(3S,4R)-3-methyl-4-phenyl-1-[(1s,4s)-4-cyano-4-(4-fluorophenyl)cyclohexyl]piperidine-4-carboxylic acid hydrochloride

• ChemBase ID: 154168
• Molecular Formular: C26H30ClFN2O2
• Molecular Mass: 456.9800032
• Monoisotopic Mass: 456.19798411
• SMILES: C[C@H]1[C@@](CCN(C1)[C@H]1CC[C@@](CC1)(c1ccc(cc1)F)C#N)(C(=O)O)c1ccccc1.Cl
• Canonical SMILES: N#C[C@@]1(CC[C@@H](CC1)N1CC[C@]([C@@H](C1)C)(C(=O)O)c1ccccc1)c1ccc(cc1)F.Cl
• 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
• InChIKey: OICFWWJHIMKBCD-VALQNVSPSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (3S,4R)-3-methyl-4-phenyl-1-[(1s,4s)-4-cyano-4-(4-fluorophenyl)cyclohexyl]piperidine-4-carboxylic acid hydrochloride
• IUPAC Traditional name: levocabastine hydrochloride
• Synonyms: (3S,4R)-1-[cis-4-Cyano-4-(4-fluorophenyl)cyclohexyl]-3-methyl-4-phenyl-4-piperidinecarboxylic Acid Hydrochloride; [3S-[1(cis),3α,4β]]-1-[4-Cyano-4-(4-fluorophenyl)cyclohexyl]-3-methyl-4-phenyl-4-piperidinecarboxylic Acid Monohydrochloride; Levocabastine Hydrochloride; Livostin; (3S,4R)-Cabastine Hydrochloride; Levophta; Levostin; R50547; [3S-[1(cis),3α,4β]]-1-[4-cyano-4-(4-fluorophenyl)cyclohexyl]-3-methyl-4-phenyl-4-piperidinecarboxylic acid; Levocabastine hydrochloride

Database IDs

• CAS Number: 79547-78-7
• MDL Number: MFCD07787408
• PubChem SID: 162248307
• PubChem CID: 54384

CALCULATED PROPERTIES

• 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

PROPERTIES

Physical Property

• Solubility: DMSO: soluble ~10 mg/mL
• Apperance: white solid

Safety Information

• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36/37/38
• Safety Statements: 26-36
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H315-H319-H335
• GHS Precautionary statements: P261-P305 + P351 + P338
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves

Product Information

• Purity: ≥99% (HPLC)
• Empirical Formula (Hill Notation): C26H29N2O2F·HCl

DETAILS

Sigma Aldrich - L3042

Biochem/physiol Actions
Non-peptide histamine H1 receptor antagonist; neurotensin NTS2 receptor ligand.

Toronto Research Chemicals - C045500

A histamine H1 receptor antagonist used in allergic conjunctivitis.

REFERENCES

• Ash, A., et al.: Br. J. Pharmacol., 27, 427 (1966)
• Davies, M., et al.: Br. J. Clin. Pharmacol., 9, 461 (1966)
• Oda, T., et al.: J. Biol. Chem., 275, 36781 (1966)
• Zhu, Y., et al.: Mol. Pharmacol., 59, 434 (1966)