fosinopril   Click here for help

GtoPdb Ligand ID: 6456

Synonyms: Monopril® | SQ-28555
Approved drug
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
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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
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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
Classification Click here for help
Compound class Synthetic organic
Approved drug? Yes (FDA (1991))
Is prodrug? Yes
Active form fosinoprilat
IUPAC Name Click here for help
(2S,4S)-4-cyclohexyl-1-[2-[[(1S)-2-methyl-1-propanoyloxypropoxy]-(4-phenylbutyl)phosphoryl]acetyl]pyrrolidine-2-carboxylic acid
International Nonproprietary Names Click here for help
INN number INN
5833 fosinopril
Synonyms Click here for help
Monopril® | SQ-28555
Database Links Click here for help
Specialist databases
Reactome Drug Reactome logo R-ALL-9619057
Reactome Reaction Reactome logo R-HSA-9619024
Other databases
CAS Registry No. 98048-97-6 (source: PubChem)
ChEMBL Ligand CHEMBL3039598
DrugBank Ligand DB00492
DrugCentral Ligand 1245, 1245
GtoPdb PubChem SID 178103071
PubChem CID 9601226
Search Google for chemical match using the InChIKey BIDNLKIUORFRQP-XYGFDPSESA-N
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Search PubMed clinical trials fosinopril
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UniChem Compound Search for chemical match using the InChIKey BIDNLKIUORFRQP-XYGFDPSESA-N
UniChem Connectivity Search for chemical match using the InChIKey BIDNLKIUORFRQP-XYGFDPSESA-N
Wikipedia Fosinopril