 Home > Encyclopedia > Fosinoprilat

Fosinoprilat

Fosinoprilat structure

CAS No:
95399-71-6
Formula:
C23H34NO5P
Chemical Name:
Fosinoprilat
Synonyms:
L-Proline,4-cyclohexyl-1-[2-[hydroxy(4-phenylbutyl)phosphinyl]acetyl]-,(4S)-;L-Proline,4-cyclohexyl-1-[[hydroxy(4-phenylbutyl)phosphinyl]acetyl]-,trans-;L-Proline,4-cyclohexyl-1-[[hydroxy(4-phenylbutyl)phosphinyl]acetyl]-,(4S)-;(4S)-4-Cyclohexyl-1-[2-[hydroxy(4-phenylbutyl)phosphinyl]acetyl]-L-proline;Fosfenopril;SQ 27519;Fosinoprilic acid;Fosinoprilat
Categories:
Analytical Chemistry > Standard

Description

White Crystalline Solid

Fosinoprilat is a phosphinic acid-containing N-acyl derivative of (4S)-cyclohexyl-L-proline. An inhibitor of angiotensin converting enzyme (ACE), it is used as the phosphinate ester pro-drug fosinopril for treatment of hypertension and chronic heart failure. It has a role as an antihypertensive agent and an EC 3.4.15.1 (peptidyl-dipeptidase A) inhibitor. It is a member of phosphinic acids and a L-proline derivative.|Fosinoprilat is the active phosphinic acid metabolite of prodrug [fosinopril], which is activated by esterases in vivo. It binds zinc with phosphinic acid group.|Fosinoprilat is an Angiotensin Converting Enzyme Inhibitor. The mechanism of action of fosinoprilat is as an Angiotensin-converting Enzyme Inhibitor.|Fosinoprilat is a phosphinic acid-containing angiotensin-converting enzyme (ACE) inhibitor with antihypertensive activity. Fosinoprilat specifically and competitively inhibits angiotensin-converting enzyme thereby decreasing the formation of the potent vasoconstrictor angiotensin II, resulting in diminished vasopressor activity. In addition, angiotensin II-mediated aldosterone secretion by adrenal cortex is decreased, which results in a decrease of sodium retention and an increase in water outflow.

Fosinoprilat Basic Attributes

Molecular Weight：

435.49

Exact Mass：

435.49

UNII：

S312EY6ZT8

NCI Thesaurus Code：

C65762

HScode：

2933995300

Characteristics

PSA：

104.72000

XLogP3：

4.09960

Density：

1.238g/cm3

Melting Point：

149-153 °C

Boiling Point：

728.9ºC at 760mmHg

Flash Point：

394.6ºC

Refractive Index：

1.564

Storage Conditions：

-20°C Freezer

Specific rotation：

D -24° (c = 1 in methanol)

Safety Information

Transport codes：

NONH for all modes of transport

wgk germany：

Drug Information

MeSH：

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. (See all compounds classified as Antihypertensive Agents.)|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. (See all compounds classified as Angiotensin-Converting Enzyme Inhibitors.)|Agents used for the treatment or prevention of cardiac arrhythmias. They may affect the polarization-repolarization phase of the action potential, its excitability or refractoriness, or impulse conduction or membrane responsiveness within cardiac fibers. Anti-arrhythmia agents are often classed into four main groups according to their mechanism of action: sodium channel blockade, beta-adrenergic blockade, repolarization prolongation, or calcium channel blockade. (See all compounds classified as Anti-Arrhythmia Agents.)

MeSH Entry Terms：

fosfenopril

Fosinoprilat Use and Manufacturing

A metabolite of Fosinopril, a phosphinic acid containing angiotensin converting enzyme (ACE) inhibitor

Computed Properties

Molecular Weight:435.5
XLogP3:3.8
Hydrogen Bond Donor Count:2
Hydrogen Bond Acceptor Count:5
Rotatable Bond Count:9
Exact Mass:435.21746018
Monoisotopic Mass:435.21746018
Topological Polar Surface Area:94.9
Heavy Atom Count:30
Complexity:627
Defined Atom Stereocenter Count:2
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes