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Zofenopril

Zofenopril structure

CAS No:
81872-10-8
Formula:
C22H23NO4S2
Chemical Name:
Zofenopril
Synonyms:
L-Proline,1-[(2S)-3-(benzoylthio)-2-methyl-1-oxopropyl]-4-(phenylthio)-,(4S)-;L-Proline,1-[3-(benzoylthio)-2-methyl-1-oxopropyl]-4-(phenylthio)-,[1(R*),2α,4α]-;(4S)-1-[(2S)-3-(Benzoylthio)-2-methyl-1-oxopropyl]-4-(phenylthio)-L-proline;Zofenopril
Categories:
Active Pharmaceutical Ingredients > Circulatory System Drugs

Description

Zofenopril is an angiotensin-converting enzyme (ACE) inhibitor with an IC50 of 81 μM.

Zofenopril is a proline derivative that is 4-(phenylsulfanyl)-L-proline in which the amine proton is replaced by a (2S)-3-(benzoylsulfanyl)-2-methylpropanoyl group. A prodrug for zofenoprilat. It has a role as an EC 3.4.15.1 (peptidyl-dipeptidase A) inhibitor, an apoptosis inhibitor, a cardioprotective agent, an anticonvulsant, a prodrug and a vasodilator agent. It is a thioester, a N-acyl-L-amino acid, an aryl sulfide and a L-proline derivative. It is a conjugate acid of a zofenopril(1-).|Zofenopril is employed as both a cardioprotective and anti-hypertensive agent. It is an angiotensin-converting enzyme (ACE) inhibitor.|Zofenopril is a sulfhydryl angiotensin-converting enzyme (ACE) inhibitor with antihypertensive activity. As a prodrug, zofenopril is hydrolyzed in vivo into its active form zofenoprilat. Zofenoprilat competitively binds to and inhibits ACE, thereby blocking the conversion of angiotensin I to angiotensin II. This prevents the potent vasoconstrictive actions of angiotensin II and results in vasodilation. Zofenoprilat also decreases angiotensin II-induced aldosterone secretion by the adrenal cortex, which leads to an increase in sodium excretion and subsequently increases water outflow.

Zofenopril Basic Attributes

Molecular Weight：

429.56

Exact Mass：

429.55

EC Number：

201-705-8

UNII：

290ZY759PI

DSSTox ID：

DTXSID0046640

NCI Thesaurus Code：

C82219

ATC Code：

C09BA15|C - Cardiovascular system

Characteristics

PSA：

125.28000

XLogP3：

3.78

Appearance：

light yellow crystalline

Density：

1.3±0.1 g/cm3

Melting Point：

42-47 °C

Boiling Point：

646.3±55.0 °C at 760 mmHg

Flash Point：

344.7±31.5 °C

Refractive Index：

1.659

Storage Conditions：

2-8°C

Specific rotation：

D25 -36.5° (c = 1 in methanol)

Safety Information

Hazard category：

IRRITANT

wgk germany：

hazard class code：

22-37/38-41

safety instructions：

23-24/25

RTECS Number：

QJ0875000

Marks：

Xn,Xi

Drug Information

Drug Indication：

Treatment of hypertension

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.)

MeSH Entry Terms：

SQ 26900

Zofenopril Use and Manufacturing

Uses

Labeled Zofenopril, intended for use as an internal standard for the quantification of Zofenopril by GC- or LC-mass spectrometry.

Use Classification：

Human Drugs -> EU pediatric investigation plans

Computed Properties

Molecular Weight:429.6
XLogP3:4.4
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:6
Rotatable Bond Count:8
Exact Mass:429.10685056
Monoisotopic Mass:429.10685056
Topological Polar Surface Area:125
Heavy Atom Count:29
Complexity:587
Defined Atom Stereocenter Count:3
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes