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

General Information of Drug (ID: DR1552)
Drug Name
Tenofovir alafenamide
Prodrug Info Tenofovir alafenamide is the prodrug of Tenofovir(TFV)
Synonyms
Tenofovir Alafenamide (GS-7340); Tenofovir Alafenamide [USAN:INN]; UNII-EL9943AG5J; UNII-J4414G3BUK; Vemlidy; Tenofovir; UNII-W4HFE001U5; W4HFE001U5; (R)-(((1-(6-AMINO-9H-PURIN-9-YL)PROPAN-2-YL)OXY)METHYL)PHOSPHONIC ACID; (R)-(1-(6-amino-9H-purin-9-yl)propan-2-yloxy)methylphosphonic acid; (R)-9-(2-Phosphonomethoxypropyl)adenine; (R)-9-[2-(Phosphonomethoxy)propyl]adenine; (R)-PMPA; ({[(2R)-1-(6-amino-9H-purin-9-yl)propan-2-yl]oxy}methyl)phosphonic acid; 147127-20-6; 9-[(R)-2-(phosphonomethoxy)propyl]adenine; Apropovir; CHEBI:63625; D,L-Tenofovir; GS-1278; PMPA; PMPA gel; (S)-Isopropyl 2-(((S)-((((R)-1-(6-amino-9H-purin-9-yl)propan-2-yl)oxy)methyl)(phenoxy)phosphoryl)amino)propanoate; 379270-37-8; AK109983; EL9943AG5J; GS 7340; GS-7339; GS-7340; GS7340; J4414G3BUK; L-Alanine, N-((S)-(((1R)-2-(6-amino-9H-purin-9-yl)-1-methylethoxy)methyl)phenoxyphosphinyl)-, 1-methylethyl ester; TENOFOVIR ALAFENAMIDE
Indication Viral hepatitis [ICD11: 1E51] Approved [1]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 476.5 Topological Polar Surface Area 144
Heavy Atom Count 33 Rotatable Bond Count 12
Hydrogen Bond Donor Count 2 Hydrogen Bond Acceptor Count 10
Cross-matching ID
PubChem CID
9574768
ChEBI ID
CHEBI:90926
CAS Number
379270-37-8
Formula
C21H29N6O5P
Canonical SMILES
CC(C)OC(=O)C(C)NP(=O)(COC(C)CN1C=NC2=C(N=CN=C21)N)OC3=CC=CC=C3
InChI
1S/C21H29N6O5P/c1-14(2)31-21(28)16(4)26-33(29,32-17-8-6-5-7-9-17)13-30-15(3)10-27-12-25-18-19(22)23-11-24-20(18)27/h5-9,11-12,14-16H,10,13H2,1-4H3,(H,26,29)(H2,22,23,24)/t15-,16+,33+/m1/s1
InChIKey
LDEKQSIMHVQZJK-CAQYMETFSA-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
Tenofovir(TFV) DM000500
464205
Hydrolysis - Hydrolyzation 1 [2]
Tenofovir-DP DM000501
5481180
Other reaction - Phosphorylation 2 [2]
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR003116 Tenofovir alafenamide Tenofovir Hydrolysis - Hydrolyzation CTSA ... [2]
MR003115 Tenofovir Tenofovir diphosphate Other reaction - Phosphorylation Unclear [2]
Drug-Metabolizing Enzyme(s) (DME) Metabolizing This Drug
DME Name DME Info Species Uniprot ID EC Number REF
Carboxylesterase 1 (CES1) DME0054 Homo sapiens
EST1_HUMAN
3.1.1.1
[2]
Cathepsin A (CTSA) DME0071 Homo sapiens
PPGB_HUMAN
3.4.16.5
[2]
Cathepsin A (CTSA) DME0071 Homo sapiens
PPGB_HUMAN
3.4.16.5
[3]
Cytochrome P450 3A4 (CYP3A4) DME0001 Homo sapiens
CP3A4_HUMAN
1.14.14.55
[4]
Unclear metabolic mechanism (DME-unclear) DME1272 Gardnerella vaginalis Not Available Not Available [5] , [6]
Unclear metabolic mechanism (DME-unclear) DME1434 Lactobacillus crispatus Not Available Not Available [5]
⏷ Show the Full List of 6  DME(s)
References
1 Tenofovir Alafenamide was approved by FDA. The 2020 official website of the U.S. Food and Drug Administration.
2 Bictegravir/Emtricitabine/Tenofovir Alafenamide: a review in HIV-1 infection. Drugs. 2018 Nov;78(17):1817-1828.
3 DrugBank(Pharmacology-Metabolism):Tenofovir alafenamide
4 FDA label of Bictegravir, emtricitabine, and tenofovir alafenamide. The 2020 official website of the U.S. Food and Drug Administration.
5 Vaginal microbiome modulates topical antiretroviral drug pharmacokinetics. JCI Insight. 2018 Jul 12;3(13). pii: 99545.
6 Vaginal bacteria modify HIV tenofovir microbicide efficacy in African women. Science. 2017 Jun 2;356(6341):938-945.

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