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    Chemistry

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    Also known as: 66564-14-5, Paxapride, Cidine, Cinitapride [inn], Cinitapride hydrogen tartrate, 4-amino-n-[1-(cyclohex-3-en-1-ylmethyl)piperidin-4-yl]-2-ethoxy-5-nitrobenzamide
    Molecular Formula
    C21H30N4O4
    Molecular Weight
    402.5  g/mol
    InChI Key
    ZDLBNXXKDMLZMF-UHFFFAOYSA-N
    FDA UNII
    R8I97I2L24
    Cinitapride
    Cinitapride is a gastroprokinetic agent and antiulcer benzamide with agonist activity at 5-HT1 and 5-HT4 receptors and antagonist activity at 5-HT2 receptors. It is marketed in Spain and Mexico.
    1 2D Structure

    Cinitapride

    2 Identification
    2.1 Computed Descriptors
    2.1.1 IUPAC Name
    4-amino-N-[1-(cyclohex-3-en-1-ylmethyl)piperidin-4-yl]-2-ethoxy-5-nitrobenzamide
    2.1.2 InChI
    InChI=1S/C21H30N4O4/c1-2-29-20-13-18(22)19(25(27)28)12-17(20)21(26)23-16-8-10-24(11-9-16)14-15-6-4-3-5-7-15/h3-4,12-13,15-16H,2,5-11,14,22H2,1H3,(H,23,26)
    2.1.3 InChI Key
    ZDLBNXXKDMLZMF-UHFFFAOYSA-N
    2.1.4 Canonical SMILES
    CCOC1=CC(=C(C=C1C(=O)NC2CCN(CC2)CC3CCC=CC3)[N+](=O)[O-])N
    2.2 Other Identifiers
    2.2.1 UNII
    R8I97I2L24
    2.3 Synonyms
    2.3.1 MeSH Synonyms

    1. 4-amino-n-(1-(3-cyclohexen-1-ylmethyl)-4-piperidyl)-2-ethoxy-5-nitrobenzamide

    2. Blaston

    3. Cidine

    4. Cinitapride Tartrate

    2.3.2 Depositor-Supplied Synonyms

    1. 66564-14-5

    2. Paxapride

    3. Cidine

    4. Cinitapride [inn]

    5. Cinitapride Hydrogen Tartrate

    6. 4-amino-n-[1-(cyclohex-3-en-1-ylmethyl)piperidin-4-yl]-2-ethoxy-5-nitrobenzamide

    7. R8i97i2l24

    8. 66564-14-5 (free Base)

    9. Cinitapride (inn)

    10. 4-amino-n-(1-(3-cyclohexen-1-ylmethyl)-4-piperidyl)-2-ethoxy-5-nitrobenzamide

    11. Cinitaprida

    12. Cinitapridum

    13. Cinitapridum [inn-latin]

    14. Cinitaprida [inn-spanish]

    15. Cidin

    16. Unii-r8i97i2l24

    17. Paxapride (tn)

    18. Cinitapride [mi]

    19. 96623-56-2

    20. Cinitapride [mart.]

    21. (non-labelled)cinitapride-d5

    22. Cinitapride [who-dd]

    23. Schembl476454

    24. Chembl2104523

    25. Schembl19235643

    26. Dtxsid60867232

    27. Chebi:135642

    28. Bcp04096

    29. Hy-b2089

    30. Akos015909742

    31. Bcp9000531

    32. Db08810

    33. Bcp0726000107

    34. Cs-0017505

    35. Ft-0665049

    36. D07700

    37. Q5121012

    2.4 Create Date
    2005-08-08
    3 Chemical and Physical Properties
    Molecular Weight 402.5 g/mol
    Molecular Formula C21H30N4O4
    XLogP33.6
    Hydrogen Bond Donor Count2
    Hydrogen Bond Acceptor Count6
    Rotatable Bond Count6
    Exact Mass402.22670545 g/mol
    Monoisotopic Mass402.22670545 g/mol
    Topological Polar Surface Area113 Ų
    Heavy Atom Count29
    Formal Charge0
    Complexity586
    Isotope Atom Count0
    Defined Atom Stereocenter Count0
    Undefined Atom Stereocenter Count1
    Defined Bond Stereocenter Count0
    Undefined Bond Stereocenter Count0
    Covalently Bonded Unit Count1
    4 Drug and Medication Information
    4.1 Drug Indication

    It is indicated to treat gastrointestinal disorders associated with motility disturbances like gastroesophageal reflux disease (GERD), non-ulcer dyspepsia and delayed gastric emptying.

    5 Pharmacology and Biochemistry
    5.1 MeSH Pharmacological Classification

    Anti-Ulcer Agents

    Various agents with different action mechanisms used to treat or ameliorate PEPTIC ULCER or irritation of the gastrointestinal tract. This has included ANTIBIOTICS to treat HELICOBACTER INFECTIONS; HISTAMINE H2 ANTAGONISTS to reduce GASTRIC ACID secretion; and ANTACIDS for symptomatic relief. (See all compounds classified as Anti-Ulcer Agents.)

    5.2 ATC Code

    A - Alimentary tract and metabolism

    A03 - Drugs for functional gastrointestinal disorders

    A03F - Propulsives

    A03FA - Propulsives

    A03FA08 - Cinitapride

    5.3 Absorption, Distribution and Excretion

    Absorption

    The absorption of cinitapride (12mg) following oral administration was rapid, with peak levels being achieved 2 h after dosing; absorption following intramuscular administration (4mg) was even more rapid, with peak levels (50% more that oral levels) being achieved 1 h after dosing.

    5.4 Biological Half-Life

    3-5 h during the first 8 h and a residual half-life greater than 15 h thereafter.

    5.5 Mechanism of Action

    Cinitapride is a substituted benzamide with 5-HT receptor antagonist and agonist activity.

    API Reference Price

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    21-Jan-2021
    22-Aug-2024
    KGS
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