Basic information
- CAS
95153-31-4- Standard SMILES
CCC[C@H](N[C@@H](C)C(=O)N1[C@H](C(=O)O)C[C@@H]2CCCC[C@@H]21)C(=O)O- InChIKey
ODAIHABQVKJNIY-PEDHHIEDSA-N- Molecular formula
- C17H28N2O5
- Average molar mass
- 340.4 g/mol
- Monoisotopic mass
- 340.199822
Overview
Perindoprilat is a dipeptide obtained by formal condensation of one of the carboxy groups of N-[(1S)-1-carboxyethyl]-L-norvaline with the amino group of (2S,3aS,7aS)-octahydroindole-2-carboxylic acid. The major active metabolite of perindopril. It has a role as an EC 3.4.15.1 (peptidyl-dipeptidase A) inhibitor, an antihypertensive agent and a drug metabolite. It is an organic heterobicyclic compound, a dicarboxylic acid, a dipeptide and a L-alanine derivative.
Names & identifiers
- Preferred name
- Perindoprilat
- IUPAC
- (2S,3aS,7aS)-1-[(2S)-2-[[(1S)-1-carboxybutyl]amino]propanoyl]-2,3,3a,4,5,6,7,7a-octahydroindole-2-carboxylic acid
- English name
- Perindoprilat
- Molecular formula
- C17H28N2O5
- Molecular weight
- 340.41
Names & synonyms
Perindoprilat95153-31-4PerindoprilatePerindoprilatoPerindoprilatumS-97802UV6ZNQ92KS 9780DTXSID90869249CHEBI:132041(2S,3aS,7aS)-1-[(2S)-2-[[(2S)-1-hydroxy-1-oxopentan-2-yl]amino]propanoyl]-2,3,3a,4,5,6,7,7a-octahydroindole-2-carboxylic acidPerindopril diacid
Show more names
Perindopril EP IMpurity BPerindopril Impurity B(2S,3aS,7aS)-1-[(2S)-2-[[(1S)-1-carboxybutyl]amino]propanoyl]octahydro-1H-indole-2-carboxylicacid(perindoprilat)Diacid formPerindoprilat ,95%PERINDOPRILAT HYDRATE
(2S,3aS,7aS)-1-((2S)-2-(((2S)-1-hydroxy-1-oxopentan-2-yl)amino)propanoyl)-2,3,3a,4,5,6,7,7a-octahydroindole-2-carboxylic acidRefChem:57070DTXCID10820872(2S,3aS,7aS)-1-((2S)-2-(((1S)-1-carboxybutyl)amino)propanoyl)-octahydro-1H-indole-2-carboxylic acid(2S,3aS,7aS)-1-((S)-2-(((S)-1-carboxybutyl)amino)propanoyl)octahydro-1H-indole-2-carboxylic acidPerindopril diacid form(2S,3aS,7aS)-1-[(2S)-2-[[(1S)-1-carboxybutyl]amino]propanoyl]-2,3,3a,4,5,6,7,7a-octahydroindole-2-carboxylic acid(2S,3aS,7aS)-1-(((S)-1-carboxybutyl)-L-alanyl)octahydro-1H-indole-2-carboxylic acid
Properties
Computed structural properties
- XLogP
- 0.2
- Topological polar surface area
- 107 Ų
- Hydrogen bond donors
- 3
- Hydrogen bond acceptors
- 6
- Rotatable bonds
- 7
- Heavy atoms
- 24
- Formal charge
- 0
- Complexity
- 495
Experimental & physicochemical properties
DrugsPharmaceuticals -> Metabolite of Perindopril
Physicochemical properties
- Melting point
- 153 · 153-155°C
- Boiling point
- 568.1 · 568.1±45.0 °C(Predicted)
- Density
- 1.222 · 1.222±0.06 g/cm3(Predicted)
- storage temp.
- -20 °C · -20°C Freezer
- solubility
- DMSO (Slightly), Methanol (Slightly)
- form
- Solid
- pka
- 2.27 · 2.27±0.20(Predicted)
- color
- White to Pale Beige
- Stability
- Hygroscopic
- CAS DataBase Reference
- 95153 · 95153-31-4
- FDA UNII
- 2 UV6ZNQ92K · 2UV6ZNQ92K
- HS Code
- 2933999552 · 2933999552
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
GHS classification
GHS Classification
Warning
H361d (100%): Suspected of damaging the unborn child [Warning Reproductive toxicity]
P203, P280, P318, P405, and P501 (click each P-code to see the statement)
The GHS information provided by 1 company from 1 notification to the ECHA C&L Inventory.
Hazard information
Hazard Classes and CategoriesRepr. 2 (100%)
Safety data
- hs_code
- 2933999552
Chemistry & industry
Pharmacology
FDA Pharmacological Classification
2UV6ZNQ92K
PERINDOPRILAT
Established Pharmacologic Class [EPC] - Angiotensin Converting Enzyme Inhibitor
Mechanisms of Action [MoA] - Angiotensin-converting Enzyme Inhibitors
Perindoprilat is an Angiotensin Converting Enzyme Inhibitor. The mechanism of action of perindoprilat is as an Angiotensin-converting Enzyme Inhibitor.
MeSH Pharmacological Classification
A class of drugs whose main indications are the treatment of hypertension and heart failure. They exert their hemodynamic effect mainly by inhibiting the renin-angiotensin system. They also modulate sympathetic nervous system activity and increase prostaglandin synthesis. They cause mainly vasodilation and mild natriuresis without affecting heart rate and contractility.
Drugs used in the treatment of acute or chronic vascular HYPERTENSION regardless of pharmacological mechanism. Among the antihypertensive agents are DIURETICS; (especially DIURETICS, THIAZIDE); ADRENERGIC BETA-ANTAGONISTS; ADRENERGIC ALPHA-ANTAGONISTS; ANGIOTENSIN-CONVERTING ENZYME INHIBITORS; CALCIUM CHANNEL BLOCKERS; GANGLIONIC BLOCKERS; and VASODILATOR AGENTS.
Tissue LocationsKidney
Cellular LocationsCytoplasm
Metabolite PathwaysPerindopril Action Pathway
Applications
UsesAn angiotensin-converting enzyme (ACE) inhibitor. Antihypertensive.
UsesPerindoprilat is the active metabolite of perindopril, an inhibitor of angiotensin converting enzyme (ACE) that has efficacy against hypertension. Perindoprilat specifically and competitively inhibits ACE in vitro with IC50 values ranging between 1.5 and 3.2 nM. Elimination of perindoprilat is decreased in the elderly and in patients with heart or renal failure.[Cayman Chemical]
Related reactions
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Compound notes
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