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Alacepril

Alacepril

Synopsis, Chemistry

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Also known as: 74258-86-9, Cetapril, Du-1219, X39tl7jdpf, 1-(d-3-acetylthio-2-methylpropanoyl)-l-prolyl-l-phenylalanine, N-(1-((s)-3-mercapto-2-methylpropionyl)-l-prolyl)-3-phenyl-l-alanine acetate (ester)

Molecular Formula

C₂₀H₂₆N₂O₅S

Molecular Weight

406.5 g/mol

InChI Key

FHHHOYXPRDYHEZ-COXVUDFISA-N

FDA UNII

X39TL7JDPF

Alacepril is a long-acting, sulfhydryl-containing angiotensin-converting enzyme (ACE) inhibitor with antihypertensive activity. As a prodrug, alacepril is rapidly metabolized to captopril; captopril 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. Captopril 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

Alacepril

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

(2S)-2-[[(2S)-1-[(2S)-3-acetylsulfanyl-2-methylpropanoyl]pyrrolidine-2-carbonyl]amino]-3-phenylpropanoic acid

2.1.2 InChI

InChI=1S/C20H26N2O5S/c1-13(12-28-14(2)23)19(25)22-10-6-9-17(22)18(24)21-16(20(26)27)11-15-7-4-3-5-8-15/h3-5,7-8,13,16-17H,6,9-12H2,1-2H3,(H,21,24)(H,26,27)/t13-,16+,17+/m1/s1

2.1.3 InChI Key

FHHHOYXPRDYHEZ-COXVUDFISA-N

2.1.4 Canonical SMILES

CC(CSC(=O)C)C(=O)N1CCCC1C(=O)NC(CC2=CC=CC=C2)C(=O)O

2.1.5 Isomeric SMILES

C[C@H](CSC(=O)C)C(=O)N1CCC[C@H]1C(=O)N[C@@H](CC2=CC=CC=C2)C(=O)O

2.2 Other Identifiers

2.2.1 UNII

X39TL7JDPF

2.3 Synonyms

2.3.1 MeSH Synonyms

1. Aracepril

2. Du 1219

3. Du-1219

4. N-(1-(3-(acetylthio)-2-methyl-1-oxopropyl)-l-prolyl)-l-phenylalanine

2.3.2 Depositor-Supplied Synonyms

1. 74258-86-9

2. Cetapril

3. Du-1219

4. X39tl7jdpf

5. 1-(d-3-acetylthio-2-methylpropanoyl)-l-prolyl-l-phenylalanine

6. N-(1-((s)-3-mercapto-2-methylpropionyl)-l-prolyl)-3-phenyl-l-alanine Acetate (ester)

7. Nsc-338157

8. Ncgc00182037-01

9. Alaceprilum [latin]

10. Alaceprilum

11. Alacepril [inn:jan]

12. 1-[(2s)-3-(acetylthio)-2-methyl-1-oxopropyl]-l-prolyl-l-phenylalanine

13. Cetapril (tn)

14. (s)-2-((s)-1-((s)-3-(acetylthio)-2-methylpropanoyl)pyrrolidine-2-carboxamido)-3-phenylpropanoic Acid

15. Unii-x39tl7jdpf

16. Nsc 338157

17. Du 1219

18. Brn 3634372

19. 1-((2s)-3-(acetylthio)-2-methyl-1-oxopropyl)-l-prolyl-l-phenylalanine

20. Alacepril [inn]

21. Alacepril [jan]

22. Alacepril [mi]

23. N-(2-((s)-3-acetylthio-2-methylpropionyl)propyl)-3-phenylalanin

24. Alacepril (jp17/inn)

25. Alacepril [mart.]

26. Alacepril [who-dd]

27. Dsstox_cid_28502

28. Dsstox_rid_82774

29. Dsstox_gsid_48576

30. Schembl34559

31. Chembl2103775

32. Dtxsid3048576

33. Chebi:31182

34. Zinc3775143

35. Tox21_112904

36. Akos015916655

37. Ks-1321

38. L-phenylalanine, N-(1-(3-(acetylthio)-2-methyl-1-oxopropyl)-l-prolyl)-, (s)-

39. (2s)-2-[[(2s)-1-[(2s)-3-acetylsulfanyl-2-methylpropanoyl]pyrrolidine-2-carbonyl]amino]-3-phenylpropanoic Acid

40. Cas-74258-86-9

41. Hy-107318

42. Cs-0028129

43. D01900

44. 258a869

45. Q3290792

46. 219554-02-6

2.4 Create Date

2005-06-24

3 Chemical and Physical Properties

Molecular Formula	C₂₀H₂₆N₂O₅S
Molecular Weight	406.5 g/mol
XLogP3	2.1
Hydrogen Bond Donor Count	2
Hydrogen Bond Acceptor Count	6
Rotatable Bond Count	9
Exact Mass	406.15624311 g/mol
Monoisotopic Mass	406.15624311 g/mol
Topological Polar Surface Area	129 Å²
Heavy Atom Count	28
Formal Charge	0
Complexity	591
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

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.)

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.)