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

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    Spirapril

    DOSSIERs // Finished Dosage Forms

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    2D Structure
    1. Also known as: Spirapril hcl, 94841-17-5, Spirapril hydrochloride [usan], Sch 33844, Occ25lm897, 83647-97-6 (free base)
    Molecular Formula
    C22H31ClN2O5S2
    Molecular Weight
    503.1  g/mol
    InChI Key
    CLDOLNORSLLQDI-OOAIBONUSA-N
    FDA UNII
    OCC25LM897
    Spirapril Hydrochloride is the hydrochloride salt form of spirapril, a prodrug and non-sulfhydryl angiotensin converting enzyme (ACE) inhibitor with antihypertensive activity. Spirapril is converted in the body to its active metabolite spiraprilat. Spiraprilat 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. Spirapril 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
    (8S)-7-[(2S)-2-[[(2S)-1-ethoxy-1-oxo-4-phenylbutan-2-yl]amino]propanoyl]-1,4-dithia-7-azaspiro[4.4]nonane-8-carboxylic acid;hydrochloride
    2.1.2 InChI
    InChI=1S/C22H30N2O5S2.ClH/c1-3-29-21(28)17(10-9-16-7-5-4-6-8-16)23-15(2)19(25)24-14-22(30-11-12-31-22)13-18(24)20(26)27;/h4-8,15,17-18,23H,3,9-14H2,1-2H3,(H,26,27);1H/t15-,17-,18-;/m0./s1
    2.1.3 InChI Key
    CLDOLNORSLLQDI-OOAIBONUSA-N
    2.1.4 Canonical SMILES
    CCOC(=O)C(CCC1=CC=CC=C1)NC(C)C(=O)N2CC3(CC2C(=O)O)SCCS3.Cl
    2.1.5 Isomeric SMILES
    CCOC(=O)[C@H](CCC1=CC=CC=C1)N[C@@H](C)C(=O)N2CC3(C[C@H]2C(=O)O)SCCS3.Cl
    2.2 Other Identifiers
    2.2.1 UNII
    OCC25LM897
    2.3 Synonyms
    2.3.1 MeSH Synonyms

    1. Quadropril

    2. Renormax

    3. Renpress

    4. Sch 33844

    5. Sch-33844

    6. Spirapril

    2.3.2 Depositor-Supplied Synonyms

    1. Spirapril Hcl

    2. 94841-17-5

    3. Spirapril Hydrochloride [usan]

    4. Sch 33844

    5. Occ25lm897

    6. 83647-97-6 (free Base)

    7. (8s)-7((s)-n-((s)-1-carboxy-3-phenylpropyl)alanyl)-1,4-dithia-7-azaspiro(4.4)nonane-8-carboxylic Acid, 1-ethyl Ester, Monohydrochloride

    8. Sch-33844

    9. (8s)-7-[(2s)-2-[[(2s)-1-ethoxy-1-oxo-4-phenylbutan-2-yl]amino]propanoyl]-1,4-dithia-7-azaspiro[4.4]nonane-8-carboxylic Acid;hydrochloride

    10. 1,4-dithia-7-azaspiro(4.4)nonane-8-carboxylic Acid, 7-(2-((1-(ethoxycarbonyl)-3-phenylpropyl)amino)-1-oxopropyl)-, Monohydrochloride, (8s-(7(r*(r*)),8r*))-

    11. Spirapril Hydrochloride (usan)

    12. (s)-7-(((s)-1-ethoxy-1-oxo-4-phenylbutan-2-yl)-l-alanyl)-1,4-dithia-7-azaspiro[4.4]nonane-8-carboxylic Acid Hydrochloride

    13. Unii-occ25lm897

    14. Renormax (tn)

    15. Spiraprilhydrochloride

    16. Ncgc00182545-01

    17. Dsstox_cid_24272

    18. Dsstox_rid_80139

    19. Dsstox_gsid_44272

    20. Schembl387353

    21. Spirapril For System Suitability

    22. Chembl1200831

    23. Dtxsid6044272

    24. Spirapril Hydrochloride [mi]

    25. Tox21_112981

    26. Akos025311425

    27. Spirapril Hydrochloride [mart.]

    28. Spirapril Hydrochloride [vandf]

    29. Spirapril Hydrochloride [who-dd]

    30. Cas-94841-17-5

    31. Spirapril Hydrochloride [orange Book]

    32. D03765

    33. A854716

    34. Q27285573

    35. (8s)-7-[(2s)-2-[[(1s)-1-(ethoxycarbonyl)-3-phenylpropyl]amino]-1-oxopropyl]-1,4-dithia-7-azaspiro[4.4]nonane-8-carboxylic Acid Monohydrochloride

    36. 1,4-dithia-7-azaspiro(4.4)nonane-8-carboxylic Acid, 7-((2s)-2-(((1s)-1-(ethoxycarbonyl)-3-phenylpropyl)amino)-1-oxopropyl)-, Hydrochloride (1:1), (8s)-

    2.4 Create Date
    2006-06-06
    3 Chemical and Physical Properties
    Molecular Weight 503.1 g/mol
    Molecular Formula C22H31ClN2O5S2
    Hydrogen Bond Donor Count3
    Hydrogen Bond Acceptor Count8
    Rotatable Bond Count10
    Exact Mass502.1362921 g/mol
    Monoisotopic Mass502.1362921 g/mol
    Topological Polar Surface Area147 Ų
    Heavy Atom Count32
    Formal Charge0
    Complexity650
    Isotope Atom Count0
    Defined Atom Stereocenter Count3
    Undefined Atom Stereocenter Count0
    Defined Bond Stereocenter Count0
    Undefined Bond Stereocenter Count0
    Covalently Bonded Unit Count2
    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.)

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