General Information of Drug (ID: DMUIE76)

Drug Name
Acetaminophen
Synonyms
acetaminophen; 4-Acetamidophenol; Paracetamol; 103-90-2; Tylenol; N-(4-Hydroxyphenyl)acetamide; APAP; Acetaminofen; Panadol; Datril; p-Hydroxyacetanilide; N-Acetyl-p-aminophenol; p-Acetamidophenol; Algotropyl; Naprinol; Lonarid; 4'-Hydroxyacetanilide; Multin; Acenol; Acamol; Anelix; p-Acetaminophenol; Liquagesic; Acetagesic; Gelocatil; Servigesic; Acetalgin; Abensanil; Pyrinazine; Injectapap; Clixodyne; Valgesic; Tussapap; Finimal; Paracet; Homoolan; Febrolin; Febrilix; Febridol; Dymadon; Anaflon; Apamide; Valadol; Tralgon; Tabalgin; Lestemp; Alvedon; Abenol; Abrol; Abrolet; Acephen; Acertol; Acetaco; Acetamol; Acetavance; Acetofen; Actamin; Actimol; Afebrin; Afebryl; Aferadol; Algesidal; Algina; Algomol; Alpiny; Alpinyl; Amadil; Aminofen; Analter; Anapap; Andox; Anhiba; Antidol; Anuphen; Apacet; Apadon; Apitrelal; Arfen; Arthralgen; Asetam; Asomal; Aspac; Asplin; Atasol; Atralidon; Babikan; Bacetamol; Banesin; Benmyo; Biocetamol; Cadafen; Calapol; Calmanticold; Calonal; Calpol; Capital; Captin; Causalon; Cefalex; Cetadol; Codabrol; Codalgin; Codapane; Codicet; Codisal; Codoliprane; Cofamol; Conacetol; Cosutone; Cuponol; Curadon; Curpol; Custodial; Dafalgan; Darocet; Darvocet; Daygrip; Deminofen; Democyl; Demogripal; Desfebre; Dhamol; Dimindol; Dirox; Disprol; Dolcor; Dolefin; Dolegrippin; Dolgesic; Doliprane; Dolko; Dolofugin; Doloreduct; Dolorfug; Dolorstop; Dolotec; Dolprone; Dorocoff; Dresan; Dristancito; Duaneo; Dularin; Duorol; Duracetamol; Durapan; Dypap; Ecosetol; Elixodyne; Empracet; Enelfa; Eneril; Excipain; Exdol; Fanalgic; Farmadol; Febranine; Febrectal; Febrectol; Febrex; Febricet; Febrin; Febrinol; Fendon; Fensum; Fepanil; Fevor; Finiweh; Fluparmol; Geluprane; Genapap; Genebs; Grippostad; Gynospasmine; Hedex; Ildamol; Inalgex; Infadrops; Janupap; Kataprin; Korum; Labamol; Lekadol; Lemgrip; Lemsip; Liqiprine; Lupocet; Lyteca; Magnidol; Malgis; Malidens; Maxadol; Medocodene; Mexalen; Minafen; Minoset; Miralgin; Momentum; NEBS; Napafen; Nealgyl; NeoCitran; Neodol; Neodolito; Neopap; Neotrend; Neuridon; NilnOcen; Nina; Nobedon; Nodolex; Noral; Ofirmev; Oltyl; Oralgan; Ortensan; Oxycocet; Paceco; Pacemo; Pacemol; Pacet; Pacimol; Paedialgon; Paedol; Painex; Paldesic; Pamol; Panacete; Panadeine; Panadiene; Panaleve; Panamax; Panasorb; Panasorbe; Panets; Panex; Panodil; Panofen; Pantalgin; Paracemol; Paracenol; Paracetamole; Paracetamolo; Paracetanol; Paracetol; Paracin; Paracod; Paracodol; Parador; Paradrops; Parakapton; Parake; Paralen; Paralief; Paralink; Paralyoc; Paramol; Paramolan; Paranox; Parapan; Parasedol; Parasin; Paraspen; Parcetol; Parelan; Parmol; Parogal; Paroma; Pasolind; Pediapirin; Pediatrix; Pedric; Perfalgan; Phendon; Phenipirin; Phogoglandin; Pinex; Piramin; Pirinasol; Plicet; Polmofen; Predimol; Predualito; Prodol; Prompt; Prontina; Puernol; Pulmofen; Pyrigesic; Pyromed; Redutemp; Reliv; Remedol; Rivalgyl; Robigesic; Rounox; RubieMol; Rubophen; Rupemol; Salzone; Sanicet; Sanicopyrine; Scanol; Scentalgyl; Schmerzex; Sedalito; Semolacin; Seskamol; Setakop; Setamol; Setol; Sifenol; Sinaspril; Sinedol; Sinmol; Stanback; Stopain; Sunetheton; Supofen; Suppap; TYL; Tachiprina; Tapanol; Tapar; Tazamol; Temlo; Tempanal; Tempra; Termacet; Termalgin; Termalgine; Termofren; Tiffy; Titralgan; Treuphadol; Tricoton; Tylex; Tylol; Tymol; Upsanol; Utragin; Valorin; Veralgina; Vermidon; Verpol; Vips; Viruflu; Vivimed; Volpan; Zatinol; Zolben; Aceta Elixir; Actifed Plus; Aspirin free anacin; Bayer Select; D oliprane; Dymadon Co; Fortalidon P; Gattaphen T; Gripin Bebe; Helon N; Influbene N; Jin Gang; Lonarid Mono; Lyteca Syrup; Malex N; Panadeine Co; Panale ve; Pasolind N; Spalt N; Supadol mono; Toximer P; Treupel N; Treupel mon; Ty lenol; Tylex CD; Anacin 3; A-Per; Accu-Tap; Ultracet
Indication
Disease Entry ICD 11 Status REF
Pain MG30-MG3Z Approved [1], [2], [3]
Therapeutic Class
Analgesics
Drug Type
Small molecular drug
Structure
3D MOL 2D MOL
#Ro5 Violations (Lipinski): 0 Molecular Weight (mw) 151.16
Topological Polar Surface Area (xlogp) 0.5
Rotatable Bond Count (rotbonds) 1
Hydrogen Bond Donor Count (hbonddonor) 2
Hydrogen Bond Acceptor Count (hbondacc) 2
ADMET Property
Absorption Tmax
The time to maximum plasma concentration (Tmax) is 90 min [4]
BDDCS Class
Biopharmaceutics Drug Disposition Classification System (BDDCS) Class 1: high solubility and high permeability [5]
Bioavailability
The bioavailability of drug is 88% [4]
Clearance
The drug present in the plasma can be removed from the body at the rate of 5 mL/min/kg [6]
Elimination
Less than 5% is excreted in the urine as free (unconjugated) acetaminophen and at least 90% of the administered dose is excreted within 24 hours [7]
Half-life
The concentration or amount of drug in body reduced by one-half in 2.5 hours [4]
Metabolism
The drug is metabolized via the liver [8]
MRTD
The Maximum Recommended Therapeutic Dose (MRTD) of drug that ensured maximising efficacy and moderate side effect is 330.76126 micromolar/kg/day [9]
Unbound Fraction
The unbound fraction of drug in plasma is 0.52% [6]
Vd
The volume of distribution (Vd) of drug is 0.9 L/kg [10]
Water Solubility
The ability of drug to dissolve in water is measured as 23.7 mg/mL [5]
Chemical Identifiers
Formula
C8H9NO2
IUPAC Name
N-(4-hydroxyphenyl)acetamide
Canonical SMILES
CC(=O)NC1=CC=C(C=C1)O
InChI
InChI=1S/C8H9NO2/c1-6(10)9-7-2-4-8(11)5-3-7/h2-5,11H,1H3,(H,9,10)
InChIKey
RZVAJINKPMORJF-UHFFFAOYSA-N
Cross-matching ID
PubChem CID
1983
ChEBI ID
CHEBI:46195
CAS Number
103-90-2
DrugBank ID
DB00316
TTD ID
D0U5QK
VARIDT ID
DR01006
INTEDE ID
DR0037
ACDINA ID
D00009

Molecular Interaction Atlas of This Drug


Drug Therapeutic Target (DTT)
DTT Name DTT ID UniProt ID MOA REF
Norepinephrine transporter (NET) TTAWNKZ SC6A2_HUMAN Inhibitor [11]
Prostaglandin G/H synthase (COX) TTK0943 PGH1_HUMAN; PGH2_HUMAN Inhibitor [12], [13], [14]
Serotonin transporter (SERT) TT3ROYC SC6A4_HUMAN Inhibitor [11]

Drug Transporter (DTP)
DTP Name DTP ID UniProt ID MOA REF
Multidrug resistance-associated protein 2 (ABCC2) DTFI42L MRP2_HUMAN Substrate [15]

Drug-Metabolizing Enzyme (DME)
DME Name DME ID UniProt ID MOA REF
Cytochrome P450 3A4 (CYP3A4) DE4LYSA CP3A4_HUMAN Substrate [16]
Cytochrome P450 2E1 (CYP2E1)
Main DME
DEVDYN7 CP2E1_HUMAN Substrate [17]
Cytochrome P450 2D6 (CYP2D6) DECB0K3 CP2D6_HUMAN Substrate [16]
Cytochrome P450 2C9 (CYP2C9) DE5IED8 CP2C9_HUMAN Substrate [18]
Cytochrome P450 1A1 (CYP1A1) DE6OQ3W CP1A1_HUMAN Substrate [19]
UDP-glucuronosyltransferase 1A1 (UGT1A1) DEYGVN4 UD11_HUMAN Substrate [20]
Glutathione S-transferase alpha-1 (GSTA1) DE4ZHS1 GSTA1_HUMAN Substrate [21]
Cytochrome P450 2A6 (CYP2A6) DEJVYAZ CP2A6_HUMAN Substrate [16]
Cytochrome P450 1A2 (CYP1A2) DEJGDUW CP1A2_HUMAN Substrate [22]
Cytochrome P450 3A5 (CYP3A5) DEIBDNY CP3A5_HUMAN Substrate [23]
UDP-glucuronosyltransferase 1A9 (UGT1A9) DE85D2P UD19_HUMAN Substrate [24]
Sulfotransferase 1A1 (SULT1A1) DEYWLRK ST1A1_HUMAN Substrate [25]
UDP-glucuronosyltransferase 1A6 (UGT1A6) DESD26P UD16_HUMAN Substrate [26]
UDP-glucuronosyltransferase 2B15 (UGT2B15) DENZ6B1 UDB15_HUMAN Substrate [27]
Cytochrome P450 102A1 (cyp102) DE4OGUF CPXB_BACMB Substrate [28]
Molecular Interaction Atlas (MIA) Jump to Detail Molecular Interaction Atlas of This Drug

Molecular Expression Atlas of This Drug

The Studied Disease Pain
ICD Disease Classification MG30-MG3Z
Molecule Name Molecule Type Gene Name p-value Fold-Change Z-score
Serotonin transporter (SERT) DTT SLC6A4 8.76E-01 7.18E-05 6.19E-04
Multidrug resistance-associated protein 2 (ABCC2) DTP MRP2 6.25E-01 8.95E-02 8.58E-01
Sulfotransferase 1A1 (SULT1A1) DME SULT1A1 2.45E-01 1.10E-01 2.25E-01
UDP-glucuronosyltransferase 1A1 (UGT1A1) DME UGT1A1 4.53E-01 4.14E-02 1.83E-01
Cytochrome P450 2E1 (CYP2E1) DME CYP2E1 9.45E-02 -1.86E-01 -9.83E-01
UDP-glucuronosyltransferase 2B15 (UGT2B15) DME UGT2B15 4.75E-01 9.00E-02 8.57E-01
Cytochrome P450 2A6 (CYP2A6) DME CYP2A6 8.99E-01 4.59E-03 2.19E-02
Cytochrome P450 1A2 (CYP1A2) DME CYP1A2 8.46E-01 -6.63E-03 -4.49E-02
Cytochrome P450 3A5 (CYP3A5) DME CYP3A5 9.57E-01 9.43E-03 1.29E-01
Cytochrome P450 2D6 (CYP2D6) DME CYP2D6 8.70E-01 2.98E-02 1.22E-01
Cytochrome P450 1A1 (CYP1A1) DME CYP1A1 7.84E-01 -1.03E-01 -4.48E-01
Cytochrome P450 2C9 (CYP2C9) DME CYP2C9 2.35E-01 2.78E-02 2.09E-01
Glutathione S-transferase alpha-1 (GSTA1) DME GSTA1 5.78E-01 3.39E-02 1.54E-01
Cytochrome P450 3A4 (CYP3A4) DME CYP3A4 1.76E-01 1.26E-01 8.27E-01
Molecular Expression Atlas (MEA) Jump to Detail Molecular Expression Atlas of This Drug

Drug-Drug Interaction (DDI) Information of This Drug

Coadministration of a Drug Treating the Same Disease as Acetaminophen
DDI Drug Name DDI Drug ID Severity Mechanism Disease REF
Prilocaine DMI7DZ2 Major Increased risk of methemoglobinemia by the combination of Acetaminophen and Prilocaine. Pain [MG30-MG3Z] [174]
Flavoxate DMKV4NL Minor Altered absorption of Acetaminophen due to GI dynamics variation caused by Flavoxate. Pain [MG30-MG3Z] [175]
Coadministration of a Drug Treating the Disease Different from Acetaminophen (Comorbidity)
DDI Drug Name DDI Drug ID Severity Mechanism Comorbidity REF
Remdesivir DMBFZ6L Moderate Increased risk of hepatotoxicity by the combination of Acetaminophen and Remdesivir. 1D6YCoronavirus Disease 2019 [1D6YCoronavirus Disease 2019] [174]
Thioguanine DM7NKEV Moderate Increased risk of hepatotoxicity by the combination of Acetaminophen and Thioguanine. Acute myeloid leukaemia [2A60] [176]
Arn-509 DMT81LZ Moderate Increased metabolism of Acetaminophen caused by Arn-509 mediated induction of UGT. Acute myeloid leukaemia [2A60] [177]
Scopolamine DMOM8AL Minor Altered absorption of Acetaminophen due to GI dynamics variation caused by Scopolamine. Addictive disorder [6C50-6C5Z] [175]
Bedaquiline DM3906J Moderate Increased risk of hepatotoxicity by the combination of Acetaminophen and Bedaquiline. Antimicrobial drug resistance [MG50-MG52] [178]
Methylphenobarbital DMDSWAG Moderate Increased metabolism of Acetaminophen caused by Methylphenobarbital mediated induction of CYP450 enzyme. Anxiety disorder [6B00-6B0Z] [179]
Oxazepam DMXNZM4 Minor Decreased metabolism of Acetaminophen caused by Oxazepam mediated inhibition of CYP450 enzyme. Anxiety disorder [6B00-6B0Z] [180]
Pexidartinib DMS2J0Z Major Increased risk of hepatotoxicity by the combination of Acetaminophen and Pexidartinib. Bone/articular cartilage neoplasm [2F7B] [181]
Secobarbital DM14RF5 Moderate Increased metabolism of Acetaminophen caused by Secobarbital mediated induction of CYP450 enzyme. Chronic insomnia [7A00] [182]
Anisindione DM2C48U Moderate Increased risk of bleeding by the combination of Acetaminophen and Anisindione. Coagulation defect [3B10] [183]
Methohexital DM7YMIT Moderate Increased metabolism of Acetaminophen caused by Methohexital mediated induction of CYP450 enzyme. Corneal disease [9A76-9A78] [182]
Thiopental DMGP8AX Moderate Increased metabolism of Acetaminophen caused by Thiopental mediated induction of CYP450 enzyme. Corneal disease [9A76-9A78] [182]
Ethanol DMDRQZU Major Increased risk of hepatotoxicity by the combination of Acetaminophen and Ethanol. Cystitis [GC00] [184]
Hyoscyamine DM804UR Minor Altered absorption of Acetaminophen due to GI dynamics variation caused by Hyoscyamine. Digestive system disease [DE2Z] [175]
Mepenzolate DM8YU2F Minor Altered absorption of Acetaminophen due to GI dynamics variation caused by Mepenzolate. Digestive system disease [DE2Z] [175]
Oxybutynine DMJPBAX Minor Altered absorption of Acetaminophen due to GI dynamics variation caused by Oxybutynine. Discovery agent [N.A.] [175]
Trihexyphenidyl DMB19L8 Minor Altered absorption of Acetaminophen due to GI dynamics variation caused by Trihexyphenidyl. Dystonic disorder [8A02] [175]
Primidone DM0WX6I Moderate Increased metabolism of Acetaminophen caused by Primidone mediated induction of CYP450 enzyme. Epilepsy/seizure [8A61-8A6Z] [182]
Mephenytoin DM5UGDK Moderate Increased metabolism of Acetaminophen caused by Mephenytoin mediated induction of CYP450 enzyme. Epilepsy/seizure [8A61-8A6Z] [185]
Fosphenytoin DMOX3LB Moderate Increased metabolism of Acetaminophen caused by Fosphenytoin mediated induction of CYP450 enzyme. Epilepsy/seizure [8A61-8A6Z] [185]
Ethotoin DMXWOCP Moderate Increased metabolism of Acetaminophen caused by Ethotoin mediated induction of CYP450 enzyme. Epilepsy/seizure [8A61-8A6Z] [185]
Phenobarbital DMXZOCG Moderate Increased metabolism of Acetaminophen caused by Phenobarbital mediated induction of CYP450 enzyme. Epilepsy/seizure [8A61-8A6Z] [182]
Carbamazepine DMZOLBI Moderate Increased metabolism of Acetaminophen caused by Carbamazepine mediated induction of CYP450 enzyme. Epilepsy/seizure [8A61-8A6Z] [186]
Cannabidiol DM0659E Moderate Increased risk of hepatotoxicity by the combination of Acetaminophen and Cannabidiol. Epileptic encephalopathy [8A62] [177]
Solifenacin DMG592Q Minor Altered absorption of Acetaminophen due to GI dynamics variation caused by Solifenacin. Functional bladder disorder [GC50] [175]
Tolterodine DMSHPW8 Minor Altered absorption of Acetaminophen due to GI dynamics variation caused by Tolterodine. Functional bladder disorder [GC50] [175]
Darifenacin DMWXLYZ Minor Altered absorption of Acetaminophen due to GI dynamics variation caused by Darifenacin. Functional bladder disorder [GC50] [175]
Propantheline DM2EN6G Minor Altered absorption of Acetaminophen due to GI dynamics variation caused by Propantheline. Gastric ulcer [DA60] [175]
Sulfinpyrazone DMEV954 Moderate Increased metabolism of Acetaminophen caused by Sulfinpyrazone mediated induction of CYP450 enzyme. Gout [FA25] [186]
Isoniazid DM5JVS3 Moderate Increased metabolism of Acetaminophen caused by Isoniazid mediated induction of CYP450 enzyme. HIV-infected patients with tuberculosis [1B10-1B14] [187]
Rifampin DMA8J1G Minor Increased risk of hepatotoxicity by the combination of Acetaminophen and Rifampin. HIV-infected patients with tuberculosis [1B10-1B14] [182]
Brentuximab vedotin DMWLC57 Moderate Increased risk of hepatotoxicity by the combination of Acetaminophen and Brentuximab vedotin. Hodgkin lymphoma [2B30] [188]
Zidovudine DM4KI7O Minor Increased risk of hepatotoxicity by the combination of Acetaminophen and Zidovudine. Human immunodeficiency virus disease [1C60-1C62] [189]
Efavirenz DMC0GSJ Moderate Increased risk of hepatotoxicity by the combination of Acetaminophen and Efavirenz. Human immunodeficiency virus disease [1C60-1C62] [190]
Fenofibrate DMFKXDY Moderate Decreased metabolism of Acetaminophen caused by Fenofibrate mediated inhibition of CYP450 enzyme. Hyper-lipoproteinaemia [5C80] [174]
Mipomersen DMGSRN1 Major Increased risk of hepatotoxicity by the combination of Acetaminophen and Mipomersen. Hyper-lipoproteinaemia [5C80] [191]
Teriflunomide DMQ2FKJ Major Increased risk of hepatotoxicity by the combination of Acetaminophen and Teriflunomide. Hyper-lipoproteinaemia [5C80] [192]
BMS-201038 DMQTAGO Major Increased risk of hepatotoxicity by the combination of Acetaminophen and BMS-201038. Hyper-lipoproteinaemia [5C80] [193]
Givosiran DM5PFIJ Moderate Decreased metabolism of Acetaminophen caused by Givosiran mediated inhibition of CYP450 enzyme. Inborn porphyrin/heme metabolism error [5C58] [194]
Belladonna DM2RBWK Minor Altered absorption of Acetaminophen due to GI dynamics variation caused by Belladonna. Infectious gastroenteritis/colitis [1A40] [175]
Amobarbital DM0GQ8N Moderate Increased metabolism of Acetaminophen caused by Amobarbital mediated induction of CYP450 enzyme. Insomnia [7A00-7A0Z] [182]
Clidinium DMUMQZ0 Minor Altered absorption of Acetaminophen due to GI dynamics variation caused by Clidinium. Irritable bowel syndrome [DD91] [175]
Dicyclomine DMZSDGX Minor Altered absorption of Acetaminophen due to GI dynamics variation caused by Dicyclomine. Irritable bowel syndrome [DD91] [175]
Methotrexate DM2TEOL Moderate Increased risk of hepatotoxicity by the combination of Acetaminophen and Methotrexate. Leukaemia [2A60-2B33] [177]
Glycerol phenylbutyrate DMDGRQO Moderate Decreased metabolism of Acetaminophen caused by Glycerol phenylbutyrate mediated inhibition of CYP450 enzyme. Liver disease [DB90-DB9Z] [177]
Ceritinib DMB920Z Moderate Decreased metabolism of Acetaminophen caused by Ceritinib mediated inhibition of CYP450 enzyme. Lung cancer [2C25] [174]
PF-06463922 DMKM7EW Moderate Increased metabolism of Acetaminophen caused by PF-06463922 mediated induction of UGT. Lung cancer [2C25] [174]
Calaspargase pegol DMQZBXI Moderate Increased risk of hepatotoxicity by the combination of Acetaminophen and Calaspargase pegol. Malignant haematopoietic neoplasm [2B33] [195]
Idelalisib DM602WT Moderate Increased risk of hepatotoxicity by the combination of Acetaminophen and Idelalisib. Mature B-cell leukaemia [2A82] [196]
Clofarabine DMCVJ86 Moderate Increased risk of hepatotoxicity by the combination of Acetaminophen and Clofarabine. Mature B-cell lymphoma [2A85] [197]
Vemurafenib DM62UG5 Moderate Decreased metabolism of Acetaminophen caused by Vemurafenib mediated inhibition of CYP450 enzyme. Melanoma [2C30] [198]
Propranolol DM79NTF Minor Decreased metabolism of Acetaminophen caused by Propranolol. Migraine [8A80] [199]
Exjade DMHPRWG Moderate Decreased metabolism of Acetaminophen caused by Exjade mediated inhibition of CYP450 enzyme. Mineral absorption/transport disorder [5C64] [200]
Imatinib DM7RJXL Moderate Increased risk of hepatotoxicity by the combination of Acetaminophen and Imatinib. Myeloproliferative neoplasm [2A20] [201]
Metoclopramide DMFA5MY Minor Altered absorption of Acetaminophen due to GI dynamics variation caused by Metoclopramide. Nausea/vomiting [MD90] [174]
Rucaparib DM9PVX8 Moderate Decreased metabolism of Acetaminophen caused by Rucaparib mediated inhibition of CYP450 enzyme. Ovarian cancer [2C73] [202]
Biperiden DME78OA Minor Altered absorption of Acetaminophen due to GI dynamics variation caused by Biperiden. Parkinsonism [8A00] [175]
Procyclidine DMHFJDT Minor Altered absorption of Acetaminophen due to GI dynamics variation caused by Procyclidine. Parkinsonism [8A00] [175]
Ranitidine DM0GUSX Minor Increased risk of hepatotoxicity by the combination of Acetaminophen and Ranitidine. Peptic ulcer [DA61] [203]
Methylscopolamine DM5VWOB Minor Altered absorption of Acetaminophen due to GI dynamics variation caused by Methylscopolamine. Peptic ulcer [DA61] [175]
Leflunomide DMR8ONJ Major Increased risk of hepatotoxicity by the combination of Acetaminophen and Leflunomide. Rheumatoid arthritis [FA20] [192]
Trabectedin DMG3Y89 Moderate Increased risk of hepatotoxicity by the combination of Acetaminophen and Trabectedin. Solid tumour/cancer [2A00-2F9Z] [177]
Epirubicin DMPDW6T Moderate Increased risk of hepatotoxicity by the combination of Acetaminophen and Epirubicin. Solid tumour/cancer [2A00-2F9Z] [174]
Pitolisant DM8RFNJ Moderate Increased metabolism of Acetaminophen caused by Pitolisant mediated induction of CYP450 enzyme. Somnolence [MG42] [177]
Naltrexone DMUL45H Moderate Increased risk of hepatotoxicity by the combination of Acetaminophen and Naltrexone. Substance abuse [6C40] [204]
Warfarin DMJYCVW Moderate Increased risk of bleeding by the combination of Acetaminophen and Warfarin. Supraventricular tachyarrhythmia [BC81] [183]
Liraglutide DM3FXPS Minor Altered absorption of Acetaminophen due to GI dynamics variation caused by Liraglutide. Type 2 diabetes mellitus [5A11] [205]
Atropine DMEN6X7 Minor Altered absorption of Acetaminophen due to GI dynamics variation caused by Atropine. Unspecific substance harmful effect [NE6Z] [175]
⏷ Show the Full List of 68 DDI Information of This Drug

Drug Inactive Ingredient(s) (DIG) and Formulation(s) of This Drug

DIG
DIG Name DIG ID PubChem CID Functional Classification
Acesulfame E00341 36573 Flavoring agent
Allura red AC dye E00338 33258 Colorant
Ascorbyl palmitate E00581 54680660 Antioxidant
Aspartame E00402 134601 Flavoring agent
Benzyl alcohol E00010 244 Antimicrobial preservative; Solvent
Butylparaben E00142 7184 Antimicrobial preservative
Calcium carbonate E00198 10112 Binding agent; Buffering agent; Diluent; Opacifying agent
D&C red no. 27 E00381 83511 Colorant
D&C red no. 30 E00456 3000709 Colorant
D&C red no. 33 E00261 19116 Colorant
DL-alpha-tocopherol E00052 2116 Antioxidant
FD&C blue no. 1 E00263 19700 Colorant
FD&C blue no. 2 E00446 2723854 Colorant
FD&C yellow no. 5 free acid E00246 16014 Colorant
Isopropyl alcohol E00070 3776 Antimicrobial preservative; Solvent
Kyselina citronova E00014 311 Acidulant; Antioxidant; Buffering agent; Complexing agent; Flavoring agent
Lauryl sulfate E00189 8778 Emulsifying agent; Modified-release agent; Penetration agent; Solubilizing agent; Surfactant; lubricant
Maltitol E00423 493591 Binding agent; Coating agent; Diluent; Flavoring agent
Mannitol E00103 6251 Diluent; Flavoring agent; Lyophilization aid; Plasticizing agent; Tonicity agent
Menthol E00050 1254 Flavoring agent
methylparaben E00149 7456 Antimicrobial preservative
Oleic acid E00421 445639 Emulsifying agent; Penetration agent; Solubilizing agent
Potassium acetate E00430 517044 Film/membrane-forming agent
Propyl 4-hydroxybenzoate E00141 7175 Antimicrobial preservative
Propylparaben sodium E00567 23679044 Antimicrobial preservative
Quinoline yellow WS E00309 24671 Colorant
Sodium benzoate E00432 517055 Antimicrobial preservative; lubricant
Sodium citrate anhydrous E00102 6224 Alkalizing agent; Buffering agent; Complexing agent; Emulsifying agent
Sodium ethylparaben E00568 23681179 Antimicrobial preservative
Sodium lauryl sulfate E00464 3423265 Emulsifying agent; Modified-release agent; Penetration agent; Solubilizing agent; Surfactant; lubricant
Sodium methylparaben E00543 23663626 Antimicrobial preservative
Stearic acid E00079 5281 Emulsifying agent; Solubilizing agent; Viscosity-controlling agent; lubricant
Sucralose E00370 71485 Flavoring agent
Sunset yellow FCF E00255 17730 Colorant
Vanillin E00049 1183 Flavoring agent
Ammonia E00007 222 Alkalizing agent
Beta-D-lactose E00099 6134 Diluent; Dry powder inhaler carrier; Lyophilization aid
Brushite E00392 104805 Diluent
Butyl alcohol E00011 263 Flavoring agent; Solvent
Calcium hydrogenphosphate E00294 24441 Diluent
Carboxymethylcellulose sodium E00621 Not Available Adsorbent; Binding agent; Disintegrant; Emulsifying agent; Suspending agent; Viscosity-controlling agent
Carmellose sodium E00625 Not Available Disintegrant
Citric acid monohydrate E00271 22230 Acidulant; Antioxidant; Buffering agent; Complexing agent; Flavoring agent
Crospovidone E00626 Not Available Disintegrant
Dextrin E00359 62698 Binding agent; Diluent; Microencapsulating agent; Stiffening agent; Suspending agent; Viscosity-controlling agent
Dextrose monohydrate E00538 22814120 Binding agent; Diluent; Flavoring agent; Tonicity agent
Edetate calcium disodium E00487 6093170 Complexing agent
Edetate disodium E00186 8759 Complexing agent
Eisenoxyd E00585 56841934 Colorant
Ferric hydroxide oxide yellow E00539 23320441 Colorant
Ferrosoferric oxide E00231 14789 Colorant
Fructose E00447 2723872 Flavoring agent
Glycerin E00026 753 Antimicrobial preservative; Emollient; Flavoring agent; Humectant; Lubricant; Plasticizing agent; Solvent; Suppository base; Tonicity agent; Viscosity-controlling agent
Hexahydric alcohol E00083 5780 Diluent; Flavoring agent; Humectant; Plasticizing agent
Hexasodium hexametaphosphate E00316 24968 Other agent
Hypromellose E00634 Not Available Coating agent
Lactose monohydrate E00393 104938 Binding agent; Diluent; Dry powder inhaler carrier; Lyophilization aid
Lithol rubin BCA E00607 135423095 Colorant
Magnesium stearate E00208 11177 lubricant
Medium-chain triglyceride E00640 Not Available Emollient; Lubricant; Surfactant
Polyethylene glycol 1000 E00647 Not Available Coating agent; Diluent; Ointment base; Plasticizing agent; Solvent; Suppository base; lubricant
Polyethylene glycol 2000 E00649 Not Available Coating agent; Diluent; Ointment base; Plasticizing agent; Solvent; Suppository base; lubricant
Polyethylene glycol 300 E00651 Not Available Coating agent; Diluent; Ointment base; Plasticizing agent; Solvent; Suppository base; lubricant
Polyethylene glycol 400 E00653 Not Available Coating agent; Diluent; Ointment base; Plasticizing agent; Solvent; Suppository base; lubricant
Polyethylene glycol 6000 E00655 Not Available Coating agent; Diluent; Ointment base; Plasticizing agent; Solvent; Suppository base; lubricant
Polysorbate 80 E00665 Not Available Dispersing agent; Emollient; Emulsifying agent; Plasticizing agent; Solubilizing agent; Surfactant; Suspending agent
Polyvinyl alcohol E00666 Not Available Coating agent; Emulsion stabilizing agent; Film/Membrane-forming agent
Potassium hydroxide E00233 14797 Alkalizing agent
Potassium sorbate E00566 23676745 Antimicrobial preservative
Povidone E00667 Not Available Binding agent; Coating agent; Disintegrant; Film/membrane-forming agent; Solubilizing agent; Suspending agent
Propylene glycol E00040 1030 Antimicrobial preservative; Humectant; Plasticizing agent; Solvent
Saccharose E00091 5988 Binding agent; Coating agent; Cryoprotectant; Diluent; Flavoring agent; Suspending agent; Viscosity-controlling agent
Silicon dioxide E00670 Not Available Anticaking agent; Opacifying agent; Viscosity-controlling agent
Sodium bicarbonate E00424 516892 Alkalizing agent; Diluent
Sodium chloride E00077 5234 Diluent; Tonicity agent
Sodium hydroxide E00234 14798 Alkalizing agent
Sodium metabisulfite E00444 656671 Antimicrobial preservative; Antioxidant
Sodium propionate E00445 2723816 Antimicrobial preservative
Talc E00520 16211421 Anticaking agent; Diluent; Glidant; lubricant
Titanium dioxide E00322 26042 Coating agent; Colorant; Opacifying agent
Triacetin E00080 5541 Humectant; Plasticizing agent; Solvent
Vinylpyrrolidone E00668 Not Available Binding agent; Coating agent; Disintegrant; Film/membrane-forming agent; Solubilizing agent; Suspending agent
Water E00035 962 Solvent
⏷ Show the Full List of 83 Pharmaceutical Excipients of This Drug
Pharmaceutical Formulation
Formulation Name Drug Dosage Dosage Form Route
Acetaminophen 500 mg tablet 500 mg Oral Tablet Oral
Acetaminophen 160 mg tablet 160 mg Disintegrating Oral Tablet Oral
Acetaminophen 160 mg tablet 160 mg Chewable Tablet Oral
Acetaminophen 325 mg tablet 325 mg Disintegrating Oral Tablet Oral
Acetaminophen 650 mg tablet 650 mg 8 HR Extended Release Tablet Oral
Acetaminophen 650 mg tablet 650 mg Extended Release Oral Tablet Oral
Acetaminophen 80 mg tablet 80 mg Disintegrating Oral Tablet Oral
Acetaminophen 80 mg tablet 80 mg Chewable Tablet Oral
Acetaminophen 500 mg capsule 500 mg Oral Capsule Oral
Acetaminophen 80 mg tablet 80 mg Oral Tablet Oral
Acetaminophen 650 mg tablet 650 mg 8 HR Extended Release Oral Tablet Oral
Acetaminophen 325 mg capsule 325 mg Oral Capsule Oral
Acetaminophen 325 mg tablet 325 mg Oral Tablet Oral
Acetaminophen 650 mg tablet 650 mg Oral Tablet Oral
Jump to Detail Pharmaceutical Formulation Page of This Drug

References

1 The Diversion of Ultram, Ultracet, and generic tramadol HCL. J Addict Dis. 2006;25(2):53-8.
2 URL: http://www.guidetopharmacology.org Nucleic Acids Res. 2015 Oct 12. pii: gkv1037. The IUPHAR/BPS Guide to PHARMACOLOGY in 2016: towards curated quantitative interactions between 1300 protein targets and 6000 ligands. (Ligand id: 5239).
3 FDA Approved Drug Products from FDA Official Website. 2009. Application Number: (NDA) 018337.
4 PharmGKB summary: pathways of acetaminophen metabolism at the therapeutic versus toxic doses. Pharmacogenet Genomics. 2015 Aug;25(8):416-26. doi: 10.1097/FPC.0000000000000150.
5 BDDCS applied to over 900 drugs
6 Trend Analysis of a Database of Intravenous Pharmacokinetic Parameters in Humans for 1352 Drug Compounds
7 An FDA phase I clinical trial of quinacrine sterilization (QS). Int J Gynaecol Obstet. 2003 Oct;83 Suppl 2:S45-9.
8 FDA approval: ado-trastuzumab emtansine for the treatment of patients with HER2-positive metastatic breast cancer. Clin Cancer Res. 2014 Sep 1;20(17):4436-41.
9 Estimating the safe starting dose in phase I clinical trials and no observed effect level based on QSAR modeling of the human maximum recommended daily dose
10 Bannwarth B, Pehourcq F: [Pharmacologic basis for using paracetamol: pharmacokinetic and pharmacodynamic issues]. Drugs. 2003;63 Spec No 2:5-13.
11 Augmentation effect of combination therapy of aripiprazole and antidepressants on forced swimming test in mice. Psychopharmacology (Berl). 2009 Sep;206(1):97-107.
12 Mechanism of action of paracetamol. Am J Ther. 2005 Jan-Feb;12(1):46-55.
13 COX-3: just another COX or the solitary elusive target of paracetamol Lancet. 2003 Mar 22;361(9362):981-2.
14 COX-3, a cyclooxygenase-1 variant inhibited by acetaminophen and other analgesic/antipyretic drugs: cloning, structure, and expression. Proc Natl Acad Sci U S A. 2002 Oct 15;99(21):13926-31.
15 Effect of acetaminophen on expression and activity of rat liver multidrug resistance-associated protein 2 and P-glycoprotein. Biochem Pharmacol. 2004 Aug 15;68(4):791-8.
16 Metabolic interactions between acetaminophen (paracetamol) and two flavonoids, luteolin and quercetin, through in-vitro inhibition studies. J Pharm Pharmacol. 2017 Dec;69(12):1762-1772.
17 Acetaminophen induced acute liver failure via oxidative stress and JNK activation: protective role of taurine by the suppression of cytochrome P450 2E1. Free Radic Res. 2010 Mar;44(3):340-55.
18 Summary of information on human CYP enzymes: human P450 metabolism data. Drug Metab Rev. 2002 Feb-May;34(1-2):83-448.
19 Preferred orientations in the binding of 4'-hydroxyacetanilide (acetaminophen) to cytochrome P450 1A1 and 2B1 isoforms as determined by 13C- and 15N-NMR relaxation studies. J Med Chem. 1994 Mar 18;37(6):860-7.
20 Effect of UDP-glucuronosyltransferase (UGT) 1A polymorphism (rs8330 and rs10929303) on glucuronidation status of acetaminophen. Dose Response. 2017 Sep 11;15(3):1559325817723731.
21 Retinoid X receptor alpha regulates the expression of glutathione s-transferase genes and modulates acetaminophen-glutathione conjugation in mouse liver. Mol Pharmacol. 2005 Dec;68(6):1590-6.
22 PharmGKB summary: pathways of acetaminophen metabolism at the therapeutic versus toxic doses. Pharmacogenet Genomics. 2015 Aug;25(8):416-26.
23 Induction of hepatic CYP2E1 by a subtoxic dose of acetaminophen in rats: increase in dichloromethane metabolism and carboxyhemoglobin elevation. Drug Metab Dispos. 2007 Oct;35(10):1754-8.
24 Polymorphic expression of UGT1A9 is associated with variable acetaminophen glucuronidation in neonates: a population pharmacokinetic and pharmacogenetic study. Clin Pharmacokinet. 2018 Oct;57(10):1325-1336.
25 Interindividual variability in acetaminophen sulfation by human fetal liver: implications for pharmacogenetic investigations of drug-induced birth defects. Birth Defects Res A Clin Mol Teratol. 2008 Mar;82(3):155-65.
26 UGT1A6 and UGT2B15 polymorphisms and acetaminophen conjugation in response to a randomized, controlled diet of select fruits and vegetables. Drug Metab Dispos. 2011 Sep;39(9):1650-7.
27 Characterization of niflumic acid as a selective inhibitor of human liver microsomal UDP-glucuronosyltransferase 1A9: application to the reaction phenotyping of acetaminophen glucuronidation. Drug Metab Dispos. 2011 Apr;39(4):644-52.
28 The bacterial P450 BM3: a prototype for a biocatalyst with human P450 activities. Trends Biotechnol. 2007 Jul;25(7):289-98.
29 Expression levels and activation of a PXR variant are directly related to drug resistance in osteosarcoma cell lines. Cancer. 2007 Mar 1;109(5):957-65.
30 Contribution of human hepatic cytochrome P450 isoforms to regioselective hydroxylation of steroid hormones. Xenobiotica. 1998 Jun;28(6):539-47.
31 Comprehensive evaluation of tamoxifen sequential biotransformation by the human cytochrome P450 system in vitro: prominent roles for CYP3A and CYP2D6. J Pharmacol Exp Ther. 2004 Sep;310(3):1062-75.
32 Isoform-specific regulation of cytochromes P450 expression by estradiol and progesterone. Drug Metab Dispos. 2013 Feb;41(2):263-9.
33 Potent mechanism-based inhibition of CYP3A4 by imatinib explains its liability to interact with CYP3A4 substrates. Br J Pharmacol. 2012 Apr;165(8):2787-98.
34 Effects of morin on the pharmacokinetics of etoposide in rats. Biopharm Drug Dispos. 2007 Apr;28(3):151-6.
35 The metabolism of zidovudine by human liver microsomes in vitro: formation of 3'-amino-3'-deoxythymidine. Biochem Pharmacol. 1994 Jul 19;48(2):267-76.
36 Substrates, inducers, inhibitors and structure-activity relationships of human Cytochrome P450 2C9 and implications in drug development. Curr Med Chem. 2009;16(27):3480-675.
37 Cytochrome P450 3A4-mediated interaction of diclofenac and quinidine. Drug Metab Dispos. 2000 Sep;28(9):1043-50.
38 Roles of cytochromes P450 1A2, 2A6, and 2C8 in 5-fluorouracil formation from tegafur, an anticancer prodrug, in human liver microsomes. Drug Metab Dispos. 2000 Dec;28(12):1457-63.
39 Effects of polyunsaturated fatty acids on prostaglandin synthesis and cyclooxygenase-mediated DNA adduct formation by heterocyclic aromatic amines in human adenocarcinoma colon cells. Mol Carcinog. 2004 Jul;40(3):180-8.
40 Endoxifen and other metabolites of tamoxifen inhibit human hydroxysteroid sulfotransferase 2A1 (hSULT2A1). Drug Metab Dispos. 2014 Nov;42(11):1843-50.
41 Cytochrome P450 1A2 (CYP1A2) activity and risk factors for breast cancer: a cross-sectional study. Breast Cancer Res. 2004;6(4):R352-65.
42 The effect of apigenin on pharmacokinetics of imatinib and its metabolite N-desmethyl imatinib in rats. Biomed Res Int. 2013;2013:789184.
43 The influence of metabolic gene polymorphisms on urinary 1-hydroxypyrene concentrations in Chinese coke oven workers. Sci Total Environ. 2007 Aug 1;381(1-3):38-46.
44 Identification of P450 enzymes involved in metabolism of verapamil in humans. Naunyn Schmiedebergs Arch Pharmacol. 1993 Sep;348(3):332-7.
45 Metabolism and metabolic inhibition of xanthotoxol in human liver microsomes. Evid Based Complement Alternat Med. 2016;2016:5416509.
46 Ontogeny and sorafenib metabolism. Clin Cancer Res. 2012 Oct 15;18(20):5788-95.
47 Functional significance of UDP-glucuronosyltransferase variants in the metabolism of active tamoxifen metabolites. Cancer Res. 2009 Mar 1;69(5):1892-900.
48 Functional characterization of human and cynomolgus monkey UDP-glucuronosyltransferase 1A1 enzymes. Life Sci. 2010 Aug 14;87(7-8):261-8.
49 UDP-glucuronosyltransferase 1A1 is the principal enzyme responsible for etoposide glucuronidation in human liver and intestinal microsomes: structural characterization of phenolic and alcoholic glucuronides of etoposide and estimation of enzyme kinetics. Drug Metab Dispos. 2007 Mar;35(3):371-80.
50 Interindividual variability in pharmacokinetics of generic nucleoside reverse transcriptase inhibitors in TB/HIV-coinfected Ghanaian patients: UGT2B7*1c is associated with faster zidovudine clearance and glucuronidation. J Clin Pharmacol. 2009 Sep;49(9):1079-90.
51 Effect of aging on glucuronidation of valproic acid in human liver microsomes and the role of UDP-glucuronosyltransferase UGT1A4, UGT1A8, and UGT1A10. Drug Metab Dispos. 2009 Jan;37(1):229-36.
52 Characterization of rat intestinal microsomal UDP-glucuronosyltransferase activity toward mycophenolic acid. Drug Metab Dispos. 2006 Sep;34(9):1632-9.
53 Drug-drug interactions for UDP-glucuronosyltransferase substrates: a pharmacokinetic explanation for typically observed low exposure (AUCi/AUC) ratios. Drug Metab Dispos. 2004 Nov;32(11):1201-8.
54 Substrate-dependent modulation of UDP-glucuronosyltransferase 1A1 (UGT1A1) by propofol in recombinant human UGT1A1 and human liver microsomes. Basic Clin Pharmacol Toxicol. 2007 Sep;101(3):211-4.
55 Identification and preliminary characterization of UDP-glucuronosyltransferases catalyzing formation of ethyl glucuronide. Anal Bioanal Chem. 2014 Apr;406(9-10):2325-32.
56 Atorvastatin glucuronidation is minimally and nonselectively inhibited by the fibrates gemfibrozil, fenofibrate, and fenofibric acid. Drug Metab Dispos. 2007 Aug;35(8):1315-24.
57 Genotoxicity of tamoxifen, tamoxifen epoxide and toremifene in human lymphoblastoid cells containing human cytochrome P450s. Carcinogenesis. 1994 Jan;15(1):5-9.
58 Psychotropic drug interactions with valproate. Clin Neuropharmacol. 2005 Mar-Apr;28(2):96-101.
59 The role of human cytochrome P450 enzymes in the formation of 2-hydroxymetronidazole: CYP2A6 is the high affinity (low Km) catalyst. Drug Metab Dispos. 2013 Sep;41(9):1686-94.
60 Possible involvement of multiple human cytochrome P450 isoforms in the liver metabolism of propofol. Br J Anaesth. 1998 Jun;80(6):788-95.
61 CYP2A6- and CYP2A13-catalyzed metabolism of the nicotine delta-5'(1')iminium ion. J Pharmacol Exp Ther. 2012 Nov;343(2):307-15.
62 Allelic variants of human cytochrome P450 1A1 (CYP1A1): effect of T461N and I462V substitutions on steroid hydroxylase specificity. Pharmacogenetics. 2000 Aug;10(6):519-30.
63 Metabolism of tamoxifen by recombinant human cytochrome P450 enzymes: formation of the 4-hydroxy, 4'-hydroxy and N-desmethyl metabolites and isomerization of trans-4-hydroxytamoxifen. Drug Metab Dispos. 2002 Aug;30(8):869-74.
64 Cytochrome P450 isoforms catalyze formation of catechol estrogen quinones that react with DNA. Metabolism. 2007 Jul;56(7):887-94.
65 Diclofenac and its derivatives as tools for studying human cytochromes P450 active sites: particular efficiency and regioselectivity of P450 2Cs. Biochemistry. 1999 Oct 26;38(43):14264-70.
66 A common CYP1B1 polymorphism is associated with 2-OHE1/16-OHE1 urinary estrone ratio. Clin Chem Lab Med. 2005;43(7):702-6.
67 Cytochromes P450 in crustacea. Comp Biochem Physiol C Pharmacol Toxicol Endocrinol. 1998 Nov;121(1-3):157-72.
68 Disruption of endogenous regulator homeostasis underlies the mechanism of rat CYP1A1 mRNA induction by metyrapone. Biochem J. 1998 Apr 1;331 ( Pt 1):273-81.
69 Pharmacogenomics in drug-metabolizing enzymes catalyzing anticancer drugs for personalized cancer chemotherapy. Curr Drug Metab. 2007 Aug;8(6):554-62.
70 Roles of CYP2A6 and CYP2B6 in nicotine C-oxidation by human liver microsomes. Arch Toxicol. 1999 Mar;73(2):65-70.
71 Progestagenic effects of tibolone are target gene-specific in human endometrial cells. J Soc Gynecol Investig. 2006 Sep;13(6):459-65.
72 Tamoxifen-induced adduct formation and cell stress in human endometrial glands. Drug Metab Dispos. 2010 Jan;38(1):200-7.
73 Proposed role of the sulfotransferase/sulfatase pathway in modulating yolk steroid effects. Integr Comp Biol. 2008 Sep;48(3):419-27.
74 Inhibition of human phenol and estrogen sulfotransferase by certain non-steroidal anti-inflammatory agents. Curr Drug Metab. 2006 Oct;7(7):745-53.
75 Natural products isolated from Mexican medicinal plants: novel inhibitors of sulfotransferases, SULT1A1 and SULT2A1. Phytomedicine. 2001 Nov;8(6):481-8.
76 Kinetic analysis of bile acid sulfation by stably expressed human sulfotransferase 2A1 (SULT2A1). Xenobiotica. 2010 Mar;40(3):184-94.
77 Characterization of human liver thermostable phenol sulfotransferase (SULT1A1) allozymes with 3,3',5-triiodothyronine as the substrate. J Endocrinol. 2001 Dec;171(3):525-32.
78 Crystal structure of human sulfotransferase SULT1A3 in complex with dopamine and 3'-phosphoadenosine 5'-phosphate. Biochem Biophys Res Commun. 2005 Sep 23;335(2):417-23.
79 Sulfation of benzyl alcohol by the human cytosolic sulfotransferases (SULTs): a systematic analysis. J Appl Toxicol. 2016 Sep;36(9):1090-4.
80 The 2.7 A resolution structure of the glycopeptide sulfotransferase Teg14. Acta Crystallogr D Biol Crystallogr. 2010 Dec;66(Pt 12):1278-86.
81 Inhibitory effects of anticancer drugs on dextromethorphan-O-demethylase activity in human liver microsomes. Cancer Chemother Pharmacol. 1993;32(6):491-5.
82 Effect of genetic polymorphism on the metabolism of endogenous neuroactive substances, progesterone and p-tyramine, catalyzed by CYP2D6. Brain Res Mol Brain Res. 2004 Oct 22;129(1-2):117-23.
83 CYP2D6 polymorphisms and tamoxifen metabolism: clinical relevance. Curr Oncol Rep. 2010 Jan;12(1):7-15.
84 Inhibition of cytochrome P450 2D6: structure-activity studies using a series of quinidine and quinine analogues. Chem Res Toxicol. 2003 Apr;16(4):450-9.
85 Effects of propofol on human hepatic microsomal cytochrome P450 activities. Xenobiotica. 1998 Sep;28(9):845-53.
86 Pharmacogenetics of schizophrenia. Am J Med Genet. 2000 Spring;97(1):98-106.
87 Structure-activity relationship for human cytochrome P450 substrates and inhibitors. Drug Metab Rev. 2002 Feb-May;34(1-2):69-82.
88 Bioactivation of the tricyclic antidepressant amitriptyline and its metabolite nortriptyline to arene oxide intermediates in human liver microsomes and recombinant P450s. Chem Biol Interact. 2008 May 9;173(1):59-67.
89 Role of glutathione S-transferase P1-1 in the cellular detoxification of cisplatin. Mol Cancer Ther. 2008 Oct;7(10):3247-55.
90 Human glutathione transferase A3-3, a highly efficient catalyst of double-bond isomerization in the biosynthetic pathway of steroid hormones. J Biol Chem. 2001 Aug 31;276(35):33061-5.
91 Comparison of basal glutathione S-transferase activities and of the influence of phenobarbital, butylated hydroxy-anisole or 5,5'-diphenylhydantoin on enzyme activity in male rodents. Comp Biochem Physiol C. 1987;88(1):91-3.
92 Characterization and formation of the glutathione conjugate of clofibric acid. Drug Metab Dispos. 1995 Jan;23(1):119-23.
93 In vitro characterization of the human biotransformation and CYP reaction phenotype of ET-743 (Yondelis, Trabectidin), a novel marine anti-cancer drug. Invest New Drugs. 2006 Jan;24(1):3-14.
94 Glutathione S-transferase M1 polymorphism: a risk factor for hepatic venoocclusive disease in bone marrow transplantation. Blood. 2004 Sep 1;104(5):1574-7.
95 Inhibition of glutathione S-transferases by antimalarial drugs possible implications for circumventing anticancer drug resistance. Int J Cancer. 2002 Feb 10;97(5):700-5.
96 Purification and biochemical properties of glutathione S-transferase from Lactuca sativa. J Biochem Mol Biol. 2005 Mar 31;38(2):232-7.
97 Combined glutathione-S-transferase M1 and T1 genetic polymorphism and tacrine hepatotoxicity. Clin Pharmacol Ther. 2000 Apr;67(4):432-7.
98 Metabolism of melphalan by rat liver microsomal glutathione S-transferase. Chem Biol Interact. 2005 Apr 15;152(2-3):101-6.
99 Drug related genetic polymorphisms affecting adverse reactions to methotrexate, vinblastine, doxorubicin and cisplatin in patients with urothelial cancer. J Urol. 2008 Dec;180(6):2389-95.
100 Human prostate CYP3A5: identification of a unique 5'-untranslated sequence and characterization of purified recombinant protein. Biochem Biophys Res Commun. 1999 Jul 14;260(3):676-81.
101 Polymorphisms in cytochrome P4503A5 (CYP3A5) may be associated with race and tumor characteristics, but not metabolism and side effects of tamoxifen in breast cancer patients. Cancer Lett. 2005 Jan 10;217(1):61-72.
102 Drug Interactions Flockhart Table
103 Urinary 6 beta-hydroxycortisol excretion in rheumatoid arthritis. Br J Rheumatol. 1997 Jan;36(1):54-8.
104 Clinical pharmacokinetics of imatinib. Clin Pharmacokinet. 2005;44(9):879-94.
105 Kinetics and regulation of cytochrome P450-mediated etoposide metabolism. Drug Metab Dispos. 2004 Sep;32(9):993-1000.
106 Differential mechanism-based inhibition of CYP3A4 and CYP3A5 by verapamil. Drug Metab Dispos. 2005 May;33(5):664-71.
107 16Alpha-hydroxylation of estrone by human cytochrome P4503A4/5. Carcinogenesis. 1998 May;19(5):867-72.
108 Chronic ethanol feeding and folate deficiency activate hepatic endoplasmic reticulum stress pathway in micropigs. Am J Physiol Gastrointest Liver Physiol. 2005 Jul;289(1):G54-63.
109 Cytochrome P450 2E1 null mice provide novel protection against cisplatin-induced nephrotoxicity and apoptosis. Kidney Int. 2003 May;63(5):1687-96.
110 A study on the metabolism of etoposide and possible interactions with antitumor or supporting agents by human liver microsomes. J Pharmacol Exp Ther. 1998 Sep;286(3):1294-300.
111 Novel metabolic pathway of estrone and 17beta-estradiol catalyzed by cytochrome P-450. Drug Metab Dispos. 2000 Feb;28(2):110-2.
112 Inhibition of cytochrome P450 2E1 by propofol in human and porcine liver microsomes. Biochem Pharmacol. 2002 Oct 1;64(7):1151-6.
113 CYP2E1 and clinical features in alcoholics. Neuropsychobiology. 2003;47(2):86-9.
114 Effects of nicotine on cytochrome P450 2A6 and 2E1 activities. Br J Clin Pharmacol. 2010 Feb;69(2):152-9.
115 Progesterone and testosterone hydroxylation by cytochromes P450 2C19, 2C9, and 3A4 in human liver microsomes. Arch Biochem Biophys. 1997 Oct 1;346(1):161-9.
116 Tamoxifen inhibits cytochrome P450 2C9 activity in breast cancer patients. J Chemother. 2006 Aug;18(4):421-4.
117 Characterization of the oxidative metabolites of 17beta-estradiol and estrone formed by 15 selectively expressed human cytochrome p450 isoforms. Endocrinology. 2003 Aug;144(8):3382-98.
118 Drug-drug interactions with imatinib: an observational study. Medicine (Baltimore). 2016 Oct;95(40):e5076.
119 Drug interactions with calcium channel blockers: possible involvement of metabolite-intermediate complexation with CYP3A. Drug Metab Dispos. 2000 Feb;28(2):125-30.
120 New insights into the structural features and functional relevance of human cytochrome P450 2C9. Part I. Curr Drug Metab. 2009 Dec;10(10):1075-126.
121 A potential role for the estrogen-metabolizing cytochrome P450 enzymes in human breast carcinogenesis. Breast Cancer Res Treat. 2003 Dec;82(3):191-7.
122 A mechanistic approach to antiepileptic drug interactions. Ann Pharmacother. 1998 May;32(5):554-63.
123 In vitro comparative inhibition profiles of major human drug metabolising cytochrome P450 isozymes (CYP2C9, CYP2D6 and CYP3A4) by HMG-CoA reductase inhibitors. Eur J Clin Pharmacol. 1996;50(3):209-15.
124 Glucuronidation of nonsteroidal anti-inflammatory drugs: identifying the enzymes responsible in human liver microsomes. Drug Metab Dispos. 2005 Jul;33(7):1027-35.
125 Pharmacokinetic interaction involving sorafenib and the calcium-channel blocker felodipine in a patient with hepatocellular carcinoma. Invest New Drugs. 2011 Dec;29(6):1511-4.
126 The evolution of population pharmacokinetic models to describe the enterohepatic recycling of mycophenolic acid in solid organ transplantation and autoimmune disease. Clin Pharmacokinet. 2011 Jan;50(1):1-24.
127 The UDP-glucuronosyltransferase 1A9 enzyme is a peroxisome proliferator-activated receptor alpha and gamma target gene. J Biol Chem. 2003 Apr 18;278(16):13975-83.
128 S-Naproxen and desmethylnaproxen glucuronidation by human liver microsomes and recombinant human UDP-glucuronosyltransferases (UGT): role of UGT2B7 in the elimination of naproxen. Br J Clin Pharmacol. 2005 Oct;60(4):423-33.
129 Ezetimibe: a review of its metabolism, pharmacokinetics and drug interactions. Clin Pharmacokinet. 2005;44(5):467-94.
130 Effect of the UGT2B15 genotype on the pharmacokinetics, pharmacodynamics, and drug interactions of intravenous lorazepam in healthy volunteers. Clin Pharmacol Ther. 2005 Jun;77(6):486-94.
131 Importance of UDP-glucuronosyltransferase 1A10 (UGT1A10) in the detoxification of polycyclic aromatic hydrocarbons: decreased glucuronidative activity of the UGT1A10139Lys isoform. Drug Metab Dispos. 2006 Jun;34(6):943-9.
132 UDP glucuronosyltransferase (UGT) 1A6 pharmacogenetics: II. Functional impact of the three most common nonsynonymous UGT1A6 polymorphisms (S7A, T181A, and R184S). J Pharmacol Exp Ther. 2005 Jun;313(3):1340-6.
133 Pharmacokinetics of propofol and extrahepatic UGT1A6 gene expression in anhepatic rats. Pharmacology. 2009;84(4):219-26.
134 Troglitazone glucuronidation in human liver and intestine microsomes: high catalytic activity of UGT1A8 and UGT1A10. Drug Metab Dispos. 2002 Dec;30(12):1462-9.
135 Polymorphisms of Aspirin-Metabolizing Enzymes CYP2C9, NAT2 and UGT1A6 in Aspirin-Intolerant Urticaria. Allergy Asthma Immunol Res. 2011 Oct;3(4):273-6.
136 Deferiprone glucuronidation by human tissues and recombinant UDP glucuronosyltransferase 1A6: an in vitro investigation of genetic and splice variants. Drug Metab Dispos. 2009 Feb;37(2):322-9.
137 Structural and functional studies of UDP-glucuronosyltransferases. Drug Metab Rev. 1999 Nov;31(4):817-99.
138 Human UGT1A6 pharmacogenetics: identification of a novel SNP, characterization of allele frequencies and functional analysis of recombinant allozymes in human liver tissue and in cultured cells. Pharmacogenetics. 2004 Aug;14(8):487-99.
139 Identification of aspartic acid and histidine residues mediating the reaction mechanism and the substrate specificity of the human UDP-glucuronosyltransferases 1A. J Biol Chem. 2007 Dec 14;282(50):36514-24.
140 Both reactivity and accessibility are important in cytochrome P450 metabolism: a combined DFT and MD study of fenamic acids in BM3 mutants. J Chem Inf Model. 2019 Feb 25;59(2):743-753.
141 acillus megaterium SF185 spores exert protective effects against oxidative stress in vivo and in vitro. Sci Rep. 2019 Aug 19;9(1):12082.
142 Wild-type CYP102A1 as a biocatalyst: turnover of drugs usually metabolised by human liver enzymes. J Biol Inorg Chem. 2007 Mar;12(3):313-23.
143 Involvement of the drug transporters p glycoprotein and multidrug resistance-associated protein Mrp2 in telithromycin transport. Antimicrob Agents Chemother. 2006 Jan;50(1):80-7.
144 Dose-dependent disposition of methotrexate in Abcc2 and Abcc3 gene knockout murine models. Drug Metab Dispos. 2011 Nov;39(11):2155-61.
145 Mammalian multidrug-resistance proteins (MRPs). Essays Biochem. 2011 Sep 7;50(1):179-207.
146 Enhancing chemosensitivity in oral squamous cell carcinoma by lentivirus vector-mediated RNA interference targeting EGFR and MRP2. Oncol Lett. 2016 Sep;12(3):2107-2114.
147 Multidrug resistance associated protein 2 mediates transport of prostaglandin E2. Liver Int. 2006 Apr;26(3):362-8.
148 Lentivirus-mediated RNAi silencing targeting ABCC2 increasing the sensitivity of a human nasopharyngeal carcinoma cell line against cisplatin. J Transl Med. 2008 Oct 4;6:55.
149 Small intestinal efflux mediated by MRP2 and BCRP shifts sulfasalazine intestinal permeability from high to low, enabling its colonic targeting. Am J Physiol Gastrointest Liver Physiol. 2009 Aug;297(2):G371-7.
150 Delineating the contribution of secretory transporters in the efflux of etoposide using Madin-Darby canine kidney (MDCK) cells overexpressing P-glycoprotein (Pgp), multidrug resistance-associated protein (MRP1), and canalicular multispecific organic anion transporter (cMOAT). Drug Metab Dispos. 2002 Apr;30(4):457-63.
151 Multidrug Resistance-Associated Protein 2 (MRP2) Mediated Transport of Oxaliplatin-Derived Platinum in Membrane Vesicles. PLoS One. 2015 Jul 1;10(7):e0130727.
152 Mammalian drug efflux transporters of the ATP binding cassette (ABC) family in multidrug resistance: A review of the past decade. Cancer Lett. 2016 Jan 1;370(1):153-64.
153 Diclofenac and NS-398, a selective cyclooxygenase-2 inhibitor, decrease agonist-induced contractions of the pig isolated ureter. Urol Res. 2000 Dec;28(6):376-82.
154 Cyclooxygenase inhibitors: instrumental drugs to understand cardiovascular homeostasis and arterial thrombosis. Cardiovasc Hematol Disord Drug Targets. 2008 Dec;8(4):268-77.
155 Comparison of the efficacy and tolerability of dexibuprofen and celecoxib in the treatment of osteoarthritis of the hip. Int J Clin Pharmacol Ther. 2003 Apr;41(4):153-64.
156 Cyclooxygenase and nitric oxide synthase dependence of cutaneous reactive hyperemia in humans. Am J Physiol Heart Circ Physiol. 2007 Jul;293(1):H425-32.
157 Interactions of PGH synthase isozymes-1 and -2 with NSAIDs. Ann N Y Acad Sci. 1994 Nov 15;744:50-7.
158 The aryl propionic acid R-flurbiprofen selectively induces p75NTR-dependent decreased survival of prostate tumor cells. Cancer Res. 2007 Apr 1;67(7):3254-62.
159 Aceclofenac spares cyclooxygenase 1 as a result of limited but sustained biotransformation to diclofenac. Clin Pharmacol Ther. 2003 Sep;74(3):222-35.
160 The analgesic NSAID lornoxicam inhibits cyclooxygenase (COX)-1/-2, inducible nitric oxide synthase (iNOS), and the formation of interleukin (IL)-6 in vitro. Inflamm Res. 1999 Jul;48(7):369-79.
161 Modulation of arachidonic acid metabolism by orally administered morniflumate in man. Agents Actions. 1991 Jul;33(3-4):233-9.
162 Topical nepafenac inhibits ocular neovascularization. Invest Ophthalmol Vis Sci. 2003 Jan;44(1):409-15.
163 Treatment of comorbid pain with serotonin norepinephrine reuptake inhibitors. CNS Spectr. 2008 Jul;13(7 Suppl 11):22-6.
164 Invivo antioxidant status: a putative target of antidepressant action. Prog Neuropsychopharmacol Biol Psychiatry. 2009 Mar 17;33(2):220-8.
165 Differential involvement of the norepinephrine, serotonin and dopamine reuptake transporter proteins in cocaine-induced taste aversion. Pharmacol Biochem Behav. 2009 Jul;93(1):75-81.
166 Clinically relevant drug interactions with new generation antidepressants and antipsychotics. Ther Umsch. 2009 Jun;66(6):485-92.
167 2008 FDA drug approvals. Nat Rev Drug Discov. 2009 Feb;8(2):93-6.
168 Antidepressants suppress production of the Th1 cytokine interferon-gamma, independent of monoamine transporter blockade. Eur Neuropsychopharmacol. 2006 Oct;16(7):481-90.
169 Multi-target therapeutics: when the whole is greater than the sum of the parts. Drug Discov Today. 2007 Jan;12(1-2):34-42.
170 Hughes B: 2009 FDA drug approvals. Nat Rev Drug Discov. 2010 Feb;9(2):89-92.
171 Drugs@FDA. U.S. Food and Drug Administration. U.S. Department of Health & Human Services.
172 Radium 223 dichloride for prostate cancer treatment. Drug Des Devel Ther. 2017 Sep 6;11:2643-2651.
173 Psychopharmacological treatment of dermatological patients--when simply talking does not help. J Dtsch Dermatol Ges. 2007 Dec;5(12):1101-6.
174 Cerner Multum, Inc. "Australian Product Information.".
175 Clark JM, Seager SJ "Gastric emptying following premedication with glycopyrrolate or atropine." Br J Anaesth 55 (1983): 1195-9. [PMID: 6652009]
176 Product Information. Aubagio (teriflunomide). Genzyme Corporation, Cambridge, MA.
177 Cerner Multum, Inc. "UK Summary of Product Characteristics.".
178 Product Information. Sirturo (bedaquiline). Janssen Pharmaceuticals, Titusville, NJ.
179 Douidar SM, Ahmed AE "A novel mechanism for the enhancement of acetaminophen hepatotoxicity by phenobarbital." J Pharmacol Exp Ther 240 (1987): 578-83. [PMID: 3806412]
180 Dybing E "Inhibition of acetaminophen glucuronidation by oxazepam." Biochem Pharmacol 25 (1976): 1421-5. [PMID: 938564]
181 Product Information. Turalio (pexidartinib). Daiichi Sankyo, Inc., Parsippany, NJ.
182 Bock KW, Wiltfang J, Blume R, Ullrich D, Bircher J "Paracetamol as a test drug to determine glucuronide formation in man: effects of inducers and of smoking." Eur J Clin Pharmacol 31 (1987): 677-83. [PMID: 3556375]
183 Antlitz AM, Mead JA Jr, Tolentino MA "Potentiation of oral anticoagulant therapy by acetaminophen." Curr Ther Res Clin Exp 10 (1968): 501-7. [PMID: 4971464]
184 Bonkovsky HL "Acetaminophen hepatotoxicity, fasting, and ethanol." JAMA 274 (1995): 301. [PMID: 7609254]
185 Bivins BA, Rapp RP, Griffen WO Jr, Blouin R, Bustrack J "Dopamine-phenytoin interaction. A cause of hypotension in the critically ill." Arch Surg 113 (1978): 245-9. [PMID: 637689]
186 Miners JO, Attwood J, Birkett DJ "Determinants of acetaminophen metabolism: effect of inducers and inhibitors of drug metabolism on acetaminophen's metabolic pathways." Clin Pharmacol Ther 35 (1984): 480-6. [PMID: 6705446]
187 Crippin JS "Acetaminophen hepatotoxicity: potentiation by isoniazid." Am J Gastroenterol 88 (1993): 590-2. [PMID: 8470644]
188 Product Information. Adcetris (brentuximab vedotin). Seattle Genetics Inc, Bothell, WA.
189 Ameer B "Acetaminophen hepatotoxicity augmented by zidovudine." Am J Med 95 (1993): 342. [PMID: 8368234]
190 Elsharkawy AM, Schwab U, McCarron B, et al. "Efavirenz induced acute liver failure requiring liver transplantation in a slow drug metaboliser." J Clin Virol 58 (2013): 331-3. [PMID: 23763943]
191 Product Information. Kynamro (mipomersen). Genzyme Corporation, Cambridge, MA.
192 Canadian Pharmacists Association.
193 Product Information. Juxtapid (lomitapide). Aegerion Pharmaceuticals Inc, Cambridge, MA.
194 Product Information. Givlaari (givosiran). Alnylam Pharmaceuticals, Cambridge, MA.
195 Al-Nawakil C, Willems L, Mauprivez C, et.al "Successful treatment of l-asparaginase-induced severe acute hepatotoxicity using mitochondrial cofactors." Leuk Lymphoma 55 (2014): 1670-4. [PMID: 24090500]
196 Product Information. Zydelig (idelalisib). Gilead Sciences, Foster City, CA.
197 Product Information. Clolar (clofarabine). sanofi-aventis, Bridgewater, NJ.
198 Product Information. Zelboraf (vemurafenib). Genentech, South San Francisco, CA.
199 Baraka OZ, Truman CA, Ford JM, Roberts CJ. The effect of propranolol on paracetamol metabolism in man.?Br J Clin Pharmacol. 1990;29(2):261-264. [PMID: 2306420]
200 Product Information. Exjade (deferasirox). Novartis Pharmaceuticals, East Hanover, NJ.
201 Lin NU, Sarantopoulos S, Stone JR, et al. "Fatal hepatic necrosis following imatinib mesylate therapy." Blood 102 (2003): 3455-6. [PMID: 14568907]
202 EMA. European Medicines Agency. European Union "EMA - List of medicines under additional monitoring.".
203 Jack D, Thomas M, Skidmore IF "Ranitidine and paracetamol metabolism." Lancet 2 (1985): 1067. [PMID: 2865542]
204 Product Information. ReVia (naltrexone). DuPont Pharmaceuticals, Wilmington, DE.
205 Product Information. Victoza (liraglutide). Novo Nordisk Pharmaceuticals Inc, Princeton, NJ.