General Information of Drug (ID: DMUIE76)

Drug Name
Acetaminophen Drug Info
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
Cross-matching ID
PubChem CID
1983
ChEBI ID
CHEBI:46195
CAS Number
CAS 103-90-2
TTD Drug ID
DMUIE76
VARIDT Drug ID
DR01006
INTEDE Drug ID
DR0037
ACDINA Drug ID
D00009

Molecule(s) Related to This Drug


Drug Therapeutic Target (DTT)
DTT Name DTT ID UniProt ID MOA REF
Norepinephrine transporter (NET) TTAWNKZ SC6A2_HUMAN Inhibitor [4]
Prostaglandin G/H synthase (COX) TTK0943 PGH1_HUMAN; PGH2_HUMAN Inhibitor [5] , [6] , [7]
Serotonin transporter (SERT) TT3ROYC SC6A4_HUMAN Inhibitor [4]

Drug Transporter (DTP)
DTP Name DTP ID UniProt ID Highest Status REF
Multidrug resistance-associated protein 2 (ABCC2) DTFI42L MRP2_HUMAN Approved [8]

Drug-Metabolizing Enzyme (DME)
DME Name DME ID UniProt ID Highest Status REF
Cytochrome P450 3A4 (CYP3A4) DE4LYSA CP3A4_HUMAN Approved [9]
Cytochrome P450 2E1 (CYP2E1) DEVDYN7 CP2E1_HUMAN Approved [10]
Cytochrome P450 2D6 (CYP2D6) DECB0K3 CP2D6_HUMAN Approved [9]
Cytochrome P450 2C9 (CYP2C9) DE5IED8 CP2C9_HUMAN Approved [11]
Cytochrome P450 1A1 (CYP1A1) DE6OQ3W CP1A1_HUMAN Approved [12]
UDP-glucuronosyltransferase 1A1 (UGT1A1) DEYGVN4 UD11_HUMAN Approved [13]
Glutathione S-transferase alpha-1 (GSTA1) DE4ZHS1 GSTA1_HUMAN Approved [14]
Cytochrome P450 2A6 (CYP2A6) DEJVYAZ CP2A6_HUMAN Approved [9]
Cytochrome P450 1A2 (CYP1A2) DEJGDUW CP1A2_HUMAN Approved [15]
Cytochrome P450 3A5 (CYP3A5) DEIBDNY CP3A5_HUMAN Approved [16]
UDP-glucuronosyltransferase 1A9 (UGT1A9) DE85D2P UD19_HUMAN Approved [17]
Sulfotransferase 1A1 (SULT1A1) DEYWLRK ST1A1_HUMAN Approved [18]
UDP-glucuronosyltransferase 1A6 (UGT1A6) DESD26P UD16_HUMAN Approved [19]
UDP-glucuronosyltransferase 2B15 (UGT2B15) DENZ6B1 UDB15_HUMAN Approved [20]
Cytochrome P450 102A1 (cyp102) DE4OGUF CPXB_BACMB Approved [21]

The Expression Level of Molecule(s) in Normal Tissue of Major ADME-Related Organs

Molecule Molecule Type Gene Name Liver Colon Kidney Small Intestine
Norepinephrine transporter (NET) DTT SLC6A2 2.459 3.426 3.322 3.35
Serotonin transporter (SERT) DTT SLC6A4 6.278 5.469 6.075 6.966
Multidrug resistance-associated protein 2 (ABCC2) DTP MRP2 7.751 4.17 6.425 6.282
Sulfotransferase 1A1 (SULT1A1) DME SULT1A1 9.814 9.348 7.196 10.468
Cytochrome P450 2E1 (CYP2E1) DME CYP2E1 12.054 3.968 2.945 4.1
UDP-glucuronosyltransferase 2B15 (UGT2B15) DME UGT2B15 9.165 4.684 3.036 5.897
Cytochrome P450 2A6 (CYP2A6) DME CYP2A6 10.644 6.631 6.598 6.937
Cytochrome P450 1A2 (CYP1A2) DME CYP1A2 10.036 5.779 6.508 6.481
Cytochrome P450 3A5 (CYP3A5) DME CYP3A5 10.08 7.207 5.403 9.211
Cytochrome P450 2D6 (CYP2D6) DME CYP2D6 3.307 5.005 3.921 5.327
Cytochrome P450 1A1 (CYP1A1) DME CYP1A1 5.952 6.384 4.897 6.293
Cytochrome P450 2C9 (CYP2C9) DME CYP2C9 11.76 5.931 6.164 9.423
Glutathione S-transferase alpha-1 (GSTA1) DME GSTA1 10.53 6.221 8.589 9.978
Cytochrome P450 3A4 (CYP3A4) DME CYP3A4 11.692 6.58 4.984 9.089
Molecule Expression Atlas in Normal Tissue of Major ADME-related organs

The Expression Level of Molecule(s) between Disease Section and Healthy Individual Tissue

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 between Disease Section and Healthy Individual Tissue

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 Augmentation effect of combination therapy of aripiprazole and antidepressants on forced swimming test in mice. Psychopharmacology (Berl). 2009 Sep;206(1):97-107.
5 Mechanism of action of paracetamol. Am J Ther. 2005 Jan-Feb;12(1):46-55.
6 COX-3: just another COX or the solitary elusive target of paracetamol Lancet. 2003 Mar 22;361(9362):981-2.
7 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.
8 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.
9 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.
10 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.
11 Summary of information on human CYP enzymes: human P450 metabolism data. Drug Metab Rev. 2002 Feb-May;34(1-2):83-448.
12 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.
13 Effect of UDP-glucuronosyltransferase (UGT) 1A polymorphism (rs8330 and rs10929303) on glucuronidation status of acetaminophen. Dose Response. 2017 Sep 11;15(3):1559325817723731.
14 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.
15 PharmGKB summary: pathways of acetaminophen metabolism at the therapeutic versus toxic doses. Pharmacogenet Genomics. 2015 Aug;25(8):416-26.
16 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.
17 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.
18 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.
19 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.
20 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.
21 The bacterial P450 BM3: a prototype for a biocatalyst with human P450 activities. Trends Biotechnol. 2007 Jul;25(7):289-98.