fosinopril   

GtoPdb Ligand ID: 6456

Synonyms: Monopril® | SQ-28555
fosinopril is an approved drug (FDA (1991))
Compound class: Synthetic organic
Comment: Fosinopril is a prodrug which is metabolised to the active drug fosinoprilat. Fosinopril belongs to the angiotensin-converting enzyme (ACE) inhibitor drug family. There is some ambiguity in the literature and on other resources as to the exact stereochemistry of fosinopril. The structure shown here matches that specified by the INN document.
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2D Structure
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Physico-chemical Properties
Hydrogen bond acceptors 8
Hydrogen bond donors 1
Rotatable bonds 16
Topological polar surface area 120.02
Molecular weight 563.3
XLogP 6.31
No. Lipinski's rules broken 2
SMILES / InChI / InChIKey
Canonical SMILES CCC(=O)OC(C(C)C)OP(=O)(CC(=O)N1CC(CC1C(=O)O)C1CCCCC1)CCCCc1ccccc1
Isomeric SMILES CCC(=O)O[C@H](C(C)C)O[P@@](=O)(CC(=O)N1C[C@@H](C[C@H]1C(=O)O)C1CCCCC1)CCCCc1ccccc1
InChI InChI=1S/C30H46NO7P/c1-4-28(33)37-30(22(2)3)38-39(36,18-12-11-15-23-13-7-5-8-14-23)21-27(32)31-20-25(19-26(31)29(34)35)24-16-9-6-10-17-24/h5,7-8,13-14,22,24-26,30H,4,6,9-12,15-21H2,1-3H3,(H,34,35)/t25-,26+,30+,39-/m1/s1
InChI Key BIDNLKIUORFRQP-XYGFDPSESA-N
Classification
Compound class Synthetic organic
Approved drug? Yes (FDA (1991))
Is prodrug? Yes
Active form fosinoprilat
IUPAC Name
(2S,4S)-4-cyclohexyl-1-[2-[[(1S)-2-methyl-1-propanoyloxypropoxy]-(4-phenylbutyl)phosphoryl]acetyl]pyrrolidine-2-carboxylic acid
International Nonproprietary Names
INN number INN
5833 fosinopril
Synonyms
Monopril® | SQ-28555
Database Links
CAS Registry No. 98048-97-6 (source: PubChem)
ChEBI CHEBI:5163
ChEMBL Ligand CHEMBL3039598
DrugBank Ligand DB00492
DrugCentral Ligand 1245
GtoPdb PubChem SID 178103071
PubChem CID 9601226
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Wikipedia Fosinopril