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Technical details about Zofenopril, learn more about the structure, uses, toxicity, action, side effects and more

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2D Structure
1. 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

2D Structure

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 Weight 429.6 g/mol
Molecular Formula C22H23NO4S2
XLogP34.4
Hydrogen Bond Donor Count1
Hydrogen Bond Acceptor Count6
Rotatable Bond Count8
Exact Mass429.10685056 g/mol
Monoisotopic Mass429.10685056 g/mol
Topological Polar Surface Area125 Ų
Heavy Atom Count29
Formal Charge0
Complexity587
Isotope Atom Count0
Defined Atom Stereocenter Count3
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently Bonded Unit Count1
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


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