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

General Information of Drug (ID: DR0745)
Drug Name
Fosamprenavir
Prodrug Info Fosamprenavir is the prodrug of Amprenavir
Synonyms
Fosamprenavir; Fosamprenavir (INN); Fosamprenavir [INN]; Telzir; Telzir(TM); VX 175; VX-175; WOU1621EEG; (3-(((4-Aminophenyl)sulfonyl)(2-methylpropyl)amino)-1-(phenylmethyl)-2-(phosphonooxy)propyl)carbamic acid C-(tetrahydro-3-furanyl) ester; Amprenavir phosphate; FOS-APV; 226700-79-4; CHEBI:82941; Carbamic acid, ((1S,2R)-3-(((4-aminophenyl)sulfonyl)(2-methylpropyl)amino)-1-(phenylmethyl)-2-(phosphonooxy)propyl)-, C-((3S)-tetrahydro-3-furanyl) ester; GW 433908; GW433908; HSDB 7340; UNII-WOU1621EEG
Indication Human immunodeficiency virus infection [ICD11: 1C60] Approved [1]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 585.6 Topological Polar Surface Area 186
Heavy Atom Count 39 Rotatable Bond Count 14
Hydrogen Bond Donor Count 4 Hydrogen Bond Acceptor Count 11
Cross-matching ID
PubChem CID
131536
PubChem SID
630866 ; 10242897 ; 14764609 ; 14911487 ; 17396671 ; 29309884 ; 46504901 ; 50070552 ; 50071323 ; 75335910 ; 103633149 ; 104375333 ; 126680953 ; 134222910 ; 134337996 ; 135111213 ; 136139133 ; 137006000 ; 142147341 ; 160964617 ; 175267520 ; 179296052 ; 210279023 ; 223447627 ; 223664897 ; 226420602 ; 251971352
ChEBI ID
CHEBI:82941
CAS Number
226700-79-4
TTD Drug ID
D0F5MT
Formula
C25H36N3O9PS
Canonical SMILES
CC(C)CN(CC(C(CC1=CC=CC=C1)NC(=O)OC2CCOC2)OP(=O)(O)O)S(=O)(=O)C3=CC=C(C=C3)N
InChI
1S/C25H36N3O9PS/c1-18(2)15-28(39(33,34)22-10-8-20(26)9-11-22)16-24(37-38(30,31)32)23(14-19-6-4-3-5-7-19)27-25(29)36-21-12-13-35-17-21/h3-11,18,21,23-24H,12-17,26H2,1-2H3,(H,27,29)(H2,30,31,32)/t21-,23-,24+/m0/s1
InChIKey
MLBVMOWEQCZNCC-OEMFJLHTSA-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
Amprenavir DM003053
65016
Unclear 1 [2]
GW549444 DM002063 N. A. Unclear 2 [2]
GW549445 DM002064 N. A. Unclear 2 [2]
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR002851 Fosamprenavir Amprenavir Unclear ALPL [2]
MR002852 Amprenavir GW549444 Unclear CYP3A4 [2]
MR002853 Amprenavir GW549445 Unclear CYP3A4 [2]
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]
References
1 Fosamprenavir was approved by FDA. The 2020 official website of the U.S. Food and Drug Administration.
2 Fosamprenavir : clinical pharmacokinetics and drug interactions of the amprenavir prodrug. Clin Pharmacokinet. 2006;45(2):137-68.

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