Details of the Drug Metabolized by Drug-Metabolizing Enzyme (DME)

General Information of Drug (ID: DR1424)
Drug Name
Rilpivirine hydrochloride
Synonyms
Rilpivirine HCl; Rilpivirine hydrochloride; Rilpivirine hydrochloride (JAN/USAN); Rilpivirine hydrochloride [USAN]; Rilpivirine; TMC 278; TMC-278; TMC278; UNII-FI96A8X663; (E)-4-((4-((4-(2-cyanovinyl)-2,6-dimethylphenyl)amino)pyrimidin-2-yl)amino)benzonitrile; 4-[[4-[[4-[(E)-2-Cyanoethenyl]-2,6-dimethyl-phenyl]amino]pyrimidin-2-yl]amino]benzonitrile; 4-{[4-({4-[(E)-2-Cyanoethenyl]-2,6-Dimethylphenyl}amino)pyrimidin-2-Yl]amino}benzonitrile; 4-{[4-({4-[(E)-2-cyanovinyl]-2,6-dimethylphenyl}amino)pyrimidin-2-yl]amino}benzonitrile; 500287-72-9; CHEBI:68606; FI96A8X663; R 278474; R278474; SB19134; SCHEMBL1831067; TMC-278-LA; TMC278 hydrochloride; TMC278-HYDROCHLORIDE; UNII-212WAX8KDD; rilpivirine monohydrochloride; 212WAX8KDD; 4-((4-((4-((1E)-2-Cyanoethenyl)-2,6-dimethylphenyl)amino)pyrimidin-2- yl)amino)benzonitrile; 700361-47-3; AKOS025149454; BC677097; BCP13350; CHEBI:68602; CHEMBL1628504; DTXSID80220320; Edurant (TN); Endurant; KZVVGZKAVZUACK-BJILWQEISA-N; R-278474
Indication Human immunodeficiency virus infection [ICD11: 1C60] Approved [1]
Structure
3D MOL is unavailable 2D MOL
Pharmaceutical Properties Molecular Weight 402.9 Topological Polar Surface Area 97.4
Heavy Atom Count 29 Rotatable Bond Count 5
Hydrogen Bond Donor Count 3 Hydrogen Bond Acceptor Count 6
Cross-matching ID
PubChem CID
11711114
ChEBI ID
CHEBI:83309
CAS Number
700361-47-3
TTD Drug ID
D0T6WN
Formula
C22H19ClN6
Canonical SMILES
CC1=CC(=CC(=C1NC2=NC(=NC=C2)NC3=CC=C(C=C3)C#N)C)C=CC#N.Cl
InChI
1S/C22H18N6.ClH/c1-15-12-18(4-3-10-23)13-16(2)21(15)27-20-9-11-25-22(28-20)26-19-7-5-17(14-24)6-8-19;/h3-9,11-13H,1-2H3,(H2,25,26,27,28);1H/b4-3+;
InChIKey
KZVVGZKAVZUACK-BJILWQEISA-N
The Metabolic Roadmap of This Drug
The Full List of Drug Metabolites (DM) of This Drug
DM Name DM ID PubChem ID Reaction DM Level REF
Rilpivirine M1 DM017910 N. A. Oxidation - Hydroxylation 1 [3]
Rilpivirine M2 DM017906 N. A. Oxidation - Hydroxylation 1 [3]
Rilpivirine M3 DM017911 N. A. Oxidation - Hydroxylation 1 [3]
Rilpivirine M4 DM017908 N. A. Oxidation - Hydroxylation 1 [3]
Rilpivirine M5 DM017912 N. A. Conjugation - Glucuronidation 1 [3]
Rilpivirine M6 DM017907 N. A. Conjugation - Glucuronidation 2 [3]
Rilpivirine M7 DM017909 N. A. Conjugation - Glucuronidation 2 [3]
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR009532 Rilpivirine hydrochloride Rilpivirine M2 Oxidation - Hydroxylation CYP3A4 ... [3]
MR009534 Rilpivirine hydrochloride Rilpivirine M4 Oxidation - Hydroxylation CYP3A4 ... [3]
MR009536 Rilpivirine hydrochloride Rilpivirine M1 Oxidation - Hydroxylation CYP3A4 ... [3]
MR009537 Rilpivirine hydrochloride Rilpivirine M3 Oxidation - Hydroxylation CYP3A4 ... [3]
MR009538 Rilpivirine hydrochloride Rilpivirine M5 Conjugation - Glucuronidation UGT1A4 [3]
MR009533 Rilpivirine M2 Rilpivirine M6 Conjugation - Glucuronidation UGT1A1 [3]
MR009535 Rilpivirine M4 Rilpivirine M7 Conjugation - Glucuronidation SLC35A2 [3]
⏷ Show the Full List of 7 MR(s)
Drug-Metabolizing Enzyme(s) (DME) Metabolizing This Drug
DME Name DME Info Species Uniprot ID EC Number REF
Cytochrome P450 3A4 (CYP3A4) DME0001 Homo sapiens
CP3A4_HUMAN
1.14.14.55
[2]
Cytochrome P450 3A5 (CYP3A5) DME0012 Homo sapiens
CP3A5_HUMAN
1.14.14.1
[3]
Mephenytoin 4-hydroxylase (CYP2C19) DME0021 Homo sapiens
CP2CJ_HUMAN
1.14.14.1
[4]
UDP-glucuronosyltransferase 1A1 (UGT1A1) DME0004 Homo sapiens
UD11_HUMAN
2.4.1.17
[3]
UDP-glucuronosyltransferase 1A4 (UGT1A4) DME0048 Homo sapiens
UD14_HUMAN
2.4.1.17
[3]
UDP-glucuronyltransferase (UGT) DMEN064 . Not Available Not Available [3]
⏷ Show the Full List of 6  DME(s)
References
1 Rilpivirine Hydrochloride was approved by FDA. The 2020 official website of the U.S. Food and Drug Administration.
2 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.
3 Human biotransformation of the nonnucleoside reverse transcriptase inhibitor rilpivirine and a cross-species metabolism comparison. Antimicrob Agents Chemother. 2013 Oct;57(10):5067-79.
4 Population pharmacokinetics and pharmacogenetics analysis of rilpivirine in HIV-1-infected individuals. Antimicrob Agents Chemother. 2016 Dec 27;61(1).

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