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Levocabastine

Levocabastine

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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

Levocabastine

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 Formula	C₂₆H₃₀ClFN₂O₂
Molecular Weight	457.0 g/mol
Hydrogen Bond Donor Count	2
Hydrogen Bond Acceptor Count	5
Rotatable Bond Count	4
Exact Mass	456.1979841 g/mol
Monoisotopic Mass	456.1979841 g/mol
Topological Polar Surface Area	64.3 Å²
Heavy Atom Count	32
Formal Charge	0
Complexity	681
Isotope Atom Count	0
Defined Atom Stereocenter Count	2
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	2

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.)