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Spirapril

Spirapril structure

CAS No:
83647-97-6
Formula:
C22H30N2O5S2
Chemical Name:
Spirapril
Synonyms:
1,4-Dithia-7-azaspiro[4.4]nonane-8-carboxylic acid,7-[(2S)-2-[[(1S)-1-(ethoxycarbonyl)-3-phenylpropyl]amino]-1-oxopropyl]-,(8S)-;1,4-Dithia-7-azaspiro[4.4]nonane-8-carboxylic acid,7-[2-[[1-(ethoxycarbonyl)-3-phenylpropyl]amino]-1-oxopropyl]-,[8S-[7[R*(R*)],8R*]]-;(8S)-7-[(2S)-2-[[(1S)-1-(Ethoxycarbonyl)-3-phenylpropyl]amino]-1-oxopropyl]-1,4-dithia-7-azaspiro[4.4]nonane-8-carboxylic acid;Sch 33844;Spirapril
Categories:
Active Pharmaceutical Ingredients > Circulatory System Drugs

Description

Solid

Spirapril is a dipeptide, a dithioketal, an azaspiro compound, a dicarboxylic acid monoester, an ethyl ester, a tertiary carboxamide, a secondary amino compound and a pyrrolidinecarboxylic acid. It has a role as a prodrug, an EC 3.4.15.1 (peptidyl-dipeptidase A) inhibitor and an antihypertensive agent. It derives from a spiraprilat.|Spirapril is an ACE inhibitor antihypertensive drug used to treat hypertension. Spirapril is converted to the active spiraprilat after administration. ACE inhibitors are used primarily in treatment of hypertension and congestive heart failure.|Spirapril is a prodrug and non-sulfhydryl angiotensin converting enzyme (ACE) inhibitor with antihypertensive activity. Spirapril is converted in the body to its active metabolite spiraprilat. Spiraprilat 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. Spiraprilat also decreases angiotensin II-induced aldosterone secretion by the adrenal cortex, which leads to an increase in sodium excretion and subsequently increases water outflow.

Spirapril Basic Attributes

Molecular Weight：

466.61

Exact Mass：

466.61

UNII：

96U2K78I3V

DSSTox ID：

DTXSID1044300

NCI Thesaurus Code：

C66560

ATC Code：

C - Cardiovascular system

Characteristics

PSA：

147

XLogP3：

2.71960

Appearance：

Solid

Density：

1.32 g/cm3

Boiling Point：

697.8ºC at 760 mmHg

Flash Point：

375.8ºC

Refractive Index：

1.621

Water Solubility：

2.93e-02 g/L

Drug Information

Drug Indication：

Spirapril is an ACE inhibitor class drug used to treat hypertension.

Pharmacology：

Spirapril is an angiotensin-converting enzyme (ACE) inhibitor. ACE is a peptidyl dipeptidase that catalyzes the conversion of angiotensin I to the vasoconstrictor substance, angiotensin II. By blocking ACE, spirapril decreases angiotensin II which is a vasoconstrictor and inducer of aldosterone. So by inhibiting the enzymes, aldosterone secreation is decreased (so less sodium is reabsorbed) and there is a decrease in vasoconstriction. Combined, this leades to a decrease in blood pressure.

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.)

Absorption：

Bioavailability is 50% following oral administration.

Metabolism/Metabolites：

Hepatic. Converted to spiraprilat following oral administration.

Biological Half-Life：

30 to 35 hours

Mechanism of Action：

Spiraprilat, the active metabolite of spirapril, competes with angiotensin I for binding at the angiotensin-converting enzyme, blocking the conversion of angiotensin I to angiotensin II. Inhibition of ACE results in decreased plasma angiotensin II. As angiotensin II is a vasoconstrictor and a negative-feedback mediator for renin activity, lower concentrations result in a decrease in blood pressure and stimulation of baroreceptor reflex mechanisms, which leads to decreased vasopressor activity and to decreased aldosterone secretion. Spiraprilat may also act on kininase II, an enzyme identical to ACE that degrades the vasodilator bradykinin.

MeSH Entry Terms：

Quadropril

Spirapril Use and Manufacturing

Uses

Angiotensin converting enzyme inhibitor. Used to treat high blood pressure.

Use Classification：

Human Drugs -> FDA Approved Drug Products with Therapeutic Equivalence Evaluations (Orange Book) -> Active Ingredients

Computed Properties

Molecular Weight:466.6
XLogP3:0.9
Hydrogen Bond Donor Count:2
Hydrogen Bond Acceptor Count:8
Rotatable Bond Count:10
Exact Mass:466.15961441
Monoisotopic Mass:466.15961441
Topological Polar Surface Area:147
Heavy Atom Count:31
Complexity:650
Defined Atom Stereocenter Count:3
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes