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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:51 UTC
Update Date2021-09-14 15:41:33 UTC
HMDB IDHMDB0015238
Secondary Accession Numbers
  • HMDB15238
Metabolite Identification
Common NameLevocabastine
DescriptionLevocabastine is only found in individuals that have used or taken this drug. It is a selective second-generation H1-receptor antagonist used for allergic conjunctivitis. Levocabastine was discovered at Janssen Pharmaceutica in 1979.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.
Structure
Data?1582753274
Synonyms
ValueSource
LevocabastinHMDB
Janssen brand OF levocabastine hydrochlorideHMDB
LevophtaHMDB
LivostinHMDB
Chauvin brand OF levocabastine hydrochlorideHMDB
Iolab brand OF levocabastine hydrochlorideHMDB
Taxandria brand OF levocabastine hydrochlorideHMDB
Ciba vision brand OF levocabastine hydrochlorideHMDB
Winzer brand OF levocabastine hydrochlorideHMDB
LévophtaHMDB
1-(4-Cyano-4-(4-fluorophenyl)cyclohexyl)-3-methyl-4-phenyl-4-piperidinecarboxylic acidHMDB
BilinaHMDB
Esteve brand OF levocabastine hydrochlorideHMDB
Levocabastine hydrochlorideHMDB
LivocabHMDB
Chemical FormulaC26H29FN2O2
Average Molecular Weight420.5191
Monoisotopic Molecular Weight420.221306387
IUPAC Name(3S,4R)-1-[4-cyano-4-(4-fluorophenyl)cyclohexyl]-3-methyl-4-phenylpiperidine-4-carboxylic acid
Traditional Namelivostin
CAS Registry Number79516-68-0
SMILES
C[C@@H]1CN(CC[C@]1(C(O)=O)C1=CC=CC=C1)C1CCC(CC1)(C#N)C1=CC=C(F)C=C1
InChI Identifier
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
InChI KeyZCGOMHNNNFPNMX-YHYDXASRSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as phenylpiperidines. Phenylpiperidines are compounds containing a phenylpiperidine skeleton, which consists of a piperidine bound to a phenyl group.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassPiperidines
Sub ClassPhenylpiperidines
Direct ParentPhenylpiperidines
Alternative Parents
Substituents
  • Phenylpiperidine
  • Piperidinecarboxylic acid
  • Cyclohexylamine
  • Fluorobenzene
  • Aralkylamine
  • Halobenzene
  • Aryl fluoride
  • Aryl halide
  • Monocyclic benzene moiety
  • Benzenoid
  • Amino acid or derivatives
  • Amino acid
  • Tertiary aliphatic amine
  • Tertiary amine
  • Carboxylic acid derivative
  • Carboxylic acid
  • Azacycle
  • Monocarboxylic acid or derivatives
  • Carbonitrile
  • Nitrile
  • Organooxygen compound
  • Hydrocarbon derivative
  • Organic nitrogen compound
  • Amine
  • Carbonyl group
  • Organic oxygen compound
  • Organopnictogen compound
  • Organic oxide
  • Organohalogen compound
  • Organofluoride
  • Organonitrogen compound
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Biological location

Source

Route of exposure

Process

Naturally occurring process

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.0035 g/LNot Available
LogP5Not Available
Experimental Spectral PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.0035 g/LALOGPS
logP10(4.56) g/LALOGPS
logP10(2.5) g/LChemAxon
logS10(-5.1) g/LALOGPS
pKa (Strongest Acidic)3.71ChemAxon
pKa (Strongest Basic)10.32ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area64.33 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity118.48 m³·mol⁻¹ChemAxon
Polarizability45.72 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Spectral Properties

Predicted Kovats Retention Indices

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Levocabastine,1TMS,#1C[C@@H]1CN(C2CCC(C#N)(C3=CC=C(F)C=C3)CC2)CC[C@]1(C(=O)O[Si](C)(C)C)C1=CC=CC=C13216.0Semi standard non polarhttps://arxiv.org/abs/1905.12712
Levocabastine,1TBDMS,#1C[C@@H]1CN(C2CCC(C#N)(C3=CC=C(F)C=C3)CC2)CC[C@]1(C(=O)O[Si](C)(C)C(C)(C)C)C1=CC=CC=C13447.3Semi standard non polarhttps://arxiv.org/abs/1905.12712
Spectra
Biological Properties
Cellular Locations
  • Membrane
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB01106 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB01106 details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID49123
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkLevocabastine
METLIN IDNot Available
PubChem Compound54385
PDB IDNot Available
ChEBI ID654467
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

Enzymes

General function:
Involved in G-protein coupled receptor protein signaling pathway
Specific function:
In peripheral tissues, the H1 subclass of histamine receptors mediates the contraction of smooth muscles, increase in capillary permeability due to contraction of terminal venules, and catecholamine release from adrenal medulla, as well as mediating neurotransmission in the central nervous system
Gene Name:
HRH1
Uniprot ID:
P35367
Molecular weight:
55783.6
References
  1. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]
  2. Sugimoto Y, Iba Y, Ishizawa K, Suzuki G, Kamei C: Effects of levocabastine on lipid mediator release from guinea pig lung fragments. Acta Med Okayama. 1999 Dec;53(6):271-4. [PubMed:10631382 ]
  3. Chalon P, Vita N, Kaghad M, Guillemot M, Bonnin J, Delpech B, Le Fur G, Ferrara P, Caput D: Molecular cloning of a levocabastine-sensitive neurotensin binding site. FEBS Lett. 1996 May 20;386(2-3):91-4. [PubMed:8647296 ]
  4. Yamada M, Yamada M, Lombet A, Forgez P, Rostene W: Distinct functional characteristics of levocabastine sensitive rat neurotensin NT2 receptor expressed in Chinese hamster ovary cells. Life Sci. 1998;62(23):PL 375-80. [PubMed:9627096 ]
  5. Betancur C, Canton M, Burgos A, Labeeuw B, Gully D, Rostene W, Pelaprat D: Characterization of binding sites of a new neurotensin receptor antagonist, [3H]SR 142948A, in the rat brain. Eur J Pharmacol. 1998 Feb 5;343(1):67-77. [PubMed:9551716 ]
  6. Akiyoshi M, Shigeoka T, Torii S, Maki E, Enomoto S, Takahashi H, Hirano F: [Pharmacological and clinical properties of levocabastine hydrochloride (eye drop and nasal spray), a selective H1 antagonist]. Nihon Yakurigaku Zasshi. 2002 Mar;119(3):175-84. [PubMed:11915520 ]
General function:
Involved in G-protein coupled receptor protein signaling pathway
Specific function:
Receptor for the tridecapeptide neurotensin. It is associated with G proteins that activate a phosphatidylinositol- calcium second messenger system
Gene Name:
NTSR2
Uniprot ID:
O95665
Molecular weight:
45412.7
References
  1. Richard F, Barroso S, Martinez J, Labbe-Jullie C, Kitabgi P: Agonism, inverse agonism, and neutral antagonism at the constitutively active human neurotensin receptor 2. Mol Pharmacol. 2001 Dec;60(6):1392-8. [PubMed:11723247 ]
  2. Chalon P, Vita N, Kaghad M, Guillemot M, Bonnin J, Delpech B, Le Fur G, Ferrara P, Caput D: Molecular cloning of a levocabastine-sensitive neurotensin binding site. FEBS Lett. 1996 May 20;386(2-3):91-4. [PubMed:8647296 ]
  3. Botto JM, Guillemare E, Vincent JP, Mazella J: Effects of SR 48692 on neurotensin-induced calcium-activated chloride currents in the Xenopus oocyte expression system: agonist-like activity on the levocabastine-sensitive neurotensin receptor and absence of antagonist effect on the levocabastine insensitive neurotensin receptor. Neurosci Lett. 1997 Feb 28;223(3):193-6. [PubMed:9080465 ]