Fosinoprilat

This drug entry is a stub and has not been fully annotated. It is scheduled to be annotated soon.

Identification

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Name
Fosinoprilat
Accession Number
DB14207
Type
Small Molecule
Groups
Experimental
Description

Fosinoprilat is the active phosphinic acid metabolite of prodrug fosinopril, which is activated by esterases in vivo. It binds zinc with phosphinic acid group.

Structure
Thumb
Synonyms
  • Fosinopril diacid
  • Fosinoprilat
  • Fosinoprilatum
  • Fosinoprilic acid
Categories
UNII
S312EY6ZT8
CAS number
95399-71-6
Weight
Average: 435.4935
Monoisotopic: 435.217459715
Chemical Formula
C23H34NO5P
InChI Key
WOIWWYDXDVSWAZ-RTWAWAEBSA-N
InChI
InChI=1S/C23H34NO5P/c25-22(17-30(28,29)14-8-7-11-18-9-3-1-4-10-18)24-16-20(15-21(24)23(26)27)19-12-5-2-6-13-19/h1,3-4,9-10,19-21H,2,5-8,11-17H2,(H,26,27)(H,28,29)/t20-,21+/m1/s1
IUPAC Name
(2S,4S)-4-cyclohexyl-1-{2-[hydroxy(4-phenylbutyl)phosphoryl]acetyl}pyrrolidine-2-carboxylic acid
SMILES
[H][C@]1(C[C@H](N(C1)C(=O)CP(O)(=O)CCCCC1=CC=CC=C1)C(O)=O)C1CCCCC1

Pharmacology

Indication
Not Available
Pharmacodynamics
Not Available
Mechanism of action
Not Available
Absorption
Not Available
Volume of distribution
Not Available
Protein binding
Not Available
Metabolism
Not Available
Route of elimination
Not Available
Half life
Not Available
Clearance
Not Available
Toxicity
Not Available
Affected organisms
Not Available
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
DrugInteraction
1-(3-Mercapto-2-Methyl-Propionyl)-Pyrrolidine-2-Carboxylic Acid1-(3-Mercapto-2-Methyl-Propionyl)-Pyrrolidine-2-Carboxylic Acid may increase the hypotensive activities of Fosinoprilat.
1-benzylimidazole1-benzylimidazole may decrease the antihypertensive activities of Fosinoprilat.
2,5-Dimethoxy-4-ethylamphetamine2,5-Dimethoxy-4-ethylamphetamine may decrease the antihypertensive activities of Fosinoprilat.
2,5-Dimethoxy-4-ethylthioamphetamine2,5-Dimethoxy-4-ethylthioamphetamine may decrease the antihypertensive activities of Fosinoprilat.
4-Bromo-2,5-dimethoxyamphetamine4-Bromo-2,5-dimethoxyamphetamine may decrease the antihypertensive activities of Fosinoprilat.
4-Methoxyamphetamine4-Methoxyamphetamine may decrease the antihypertensive activities of Fosinoprilat.
5-methoxy-N,N-dimethyltryptamine5-methoxy-N,N-dimethyltryptamine may decrease the antihypertensive activities of Fosinoprilat.
7,8-Dichloro-1,2,3,4-tetrahydroisoquinoline7,8-Dichloro-1,2,3,4-tetrahydroisoquinoline may increase the hypotensive activities of Fosinoprilat.
AbediterolAbediterol may decrease the antihypertensive activities of Fosinoprilat.
AcebutololThe risk or severity of hyperkalemia can be increased when Acebutolol is combined with Fosinoprilat.
Additional Data Available
  • Extended Description
    Extended Description

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  • Severity
    Severity

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  • Evidence Level
    Evidence Level

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  • Action
    Action

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Food Interactions
Not Available

References

General References
Not Available
External Links
KEGG Drug
D03772
ChemSpider
56667
BindingDB
50018849
ChEBI
116962
ChEMBL
CHEMBL581
Wikipedia
Fosinopril

Clinical Trials

Clinical Trials
Not Available

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Not Available
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.00447 mg/mLALOGPS
logP3.7ALOGPS
logP3.34ChemAxon
logS-5ALOGPS
pKa (Strongest Acidic)1.76ChemAxon
pKa (Strongest Basic)-4.7ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area94.91 Å2ChemAxon
Rotatable Bond Count9ChemAxon
Refractivity116.03 m3·mol-1ChemAxon
Polarizability47.35 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted ADMET features
Not Available

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available

Taxonomy

Description
This compound belongs to the class of organic compounds known as proline and derivatives. These 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
N-acyl-L-alpha-amino acids / Pyrrolidine carboxylic acids / N-acylpyrrolidines / Benzene and substituted derivatives / Tertiary carboxylic acid amides / Monocarboxylic acids and derivatives / Carboxylic acids / Azacyclic compounds / Organopnictogen compounds / Organophosphorus compounds
show 4 more
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 / Monocyclic benzene moiety / Benzenoid / Tertiary carboxylic acid amide
show 16 more
Molecular Framework
Aromatic heteromonocyclic compounds
External Descriptors
L-proline derivative, phosphinic acids (CHEBI:116962)

Drug created on July 04, 2018 11:27 / Updated on May 01, 2019 11:58