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Chemistry

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Also known as: Spirapril hcl, 94841-17-5, Spirapril hydrochloride [usan], Sch 33844, Occ25lm897, 83647-97-6 (free base)
Molecular Formula
C22H31ClN2O5S2
Molecular Weight
503.1  g/mol
InChI Key
CLDOLNORSLLQDI-OOAIBONUSA-N
FDA UNII
OCC25LM897

Spirapril
Spirapril Hydrochloride is the hydrochloride salt form of spirapril, 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. Spirapril also decreases angiotensin II-induced aldosterone secretion by the adrenal cortex, which leads to an increase in sodium excretion and subsequently increases water outflow.
1 2D Structure

Spirapril

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
(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;hydrochloride
2.1.2 InChI
InChI=1S/C22H30N2O5S2.ClH/c1-3-29-21(28)17(10-9-16-7-5-4-6-8-16)23-15(2)19(25)24-14-22(30-11-12-31-22)13-18(24)20(26)27;/h4-8,15,17-18,23H,3,9-14H2,1-2H3,(H,26,27);1H/t15-,17-,18-;/m0./s1
2.1.3 InChI Key
CLDOLNORSLLQDI-OOAIBONUSA-N
2.1.4 Canonical SMILES
CCOC(=O)C(CCC1=CC=CC=C1)NC(C)C(=O)N2CC3(CC2C(=O)O)SCCS3.Cl
2.1.5 Isomeric SMILES
CCOC(=O)[C@H](CCC1=CC=CC=C1)N[C@@H](C)C(=O)N2CC3(C[C@H]2C(=O)O)SCCS3.Cl
2.2 Other Identifiers
2.2.1 UNII
OCC25LM897
2.3 Synonyms
2.3.1 MeSH Synonyms

1. Quadropril

2. Renormax

3. Renpress

4. Sch 33844

5. Sch-33844

6. Spirapril

2.3.2 Depositor-Supplied Synonyms

1. Spirapril Hcl

2. 94841-17-5

3. Spirapril Hydrochloride [usan]

4. Sch 33844

5. Occ25lm897

6. 83647-97-6 (free Base)

7. (8s)-7((s)-n-((s)-1-carboxy-3-phenylpropyl)alanyl)-1,4-dithia-7-azaspiro(4.4)nonane-8-carboxylic Acid, 1-ethyl Ester, Monohydrochloride

8. Sch-33844

9. (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;hydrochloride

10. 1,4-dithia-7-azaspiro(4.4)nonane-8-carboxylic Acid, 7-(2-((1-(ethoxycarbonyl)-3-phenylpropyl)amino)-1-oxopropyl)-, Monohydrochloride, (8s-(7(r*(r*)),8r*))-

11. Spirapril Hydrochloride (usan)

12. (s)-7-(((s)-1-ethoxy-1-oxo-4-phenylbutan-2-yl)-l-alanyl)-1,4-dithia-7-azaspiro[4.4]nonane-8-carboxylic Acid Hydrochloride

13. Unii-occ25lm897

14. Renormax (tn)

15. Spiraprilhydrochloride

16. Ncgc00182545-01

17. Dsstox_cid_24272

18. Dsstox_rid_80139

19. Dsstox_gsid_44272

20. Schembl387353

21. Spirapril For System Suitability

22. Chembl1200831

23. Dtxsid6044272

24. Spirapril Hydrochloride [mi]

25. Tox21_112981

26. Akos025311425

27. Spirapril Hydrochloride [mart.]

28. Spirapril Hydrochloride [vandf]

29. Spirapril Hydrochloride [who-dd]

30. Cas-94841-17-5

31. Spirapril Hydrochloride [orange Book]

32. D03765

33. A854716

34. Q27285573

35. (8s)-7-[(2s)-2-[[(1s)-1-(ethoxycarbonyl)-3-phenylpropyl]amino]-1-oxopropyl]-1,4-dithia-7-azaspiro[4.4]nonane-8-carboxylic Acid Monohydrochloride

36. 1,4-dithia-7-azaspiro(4.4)nonane-8-carboxylic Acid, 7-((2s)-2-(((1s)-1-(ethoxycarbonyl)-3-phenylpropyl)amino)-1-oxopropyl)-, Hydrochloride (1:1), (8s)-

2.4 Create Date
2006-06-06
3 Chemical and Physical Properties
Molecular Weight 503.1 g/mol
Molecular Formula C22H31ClN2O5S2
Hydrogen Bond Donor Count3
Hydrogen Bond Acceptor Count8
Rotatable Bond Count10
Exact Mass502.1362921 g/mol
Monoisotopic Mass502.1362921 g/mol
Topological Polar Surface Area147 Ų
Heavy Atom Count32
Formal Charge0
Complexity650
Isotope Atom Count0
Defined Atom Stereocenter Count3
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently Bonded Unit Count2
4 Pharmacology and Biochemistry
4.1 MeSH Pharmacological Classification

Angiotensin-Converting Enzyme Inhibitors

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.)


Antihypertensive Agents

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.)


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