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

General Information of Drug (ID: DR0671)
Drug Name
Etravirine
Synonyms
Etravirine; Etravirine (TMC125); Intelence; R-165335; R165335; TMC 125; TMC-125; TMC125; 0C50HW4FO1; 269055-15-4; 4-((6-Amino-5-bromo-2-((4-cyanophenyl)amino)pyrimidin-4-yl)oxy)-3,5-dimethylbenzonitrile; 4-({6-AMINO-5-BROMO-2-[(4-CYANOPHENYL)AMINO]PYRIMIDIN-4-YL}OXY)-3,5-DIMETHYLBENZONITRILE; 4-[[6-AMINO-5-BROMO-2-[(4-CYANOPHENYL)AMINO]-4-PYRIMIDINYL]OXY]-3,5-DIMETHYLBENZONITRILE; C20H15BrN6O; CHEBI:63589; CHEMBL308954; UNII-0C50HW4FO1
Indication Human immunodeficiency virus infection [ICD11: 1C60] Approved [1]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 435.3 Topological Polar Surface Area 121
Heavy Atom Count 28 Rotatable Bond Count 4
Hydrogen Bond Donor Count 2 Hydrogen Bond Acceptor Count 7
Cross-matching ID
PubChem CID
193962
PubChem SID
642445 ; 832707 ; 7885445 ; 10261828 ; 12015430 ; 14856802 ; 33514683 ; 47206062 ; 50755335 ; 57397726 ; 58108352 ; 92765305 ; 92765307 ; 93375510 ; 93619697 ; 99443662 ; 103268452 ; 103999716 ; 113457302 ; 118844113 ; 125346599 ; 126617154 ; 126632876 ; 126665857 ; 131308179 ; 134224563 ; 134338670 ; 135171617 ; 135611140 ; 135693135 ; 136946574 ; 136980023 ; 137006543 ; 139263775 ; 143497676 ; 144115317 ; 152035774 ; 152234808 ; 152258935 ; 160647779 ; 160658773 ; 160968275 ; 162009794 ; 162011438 ; 162200353 ; 162849709 ; 163894003 ; 164831834 ; 170483270 ; 170503235
ChEBI ID
CHEBI:63589
CAS Number
269055-15-4
TTD Drug ID
D0BP9C
Formula
C20H15BrN6O
Canonical SMILES
CC1=CC(=CC(=C1OC2=NC(=NC(=C2Br)N)NC3=CC=C(C=C3)C#N)C)C#N
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
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
Etravirine metabolite M1 DM000953
135390905
Oxidation - Hydroxylation 1 [3] , [4]
Etravirine metabolite M3 DM000951
71750800
Oxidation - Hydroxylation 1 [3] , [4]
Etravirine metabolite M4 DM000952
71316232
Oxidation - Hydroxylation 2 [4]
Etravirine metabolite M5/6 DM000954
155928853
Oxidation - Hydroxylation 2 [4]
Etravirine metabolite M6/5 DM000955
155928807
Oxidation - Hydroxylation 2 [4]
Etravirine metabolite M7 DM000956 N. A. Conjugation - Glucuronidation 2 [4]
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR000989 Etravirine Etravirine metabolite M3 Oxidation - Hydroxylation CYP2C19 [3], [4]
MR000990 Etravirine Etravirine metabolite M1 Oxidation - Hydroxylation CYP3A4 [3], [4]
MR000986 Etravirine metabolite M1 Etravirine metabolite M5/6 Oxidation - Hydroxylation CYP2C9 [4]
MR000987 Etravirine metabolite M1 Etravirine metabolite M6/5 Oxidation - Hydroxylation CYP2C9 [4]
MR000988 Etravirine metabolite M1 Etravirine metabolite M7 Conjugation - Glucuronidation UGT1A3 ... [4]
MR000985 Etravirine metabolite M3 Etravirine metabolite M4 Oxidation - Hydroxylation CYP2C19 [4]
⏷ Show the Full List of 6 MR(s)
Drug-Metabolizing Enzyme(s) (DME) Metabolizing This Drug
DME Name DME Info Species Uniprot ID EC Number REF
Cytochrome P450 2C9 (CYP2C9) DME0019 Homo sapiens
CP2C9_HUMAN
1.14.14.1
[2]
Cytochrome P450 3A4 (CYP3A4) DME0001 Homo sapiens
CP3A4_HUMAN
1.14.14.55
[2]
Mephenytoin 4-hydroxylase (CYP2C19) DME0021 Homo sapiens
CP2CJ_HUMAN
1.14.14.1
[3]
UDP-glucuronosyltransferase 1A3 (UGT1A3) DME0041 Homo sapiens
UD13_HUMAN
2.4.1.17
[3]
UDP-glucuronosyltransferase 1A8 (UGT1A8) DME0064 Homo sapiens
UD18_HUMAN
2.4.1.17
[3]
References
1 Etravirine was approved by FDA. The 2020 official website of the U.S. Food and Drug Administration.
2 Pharmacokinetic interactions between etravirine and non-antiretroviral drugs. Clin Pharmacokinet. 2011 Jan;50(1):25-39.
3 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.
4 Clinical pharmacokinetics and pharmacodynamics of etravirine. Clin Pharmacokinet. 2009;48(9):561-74.

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