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Fosinoprilat

Fosinoprilat

Synopsis, Chemistry

REF. STANDARDS & IMPURITIES

1 BioAnalytical Methods

1 BioAnalytical Methods

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Also known as: Fosinopril diacid, 95399-71-6, Fosinoprilic acid, Fosfenopril, Fosinoprilatum, Sq 27,519

Molecular Formula

C₂₃H₃₄NO₅P

Molecular Weight

435.5 g/mol

InChI Key

WOIWWYDXDVSWAZ-RTWAWAEBSA-N

FDA UNII

S312EY6ZT8

Fosinoprilat is a phosphinic acid-containing angiotensin-converting enzyme (ACE) inhibitor with antihypertensive activity. Fosinoprilat specifically and competitively inhibits angiotensin-converting enzyme thereby decreasing the formation of the potent vasoconstrictor angiotensin II, resulting in diminished vasopressor activity. In addition, angiotensin II-mediated aldosterone secretion by adrenal cortex is decreased, which results in a decrease of sodium retention and an increase in water outflow.

Fosinoprilat is an Angiotensin Converting Enzyme Inhibitor. The mechanism of action of fosinoprilat is as an Angiotensin-converting Enzyme Inhibitor.

1 2D Structure

Fosinoprilat

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

(2S,4S)-4-cyclohexyl-1-[2-[hydroxy(4-phenylbutyl)phosphoryl]acetyl]pyrrolidine-2-carboxylic acid

2.1.2 InChI

InChI=1S/C23H34NO5P/c25-22(17-30(28,29)14-8-7-11-18-9-3-1-4-10-18)24-16-20(15-21(24)23(26)27)19-12-5-2-6-13-19/h1,3-4,9-10,19-21H,2,5-8,11-17H2,(H,26,27)(H,28,29)/t20-,21+/m1/s1

2.1.3 InChI Key

WOIWWYDXDVSWAZ-RTWAWAEBSA-N

2.1.4 Canonical SMILES

C1CCC(CC1)C2CC(N(C2)C(=O)CP(=O)(CCCCC3=CC=CC=C3)O)C(=O)O

2.1.5 Isomeric SMILES

C1CCC(CC1)[C@@H]2C[C@H](N(C2)C(=O)CP(=O)(CCCCC3=CC=CC=C3)O)C(=O)O

2.2 Other Identifiers

2.2.1 UNII

S312EY6ZT8

2.3 Synonyms

2.3.1 MeSH Synonyms

1. Fosfenopril

2. Fosinoprilic Acid

3. Sq 27519

4. Sq-27,519

5. Sq-27519

2.3.2 Depositor-Supplied Synonyms

1. Fosinopril Diacid

2. 95399-71-6

3. Fosinoprilic Acid

4. Fosfenopril

5. Fosinoprilatum

6. Sq 27,519

7. Sq-27519

8. (4s)-4-cyclohexyl-1-((hydroxy(4-phenylbutyl)phosphinyl)acetyl)-l-proline

9. Chembl581

10. Fosinopril Related Compound A

11. S312ey6zt8

12. Chebi:116962

13. So-27519

14. L-proline, 4-cyclohexyl-1-((hydroxy(4-phenylbutyl)phosphinyl)acetyl)-, Trans-

15. 4-cyclohexyl-1-{2-[hydroxy-(4-phenyl-butyl)-phosphinoyl]-acetyl}-pyrrolidine-2-carboxylic Acid

16. (2s,4s)-4-cyclohexyl-1-(2-(hydroxy(4-phenylbutyl)phosphoryl)acetyl)pyrrolidine-2-carboxylic Acid

17. (2s,4s)-4-cyclohexyl-1-[2-[hydroxy(4-phenylbutyl)phosphoryl]acetyl]pyrrolidine-2-carboxylic Acid

18. (4s)-4-cyclohexyl-[(4-phenylbutyl)phosphinyl]acetyl-l-proline

19. (4s)-4-cyclohexyl-1-{[hydroxy(4-phenylbutyl)phosphoryl]acetyl}-l-proline

20. L-proline, 4-cyclohexyl-1-[[hydroxy(4-phenylbutyl)phosphinyl]acetyl]-,(4s)-

21. Fosinoprilat [usan:inn]

22. Fosinoprilatum [inn-latin]

23. (2s,4s)-4-cyclohexyl-1-{2-[hydroxy(4-phenylbutyl)phosphoryl]acetyl}pyrrolidine-2-carboxylic Acid

24. (2s,4s)-4-cyclohexyl-1-{2-[hydroxy-(4-phenyl-butyl)-phosphinoyl]-acetyl}-pyrrolidine-2-carboxylic Acid

25. Unii-s312ey6zt8

26. Forsinoprilat

27. Ks8

28. Fosinopril Impurity A

29. Sq-27,519

30. Pu6ba2d2md

31. Fosinoprilat (usan/inn)

32. Fosinoprilat [inn]

33. Fosinoprilat [usan]

34. Schembl124537

35. Fosinopril Diacid [mi]

36. Gtpl6457

37. Dtxsid80869253

38. Zinc4213382

39. Bdbm50018849

40. Db14207

41. Sq27,519

42. Hy-107352

43. So 27,519

44. Cs-0028200

45. C21542

46. D03772

47. Fosinopril Related Compound A [usp-rs]

48. Fosinopril Sodium Impurity A [ep Impurity]

49. Fosinopril Related Compound A [usp Impurity]

50. Q27077720

51. 1[{hydroxy(4-phenylbutyl)phosphinyl}acetyl]-(trans)-4-cyclohexyl-l-proline

52. Trans-4-cyclohexyl-1-[[hydroxy(4-phenylbutyl)phosphinyl]acetyl]-l-proline

53. L-proline,4-cyclohexyl-1-[2-[hydroxy(4-phenylbutyl)phosphinyl]acetyl]-,(4s)-

54. (2s,4s)-4-cyclohexyl-1-((hydroxy(4-phenylbutyl)phosphoryl)acetyl)pyrrolidine-2-carboxylic Acid

55. (2s,4s)-4-cyclohexyl-1-[2-(hydroxy-(4-phenylbutyl)phosphoryl)acetyl]pyrrolidine-2-carboxylic Acid

2.4 Create Date

2005-08-08

3 Chemical and Physical Properties

Molecular Formula	C₂₃H₃₄NO₅P
Molecular Weight	435.5 g/mol
XLogP3	3.8
Hydrogen Bond Donor Count	2
Hydrogen Bond Acceptor Count	5
Rotatable Bond Count	9
Exact Mass	435.21746018 g/mol
Monoisotopic Mass	435.21746018 g/mol
Topological Polar Surface Area	94.9 Å²
Heavy Atom Count	30
Formal Charge	0
Complexity	627
Isotope Atom Count	0
Defined Atom Stereocenter Count	2
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.)

Anti-Arrhythmia Agents

Agents used for the treatment or prevention of cardiac arrhythmias. They may affect the polarization-repolarization phase of the action potential, its excitability or refractoriness, or impulse conduction or membrane responsiveness within cardiac fibers. Anti-arrhythmia agents are often classed into four main groups according to their mechanism of action: sodium channel blockade, beta-adrenergic blockade, repolarization prolongation, or calcium channel blockade. (See all compounds classified as Anti-Arrhythmia Agents.)

4.2 FDA Pharmacological Classification

4.2.1 Active Moiety

FOSINOPRILAT

4.2.2 FDA UNII

S312EY6ZT8

4.2.3 Pharmacological Classes

Mechanisms of Action [MoA] - Angiotensin-converting Enzyme Inhibitors