Details of the Drug

General Information of Drug (ID: DMGV8QU)

Drug Name
Etravirine
Synonyms
Intelence; DAPY deriv; Diaminopyrimidine deriv; R 165335; R165335; TMC 125; TMC125; Intelence (TN); Intelence(TM); R-165335; R165335-TMC125; TMC-125; Etravirine (JAN/USAN/INN); TMC-125/R-165335; 4-((6-amino-5-bromo-2-((4-cyanophenyl)amino)-4-pyrimidinyl)oxy)-3,5-dimethyl-benzonitrile; 4-({6-AMINO-5-BROMO-2-[(4-CYANOPHENYL)AMINO]PYRIMIDIN-4-YL}OXY)-3,5-DIMETHYLBENZONITRILE; 4-[6-amino-5-bromo-2-(4-cyanoanilino)pyrimidin-4-yl]oxy-3,5-dimethylbenzonitrile; 65B; ETR
Indication
Disease Entry ICD 11 Status REF
Human immunodeficiency virus-1 infection 1C62 Approved [1], [2]
Drug Type
Small molecular drug
Structure
3D MOL 2D MOL
#Ro5 Violations (Lipinski): 0 Molecular Weight (mw) 435.3
Topological Polar Surface Area (xlogp) 4.5
Rotatable Bond Count (rotbonds) 4
Hydrogen Bond Donor Count (hbonddonor) 2
Hydrogen Bond Acceptor Count (hbondacc) 7
ADMET Property
BDDCS Class
Biopharmaceutics Drug Disposition Classification System (BDDCS) Class 2: low solubility and high permeability [3]
Elimination
0% of drug is excreted from urine in the unchanged form [3]
Half-life
The concentration or amount of drug in body reduced by one-half in 9.05 - 41 hours [4]
Metabolism
The drug is metabolized via the liver [5]
MRTD
The Maximum Recommended Therapeutic Dose (MRTD) of drug that ensured maximising efficacy and moderate side effect is 6.5638 micromolar/kg/day [6]
Chemical Identifiers
Formula
C20H15BrN6O
IUPAC Name
4-[6-amino-5-bromo-2-(4-cyanoanilino)pyrimidin-4-yl]oxy-3,5-dimethylbenzonitrile
Canonical SMILES
CC1=CC(=CC(=C1OC2=NC(=NC(=C2Br)N)NC3=CC=C(C=C3)C#N)C)C#N
InChI
InChI=1S/C20H15BrN6O/c1-11-7-14(10-23)8-12(2)17(11)28-19-16(21)18(24)26-20(27-19)25-15-5-3-13(9-22)4-6-15/h3-8H,1-2H3,(H3,24,25,26,27)
InChIKey
PYGWGZALEOIKDF-UHFFFAOYSA-N
Cross-matching ID
PubChem CID
193962
ChEBI ID
CHEBI:63589
CAS Number
269055-15-4
DrugBank ID
DB06414
TTD ID
D0BP9C
VARIDT ID
DR00597
INTEDE ID
DR0671
ACDINA ID
D00259

Molecular Interaction Atlas of This Drug


Drug Therapeutic Target (DTT)
DTT Name DTT ID UniProt ID MOA REF
Human immunodeficiency virus Reverse transcriptase (HIV RT) TT84ETX POL_HV1B1 Modulator [2]

Drug Transporter (DTP)
DTP Name DTP ID UniProt ID MOA REF
Multidrug resistance-associated protein 3 (ABCC3) DTQ3ZHF MRP3_HUMAN Substrate [7]

Drug-Metabolizing Enzyme (DME)
DME Name DME ID UniProt ID MOA REF
Cytochrome P450 3A4 (CYP3A4)
Main DME 		DE4LYSA CP3A4_HUMAN Substrate [8]
Cytochrome P450 2C9 (CYP2C9)
Main DME 		DE5IED8 CP2C9_HUMAN Substrate [8]
Mephenytoin 4-hydroxylase (CYP2C19)
Main DME 		DEGTFWK CP2CJ_HUMAN Substrate [9]
Molecular Interaction Atlas (MIA) Jump to Detail Molecular Interaction Atlas of This Drug

Drug-Drug Interaction (DDI) Information of This Drug

Coadministration of a Drug Treating the Same Disease as Etravirine
DDI Drug Name DDI Drug ID Severity Mechanism Disease REF
MK-1439 DM215WE Major Increased metabolism of Etravirine caused by MK-1439 mediated induction of CYP450 enzyme. Human immunodeficiency virus disease [1C60-1C62] [51]
Fostemsavir DM50ILT Minor Increased metabolism of Etravirine caused by Fostemsavir mediated induction of CYP450 enzyme. Human immunodeficiency virus disease [1C60-1C62] [52]
Cobicistat DM6L4H2 Moderate Decreased metabolism of Etravirine caused by Cobicistat mediated inhibition of CYP450 enzyme. Human immunodeficiency virus disease [1C60-1C62] [53]
Dolutegravir DMCZGRE Major Increased metabolism of Etravirine caused by Dolutegravir mediated induction of UGT. Human immunodeficiency virus disease [1C60-1C62] [53]
Elvitegravir DMG9B1U Moderate Increased metabolism of Etravirine caused by Elvitegravir mediated induction of CYP450 enzyme. Human immunodeficiency virus disease [1C60-1C62] [53]
Coadministration of a Drug Treating the Disease Different from Etravirine (Comorbidity)
DDI Drug Name DDI Drug ID Severity Mechanism Comorbidity REF
Ivosidenib DM8S6T7 Moderate Increased metabolism of Etravirine caused by Ivosidenib mediated induction of CYP450 enzyme. Acute myeloid leukaemia [2A60] [54]
Midostaurin DMI6E0R Moderate Increased metabolism of Etravirine caused by Midostaurin mediated induction of CYP450 enzyme. Acute myeloid leukaemia [2A60] [55]
Arn-509 DMT81LZ Major Increased metabolism of Etravirine caused by Arn-509 mediated induction of CYP450 enzyme. Acute myeloid leukaemia [2A60] [54]
Gilteritinib DMWQ4MZ Moderate Increased metabolism of Etravirine caused by Gilteritinib mediated induction of CYP450 enzyme. Acute myeloid leukaemia [2A60] [56]
Oliceridine DM6MDCF Major Increased metabolism of Etravirine caused by Oliceridine mediated induction of CYP450 enzyme. Acute pain [MG31] [57]
Ivabradine DM0L594 Moderate Increased metabolism of Etravirine caused by Ivabradine mediated induction of CYP450 enzyme. Angina pectoris [BA40] [58]
Bedaquiline DM3906J Major Increased metabolism of Etravirine caused by Bedaquiline mediated induction of CYP450 enzyme. Antimicrobial drug resistance [MG50-MG52] [58]
Troleandomycin DMUZNIG Moderate Increased metabolism of Etravirine caused by Troleandomycin mediated induction of CYP450 enzyme. Bacterial infection [1A00-1C4Z] [54]
Erdafitinib DMI782S Major Increased metabolism of Etravirine caused by Erdafitinib mediated induction of CYP450 enzyme. Bladder cancer [2C94] [59]
Pexidartinib DMS2J0Z Moderate Increased metabolism of Etravirine caused by Pexidartinib mediated induction of CYP450 enzyme. Bone/articular cartilage neoplasm [2F7B] [54]
HKI-272 DM6QOVN Major Increased metabolism of Etravirine caused by HKI-272 mediated induction of CYP450 enzyme. Breast cancer [2C60-2C6Y] [53]
LY2835219 DM93VBZ Moderate Increased metabolism of Etravirine caused by LY2835219 mediated induction of CYP450 enzyme. Breast cancer [2C60-2C6Y] [60]
Tucatinib DMBESUA Moderate Increased metabolism of Etravirine caused by Tucatinib mediated induction of CYP450 enzyme. Breast cancer [2C60-2C6Y] [61]
Palbociclib DMD7L94 Moderate Increased metabolism of Etravirine caused by Palbociclib mediated induction of CYP450 enzyme. Breast cancer [2C60-2C6Y] [53]
Alpelisib DMEXMYK Moderate Increased metabolism of Etravirine caused by Alpelisib mediated induction of CYP450 enzyme. Breast cancer [2C60-2C6Y] [62]
Cabazitaxel DMPAZHC Moderate Increased metabolism of Etravirine caused by Cabazitaxel mediated induction of CYP450 enzyme. Breast cancer [2C60-2C6Y] [63]
Bosutinib DMTI8YE Major Increased metabolism of Etravirine caused by Bosutinib mediated induction of CYP450 enzyme. Breast cancer [2C60-2C6Y] [64]
Macitentan DMP79A1 Moderate Increased metabolism of Etravirine caused by Macitentan mediated induction of CYP450 enzyme. Cardiovascular disease [BA00-BE2Z] [65]
PF-04449913 DMSB068 Major Increased metabolism of Etravirine caused by PF-04449913 mediated induction of CYP450 enzyme. Chronic myelomonocytic leukaemia [2A40] [66]
Ulipristal DMBNI20 Moderate Increased metabolism of Etravirine caused by Ulipristal mediated induction of CYP450 enzyme. Contraceptive management [QA21] [58]
Osilodrostat DMIJC9X Moderate Decreased metabolism of Etravirine caused by Osilodrostat mediated inhibition of CYP450 enzyme. Cushing syndrome [5A70] [54]
Lumacaftor DMCLWDJ Major Increased metabolism of Etravirine caused by Lumacaftor mediated induction of CYP450 enzyme. Cystic fibrosis [CA25] [67]
Vilazodone DM4LECQ Moderate Increased metabolism of Etravirine caused by Vilazodone mediated induction of CYP450 enzyme. Depression [6A70-6A7Z] [68]
Vortioxetine DM6F1PU Moderate Increased metabolism of Etravirine caused by Vortioxetine mediated induction of CYP450 enzyme. Depression [6A70-6A7Z] [69]
OPC-34712 DMHG57U Moderate Increased metabolism of Etravirine caused by OPC-34712 mediated induction of CYP450 enzyme. Depression [6A70-6A7Z] [54]
Stiripentol DMMSDOY Moderate Increased metabolism of Etravirine caused by Stiripentol mediated induction of CYP450 enzyme. Epilepsy/seizure [8A61-8A6Z] [58]
Eslicarbazepine DMZREFQ Moderate Increased metabolism of Etravirine caused by Eslicarbazepine mediated induction of CYP450 enzyme. Epilepsy/seizure [8A61-8A6Z] [54]
Bay 80-6946 DMLOS5R Moderate Increased metabolism of Etravirine caused by Bay 80-6946 mediated induction of CYP450 enzyme. Follicular lymphoma [2A80] [70]
Tazemetostat DMWP1BH Major Increased metabolism of Etravirine caused by Tazemetostat mediated induction of CYP450 enzyme. Follicular lymphoma [2A80] [71]
Mirabegron DMS1GYT Minor Increased metabolism of Etravirine caused by Mirabegron mediated induction of CYP450 enzyme. Functional bladder disorder [GC50] [72]
Ripretinib DM958QB Moderate Increased metabolism of Etravirine caused by Ripretinib mediated induction of CYP450 enzyme. Gastrointestinal stromal tumour [2B5B] [53]
Avapritinib DMK2GZX Major Increased metabolism of Etravirine caused by Avapritinib mediated induction of CYP450 enzyme. Gastrointestinal stromal tumour [2B5B] [58]
Boceprevir DMBSHMF Moderate Increased metabolism of Etravirine caused by Boceprevir mediated induction of CYP450 enzyme. Hepatitis virus infection [1E50-1E51] [54]
Daclatasvir DMSFK9V Major Increased metabolism of Etravirine caused by Daclatasvir mediated induction of CYP450 enzyme. Hepatitis virus infection [1E50-1E51] [53]
Brentuximab vedotin DMWLC57 Moderate Increased risk of peripheral neuropathy by the combination of Etravirine and Brentuximab vedotin. Hodgkin lymphoma [2B30] [73]
Levamlodipine DM92S6N Moderate Increased metabolism of Etravirine caused by Levamlodipine mediated induction of CYP450 enzyme. Hypertension [BA00-BA04] [54]
Berotralstat DMWA2DZ Major Decreased clearance of Etravirine due to the transporter inhibition by Berotralstat. Innate/adaptive immunodeficiency [4A00] [74]
Suvorexant DM0E6S3 Moderate Increased metabolism of Etravirine caused by Suvorexant mediated induction of CYP450 enzyme. Insomnia [7A00-7A0Z] [75]
Tasimelteon DMLOQ1V Moderate Increased metabolism of Etravirine caused by Tasimelteon mediated induction of CYP450 enzyme. Insomnia [7A00-7A0Z] [76]
Naloxegol DML0B41 Moderate Increased metabolism of Etravirine caused by Naloxegol mediated induction of CYP450 enzyme. Large intestine motility disorder [DB32] [77]
Pemigatinib DM819JF Major Increased metabolism of Etravirine caused by Pemigatinib mediated induction of CYP450 enzyme. Liver cancer [2C12] [58]
Crizotinib DM4F29C Moderate Decreased metabolism of Etravirine caused by Crizotinib mediated inhibition of CYP450 enzyme. Lung cancer [2C25] [54]
Brigatinib DM7W94S Major Increased metabolism of Etravirine caused by Brigatinib mediated induction of CYP450 enzyme. Lung cancer [2C25] [53]
Ceritinib DMB920Z Moderate Increased metabolism of Etravirine caused by Ceritinib mediated induction of CYP450 enzyme. Lung cancer [2C25] [54]
Lurbinectedin DMEFRTZ Major Decreased metabolism of Etravirine caused by Lurbinectedin mediated inhibition of CYP450 enzyme. Lung cancer [2C25] [78]
PF-06463922 DMKM7EW Major Increased metabolism of Etravirine caused by PF-06463922 mediated induction of CYP450 enzyme. Lung cancer [2C25] [79]
Osimertinib DMRJLAT Moderate Increased metabolism of Etravirine caused by Osimertinib mediated induction of CYP450 enzyme. Lung cancer [2C25] [80]
Pralsetinib DMWU0I2 Moderate Increased metabolism of Etravirine caused by Pralsetinib mediated induction of CYP450 enzyme. Lung cancer [2C25] [81]
Capmatinib DMYCXKL Major Increased metabolism of Etravirine caused by Capmatinib mediated induction of CYP450 enzyme. Lung cancer [2C25] [82]
Artemether DM48QOT Major Increased metabolism of Etravirine caused by Artemether mediated induction of CYP450 enzyme. Malaria [1F40-1F45] [53]
Idelalisib DM602WT Moderate Decreased metabolism of Etravirine caused by Idelalisib mediated inhibition of CYP450 enzyme. Mature B-cell leukaemia [2A82] [54]
GDC-0199 DMH0QKA Major Increased metabolism of Etravirine caused by GDC-0199 mediated induction of CYP450 enzyme. Mature B-cell leukaemia [2A82] [83]
Acalabrutinib DM7GCVW Moderate Increased metabolism of Etravirine caused by Acalabrutinib mediated induction of CYP450 enzyme. Mature B-cell lymphoma [2A85] [84]
Ibrutinib DMHZCPO Moderate Increased metabolism of Etravirine caused by Ibrutinib mediated induction of CYP450 enzyme. Mature B-cell lymphoma [2A85] [85]
Ponatinib DMYGJQO Moderate Increased metabolism of Etravirine caused by Ponatinib mediated induction of CYP450 enzyme. Mature B-cell lymphoma [2A85] [53]
Vemurafenib DM62UG5 Moderate Increased metabolism of Etravirine caused by Vemurafenib mediated induction of CYP450 enzyme. Melanoma [2C30] [54]
Selumetinib DMC7W6R Major Increased metabolism of Etravirine caused by Selumetinib mediated induction of CYP450 enzyme. Melanoma [2C30] [86]
LGX818 DMNQXV8 Major Increased metabolism of Etravirine caused by LGX818 mediated induction of CYP450 enzyme. Melanoma [2C30] [87]
Dabrafenib DMX6OE3 Moderate Increased metabolism of Etravirine caused by Dabrafenib mediated induction of CYP450 enzyme. Melanoma [2C30] [54]
Ubrogepant DM749I3 Moderate Increased metabolism of Etravirine caused by Ubrogepant mediated induction of CYP450 enzyme. Migraine [8A80] [88]
Rimegepant DMHOAUG Major Increased metabolism of Etravirine caused by Rimegepant mediated induction of CYP450 enzyme. Migraine [8A80] [89]
Panobinostat DM58WKG Moderate Increased metabolism of Etravirine caused by Panobinostat mediated induction of CYP450 enzyme. Multiple myeloma [2A83] [90]
Siponimod DM2R86O Major Increased metabolism of Etravirine caused by Siponimod mediated induction of CYP450 enzyme. Multiple sclerosis [8A40] [53]
Deflazacort DMV0RNS Major Increased metabolism of Etravirine caused by Deflazacort mediated induction of CYP450 enzyme. Muscular dystrophy [8C70] [58]
Fedratinib DM4ZBK6 Major Increased metabolism of Etravirine caused by Fedratinib mediated induction of CYP450 enzyme. Myeloproliferative neoplasm [2A20] [58]
Ruxolitinib DM7Q98D Moderate Increased metabolism of Etravirine caused by Ruxolitinib mediated induction of CYP450 enzyme. Myeloproliferative neoplasm [2A20] [91]
Rolapitant DM8XP26 Moderate Increased metabolism of Etravirine caused by Rolapitant mediated induction of CYP450 enzyme. Nausea/vomiting [MD90] [58]
Netupitant DMEKAYI Moderate Decreased metabolism of Etravirine caused by Netupitant mediated inhibition of CYP450 enzyme. Nausea/vomiting [MD90] [54]
E-2007 DMJDYNQ Moderate Increased metabolism of Etravirine caused by E-2007 mediated induction of CYP450 enzyme. Neuropathy [8C0Z] [58]
Entrectinib DMMPTLH Major Increased metabolism of Etravirine caused by Entrectinib mediated induction of CYP450 enzyme. Non-small cell lung cancer [2C25] [92]
S-297995 DM26IH8 Moderate Increased metabolism of Etravirine caused by S-297995 mediated induction of CYP450 enzyme. Opioid use disorder [6C43] [58]
Olaparib DM8QB1D Major Increased metabolism of Etravirine caused by Olaparib mediated induction of CYP450 enzyme. Ovarian cancer [2C73] [53]
Rucaparib DM9PVX8 Moderate Decreased metabolism of Etravirine caused by Rucaparib mediated inhibition of CYP450 enzyme. Ovarian cancer [2C73] [54]
Istradefylline DM20VSK Moderate Increased metabolism of Etravirine caused by Istradefylline mediated induction of CYP450 enzyme. Parkinsonism [8A00] [54]
Abametapir DM2RX0I Moderate Decreased metabolism of Etravirine caused by Abametapir mediated inhibition of CYP450 enzyme. Pediculosis [1G00] [93]
Lanreotide acetate DMG6ZU4 Moderate Decreased metabolism of Etravirine caused by Lanreotide acetate mediated inhibition of CYP450 enzyme. Pituitary gland disorder [5A60-5A61] [54]
Macimorelin DMQYJIR Moderate Increased metabolism of Etravirine caused by Macimorelin mediated induction of CYP450 enzyme. Pituitary gland disorder [5A60-5A61] [94]
Lefamulin DME6G97 Major Increased metabolism of Etravirine caused by Lefamulin mediated induction of CYP450 enzyme. Pneumonia [CA40] [95]
Lonafarnib DMGM2Z6 Major Increased metabolism of Etravirine caused by Lonafarnib mediated induction of CYP450 enzyme. Premature ageing appearance [LD2B] [96]
Enzalutamide DMGL19D Major Increased metabolism of Etravirine caused by Enzalutamide mediated induction of CYP450 enzyme. Prostate cancer [2C82] [54]
Darolutamide DMV7YFT Moderate Increased metabolism of Etravirine caused by Darolutamide mediated induction of CYP450 enzyme. Prostate cancer [2C82] [97]
Riociguat DMXBLMP Moderate Increased metabolism of Etravirine caused by Riociguat mediated induction of CYP450 enzyme. Pulmonary hypertension [BB01] [98]
Axitinib DMGVH6N Major Increased metabolism of Etravirine caused by Axitinib mediated induction of CYP450 enzyme. Renal cell carcinoma [2C90] [99]
Upadacitinib DM32B5U Moderate Increased metabolism of Etravirine caused by Upadacitinib mediated induction of CYP450 enzyme. Rheumatoid arthritis [FA20] [100]
Tofacitinib DMBS370 Moderate Increased metabolism of Etravirine caused by Tofacitinib mediated induction of CYP450 enzyme. Rheumatoid arthritis [FA20] [53]
Voxelotor DMCS6M5 Major Increased metabolism of Etravirine caused by Voxelotor mediated induction of CYP450 enzyme. Sickle-cell disorder [3A51] [101]
LDE225 DMM9F25 Major Increased metabolism of Etravirine caused by LDE225 mediated induction of CYP450 enzyme. Skin cancer [2C30-2C37] [102]
Telotristat ethyl DMDIYFZ Moderate Increased metabolism of Etravirine caused by Telotristat ethyl mediated induction of CYP450 enzyme. Small intestine developmental anomaly [DA90] [58]
Larotrectinib DM26CQR Moderate Decreased metabolism of Etravirine caused by Larotrectinib mediated inhibition of CYP450 enzyme. Solid tumour/cancer [2A00-2F9Z] [54]
LEE011 DMMX75K Moderate Increased metabolism of Etravirine caused by LEE011 mediated induction of CYP450 enzyme. Solid tumour/cancer [2A00-2F9Z] [54]
Fostamatinib DM6AUHV Moderate Increased metabolism of Etravirine caused by Fostamatinib mediated induction of CYP450 enzyme. Thrombocytopenia [3B64] [54]
Lusutrombopag DMH6IKO Moderate Decreased clearance of Etravirine due to the transporter inhibition by Lusutrombopag. Thrombocytopenia [3B64] [103]
Apixaban DM89JLN Moderate Increased metabolism of Etravirine caused by Apixaban mediated induction of CYP450 enzyme. Thrombosis [DB61-GB90] [104]
Brilinta DMBR01X Moderate Increased metabolism of Etravirine caused by Brilinta mediated induction of CYP450 enzyme. Thrombosis [DB61-GB90] [57]
Cabozantinib DMIYDT4 Moderate Increased metabolism of Etravirine caused by Cabozantinib mediated induction of CYP450 enzyme. Thyroid cancer [2D10] [105]
Linagliptin DMWFJTR Moderate Increased metabolism of Etravirine caused by Linagliptin mediated induction of CYP450 enzyme. Type 2 diabetes mellitus [5A11] [106]
Elagolix DMB2C0E Moderate Increased metabolism of Etravirine caused by Elagolix mediated induction of CYP450 enzyme. Uterine fibroid [2E86] [54]
⏷ Show the Full List of 97 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
Carmellose sodium E00625 Not Available Disintegrant
Hypromellose E00634 Not Available Coating agent
Lactose monohydrate E00393 104938 Binding agent; Diluent; Dry powder inhaler carrier; Lyophilization aid
Magnesium stearate E00208 11177 lubricant
Silicon dioxide E00670 Not Available Anticaking agent; Opacifying agent; Viscosity-controlling agent
Pharmaceutical Formulation
Formulation Name Drug Dosage Dosage Form Route
Etravirine 100 mg tablet 100 mg Oral Tablet Oral
Etravirine 200 mg tablet 200 mg Oral Tablet Oral
Jump to Detail Pharmaceutical Formulation Page of This Drug

References

1 Emerging antiviral drugs. Expert Opin Emerg Drugs. 2008 Sep;13(3):393-416.
2 2008 FDA drug approvals. Nat Rev Drug Discov. 2009 Feb;8(2):93-6.
3 BDDCS applied to over 900 drugs
4 Trend Analysis of a Database of Intravenous Pharmacokinetic Parameters in Humans for 1352 Drug Compounds
5 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.
6 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
7 Interaction potential of etravirine with drug transporters assessed in vitro. Antimicrob Agents Chemother. 2011 Mar;55(3):1282-4.
8 Pharmacokinetic interactions between etravirine and non-antiretroviral drugs. Clin Pharmacokinet. 2011 Jan;50(1):25-39.
9 Biotransformation of the antiretroviral drug etravirine: metabolite identification, reaction phenotyping, and characterization of autoinduction of cytochrome P450-dependent metabolism. Drug Metab Dispos. 2012 Apr;40(4):803-14.
10 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.
11 Contribution of human hepatic cytochrome P450 isoforms to regioselective hydroxylation of steroid hormones. Xenobiotica. 1998 Jun;28(6):539-47.
12 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.
13 Isoform-specific regulation of cytochromes P450 expression by estradiol and progesterone. Drug Metab Dispos. 2013 Feb;41(2):263-9.
14 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.
15 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.
16 Effects of morin on the pharmacokinetics of etoposide in rats. Biopharm Drug Dispos. 2007 Apr;28(3):151-6.
17 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.
18 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.
19 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.
20 Tamoxifen inhibits cytochrome P450 2C9 activity in breast cancer patients. J Chemother. 2006 Aug;18(4):421-4.
21 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.
22 Summary of information on human CYP enzymes: human P450 metabolism data. Drug Metab Rev. 2002 Feb-May;34(1-2):83-448.
23 Drug-drug interactions with imatinib: an observational study. Medicine (Baltimore). 2016 Oct;95(40):e5076.
24 Drug interactions with calcium channel blockers: possible involvement of metabolite-intermediate complexation with CYP3A. Drug Metab Dispos. 2000 Feb;28(2):125-30.
25 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.
26 A potential role for the estrogen-metabolizing cytochrome P450 enzymes in human breast carcinogenesis. Breast Cancer Res Treat. 2003 Dec;82(3):191-7.
27 A mechanistic approach to antiepileptic drug interactions. Ann Pharmacother. 1998 May;32(5):554-63.
28 High-dose rabeprazole/amoxicillin therapy as the second-line regimen after failure to eradicate H. pylori by triple therapy with the usual doses of a proton pump inhibitor, clarithromycin and amoxicillin. Hepatogastroenterology. 2003 Nov-Dec;50(54):2274-8.
29 Cytochrome P450 pharmacogenetics and cancer. Oncogene. 2006 Mar 13;25(11):1679-91.
30 CYP2C19*17 is associated with decreased breast cancer risk. Breast Cancer Res Treat. 2009 May;115(2):391-6.
31 Cytochromes of the P450 2C subfamily are the major enzymes involved in the O-demethylation of verapamil in humans. Naunyn Schmiedebergs Arch Pharmacol. 1995 Dec;353(1):116-21.
32 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.
33 Organic anion-transporting polypeptide B (OATP-B) and its functional comparison with three other OATPs of human liver. Gastroenterology. 2001 Feb;120(2):525-33.
34 Possible involvement of multiple human cytochrome P450 isoforms in the liver metabolism of propofol. Br J Anaesth. 1998 Jun;80(6):788-95.
35 Multidrug resistance protein (MRP) 1 and MRP3 attenuate cytotoxic and transactivating effects of the cyclopentenone prostaglandin, 15-deoxy-Delta(12,14)prostaglandin J2 in MCF7 breast cancer cells. Biochemistry. 2003 May 13;42(18):5429-37.
36 Transport of methotrexate (MTX) and folates by multidrug resistance protein (MRP) 3 and MRP1: effect of polyglutamylation on MTX transport. Cancer Res. 2001 Oct 1;61(19):7225-32.
37 ATP-binding cassette C transporters in human pancreatic carcinoma cell lines. Upregulation in 5-fluorouracil-resistant cells. Pancreatology. 2009;9(1-2):136-44.
38 Functional reconstitution of human ABCC3 into proteoliposomes reveals a transport mechanism with positive cooperativity. Biochemistry. 2009 May 26;48(20):4423-30.
39 Complex pharmacokinetic behavior of ezetimibe depends on abcc2, abcc3, and abcg2. Drug Metab Dispos. 2009 Aug;37(8):1698-702.
40 Transport of glyburide by placental ABC transporters: implications in fetal drug exposure. Placenta. 2006 Nov-Dec;27(11-12):1096-102.
41 Multidrug resistance-associated proteins 3, 4, and 5. Pflugers Arch. 2007 Feb;453(5):661-73.
42 Oral availability of cefadroxil depends on ABCC3 and ABCC4. Drug Metab Dispos. 2012 Mar;40(3):515-21.
43 Characterization of drug transport by the human multidrug resistance protein 3 (ABCC3). J Biol Chem. 2001 Dec 7;276(49):46400-7.
44 Involvement of multiple efflux transporters in hepatic disposition of fexofenadine. Mol Pharmacol. 2008 May;73(5):1474-83.
45 Antiviral drugs in current clinical use. J Clin Virol. 2004 Jun;30(2):115-33.
46 HIV-1 reverse transcriptase complex with DNA and nevirapine reveals non-nucleoside inhibition mechanism.Nat Struct Mol Biol.2012 Jan 22;19(2):253-9.
47 A peptide inhibitor of HIV-1 reverse transcriptase using alpha,beta-dehydro residues: a structure-based computer model. J Biomol Struct Dyn. 1998 Oct;16(2):347-54.
48 Drugs@FDA. U.S. Food and Drug Administration. U.S. Department of Health & Human Services.
49 Quadruple nucleos(t)ide reverse transcriptase inhibitors-only regimen of tenofovir plus zidovudine/lamivudine/abacavir in heavily pre-treated HIV-1 infected patients: salvage therapy or backbone only Curr HIV Res. 2009 May;7(3):320-6.
50 2018 FDA drug approvals.Nat Rev Drug Discov. 2019 Feb;18(2):85-89.
51 Product Information. Pifeltro (doravirine). Merck & Company Inc, Whitehouse Station, NJ.
52 Product Information. Rukobia (fostemsavir). ViiV Healthcare, Research Triangle Park, NC.
53 Cerner Multum, Inc. "Australian Product Information.".
54 Product Information. Intelence (etravirine). Ortho Biotech Inc, Bridgewater, NJ.
55 Dutreix C, Munarini F, Lorenzo S, Roesel J, Wang Y "Investigation into CYP3A4-mediated drug-drug interactions on midostaurin in healthy volunteers." Cancer Chemother Pharmacol 72 (2013): 1223-34. [PMID: 24085261]
56 Product Information. Xospata (gilteritinib). Astellas Pharma US, Inc, Deerfield, IL.
57 Canadian Pharmacists Association.
58 Cerner Multum, Inc. "UK Summary of Product Characteristics.".
59 Product Information. Balversa (erdafitinib). Janssen Products, LP, Horsham, PA.
60 Product Information. Verzenio (abemaciclib). Lilly, Eli and Company, Indianapolis, IN.
61 Product Information. Tukysa (tucatinib). Seattle Genetics Inc, Bothell, WA.
62 Product Information. Piqray (alpelisib). Novartis Pharmaceuticals, East Hanover, NJ.
63 Product Information. Jevtana (cabazitaxel). sanofi-aventis , Bridgewater, NJ.
64 Product Information. Bosulif (bosutinib). Pfizer U.S. Pharmaceuticals Group, New York, NY.
65 Bruderer S, Aanismaa P, Homery MC, et al. "Effect of cyclosporine and rifampin on the pharmacokinetics of macitentan, a tissue-targeting dual endothelin receptor antagonist." AAPS J 14 (2012): 68-78. [PMID: 22189899]
66 Product Information. Daurismo (glasdegib). Pfizer U.S. Pharmaceuticals Group, New York, NY.
67 Patel S, Robinson R, Burk M "Hypertensive crisis associated with St. John's Wort." Am J Med 112 (2002): 507-8. [PMID: 11959071]
68 Product Information. Viibryd (vilazodone). Trovis Pharmaceuticals LLC, New Haven, CT.
69 Product Information. Brintellix (vortioxetine). Takeda Pharmaceuticals America, Lincolnshire, IL.
70 Product Information. Aliqopa (copanlisib). Bayer Pharmaceutical Inc, West Haven, CT.
71 Product Information. Tazverik (tazemetostat). Epizyme, Inc, Cambridge, MA.
72 Product Information. Myrbetriq (mirabegron). Astellas Pharma US, Inc, Deerfield, IL.
73 Carrion C, Espinosa E, Herrero A, Garcia B "Possible vincristine-isoniazid interaction." Ann Pharmacother 29 (1995): 201. [PMID: 7756727]
74 Product Information. Orladeyo (berotralstat). BioCryst Pharmaceuticals Inc, Durham, NC.
75 Product Information. Belsomra (suvorexant). Merck & Company Inc, Whitehouse Station, NJ.
76 Product Information. Hetlioz (tasimelteon). Vanda Pharmaceuticals Inc, Rockville, MD.
77 Product Information. Movantik (naloxegol). Astra-Zeneca Pharmaceuticals, Wilmington, DE.
78 Product Information. Zepzelca (lurbinectedin). Jazz Pharmaceuticals, Palo Alto, CA.
79 Product Information. Lorbrena (lorlatinib). Pfizer U.S. Pharmaceuticals Group, New York, NY.
80 Product Information. Tagrisso (osimertinib). Astra-Zeneca Pharmaceuticals, Wilmington, DE.
81 Product Information. Gavreto (pralsetinib). Blueprint Medicines Corporation, Cambridge, MA.
82 Product Information. Tabrecta (capmatinib). Novartis Pharmaceuticals, East Hanover, NJ.
83 Product Information. Venclexta (venetoclax). AbbVie US LLC, North Chicago, IL.
84 Product Information. Calquence (acalabrutinib). Astra-Zeneca Pharmaceuticals, Wilmington, DE.
85 Product Information. Imbruvica (ibrutinib). Pharmacyclics Inc, Sunnyvale, CA.
86 Product Information. Koselugo (selumetinib). Astra-Zeneca Pharmaceuticals, Wilmington, DE.
87 Product Information. Braftovi (encorafenib). Array BioPharma Inc., Boulder, CO.
88 Product Information. Ubrelvy (ubrogepant). Allergan Inc, Irvine, CA.
89 Product Information. Nurtec ODT (rimegepant). Biohaven Pharmaceuticals, New Haven, CT.
90 Product Information. Farydak (panobinostat). Novartis Pharmaceuticals, East Hanover, NJ.
91 Product Information. Jakafi (ruxolitinib). Incyte Corporation, Wilmington, DE.
92 Product Information. Rozlytrek (entrectinib). Genentech, South San Francisco, CA.
93 Product Information. Xeglyze (abametapir topical). Dr. Reddy's Laboratories Inc, Upper Saddle River, NJ.
94 Product Information. Macrilen (macimorelin). Aeterna Zentaris, Charleston, SC.
95 Product Information. Xenleta (lefamulin). Nabriva Therapeutics US, Inc., King of Prussia, PA.
96 Product Information. Zokinvy (lonafarnib). Eiger BioPharmaceuticals, Palo Alto, CA.
97 Product Information. Nubeqa (darolutamide). Bayer HealthCare Pharmaceuticals Inc., Whippany, NJ.
98 Product Information. Adempas (riociguat). Bayer Pharmaceutical Inc, West Haven, CT.
99 Pithavala YK, Tortorici M, Toh M, et al "Effect of rifampin on the pharmacokinetics of axitinib (AG-013736) in Japanese and Caucasian healthy volunteers." Cancer Chemother Pharmacol 65 (2010): 563-70. [PMID: 19603168]
100 Product Information. Rinvoq (upadacitinib). AbbVie US LLC, North Chicago, IL.
101 Product Information. Oxbryta (voxelotor). Global Blood Therapeutics, Inc., South San Francisco, CA.
102 Product Information. Odomzo (sonidegib). Novartis Pharmaceuticals, East Hanover, NJ.
103 EMA. European Medicines Agency. European Union "EMA - List of medicines under additional monitoring.".
104 Product Information. Eliquis (apixaban). Bristol-Myers Squibb Canada Inc, Montreal, IN.
105 Product Information. Cabometyx (cabozantinib). Exelixis Inc, S San Francisco, CA.
106 Product Information. Tradjenta (linagliptin). Boehringer Ingelheim, Ridgefield, CT.