fostemsavir   Click here for help

GtoPdb Ligand ID: 11100

Abbreviated name: FTR
Synonyms: BMS-663068 | BMS663068 | compound 35 [PMID: 29271653] | GSK-3684934 | GSK3684934 | Rukobia®
Approved drug
fostemsavir is an approved drug (FDA (2020), EMA (2021))
Compound class: Synthetic organic
Comment: Fostemsavir is a phosphonooxymethyl prodrug of temsavir (BMS-626529) [4-5]. It is classified as an attachment inhibitor [2]. Temsavir binds to HIV envelope glycoprotein 120 (gp120) and thereby blocks viral attachment to the host CD4 molecule on T-lymphocytes. Naturally ocurring HIV-1 gp120 polymorphisms that could impart resistance to fostemsavir are uncommon [1].
2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 12
Hydrogen bond donors 2
Rotatable bonds 10
Topological polar surface area 191.5
Molecular weight 583.16
XLogP 0.13
No. Lipinski's rules broken 1
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Canonical SMILES COc1cnc(c2c1c(cn2COP(=O)(O)O)C(=O)C(=O)N1CCN(CC1)C(=O)c1ccccc1)n1cnc(n1)C
Isomeric SMILES COc1cnc(c2c1c(cn2COP(=O)(O)O)C(=O)C(=O)N1CCN(CC1)C(=O)c1ccccc1)n1cnc(n1)C
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)
Classification Click here for help
Compound class Synthetic organic
Approved drug? Yes (FDA (2020), EMA (2021))
IUPAC Name Click here for help
[3-[2-(4-benzoylpiperazin-1-yl)-2-oxoacetyl]-4-methoxy-7-(3-methyl-1,2,4-triazol-1-yl)pyrrolo[2,3-c]pyridin-1-yl]methyl dihydrogen phosphate
International Nonproprietary Names Click here for help
INN number INN
10292 fostemsavir
Synonyms Click here for help
BMS-663068 | BMS663068 | compound 35 [PMID: 29271653] | GSK-3684934 | GSK3684934 | Rukobia®
Database Links Click here for help
CAS Registry No. 864953-29-7 (source: WHO INN record)
ChEMBL Ligand CHEMBL3301594
DrugBank Ligand DB11796
DrugCentral Ligand 5401
GtoPdb PubChem SID 434122161
PubChem CID 11319217
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UniChem Compound Search for chemical match using the InChIKey SWMDAPWAQQTBOG-UHFFFAOYSA-N
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