General Information of Drug (ID: DMJ0QOW)

Drug Name
Rilpivirine Drug Info
Synonyms
500287-72-9; TMC278; Edurant; TMC 278; UNII-FI96A8X663; R278474; TMC-278; 4-{[4-({4-[(E)-2-Cyanoethenyl]-2,6-Dimethylphenyl}amino)pyrimidin-2-Yl]amino}benzonitrile; CHEBI:68606; FI96A8X663; R 278474; 4-{[4-({4-[(E)-2-cyanovinyl]-2,6-dimethylphenyl}amino)pyrimidin-2-yl]amino}benzonitrile; (E)-4-((4-((4-(2-cyanovinyl)-2,6-dimethylphenyl)amino)pyrimidin-2-yl)amino)benzonitrile; (E)-4-(4-(4-(2-cyanovinyl)-2,6-dimethylphenylamino)pyrimidin-2-ylamino)benzonitrile; W-202888; RPV; Mu O-conotoxin
Indication
Disease Entry ICD 11 Status REF
Human immunodeficiency virus infection 1C62 Approved [1]
Pain MG30-MG3Z Investigative [2]
Cross-matching ID
PubChem CID
6451164
ChEBI ID
CHEBI:68606
CAS Number
CAS 500287-72-9
TTD Drug ID
DMJ0QOW
INTEDE Drug ID
DR1424
ACDINA Drug ID
D00594

Molecule-Related Drug Atlas

Molecule-Related Drug Atlas
Molecule Type:
DTT
DME
Drug Status:
Approved Drug(s)
Clinical Trial Drug(s)
Investigative Drug(s)
Drug Name Drug ID Indication ICD 11 Highest Status REF
Zidovudine DM4KI7O Human immunodeficiency virus infection 1C62 Approved [7]
Nevirapine DM6HX9B Human immunodeficiency virus infection 1C62 Approved [8]
Zalcitabine DMH7MUV Human immunodeficiency virus infection 1C62 Approved [9]
Tenofovir DM1IS6U Chronic hepatitis B virus infection Approved [7]
Lamivudine DMI347A Chronic HBV infection 1E51.0Z Approved [10]
Abacavir DMMN36E Human immunodeficiency virus infection 1C62 Approved [11]
Delavirdine DM3NF5G Human immunodeficiency virus infection 1C62 Approved [10]
Efavirenz DMC0GSJ Human immunodeficiency virus infection 1C62 Approved [10]
Etravirine DMGV8QU Human immunodeficiency virus-1 infection 1C62 Approved [12]
MK-1439 DM215WE Human immunodeficiency virus infection 1C62 Approved [13]
⏷ Show the Full List of 10 Drug(s)
Drug Name Drug ID Indication ICD 11 Highest Status REF
Ropivacaine DMSPJG2 Anaesthesia 9A78.6 Approved [10]
Bupivacaine DM4PRFC Anaesthesia 9A78.6 Approved [10]
Tiapride DMN6CAG Alcohol dependence 6C40.2 Approved [14]
Tetracaine DM9J6C2 Spinal anesthesia MB40.3 Approved [15]
Proparacaine DMLS39E Anaesthesia 9A78.6 Approved [10]
Conatumumab DM2UOSN Colorectal cancer 2B91.Z Phase 2 [16]
VX-150 DMGDB21 Neuropathic pain 8E43.0 Phase 2 [17]
DSP-2230 DM0WTMD Neuropathic pain 8E43.0 Phase 1 [18]
PF-01247324 DM93LMS Pain MG30-MG3Z Phase 1 [19]
VX-128 DMC8J0G Pain MG30-MG3Z Phase 1 [17]
⏷ Show the Full List of 10 Drug(s)
Drug(s) Metabolized By Cytochrome P450 3A4 (CYP3A4)
Drug Name Drug ID Indication ICD 11 Highest Status REF
Doxorubicin DMVP5YE Acute myelogenous leukaemia 2A41 Approved [20]
Progesterone DMUY35B Amenorrhea GA20.0 Approved [21]
Tamoxifen DMLB0EZ Breast cancer 2C60-2C65 Approved [22]
Estradiol DMUNTE3 Acne vulgaris ED80 Approved [23]
Acetaminophen DMUIE76 Allergic rhinitis CA08.0 Approved [24]
Imatinib DM7RJXL Acute lymphoblastic leukaemia 2A85 Approved [25]
Etoposide DMNH3PG Acute myelogenous leukaemia 2A41 Approved [26]
Zidovudine DM4KI7O Human immunodeficiency virus infection 1C62 Approved [27]
Prasterone DM67VKL Chronic obstructive pulmonary disease CA22 Approved [21]
Verapamil DMA7PEW Angina pectoris BA40 Approved [28]
⏷ Show the Full List of 10 Drug(s)
Drug Name Drug ID Indication ICD 11 Highest Status REF
Tamoxifen DMLB0EZ Breast cancer 2C60-2C65 Approved [29]
Estradiol DMUNTE3 Acne vulgaris ED80 Approved [30]
Acetaminophen DMUIE76 Allergic rhinitis CA08.0 Approved [31]
Etoposide DMNH3PG Acute myelogenous leukaemia 2A41 Approved [32]
Zidovudine DM4KI7O Human immunodeficiency virus infection 1C62 Approved [33]
Valproate DMCFE9I Epilepsy 8A60-8A68 Approved [34]
Mycophenolate mofetil DMPQAGE Hepatosplenic T-cell lymphoma Approved [35]
Metronidazole DMTIVEN Abscess Approved [36]
Propofol DMB4OLE Anaesthesia 9A78.6 Approved [37]
Ethanol DMDRQZU Chronic pain MG30 Approved [38]
⏷ Show the Full List of 10 Drug(s)
Drug(s) Metabolized By Mephenytoin 4-hydroxylase (CYP2C19)
Drug Name Drug ID Indication ICD 11 Highest Status REF
Amoxicillin DMUYNEI Acute otitis media AB00 Approved [39]
Progesterone DMUY35B Amenorrhea GA20.0 Approved [40]
Tamoxifen DMLB0EZ Breast cancer 2C60-2C65 Approved [41]
Estradiol DMUNTE3 Acne vulgaris ED80 Approved [42]
Zidovudine DM4KI7O Human immunodeficiency virus infection 1C62 Approved [43]
Verapamil DMA7PEW Angina pectoris BA40 Approved [44]
Diclofenac DMPIHLS Chronic renal failure GB61.Z Approved [45]
Valproate DMCFE9I Epilepsy 8A60-8A68 Approved [46]
Quinine DMSWYF5 Malaria 1F40-1F45 Approved [47]
Propofol DMB4OLE Anaesthesia 9A78.6 Approved [48]
⏷ Show the Full List of 10 Drug(s)
Drug Name Drug ID Indication ICD 11 Highest Status REF
Lorlatinib DMICDLV Non-small-cell lung cancer 2C25.Y Approved [49]
Lamotrigine DM8SXYG Bipolar disorder 6A60 Approved [50]
Calcitriol DM8ZVJ7 Congenital alopecia LC30 Approved [51]
Bevirimat DML2D8Q Human immunodeficiency virus infection 1C62 Phase 2 [52]
LM-94 DMW3QGJ N. A. N. A. Phase 1/2 [53]
UDP-glucuronic acid DMW16X2 Discovery agent N.A. Investigative [53]
⏷ Show the Full List of 6 Drug(s)

Molecular Interaction Atlas of This Drug

Molecular Interaction Atlas

Drug Therapeutic Target (DTT)
DTT Name DTT ID UniProt ID MOA REF
Human immunodeficiency virus Reverse transcriptase (HIV RT) TT84ETX POL_HV1B1 Inhibitor [3]
Voltage-gated sodium channel alpha Nav1.8 (SCN10A) TT90XZ8 SCNAA_HUMAN Inhibitor [2]

Drug-Metabolizing Enzyme (DME)
DME Name DME ID UniProt ID MOA REF
Cytochrome P450 3A4 (CYP3A4) Main DME DE4LYSA CP3A4_HUMAN Substrate [4]
UDP-glucuronosyltransferase 1A1 (UGT1A1) DEYGVN4 UD11_HUMAN Substrate [5]
Mephenytoin 4-hydroxylase (CYP2C19) DEGTFWK CP2CJ_HUMAN Substrate [6]
UDP-glucuronosyltransferase 1A4 (UGT1A4) DELOY3P UD14_HUMAN Substrate [5]

References

1 2011 FDA drug approvals. Nat Rev Drug Discov. 2012 Feb 1;11(2):91-4.
2 Structures of muO-conotoxins from Conus marmoreus. I nhibitors of tetrodotoxin (TTX)-sensitive and TTX-resistant sodium channels in mammalian senso... J Biol Chem. 2004 Jun 11;279(24):25774-82.
3 Emerging antiviral drugs. Expert Opin Emerg Drugs. 2008 Sep;13(3):393-416.
4 Potential of the novel antiretroviral drug rilpivirine to modulate the expression and function of drug transporters and drug-metabolising enzymes in vitro. Int J Antimicrob Agents. 2013 May;41(5):484-7.
5 Human biotransformation of the nonnucleoside reverse transcriptase inhibitor rilpivirine and a cross-species metabolism comparison. Antimicrob Agents Chemother. 2013 Oct;57(10):5067-79.
6 Population pharmacokinetics and pharmacogenetics analysis of rilpivirine in HIV-1-infected individuals. Antimicrob Agents Chemother. 2016 Dec 27;61(1).
7 Antiviral drugs in current clinical use. J Clin Virol. 2004 Jun;30(2):115-33.
8 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.
9 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.
10 Drugs@FDA. U.S. Food and Drug Administration. U.S. Department of Health & Human Services.
11 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.
12 2008 FDA drug approvals. Nat Rev Drug Discov. 2009 Feb;8(2):93-6.
13 2018 FDA drug approvals.Nat Rev Drug Discov. 2019 Feb;18(2):85-89.
14 Emerging drugs in neuropathic pain. Expert Opin Emerg Drugs. 2007 Mar;12(1):113-26.
15 Heterologous expression and functional analysis of rat Nav1.8 (SNS) voltage-gated sodium channels in the dorsal root ganglion neuroblastoma cell line ND7-23. Neuropharmacology. 2004 Mar;46(3):425-38.
16 Pathobiology of visceral pain: molecular mechanisms and therapeutic implications. II. Genetic approaches to pain therapy. Am J Physiol Gastrointest Liver Physiol. 2000 Apr;278(4):G507-12.
17 Clinical pipeline report, company report or official report of the Pharmaceutical Research and Manufacturers of America (PhRMA)
18 Antibodies and venom peptides: new modalities for ion channels. Nat Rev Drug Discov. 2019 May;18(5):339-357.
19 Oral Administration of PF-01247324, a Subtype-Selective Nav1.8 Blocker, Reverses Cerebellar Deficits in a Mouse Model of Multiple Sclerosis. PLoS One. 2015; 10(3): e0119067.
20 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.
21 Contribution of human hepatic cytochrome P450 isoforms to regioselective hydroxylation of steroid hormones. Xenobiotica. 1998 Jun;28(6):539-47.
22 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.
23 Isoform-specific regulation of cytochromes P450 expression by estradiol and progesterone. Drug Metab Dispos. 2013 Feb;41(2):263-9.
24 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.
25 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.
26 Effects of morin on the pharmacokinetics of etoposide in rats. Biopharm Drug Dispos. 2007 Apr;28(3):151-6.
27 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.
28 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.
29 Functional significance of UDP-glucuronosyltransferase variants in the metabolism of active tamoxifen metabolites. Cancer Res. 2009 Mar 1;69(5):1892-900.
30 Functional characterization of human and cynomolgus monkey UDP-glucuronosyltransferase 1A1 enzymes. Life Sci. 2010 Aug 14;87(7-8):261-8.
31 Effect of UDP-glucuronosyltransferase (UGT) 1A polymorphism (rs8330 and rs10929303) on glucuronidation status of acetaminophen. Dose Response. 2017 Sep 11;15(3):1559325817723731.
32 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.
33 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.
34 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.
35 Characterization of rat intestinal microsomal UDP-glucuronosyltransferase activity toward mycophenolic acid. Drug Metab Dispos. 2006 Sep;34(9):1632-9.
36 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.
37 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.
38 Identification and preliminary characterization of UDP-glucuronosyltransferases catalyzing formation of ethyl glucuronide. Anal Bioanal Chem. 2014 Apr;406(9-10):2325-32.
39 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.
40 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.
41 Cytochrome P450 pharmacogenetics and cancer. Oncogene. 2006 Mar 13;25(11):1679-91.
42 CYP2C19*17 is associated with decreased breast cancer risk. Breast Cancer Res Treat. 2009 May;115(2):391-6.
43 Summary of information on human CYP enzymes: human P450 metabolism data. Drug Metab Rev. 2002 Feb-May;34(1-2):83-448.
44 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.
45 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.
46 A mechanistic approach to antiepileptic drug interactions. Ann Pharmacother. 1998 May;32(5):554-63.
47 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.
48 Possible involvement of multiple human cytochrome P450 isoforms in the liver metabolism of propofol. Br J Anaesth. 1998 Jun;80(6):788-95.
49 FDA label of Lorlatinib. The 2020 official website of the U.S. Food and Drug Administration.
50 Studies on induction of lamotrigine metabolism in transgenic UGT1 mice. Xenobiotica. 2009 Nov;39(11):826-35.
51 Identification of human UDP-glucuronosyltransferases catalyzing hepatic 1alpha,25-dihydroxyvitamin D3 conjugation. Biochem Pharmacol. 2008 Mar 1;75(5):1240-50.
52 Bevirimat: a novel maturation inhibitor for the treatment of HIV-1 infection. Antivir Chem Chemother. 2008;19(3):107-13.
53 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.