Finished Dosage Form (FDF) export of Spirapril obtained from Indian Custom Trade Statistics

Spirapril

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FINISHED DOSAGE FORMULATIONS

4 FDF Dossiers, 4 FDA Orange Book

4 FDF Dossiers
4 FDA Orange Book

Synopsis

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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 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 Formula	C₂₂H₃₁ClN₂O₅S₂
Molecular Weight	503.1 g/mol
Hydrogen Bond Donor Count	3
Hydrogen Bond Acceptor Count	8
Rotatable Bond Count	10
Exact Mass	502.1362921 g/mol
Monoisotopic Mass	502.1362921 g/mol
Topological Polar Surface Area	147 Å²
Heavy Atom Count	32
Formal Charge	0
Complexity	650
Isotope Atom Count	0
Defined Atom Stereocenter Count	3
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	2

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.)

FDF Dossiers