ChemFOnt: Showing chemical card for Fosinopril (CFc000008993)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 18:55:59 UTC

Chemfont ID

CFc000008993

Molecule Identification

Common Name

Fosinopril

Definition

Fosinopril is a phosphinic acid-containing ester prodrug that belongs to the angiotensin-converting enzyme (ACE) inhibitor class of medications. It is rapidly hydrolyzed to fosinoprilat, its principle active metabolite. Fosinoprilat inhibits ACE, the enzyme responsible for the conversion of angiotensin I (ATI) to angiotensin II (ATII). ATII regulates blood pressure and is a key component of the renin-angiotensin-aldosterone system (RAAS). Fosinopril may be used to treat mild to moderate hypertension, as an adjunct in the treatment of congestive heart failure, and to slow the rate of progression of renal disease in hypertensive individuals with diabetes mellitus and microalbuminuria or overt nephropathy.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
(2S,4S)-4-Cyclohexyl-1-[2-[(2-methyl-1-propanoyloxypropoxy)-(4-phenylbutyl)phosphoryl]acetyl]pyrrolidine-2-carboxylic acid	ChEBI
(2S,4S)-4-Cyclohexyl-1-{2-[(2-methyl-1-propionyloxy-propoxy)-(4-phenyl-butyl)-phosphinoyl]-acetyl}-pyrrolidine-2-carboxylic acid	ChEBI
(S)-4-Cyclohexyl-1-{2-[(2-methyl-1-propionyloxy-propoxy)-(4-phenyl-butyl)-phosphinoyl]-acetyl}-pyrrolidine-2-carboxylic acid	ChEBI
(2S,4S)-4-Cyclohexyl-1-[2-[(2-methyl-1-propanoyloxypropoxy)-(4-phenylbutyl)phosphoryl]acetyl]pyrrolidine-2-carboxylate	Generator
(2S,4S)-4-Cyclohexyl-1-{2-[(2-methyl-1-propionyloxy-propoxy)-(4-phenyl-butyl)-phosphinoyl]-acetyl}-pyrrolidine-2-carboxylate	Generator
(S)-4-Cyclohexyl-1-{2-[(2-methyl-1-propionyloxy-propoxy)-(4-phenyl-butyl)-phosphinoyl]-acetyl}-pyrrolidine-2-carboxylate	Generator
Fosinopril sodium	HMDB
Monopril	HMDB
Newace	HMDB
Squibb brand OF fosinopril sodium	HMDB
Staril	HMDB
Bristol-myers squibb brand OF fosinopril sodium	HMDB
Dynacil	HMDB
Fosenopril	HMDB
Fosinopril, (1(s(r)),2 alpha,4 beta)-isomer	HMDB
Fosinopril, (1(s(s)),2 alpha,4 beta)-isomer	HMDB
Fositens	HMDB
Sanol brand OF fosinopril sodium	HMDB
Sodium, fosinopril	HMDB
Tensocardil	HMDB
Bristol myers squibb brand OF fosinopril sodium	HMDB
Ferrer brand OF fosinopril sodium	HMDB
Fosinil	HMDB
Fosinorm	HMDB
Schwarz brand OF fosinopril sodium	HMDB
Esteve brand OF fosinopril sodium	HMDB
Fosinopril, (1(s(r)),2 alpha,4 alpha)-(D-pro)-isomer	HMDB
Fozitec	HMDB
Hiperlex	HMDB
Merck lipha santé brand OF fosinopril	HMDB
Tenso stop	HMDB

Chemical Formula

C₃₀H₄₆NO₇P

Average Molecular Weight

563.6625

Monoisotopic Molecular Weight

563.301189343

IUPAC Name

(2S,4S)-4-cyclohexyl-1-(2-{[2-methyl-1-(propanoyloxy)propoxy](4-phenylbutyl)phosphoryl}acetyl)pyrrolidine-2-carboxylic acid

Traditional Name

fosinopril

CAS Registry Number

98048-97-6

SMILES

CCC(=O)OC(OP(=O)(CCCCC1=CC=CC=C1)CC(=O)N1C[C@@H](C[C@H]1C(O)=O)C1CCCCC1)C(C)C

InChI Identifier

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-FKDWWROVSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as proline and derivatives. Proline and derivatives are compounds containing proline or a derivative thereof resulting from reaction of proline at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

Proline and derivatives

Alternative Parents

Substituents

N-acyl-alpha-amino acid
N-acyl-alpha amino acid or derivatives
N-acyl-l-alpha-amino acid
Proline or derivatives
N-acylpyrrolidine
Pyrrolidine carboxylic acid
Pyrrolidine carboxylic acid or derivatives
Dicarboxylic acid or derivatives
Monocyclic benzene moiety
Benzenoid
Tertiary carboxylic acid amide
Pyrrolidine
Carboxylic acid ester
Carboxamide group
Phosphinic acid ester
Organoheterocyclic compound
Carboxylic acid
Azacycle
Organophosphorus compound
Organooxygen compound
Organonitrogen compound
Organic oxygen compound
Organic nitrogen compound
Organic oxide
Organopnictogen compound
Hydrocarbon derivative
Carbonyl group
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

L-proline derivative (CHEBI:5163 )
phosphinic ester (CHEBI:5163 )

Functional Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 21059682)

Excreta

Biofluid or Excreta

Urine (PMID: 21059682)

Cellular substructure

Extracellular (HMDB: HMDB0014635)
Membrane (HMDB: HMDB0014635)

Source

Exogenous

Exogenous (HMDB: HMDB0014635)

Process

Naturally occurring process

Biological process

Biochemical pathway

Drug action pathway

Fosinopril Action Pathway (PathBank: SMP0000149)

Metabolic pathway

Fosinopril Metabolism Pathway (PathBank: SMP0000594)

Role

Not Available

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	0.001 g/L	ALOGPS
logP	4.71	ALOGPS
logP	5.49	ChemAxon
logS	-5.8	ALOGPS
pKa (Strongest Acidic)	3.87	ChemAxon
pKa (Strongest Basic)	-4.4	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	110.21 Å²	ChemAxon
Rotatable Bond Count	15	ChemAxon
Refractivity	149.12 m³·mol⁻¹	ChemAxon
Polarizability	61.17 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon