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

Identification

Generic Name
Fosinoprilat
DrugBank Accession Number
DB14207
Background

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

Type
Small Molecule
Groups
Experimental
Structure
Thumb
Weight
Average: 435.4935
Monoisotopic: 435.217459715
Chemical Formula
C23H34NO5P
Synonyms
  • Fosinopril diacid
  • Fosinoprilat
  • Fosinoprilatum
  • Fosinoprilic acid

Pharmacology

Indication

Not Available

Pharmacology
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Contraindications & Blackbox Warnings
Contraindications
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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

Adverse Effects
Adverseeffects
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Toxicity

Not Available

Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
DrugInteraction
AcebutololAcebutolol may increase the arrhythmogenic activities of Fosinoprilat.
AceclofenacThe risk or severity of renal failure, hyperkalemia, and hypertension can be increased when Aceclofenac is combined with Fosinoprilat.
AcemetacinThe risk or severity of renal failure, hyperkalemia, and hypertension can be increased when Acemetacin is combined with Fosinoprilat.
AcetyldigitoxinAcetyldigitoxin may increase the arrhythmogenic activities of Fosinoprilat.
Acetylsalicylic acidThe therapeutic efficacy of Fosinoprilat can be decreased when used in combination with Acetylsalicylic acid.
AdenosineAdenosine may increase the arrhythmogenic activities of Fosinoprilat.
Agrostis gigantea pollenThe risk or severity of adverse effects can be increased when Fosinoprilat is combined with Agrostis gigantea pollen.
Agrostis stolonifera pollenThe risk or severity of adverse effects can be increased when Fosinoprilat is combined with Agrostis stolonifera pollen.
AjmalineAjmaline may increase the arrhythmogenic activities of Fosinoprilat.
AlclofenacThe risk or severity of renal failure, hyperkalemia, and hypertension can be increased when Alclofenac is combined with Fosinoprilat.
Interactions
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Food Interactions
Not Available

Categories

Drug Categories
Chemical TaxonomyProvided by Classyfire
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
Aromatic heteromonocyclic compound / Azacycle / Benzenoid / Carbonyl group / Carboxamide group / Carboxylic acid / Hydrocarbon derivative / Monocarboxylic acid or derivatives / Monocyclic benzene moiety / N-acyl-alpha amino acid or derivatives
show 16 more
Molecular Framework
Aromatic heteromonocyclic compounds
External Descriptors
L-proline derivative, phosphinic acids (CHEBI:116962)
Affected organisms
Not Available

Chemical Identifiers

UNII
S312EY6ZT8
CAS number
95399-71-6
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

References

General References
Not Available
KEGG Drug
D03772
ChemSpider
56667
BindingDB
50018849
RxNav
1546393
ChEBI
116962
ChEMBL
CHEMBL581
ZINC
ZINC000004213382
PDBe Ligand
KS8
Wikipedia
Fosinopril
PDB Entries
6s1z

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount

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

Drug created at July 04, 2018 17:27 / Updated at February 21, 2021 18:54