Levocabastine
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Identification
- Summary
Levocabastine is a selective histamine H1 receptor antagonist indicated for the management of seasonal allergic conjunctivitis symptoms.
- Brand Names
- Livostin
- Generic Name
- Levocabastine
- DrugBank Accession Number
- DB01106
- Background
Levocabastine is a selective second-generation H1-receptor antagonist used for allergic conjunctivitis. Levocabastine was discovered at Janssen Pharmaceutica in 1979.
- Type
- Small Molecule
- Groups
- Approved, Investigational
- Structure
- Weight
- Average: 420.528
Monoisotopic: 420.221306345 - Chemical Formula
- C26H29FN2O2
- Synonyms
- Levocabastina
- Levocabastine
- Levocabastinum
Pharmacology
- 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.
Reduce drug development failure ratesBuild, train, & validate machine-learning modelswith evidence-based and structured datasets.Build, train, & validate predictive machine-learning models with structured datasets.- Associated Conditions
Indication Type Indication Combined Product Details Approval Level Age Group Patient Characteristics Dose Form Symptomatic treatment of Allergic rhinitis •••••••••••• Symptomatic treatment of Conjunctivitis allergic ••• ••• ••••••••• •••••••• • •••••• ••••••••••• •••••••••• • ••••• - Contraindications & Blackbox Warnings
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- 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.
Target Actions Organism AHistamine H1 receptor antagonistHumans ANeurotensin receptor type 2 partial antagonistHumans - Absorption
After instillation in the eye, levocabastine is systemically absorbed, albeit at low levels.
- Volume of distribution
Not Available
- Protein binding
Not Available
- Metabolism
Mostly unchanged. 10 to 20% is metabolized to the acylglucuronide of levocabastine.
- Route of elimination
Not Available
- Half-life
36 hours (after oral administration)
- Clearance
Not Available
- Adverse Effects
- Improve decision support & research outcomesWith structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates. View sample adverse effects data in our new Data Library!Improve decision support & research outcomes with our structured adverse effects data.
- Toxicity
Adverse effects include visual disturbances, dry mouth, cough, nausea, eyelid edema and lacrimation.
- Pathways
Pathway Category Levocabastine H1-Antihistamine Action Drug action - Pharmacogenomic Effects/ADRs
- Not Available
Interactions
- Drug Interactions
- This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
Drug Interaction Integrate drug-drug
interactions in your softwareAcrivastine The risk or severity of QTc prolongation can be increased when Levocabastine is combined with Acrivastine. Adenosine The risk or severity of QTc prolongation can be increased when Levocabastine is combined with Adenosine. Ajmaline The risk or severity of QTc prolongation can be increased when Levocabastine is combined with Ajmaline. Albuterol The risk or severity of QTc prolongation can be increased when Salbutamol is combined with Levocabastine. Alfuzosin The risk or severity of QTc prolongation can be increased when Alfuzosin is combined with Levocabastine. - Food Interactions
- No interactions found.
Products
- Drug product information from 10+ global regionsOur datasets provide approved product information including:dosage, form, labeller, route of administration, and marketing period.Access drug product information from over 10 global regions.
- Product Ingredients
Ingredient UNII CAS InChI Key Levocabastine hydrochloride 124XMA6YEI 79547-78-7 OICFWWJHIMKBCD-VALQNVSPSA-N - Brand Name Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Livostin Suspension 0.5 mg/1mL Ophthalmic Novartis Ophthalmics 2006-01-12 Not applicable US Livostin Suspension 0.5 mg/1mL Ophthalmic Physicians Total Care, Inc. 2004-04-28 2006-06-30 US Livostin Eye Drops Solution / drops; Suspension 0.5 mg / mL Ophthalmic Novartis 1995-12-31 2011-06-27 Canada Livostin Sus Nas 0.5mg/ml Spray; Suspension 0.05 mg / act Nasal Janssen Pharmaceuticals 1993-12-31 2020-12-22 Canada
Categories
- ATC Codes
- R01AC02 — Levocabastine
- R01AC — Antiallergic agents, excl. corticosteroids
- R01A — DECONGESTANTS AND OTHER NASAL PREPARATIONS FOR TOPICAL USE
- R01 — NASAL PREPARATIONS
- R — RESPIRATORY SYSTEM
- Drug Categories
- Anti-Allergic Agents
- Antiallergic Agents, Excl. Corticosteroids
- Central Nervous System Depressants
- Decongestants and Antiallergics
- Histamine Agents
- Histamine Antagonists
- Histamine H1 Antagonists
- Histamine H1 Antagonists, Non-Sedating
- Nasal Preparations
- Neurotransmitter Agents
- Ophthalmologicals
- Potential QTc-Prolonging Agents
- QTc Prolonging Agents
- Sensory Organs
- Chemical TaxonomyProvided by Classyfire
- Description
- This compound belongs to the class of organic compounds known as phenylpiperidines. These are compounds containing a phenylpiperidine skeleton, which consists of a piperidine bound to a phenyl group.
- Kingdom
- Organic compounds
- Super Class
- Organoheterocyclic compounds
- Class
- Piperidines
- Sub Class
- Phenylpiperidines
- Direct Parent
- Phenylpiperidines
- Alternative Parents
- Piperidinecarboxylic acids / Aralkylamines / Fluorobenzenes / Cyclohexylamines / Aryl fluorides / Trialkylamines / Amino acids / Nitriles / Monocarboxylic acids and derivatives / Azacyclic compounds show 6 more
- Substituents
- Amine / Amino acid / Amino acid or derivatives / Aralkylamine / Aromatic heteromonocyclic compound / Aryl fluoride / Aryl halide / Azacycle / Benzenoid / Carbonitrile show 22 more
- Molecular Framework
- Aromatic heteromonocyclic compounds
- External Descriptors
- Not Available
- Affected organisms
- Humans and other mammals
Chemical Identifiers
- UNII
- H68BP06S81
- CAS number
- 79516-68-0
- InChI Key
- ZCGOMHNNNFPNMX-KYTRFIICSA-N
- 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
- IUPAC Name
- (3S,4R)-3-methyl-4-phenyl-1-[(1s,4s)-4-cyano-4-(4-fluorophenyl)cyclohexyl]piperidine-4-carboxylic acid
- SMILES
- C[C@@H]1CN(CC[C@]1(C(O)=O)C1=CC=CC=C1)[C@H]1CC[C@](CC1)(C#N)C1=CC=C(F)C=C1
References
- General References
- Not Available
- External Links
- KEGG Drug
- D01717
- PubChem Compound
- 54385
- PubChem Substance
- 46505909
- ChemSpider
- 16736421
- BindingDB
- 50019405
- 28627
- ChEBI
- 135679
- ChEMBL
- CHEMBL1615438
- ZINC
- ZINC000100089496
- Therapeutic Targets Database
- DAP000335
- PharmGKB
- PA164742988
- Guide to Pharmacology
- GtP Drug Page
- RxList
- RxList Drug Page
- Drugs.com
- Drugs.com Drug Page
- Wikipedia
- Levocabastine
Clinical Trials
- Clinical Trials
Clinical Trial & Rare Diseases Add-on Data Package
Explore 4,000+ rare diseases, orphan drugs & condition pairs, clinical trial why stopped data, & more. Preview package Phase Status Purpose Conditions Count Start Date Why Stopped 100+ additional columns Unlock 175K+ rows when you subscribe.View sample dataNot Available Unknown Status Treatment Determination of the Efficacy of Different Medications for Idiopathic Rhinitis / Impact of Different Medications on Biomarkers of Idiopathic Rhinitis / Safety and Tolerance of Different Medications for Idiopathic Rhinitis 1 somestatus stop reason just information to hide 3 Completed Treatment Perennial Allergic Rhinitis (PAR) 1 somestatus stop reason just information to hide 2 Completed Treatment Rhinitis, Allergic, Perennial and Seasonal 2 somestatus stop reason just information to hide
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Novartis AG
- OMJ Pharmaceuticals
- Physicians Total Care Inc.
- Dosage Forms
Form Route Strength Suspension / drops Ophthalmic 0.5 mg/ml Spray, suspension Nasal 0.5 mg/ml Spray Nasal Solution / drops Ophthalmic Suspension Ophthalmic 0.5 mg/1mL Solution / drops Ophthalmic 0.5 mg/ml Spray Nasal 0.5 mg/ml Solution / drops; suspension Ophthalmic 0.5 mg / mL Spray; suspension Nasal 0.05 mg / act - Prices
- Not Available
- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
Property Value Source water solubility >0.5 mg/mL Not Available logP 5 Not Available - Predicted Properties
Property Value Source Water Solubility 0.00347 mg/mL ALOGPS logP 4.56 ALOGPS logP 2.5 Chemaxon logS -5.1 ALOGPS pKa (Strongest Acidic) 3.71 Chemaxon pKa (Strongest Basic) 10.32 Chemaxon Physiological Charge 0 Chemaxon Hydrogen Acceptor Count 4 Chemaxon Hydrogen Donor Count 1 Chemaxon Polar Surface Area 64.33 Å2 Chemaxon Rotatable Bond Count 4 Chemaxon Refractivity 118.48 m3·mol-1 Chemaxon Polarizability 45.58 Å3 Chemaxon Number of Rings 4 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter Yes Chemaxon Veber's Rule No Chemaxon MDDR-like Rule No Chemaxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption + 0.9811 Blood Brain Barrier + 0.8388 Caco-2 permeable + 0.5747 P-glycoprotein substrate Substrate 0.7325 P-glycoprotein inhibitor I Inhibitor 0.5 P-glycoprotein inhibitor II Non-inhibitor 0.5682 Renal organic cation transporter Non-inhibitor 0.5526 CYP450 2C9 substrate Non-substrate 0.7708 CYP450 2D6 substrate Non-substrate 0.6679 CYP450 3A4 substrate Substrate 0.5153 CYP450 1A2 substrate Non-inhibitor 0.9046 CYP450 2C9 inhibitor Non-inhibitor 0.9071 CYP450 2D6 inhibitor Inhibitor 0.8932 CYP450 2C19 inhibitor Non-inhibitor 0.9026 CYP450 3A4 inhibitor Non-inhibitor 0.8309 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.9046 Ames test Non AMES toxic 0.7503 Carcinogenicity Non-carcinogens 0.9196 Biodegradation Not ready biodegradable 1.0 Rat acute toxicity 2.9608 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.9404 hERG inhibition (predictor II) Inhibitor 0.625
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS splash10-00di-0000900000-99612e4d1c9b496df1eb Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS splash10-014i-0009700000-a0567a86cdc2d2fcbf11 Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS splash10-0umi-0008900000-27a804818b72c830bc7c Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS splash10-05r1-0009200000-88ce5da1319fb735760f Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS splash10-00dl-2549300000-fdc10e06758ed38c462e Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS splash10-002b-0239200000-c55b7277df47f5270137 Predicted 1H NMR Spectrum 1D NMR Not Applicable Predicted 13C NMR Spectrum 1D NMR Not Applicable - Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 195.15028 predictedDeepCCS 1.0 (2019) [M+H]+ 197.54585 predictedDeepCCS 1.0 (2019) [M+Na]+ 203.45836 predictedDeepCCS 1.0 (2019)
Targets
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Antagonist
- General Function
- G-protein-coupled receptor for histamine, a biogenic amine that functions as an immune modulator and a neurotransmitter (PubMed:33828102, PubMed:8280179). Through the H1 receptor, histamine mediates the contraction of smooth muscles and increases capillary permeability due to contraction of terminal venules. Also mediates neurotransmission in the central nervous system and thereby regulates circadian rhythms, emotional and locomotor activities as well as cognitive functions (By similarity)
- Specific Function
- G protein-coupled serotonin receptor activity
- Gene Name
- HRH1
- Uniprot ID
- P35367
- Uniprot Name
- Histamine H1 receptor
- Molecular Weight
- 55783.61 Da
References
- Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [Article]
- 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. [Article]
- 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. [Article]
- 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. [Article]
- 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. [Article]
- 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. [Article]
- Zhou Y, Zhang Y, Zhao D, Yu X, Shen X, Zhou Y, Wang S, Qiu Y, Chen Y, Zhu F: TTD: Therapeutic Target Database describing target druggability information. Nucleic Acids Res. 2024 Jan 5;52(D1):D1465-D1477. doi: 10.1093/nar/gkad751. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Partial antagonist
- General Function
- Receptor for the tridecapeptide neurotensin. It is associated with G proteins that activate a phosphatidylinositol-calcium second messenger system
- Specific Function
- G protein-coupled neurotensin receptor activity
- Gene Name
- NTSR2
- Uniprot ID
- O95665
- Uniprot Name
- Neurotensin receptor type 2
- Molecular Weight
- 45384.635 Da
References
- 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. [Article]
- 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. [Article]
- 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. [Article]
Drug created at June 13, 2005 13:24 / Updated at October 21, 2024 08:50