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Zofenopril

Synopsis, Chemistry

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Also known as: 81872-10-8, Zofenoprilum, Zofenil, Chembl331378, Chebi:78539, 290zy759pi

Molecular Formula

C₂₂H₂₃NO₄S₂

Molecular Weight

429.6 g/mol

InChI Key

IAIDUHCBNLFXEF-MNEFBYGVSA-N

FDA UNII

290ZY759PI

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.

1 2D Structure

Zofenopril

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

(2S,4S)-1-[(2S)-3-benzoylsulfanyl-2-methylpropanoyl]-4-phenylsulfanylpyrrolidine-2-carboxylic acid

2.1.2 InChI

InChI=1S/C22H23NO4S2/c1-15(14-28-22(27)16-8-4-2-5-9-16)20(24)23-13-18(12-19(23)21(25)26)29-17-10-6-3-7-11-17/h2-11,15,18-19H,12-14H2,1H3,(H,25,26)/t15-,18+,19+/m1/s1

2.1.3 InChI Key

IAIDUHCBNLFXEF-MNEFBYGVSA-N

2.1.4 Canonical SMILES

CC(CSC(=O)C1=CC=CC=C1)C(=O)N2CC(CC2C(=O)O)SC3=CC=CC=C3

2.1.5 Isomeric SMILES

C[C@H](CSC(=O)C1=CC=CC=C1)C(=O)N2C[C@H](C[C@H]2C(=O)O)SC3=CC=CC=C3

2.2 Other Identifiers

2.2.1 UNII

290ZY759PI

2.3 Synonyms

2.3.1 MeSH Synonyms

1. Sq 26900

2. Sq 26991

3. Sq-26900

4. Sq-26991

5. Zofenil

6. Zofenopril, Calcium Salt, (1(r*),2alpha,4alpha)-isomer

7. Zofil

2.3.2 Depositor-Supplied Synonyms

1. 81872-10-8

2. Zofenoprilum

3. Zofenil

4. Chembl331378

5. Chebi:78539

6. 290zy759pi

7. Zofenopril (inn)

8. (2s,4s)-1-[(2s)-3-benzoylsulfanyl-2-methylpropanoyl]-4-phenylsulfanylpyrrolidine-2-carboxylic Acid

9. Zofenopril [inn]

10. Zofenoprilum [latin]

11. Zofenopril [inn:ban]

12. Unii-290zy759pi

13. Zofenopril-calcium

14. Ncgc00167455-01

15. Zofenil (tn)

16. Sq-26900

17. Zofenopril [mi]

18. Zofenopril [who-dd]

19. Schembl37298

20. 1-[3-(benzoylsulfanyl)-2-methylpropanoyl]-4-(phenylsulfanyl)proline

21. Gtpl6462

22. Dtxsid0046640

23. Zinc3775162

24. Bdbm50084629

25. Cs-7911

26. Db13166

27. (2s,4s)-1-[(2s)-3-benzoylsulfanyl-2-methyl-propanoyl]-4-phenylsulfanyl-pyrrolidine-2-carboxylic Acid

28. L-proline, 1-(3-(benzoylthio)-2-methyl-1-oxopropyl)-4-(phenylthio)-, (1(r*),2alpha,4alpha)-

29. So-26991

30. Hy-108321

31. D08688

32. 872z108

33. A840209

34. Ar-270/43507827

35. Q218284

36. (4s)-1-[(2s)-3-(benzoylsulfanyl)-2-methylpropanoyl]-4-(phenylsulfanyl)-l-proline

37. (2s,4s)-1-((s)-3-(benzoylthio)-2-methylpropanoyl)-4-(phenylthio)pyrrolidine-2-carboxylic Acid

38. (2s,4s)-1-[(2s)-3-(benzoylsulfanyl)-2-methylpropanoyl]-4-(phenylsulfanyl)pyrrolidine-2-carboxylic Acid

39. (2s,4s)-1-[(2s)-3-(benzoylsulfanyl)-2-methylpropanoyl]-4-phenylsulfanylpyrrolidine-2-carboxylic Acid

40. (4s)-n-((s)-3-mercapto-2-methylpropionyl)-4-(phenylthio)-r-proline Benzoate (ester)

41. 1-(3-benzoylsulfanyl-2-methyl-propionyl)-4-phenylsulfanyl-pyrrolidine-2-carboxylic Acid(zofenopril)

42. R-proline, 1-(3-(benzoylthio)-2-methyl-1-oxopropyl)-4-(phenylthio)-, (1(r*),2.alpha.,4.alpha.)-

2.4 Create Date

2005-08-08

3 Chemical and Physical Properties

Molecular Formula	C₂₂H₂₃NO₄S₂
Molecular Weight	429.6 g/mol
XLogP3	4.4
Hydrogen Bond Donor Count	1
Hydrogen Bond Acceptor Count	6
Rotatable Bond Count	8
Exact Mass	429.10685056 g/mol
Monoisotopic Mass	429.10685056 g/mol
Topological Polar Surface Area	125 Å²
Heavy Atom Count	29
Formal Charge	0
Complexity	587
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	1

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.)

4.2 ATC Code

C09BA15

S76 | LUXPHARMA | Pharmaceuticals Marketed in Luxembourg | Pharmaceuticals marketed in Luxembourg, as published by d'Gesondheetskeess (CNS, la caisse nationale de sante, www.cns.lu), mapped by name to structures using CompTox by R. Singh et al. (in prep.). List downloaded from https://cns.public.lu/en/legislations/textes-coordonnes/liste-med-comm.html. Dataset DOI:10.5281/zenodo.4587355

C - Cardiovascular system

C09 - Agents acting on the renin-angiotensin system

C09A - Ace inhibitors, plain

C09AA - Ace inhibitors, plain

C09AA15 - Zofenopril