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    Fosinoprilat

    ANALYTICAL

    PharmaCompass
    Xls

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    2D Structure
    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

    2D Structure

    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 Weight 435.5 g/mol
    Molecular Formula C23H34NO5P
    XLogP33.8
    Hydrogen Bond Donor Count2
    Hydrogen Bond Acceptor Count5
    Rotatable Bond Count9
    Exact Mass435.21746018 g/mol
    Monoisotopic Mass435.21746018 g/mol
    Topological Polar Surface Area94.9 Ų
    Heavy Atom Count30
    Formal Charge0
    Complexity627
    Isotope Atom Count0
    Defined Atom Stereocenter Count2
    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.)

    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