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    CAS 80830-42-8

    PharmaCompass
    Xls

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    2D Structure
    Also known as: Fentiapril, 80830-42-8, Rentiapril [inn], Sa 466, D0tam1017b, (2r,4r)-2-(2-hydroxyphenyl)-3-(3-sulfanylpropanoyl)-1,3-thiazolidine-4-carboxylic acid
    Molecular Formula
    C13H15NO4S2
    Molecular Weight
    313.4  g/mol
    InChI Key
    BSHDUMDXSRLRBI-JOYOIKCWSA-N
    FDA UNII
    D0TAM1017B
    Rentiapril is a potent angiotensin-converting enzyme (ACE) inhibitor with antihypertensive activity. Rentiapril 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. Rentiapril 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
    (2R,4R)-2-(2-hydroxyphenyl)-3-(3-sulfanylpropanoyl)-1,3-thiazolidine-4-carboxylic acid
    2.1.2 InChI
    InChI=1S/C13H15NO4S2/c15-10-4-2-1-3-8(10)12-14(11(16)5-6-19)9(7-20-12)13(17)18/h1-4,9,12,15,19H,5-7H2,(H,17,18)/t9-,12+/m0/s1
    2.1.3 InChI Key
    BSHDUMDXSRLRBI-JOYOIKCWSA-N
    2.1.4 Canonical SMILES
    C1C(N(C(S1)C2=CC=CC=C2O)C(=O)CCS)C(=O)O
    2.1.5 Isomeric SMILES
    C1[C@H](N([C@H](S1)C2=CC=CC=C2O)C(=O)CCS)C(=O)O
    2.2 Other Identifiers
    2.2.1 UNII
    D0TAM1017B
    2.3 Synonyms
    2.3.1 MeSH Synonyms

    1. 2-(2'-hydroxyphenyl)-3-(3-mercaptopropanoyl)-4-thiazolidine Carboxylic Acid

    2. Rentiapril, (2r-cis)-isomer

    3. Sa 446

    4. Sa-446

    2.3.2 Depositor-Supplied Synonyms

    1. Fentiapril

    2. 80830-42-8

    3. Rentiapril [inn]

    4. Sa 466

    5. D0tam1017b

    6. (2r,4r)-2-(2-hydroxyphenyl)-3-(3-sulfanylpropanoyl)-1,3-thiazolidine-4-carboxylic Acid

    7. Prescrin

    8. Sa 446

    9. 4-thiazolidinecarboxylicacid, 2-(2-hydroxyphenyl)-3-(3-mercapto-1-oxopropyl)-, (2r,4r)-

    10. Rentiaprilum [latin]

    11. Rentiaprilum

    12. Sa-446

    13. Ccris 2341

    14. Brn 5762860

    15. Unii-d0tam1017b

    16. Rentiapril [jan]

    17. (2r,4r)-2-(o-hydroxyphenyl)-3-(3-mercaptopropionyl)-4-thiazolidinecarboxylic Acid

    18. Schembl294980

    19. Chembl309962

    20. Dtxsid80230646

    21. Zinc3814177

    22. Bdbm50406931

    23. De-040

    24. 4-thiazolidinecarboxylic Acid, 2-(2-hydroxyphenyl)-3-(3-mercapto-1-oxopropyl)-, (2r-cis)-

    25. Hy-106446

    26. Cs-0025839

    27. Q7313544

    28. (2r,4r)-2-(2-hydroxyphenyl)-3-(3-mercaptopropanoyl)thiazolidine-4-carboxylic Acid

    29. (2r,4r)--2--(2--hydroxyphenyl) --3--(3--mercaptopropionyl)--4--thiazolidinecarboxylic Acid

    2.4 Create Date
    2005-08-08
    3 Chemical and Physical Properties
    Molecular Weight 313.4 g/mol
    Molecular Formula C13H15NO4S2
    XLogP31.3
    Hydrogen Bond Donor Count3
    Hydrogen Bond Acceptor Count6
    Rotatable Bond Count4
    Exact Mass313.04425031 g/mol
    Monoisotopic Mass313.04425031 g/mol
    Topological Polar Surface Area104 Ų
    Heavy Atom Count20
    Formal Charge0
    Complexity379
    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.)