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    Zofenopril

    ACTIVE PHARMA INGREDIENTS

    FINISHED DOSAGE FORMULATIONS

    GLOBAL SALES INFORMATION

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    $ API Ref.Price (USD/KG) : 896Xls

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    2D Structure
    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