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

General Information of Drug (ID: DR5348)
Drug Name
Fostemsavir
Prodrug Info Fostemsavir is the prodrug of Temsavir
Synonyms
BMS-216; BMS-248; BMS-378806; BMS-626529; BMS-705; BMS-806; BMS-806 series; BMS-853; HIV-1 attachment inhibitors, BMS; HIV-1 entry inhibitors, BMS; BMS-488043 follow-on compounds, BMS; HIV-1 attachment inhibitors, Bristol-Myers Squibb
Indication Human immunodeficiency virus infection [ICD11: 1C60-1C62] Approved [1]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 583.5 Topological Polar Surface Area 182
Heavy Atom Count 41 Rotatable Bond Count 8
Hydrogen Bond Donor Count 2 Hydrogen Bond Acceptor Count 11
Cross-matching ID
PubChem CID
11319217
CAS Number
864953-29-7
TTD Drug ID
D00ZCT
Formula
C25H26N7O8P
Canonical SMILES
CC1=NN(C=N1)C2=NC=C(C3=C2N(C=C3C(=O)C(=O)N4CCN(CC4)C(=O)C5=CC=CC=C5)COP(=O)(O)O)OC
InChI
InChI=1S/C25H26N7O8P/c1-16-27-14-32(28-16)23-21-20(19(39-2)12-26-23)18(13-31(21)15-40-41(36,37)38)22(33)25(35)30-10-8-29(9-11-30)24(34)17-6-4-3-5-7-17/h3-7,12-14H,8-11,15H2,1-2H3,(H2,36,37,38)
InChIKey
SWMDAPWAQQTBOG-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
Temsavir DM005063
11317439
Hydrolysis - Hydrolysis 1 [2]
BMS-646915 DM005081 N. A. Unclear 2 [2]
BMS-930644 DM005080 N. A. Oxidation - N-dealkylation 2 [2]
Fostemsavir M10 DM005069 N. A. Unclear 2 [2]
Fostemsavir M18 DM005078 N. A. Oxidation - Mono-oxidation 2 [2]
Fostemsavir M19 DM005084 N. A. Unclear 2 [2]
Fostemsavir M20 DM005070 N. A. Unclear 2 [2]
Fostemsavir M27 DM005064 N. A. Oxidation - Mono-oxidation 2 [2]
Fostemsavir M28 DM005067 N. A. Unclear 2 [2]
Fostemsavir M4 DM005073
67963447
Hydrolysis - Amide hydrolysis 2 [2]
Fostemsavir M6 DM005083 N. A. Unclear 2 [2]
Fostemsavir M8 DM005082 N. A. Unclear 2 [2]
Fostemsavir M1 DM005075 N. A. Unclear 3 [2]
Fostemsavir M10 DM005069 N. A. Unclear 3 [2]
Fostemsavir M13 DM005068 N. A. Unclear 3 [2]
Fostemsavir M14 DM005072 N. A. Unclear 3 [2]
Fostemsavir M16 DM005074 N. A. Unclear 3 [2]
Fostemsavir M2 DM005076 N. A. Unclear 3 [2]
Fostemsavir M22 DM005065 N. A. Unclear 3 [2]
Fostemsavir M23 DM005071 N. A. Oxidation - Oxidationn 3 [2]
Fostemsavir M3 DM005077 N. A. Unclear 3 [2]
Fostemsavir M30 DM005079 N. A. Unclear 3 [2]
Fostemsavir M31 DM005066 N. A. Unclear 4 [2]
⏷ Show the Full List of 23  DM(s)
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR005490 Fostemsavir Temsavir Hydrolysis - Hydrolysis ALPI [2]
MR005496 Fostemsavir M27 Fostemsavir M10 Unclear Unclear [2]
MR005491 Temsavir Fostemsavir M27 Oxidation - Mono-oxidation Unclear [2]
MR005494 Temsavir Fostemsavir M28 Unclear CYP3A4 [2]
MR005497 Temsavir Fostemsavir M20 Unclear Unclear [2]
MR005501 Temsavir Fostemsavir M4 Hydrolysis - Amide hydrolysis Unclear [2]
MR005506 Temsavir Fostemsavir M18 Oxidation - Mono-oxidation Unclear [2]
MR005508 Temsavir BMS-930644 Oxidation - N-dealkylation CYP3A4 [2]
MR005509 Temsavir BMS-646915 Unclear Unclear [2]
MR005510 Temsavir Fostemsavir M8 Unclear Unclear [2]
MR005511 Temsavir Fostemsavir M6 Unclear Unclear [2]
MR005512 Temsavir Fostemsavir M19 Unclear Unclear [2]
MR005507 Fostemsavir M18 Fostemsavir M30 Unclear Unclear [2]
MR005498 Fostemsavir M20 Fostemsavir M10 Unclear Unclear [2]
MR005499 Fostemsavir M20 Fostemsavir M23 Oxidation - Oxidationn Unclear [2]
MR005500 Fostemsavir M20 Fostemsavir M14 Unclear CYP3A4 [2]
MR005492 Fostemsavir M27 Fostemsavir M22 Unclear CYP3A4 [2]
MR005495 Fostemsavir M28 Fostemsavir M13 Unclear CYP3A4 [2]
MR005502 Fostemsavir M4 Fostemsavir M16 Unclear CYP3A4 [2]
MR005503 Fostemsavir M4 Fostemsavir M1 Unclear Unclear [2]
MR005504 Fostemsavir M4 Fostemsavir M2 Unclear Unclear [2]
MR005505 Fostemsavir M4 Fostemsavir M3 Unclear Unclear [2]
MR005493 Fostemsavir M22 Fostemsavir M31 Unclear Unclear [2]
⏷ Show the Full List of 23 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 3A4 (CYP3A4) DME0001 Homo sapiens
CP3A4_HUMAN
1.14.14.55
[3]
Intestinal-type alkaline phosphatase (ALPI) DMEN257 Homo sapiens
PPBI_HUMAN
3.1.3.1
[2]
Intestinal-type alkaline phosphatase (ALPI) DMEN257 Homo sapiens
PPBI_HUMAN
3.1.3.1
[4]
UDP-glucuronyltransferase (UGT) DMEN064 . Not Available Not Available [3]
References
1 Drugs@FDA. U.S. Food and Drug Administration. U.S. Department of Health & Human Services. 2020
2 Pharmacokinetics, metabolism and excretion of radiolabeled fostemsavir administered with or without ritonavir in healthy male subjects
3 Pharmacokinetics of Temsavir, the Active Moiety of the HIV-1 Attachment Inhibitor Prodrug, Fostemsavir, Coadministered with Cobicistat, Etravirine, Darunavir/Cobicistat, or Darunavir/Ritonavir with or without Etravirine in Healthy Participants
4 Discovery of the Human Immunodeficiency Virus Type 1 (HIV-1) Attachment Inhibitor Temsavir and Its Phosphonooxymethyl Prodrug Fostemsavir

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