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

General Information of Drug (ID: DR0533)
Drug Name
Doravirine
Synonyms
Doravirine; Doravirine [USAN:INN]; MK 1439; MK-1439; MK1439; Pifeltro (TN); 1338225-97-0; 3-Chloro-5-((1-((4-methyl-5-oxo-4,5-dihydro-1H-1,2,4-triazol-3-yl)methyl)-2-oxo-4-(trifluoromethyl)-1,2-dihydropyridin-3-yl)oxy)benzonitrile; 3-Chloro-5-({1-[(4-Methyl-5-Oxo-4,5-Dihydro-1h-1,2,4-Triazol-3-Yl)methyl]-2-Oxo-4-(Trifluoromethyl)-1,2-Dihydropyridin-3-Yl}oxy)benzonitrile; 3-chloro-5-[1-[(4-methyl-5-oxo-1H-1,2,4-triazol-3-yl)methyl]-2-oxo-4-(trifluoromethyl)pyridin-3-yl]oxybenzonitrile; 4ncg; 913P6LK81M; UNII-913P6LK81M
Indication Human immunodeficiency virus infection [ICD11: 1C60] Approved [1]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 425.7 Topological Polar Surface Area 98
Heavy Atom Count 29 Rotatable Bond Count 4
Hydrogen Bond Donor Count 1 Hydrogen Bond Acceptor Count 8
Cross-matching ID
PubChem CID
58460047
PubChem SID
138785402 ; 162109074 ; 163370732 ; 163662251 ; 164147214 ; 172132099 ; 198985579 ; 224534916 ; 228614684
CAS Number
1338225-97-0
TTD Drug ID
D0R0TS
Formula
C17H11ClF3N5O3
Canonical SMILES
CN1C(=NNC1=O)CN2C=CC(=C(C2=O)OC3=CC(=CC(=C3)C#N)Cl)C(F)(F)F
InChI
1S/C17H11ClF3N5O3/c1-25-13(23-24-16(25)28)8-26-3-2-12(17(19,20)21)14(15(26)27)29-11-5-9(7-22)4-10(18)6-11/h2-6H,8H2,1H3,(H,24,28)
InChIKey
ZIAOVIPSKUPPQW-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
Doravirine M9 Metabolite DM006189
156613627
Oxidation - Oxidationn 1 [3]
Doravirine Metabolite M11 DM006196
58460048
Unclear 1 [2]
Doravirine Metabolite M15 DM006198 N. A. Conjugation - N-acetyl cysteine conjugation 1 [2]
Doravirine Metabolite M18 DM006194 N. A. Unclear 1 [2]
Doravirine Metabolite M18 DM006194 N. A. Oxidation - Oxidationn 1 [2]
Doravirine Metabolite M19 DM006195 N. A. Unclear 1 [2]
Doravirine Metabolite M5 DM006192 N. A. Unclear 1 [2]
Doravirine Metabolite M8 DM006197
136245093
Oxidation - Oxidationn 1 [2]
Doravirine Metabolite M10 DM006193 N. A. Oxidation - Oxidationn 2 [2]
Doravirine Metabolite M14 DM006191 N. A. Unclear 2 [2]
Doravirine Metabolite M7 DM006190 N. A. Conjugation - Glucuronidation 2 [2]
⏷ Show the Full List of 11  DM(s)
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR006637 Doravirine Doravirine M9 Metabolite Oxidation - Oxidationn CYP3A4 ... [3]
MR006640 Doravirine Doravirine Metabolite M5 Unclear Unclear [2]
MR006642 Doravirine Doravirine Metabolite M18 Oxidation - Oxidationn Unclear [2]
MR006643 Doravirine Doravirine Metabolite M19 Unclear Unclear [2]
MR006644 Doravirine Doravirine Metabolite M11 Unclear Unclear [2]
MR006645 Doravirine Doravirine Metabolite M8 Oxidation - Oxidationn Unclear [2]
MR006646 Doravirine Doravirine Metabolite M15 Conjugation - N-acetyl cysteine conjugation Unclear [2]
MR006638 Doravirine M9 Metabolite Doravirine Metabolite M7 Conjugation - Glucuronidation Unclear [2]
MR006639 Doravirine M9 Metabolite Doravirine Metabolite M14 Unclear Unclear [2]
MR006641 Doravirine Metabolite M5 Doravirine Metabolite M10 Oxidation - Oxidationn Unclear [2]
⏷ Show the Full List of 10 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
[2]
References
1 Doravirine was approved by FDA. The 2020 official website of the U.S. Food and Drug Administration.
2 Characterisation of the absorption, distribution, metabolism, excretion and mass balance of doravirine, a non-nucleoside reverse transcriptase inhibitor in humans. Xenobiotica. 2019 Apr;49(4):422-432.
3 DrugBank(Pharmacology-Metabolism): Doravirine

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