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    Levocabastine

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    2D Structure
    Also known as: Levocabastine hcl, Livostin, 79547-78-7, Livostin (tn), R 50,547, 124xma6yei
    Molecular Formula
    C26H30ClFN2O2
    Molecular Weight
    457.0  g/mol
    InChI Key
    OICFWWJHIMKBCD-SFUPJVRMSA-N
    FDA UNII
    124XMA6YEI
    Levocabastine Hydrochloride is the hydrochloride salt form of levocabastine, a synthetic piperidine derivative with antihistaminic properties. Levocabastine is a second generation histamine-1 receptor antagonist. When applied locally to the eye as a topical solution, this agent reduces itching, rhinorrhea, and symptoms of allergic rhinitis or conjunctivitis.
    1 2D Structure

    2D Structure

    2 Identification
    2.1 Computed Descriptors
    2.1.1 IUPAC Name
    (3S,4R)-1-[4-cyano-4-(4-fluorophenyl)cyclohexyl]-3-methyl-4-phenylpiperidine-4-carboxylic acid;hydrochloride
    2.1.2 InChI
    InChI=1S/C26H29FN2O2.ClH/c1-19-17-29(16-15-26(19,24(30)31)21-5-3-2-4-6-21)23-11-13-25(18-28,14-12-23)20-7-9-22(27)10-8-20;/h2-10,19,23H,11-17H2,1H3,(H,30,31);1H/t19-,23?,25?,26-;/m1./s1
    2.1.3 InChI Key
    OICFWWJHIMKBCD-SFUPJVRMSA-N
    2.1.4 Canonical SMILES
    CC1CN(CCC1(C2=CC=CC=C2)C(=O)O)C3CCC(CC3)(C#N)C4=CC=C(C=C4)F.Cl
    2.1.5 Isomeric SMILES
    C[C@@H]1CN(CC[C@@]1(C2=CC=CC=C2)C(=O)O)C3CCC(CC3)(C#N)C4=CC=C(C=C4)F.Cl
    2.2 Other Identifiers
    2.2.1 UNII
    124XMA6YEI
    2.3 Synonyms
    2.3.1 MeSH Synonyms

    1. 1-(4-cyano-4-(4-fluorophenyl)cyclohexyl)-3-methyl-4-phenyl-4-piperidinecarboxylic Acid

    2. Bilina

    3. Lvophta

    4. Levocabastine

    5. Levophta

    6. Livocab

    7. Livostin

    2.3.2 Depositor-Supplied Synonyms

    1. Levocabastine Hcl

    2. Livostin

    3. 79547-78-7

    4. Livostin (tn)

    5. R 50,547

    6. 124xma6yei

    7. Levocabastine (hydrochloride)

    8. Levophta

    9. (-)-trans-1-(cis-4-cyano-4-(p-fluorophenyl)cyclohexyl)-3-methyl-4-phenylisonipecotic Acid Monohydrochloride

    10. Dsstox_cid_25508

    11. Dsstox_rid_80921

    12. Dsstox_gsid_45508

    13. R-50547

    14. (3s,4r)-1-((1s,4r)-4-cyano-4-(4-fluorophenyl)cyclohexyl)-3-methyl-4-phenylpiperidine-4-carboxylic Acid Hydrochloride

    15. Levocabastine Hydrochloride [usan]

    16. Unii-124xma6yei

    17. (3s,4r)-cabastine Hydrochloride

    18. Levocabastine Hydrochloride [usan:usp]

    19. Ncgc00016939-01

    20. Cas-79547-78-7

    21. Schembl99969

    22. Schembl99970

    23. Mls002154116

    24. Chembl1237102

    25. Dtxsid9045508

    26. Chebi:31777

    27. Hms1571o19

    28. Tox21_110695

    29. Hy-14277a

    30. Levocabastine Hydrochloride (jan/usp)

    31. Tox21_110695_1

    32. At25912

    33. Ccg-221039

    34. Levocabastine Hydrochloride [jan]

    35. Ncgc00179240-04

    36. 4-piperidinecarboxylic Acid, 1-(4-cyano-4-(4-fluorophenyl)cyclohexyl)-3-methyl-4-phenyl-, Monohydrochloride, (-)-(1(cis),3alpha,4beta)-

    37. 4-piperidinecarboxylic Acid, 1-(cis-4-cyano-4-(4-fluorophenyl)cyclohexyl)-3-methyl-4-phenyl-, Monohydrochloride, (3s,4r)-

    38. Smr001233423

    39. Levocabastine Hydrochloride [mart.]

    40. Levocabastine Hydrochloride [vandf]

    41. Levocabastine Hydrochloride [usp-rs]

    42. Levocabastine Hydrochloride [who-dd]

    43. Cs-0031223

    44. D01717

    45. Levocabastine Hydrochloride [ep Impurity]

    46. Levocabastine Hydrochloride [orange Book]

    47. Levocabastine Hydrochloride [ep Monograph]

    48. Levocabastine Hydrochloride [usp Impurity]

    49. Levocabastine Hydrochloride [usp Monograph]

    50. Levocabastine Hydrochloride, >=99% (hplc), Solid

    51. Q27251370

    52. Levocabastine Hydrochloride, European Pharmacopoeia (ep) Reference Standard

    53. Levocabastine For System Suitability 2, European Pharmacopoeia (ep) Reference Standard

    54. Levocabastine Hydrochloride, United States Pharmacopeia (usp) Reference Standard

    55. (3s,4r)-1-[4-cyano-4-(4-fluorophenyl)cyclohexyl]-3-methyl-4-phenylpiperidine-4-carboxylic Acid;hydrochloride

    56. 4-piperidinecarboxylic Acid, 1-(4-cyano-4-(4-fluorophenyl)cyclohexyl)-3-methyl-4-phenyl-, Monohydrochloride, (-)-(1(cis),3.alpha.,4.beta.)-

    2.4 Create Date
    2005-06-24
    3 Chemical and Physical Properties
    Molecular Weight 457.0 g/mol
    Molecular Formula C26H30ClFN2O2
    Hydrogen Bond Donor Count2
    Hydrogen Bond Acceptor Count5
    Rotatable Bond Count4
    Exact Mass456.1979841 g/mol
    Monoisotopic Mass456.1979841 g/mol
    Topological Polar Surface Area64.3 Ų
    Heavy Atom Count32
    Formal Charge0
    Complexity681
    Isotope Atom Count0
    Defined Atom Stereocenter Count2
    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

    Histamine H1 Antagonists, Non-Sedating

    A class of non-sedating drugs that bind to but do not activate histamine receptors (DRUG INVERSE AGONISM), thereby blocking the actions of histamine or histamine agonists. These antihistamines represent a heterogenous group of compounds with differing chemical structures, adverse effects, distribution, and metabolism. Compared to the early (first generation) antihistamines, these non-sedating antihistamines have greater receptor specificity, lower penetration of BLOOD-BRAIN BARRIER, and are less likely to cause drowsiness or psychomotor impairment. (See all compounds classified as Histamine H1 Antagonists, Non-Sedating.)