Spirapril
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Grundinformationen
- CAS
83647-97-6- Standard-SMILES
CCOC(=O)[C@H](CCc1ccccc1)N[C@@H](C)C(=O)N1CC2(C[C@H]1C(=O)O)SCCS2- InChIKey
HRWCVUIFMSZDJS-SZMVWBNQSA-N- Summenformel
- C22H30N2O5S2
- Durchschnittliche Molmasse
- 466,6 g/mol
- Monoisotopische Masse
- 466,15961406
Überblick
Spirapril is an azaspiro compound resulting from the formal condensation of the amino group of (8S)-1,4-dithia-7-azaspiro[4.4]nonane-8-carboxylic acid with the carboxy group of N-[(2S)-1-ethoxy-1-oxo-4-phenylbutan-2-yl]-L-alanine. It is a prodrug for the antihypertensive drug spiraprilat. It has a role as an EC 3.4.15.1 (peptidyl-dipeptidase A) inhibitor, an antihypertensive agent and a prodrug. It is a tertiary carboxamide, an ethyl ester, an azaspiro compound, a dicarboxylic acid monoester, a dipeptide, a pyrrolidinecarboxylic acid, a secondary amino compound and a dithioketal. It is functionally related to a spiraprilat.
Namen und Bezeichner
- Bevorzugter Name
- Spirapril
- IUPAC
- (8S)-7-[(2S)-2-[[(2S)-1-ethoxy-1-oxo-4-phenylbutan-2-yl]amino]propanoyl]-1,4-dithia-7-azaspiro[4.4]nonane-8-carboxylic acid
- Englischer Name
- Spirapril
- Summenformel
- C22H30N2O5S2
- Molmasse
- 466.61
Namen und Synonyme
Spirapril83647-97-6EspiraprilSpiraprilum96U2K78I3VDTXSID1044300(8S)-7-[(2S)-2-{[(2S)-1-ethoxy-1-oxo-4-phenylbutan-2-yl]amino}propanoyl]-1,4-dithia-7-azaspiro[4.4]nonane-8-carboxylic acid(8S)-7-[(2S)-2-[[(2S)-1-ethoxy-1-oxo-4-phenylbutan-2-yl]amino]propanoyl]-1,4-dithia-7-azaspiro[4.4]nonane-8-carboxylic acid(7S)-8-((2S)-2-(((2S)-1-ethoxy-1-oxo-4-phenylbutan-2-yl)amino)propanoyl)-1,4-dithia-8-azaspiro(4.4)nonane-7-carboxylic acid(7S)-8-[(2S)-2-[[(2S)-1-ethoxy-1-oxo-4-phenylbutan-2-yl]amino]propanoyl]-1,4-dithia-8-azaspiro[4.4]nonane-7-carboxylic acid(8S)-7-((2S)-2-(((2S)-1-ethoxy-1-oxo-4-phenylbutan-2-yl)amino)propanoyl)-1,4-dithia-7-azaspiro(4.4)nonane-8-carboxylic acidRefChem:184748
Weitere Namen anzeigen
SandopfilSch-33844Brn 4277924Spiraprilic acidSpirapril [inn:ban]Spirapril USP/EP/BP
DTXCID9024300C09AA111,4-Dithia-7-azaspiro(4.4)nonane-8-carboxylic acid, 7-(2-((1-(ethoxycarbonyl)-3-phenylpropyl)amino)-1-oxopropyl)-, (8S-(7(R*(R*)),8R*))-Spirapril (INN)CHEMBL431Spiraprilum [Latin]SetrilanEspirapril [Spanish]
Eigenschaften
Berechnete StruktureigenschaftenWird ergänzt
- XLogP
- 0,9
- Polarare Oberfläche (TPSA)
- 147 Ų
- H-Brücken-Donoren
- 2
- H-Brücken-Akzeptoren
- 8
- Frei drehbare Bindungen
- 10
- Schwere Atome
- 31
- Formalladung
- 0
- Komplexität
- 650
Experimentelle und physikochemische Eigenschaften
DrugsPharmaceuticals -> Listed in ZINC15
Solubility2.93e-02 g/L
Physical DescriptionSolid
Physikochemische Eigenschaften
- Siedepunkt
- 697.8 · 697.8±55.0 °C(Predicted)
- Dichte
- 1.32 · 1.32±0.1 g/cm3(Predicted)
- storage temp.
- 2 · 2-8°C
- pka
- 2.99 · 2.99±0.20(Predicted)
Chemie und Industrie
Pharmakologische Informationen
ATC Code
C - Cardiovascular system
QC - Cardiovascular system
Pharmacodynamics
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.
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.
Biological Half-Life30 to 35 hours
Metabolism/MetabolitesHepatic. Converted to spiraprilat following oral administration.
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.
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