(3S,4R)-1-[4-cyano-4-(4-fluorophenyl)cyclohexyl]-3-methyl-4-phenylpiperidine-4-carboxylic acid

• ChemBase ID: 977
• Molecular Formular: C26H29FN2O2
• Molecular Mass: 420.5190632
• Monoisotopic Mass: 420.2213064
• SMILES: Fc1ccc(C2(CCC(N3C[C@H]([C@](CC3)(c3ccccc3)C(=O)O)C)CC2)C#N)cc1
• Canonical SMILES: N#CC1(CCC(CC1)N1CC[C@]([C@@H](C1)C)(C(=O)O)c1ccccc1)c1ccc(cc1)F
• InChI: InChI=1S/C26H29FN2O2/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)/t19-,23?,25?,26-/m1/s1
• InChIKey: ZCGOMHNNNFPNMX-YHYDXASRSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (3S,4R)-1-[4-cyano-4-(4-fluorophenyl)cyclohexyl]-3-methyl-4-phenylpiperidine-4-carboxylic acid
• IUPAC Traditional name: bilina; livostin
• Brand Name: Livostin
• Synonyms: Levocabastina [Spanish]; Levocabastin; Levocabastinum [Latin]; Levocabastine; (3S,4R)-1-(4-Cyano-4-(4-fluorophenyl)cyclohexyl)-3-Methyl-4-phenylpiperidine-4-carboxylic acid

Database IDs

• CAS Number: 79516-68-0
• PubChem SID: 160964440; 46505909
• PubChem CID: 54385

CALCULATED PROPERTIES

JChem

• Acid pKa: 3.7128966
• H Acceptors: 4
• H Donor: 1
• LogD (pH = 5.5): 2.4939494
• LogD (pH = 7.4): 2.499277
• Log P: 2.4994276
• Molar Refractivity: 118.4834 cm^3
• Polarizability: 45.76977 Å^3
• Polar Surface Area: 64.33 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 4.56
• LOG S: -5.08
• Solubility (Water): 3.47e-03 g/l

PROPERTIES

Physical Property

• Solubility: >0.5 mg/mL
• Hydrophobicity(logP): 5

Product Information

• Purity: 98%

DETAILS

DrugBank - DB01106

• Drug Groups: approved
• Description: Levocabastine is a selective second-generation H1-receptor antagonist used for allergic conjunctivitis. Levocabastine was discovered at Janssen Pharmaceutica in 1979.
• Indication: As an ophthalmic for the temporary relief of the signs and symptoms of seasonal allergic conjunctivitis. Also used as a nasal spray for allergic rhinitis.
• Pharmacology: Levocabastine is a selective histamine H1-receptor antagonist exerting inhibitory effects on the release of chemical mediators from mast cells and on the chemotaxis of polymorphonuclear leukocytes and eosinophils. Both histamine and antigens induced conjunctivitis can be inhibited by levocabastine. Levocabastine can also reduce symptoms of allergic rhinitis by preventing an increase in vascular permeability of nasal mucosa.
• Toxicity: Adverse effects include visual disturbances, dry mouth, cough, nausea, eyelid edema and lacrimation.
• Affected Organisms: Humans and other mammals
• Biotransformation: Mostly unchanged. 10 to 20% is metabolized to the acylglucuronide of levocabastine.
• Absorption: After instillation in the eye, levocabastine is systemically absorbed, albeit at low levels.
• Half Life: 36 hours (after oral administration)
• External Links: Wikipedia; RxList; Drugs.com