Levocabastine
Basic information
- CAS
79449-98-2- Standard SMILES
C[C@@H]1CN(C2CCC(C#N)(c3ccc(F)cc3)CC2)CC[C@]1(C(=O)O)c1ccccc1- InChIKey
ZCGOMHNNNFPNMX-KYTRFIICSA-N- Molecular formula
- C26H29FN2O2
- Average molar mass
- 420.5 g/mol
- Monoisotopic mass
- 420.22130633
Overview
Levocabastine is a member of piperidines.
Names & identifiers
- Preferred name
- Levocabastine
- IUPAC
- (3S,4R)-1-[4-cyano-4-(4-fluorophenyl)cyclohexyl]-3-methyl-4-phenylpiperidine-4-carboxylic acid
- English name
- Cabastine
- Molecular formula
- C26H29FN2O2
- Molecular weight
- 420.52
Names & synonyms
levocabastine79516-68-0Levocabastinum [Latin]Levocabastina [Spanish]LevocabastinaCabastineCabastine [INN]79449-98-2(3S,4R)-1-[4-cyano-4-(4-fluorophenyl)cyclohexyl]-3-methyl-4-phenylpiperidine-4-carboxylic acidLevocabastine (INN)105452-51-5COU3RRH769
Show more names
R-48756ZCGOMHNNNFPNMX-KYTRFIICSA-N4-Piperidinecarboxylic acid, 1-[cis-4-cyano-4-(4-fluorophenyl)cyclohexyl]-3-methyl-4-phenyl-, (3R,4S)-rel-
H68BP06S81LevocabastinLevocabastinumtrans-4-Cyano CabastineLEVOCABASTINE [INN]Levocabastine [INN:BAN]CabastinumR-50547
Database identifiers
- CAS
79449-98-2、79516-68-0- PubChem CID
- 54385
- DTXSID
DTXSID001024637- ChEMBL
CHEMBL2218900- ChEBI
CHEBI:135679- UNII
- COU3RRH769、H68BP06S81
- Nikkaji
- J358.848C
Properties
Computed structural properties
- XLogP
- 2.5
- Topological polar surface area
- 64.3 Ų
- Hydrogen bond donors
- 1
- Hydrogen bond acceptors
- 5
- Rotatable bonds
- 4
- Heavy atoms
- 31
- Formal charge
- 0
- Complexity
- 681
Experimental & physicochemical properties
Drugs
Pharmaceuticals -> Respiratory system -> Nasal preparations
Pharmaceuticals -> Listed in ZINC15
LogP5
Solubility
>0.5 mg/mL
3.47e-03 g/L
Physical DescriptionSolid
Physicochemical properties
- Boiling point
- 589.867 · 589.867±50.00 °C(Press: 760.00 Torr)(predicted)
- Density
- 1.232 · 1.232±0.10 g/cm3(Temp: 25 °C; Press: 760 Torr)(predicted)
- pka
- 3.573 · 3.573±0.40(predicted)
- FDA UNII
- 3 RRH769 · COU3RRH769
Chemistry & industry
Pharmacology
ATC CodeS01GX02
Pharmacodynamics
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.
Mechanism of Action
Levocabastine is a potent, selective histamine H1-receptor antagonist. It works by competing with histamine for H1-receptor sites on effector cells. It thereby prevents, but does not reverse, responses mediated by histamine alone. Levocabastine does not block histamine release but, rather, prevents histamine binding and activity. Levocabastine also binds neurotensin 2 receptors and serves as a neurotensin agonist. This can induce some degree of analgesia.
Biological Half-Life36 hours (after oral administration)
Metabolism/MetabolitesMostly unchanged. 10 to 20% is metabolized to the acylglucuronide of levocabastine.
Absorption, Distribution and ExcretionAfter instillation in the eye, levocabastine is systemically absorbed, albeit at low levels.
Cellular LocationsMembrane
Metabolite PathwaysLevocabastine H1-Antihistamine Action
Additional notes
DefinitionChEBI: Levocabastine is a member of piperidines.
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