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Details

Stereochemistry RACEMIC
Molecular Formula C26H29FN2O2
Molecular Weight 420.5191
Optical Activity ( + / - )
Defined Stereocenters 4 / 4
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of CABASTINE

SMILES

C[C@@H]1CN(CC[C@]1(C(O)=O)C2=CC=CC=C2)[C@H]3CC[C@](CC3)(C#N)C4=CC=C(F)C=C4

InChI

InChIKey=ZCGOMHNNNFPNMX-KYTRFIICSA-N
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

HIDE SMILES / InChI

Molecular Formula C26H29FN2O2
Molecular Weight 420.5191
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 4 / 4
E/Z Centers 0
Optical Activity UNSPECIFIED

Description
Curator's Comment: description was created based on several sources, including http://www.rxlist.com/livostin-side-effects-drug-center.htm

Levocabastine (trade name Livo) is a selective second-generation H1-receptor antagonist used for allergic conjunctivitis. Levocabastine binds the G protein-coupled neurotensin receptor 2 (NTR2), but not NTR1, where it behaves as a weak partial inverse agonist. In an environmental study, LIVOSTIN 0.05% (levocabastine hydrochloride ophthalmic suspension) instilled four times daily was shown to be significantly more effective than its vehicle in reducing ocular itching associated with seasonal allergic conjunctivitis. After instillation in the eye, levocabastine is systemically absorbed. However, the amount of systemically absorbed levocabastine after therapeutic ocular doses is low (mean plasma concentrations in the range of 1-2 ng/mL). Brand name Livostin is no longer available in the U.S., but generic versions may still be available. Common side effects include burning, stinging, itching, or watering of the eyes, eye irritation or discomfort, blurred vision, dry or puffy eyes, headache, nosebleed, nausea, or fatigue.

Originator

Curator's Comment: # Janssen Pharmaceutical

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Target ID: O95665
Gene ID: 23620.0
Gene Symbol: NTSR2
Target Organism: Homo sapiens (Human)
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Palliative
LIVOSTIN

Approved Use

LIVOSTIN™ 0.05% (levocabastine hydrochloride ophthalmic suspension) is indicated for the temporary relief of the signs and symptoms of seasonal allergic conjunctivitis.

Launch Date

1993
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
7.4 ng/mL
0.5 mg single, oral
dose: 0.5 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
LEVOCABASTINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FED
7.3 μg/L
0.5 mg single, oral
dose: 0.5 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
LEVOCABASTINE plasma
Homo sapiens
population: HEALTHY
age: UNKNOWN
sex: UNKNOWN
food status: UNKNOWN
12.1 μg/L
1 mg single, oral
dose: 1 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
LEVOCABASTINE plasma
Homo sapiens
population: HEALTHY
age: UNKNOWN
sex: UNKNOWN
food status: UNKNOWN
22.2 μg/L
2 mg single, oral
dose: 2 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
LEVOCABASTINE plasma
Homo sapiens
population: HEALTHY
age: UNKNOWN
sex: UNKNOWN
food status: UNKNOWN
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
319 ng × h/mL
0.5 mg single, oral
dose: 0.5 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
LEVOCABASTINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FED
337 μg × h/L
0.5 mg single, oral
dose: 0.5 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
LEVOCABASTINE plasma
Homo sapiens
population: HEALTHY
age: UNKNOWN
sex: UNKNOWN
food status: UNKNOWN
580 μg × h/L
1 mg single, oral
dose: 1 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
LEVOCABASTINE plasma
Homo sapiens
population: HEALTHY
age: UNKNOWN
sex: UNKNOWN
food status: UNKNOWN
1142 μg × h/L
2 mg single, oral
dose: 2 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
LEVOCABASTINE plasma
Homo sapiens
population: HEALTHY
age: UNKNOWN
sex: UNKNOWN
food status: UNKNOWN
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
35.7 h
0.5 mg single, oral
dose: 0.5 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
LEVOCABASTINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FED
37.5 h
0.5 mg single, oral
dose: 0.5 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
LEVOCABASTINE plasma
Homo sapiens
population: HEALTHY
age: UNKNOWN
sex: UNKNOWN
food status: UNKNOWN
37.5 h
1 mg single, oral
dose: 1 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
LEVOCABASTINE plasma
Homo sapiens
population: HEALTHY
age: UNKNOWN
sex: UNKNOWN
food status: UNKNOWN
Funbound

Funbound

ValueDoseCo-administeredAnalytePopulation
45%
0.5 mg single, oral
dose: 0.5 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
LEVOCABASTINE plasma
Homo sapiens
population: HEALTHY
age: UNKNOWN
sex: UNKNOWN
food status: UNKNOWN
45%
1 mg single, oral
dose: 1 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
LEVOCABASTINE plasma
Homo sapiens
population: HEALTHY
age: UNKNOWN
sex: UNKNOWN
food status: UNKNOWN
45%
2 mg single, oral
dose: 2 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
LEVOCABASTINE plasma
Homo sapiens
population: HEALTHY
age: UNKNOWN
sex: UNKNOWN
food status: UNKNOWN
Doses

Doses

DosePopulationAdverse events​
0.05 % 4 times / day multiple, ophthalmic
Recommended
Dose: 0.05 %, 4 times / day
Route: ophthalmic
Route: multiple
Dose: 0.05 %, 4 times / day
Sources:
unhealthy, 5 - 17 years
Health Status: unhealthy
Age Group: 5 - 17 years
Sex: M+F
Sources:
Disc. AE: Headache, Blepharoconjunctivitis...
AEs leading to
discontinuation/dose reduction:
Headache (3 patients)
Blepharoconjunctivitis (3 patients)
Sources:
0.5 mg/mL 2 times / day multiple, ophthalmic
Recommended
unhealthy, < 12 years
Other AEs: Eye disorders NEC...
0.5 mg/mL 2 times / day multiple, ophthalmic
Recommended
unhealthy, > 12 years
Other AEs: Eye disorders NEC...
0.05 % 4 times / day multiple, ophthalmic
Recommended
Dose: 0.05 %, 4 times / day
Route: ophthalmic
Route: multiple
Dose: 0.05 %, 4 times / day
Sources:
unhealthy, adult
Health Status: unhealthy
Age Group: adult
Sex: unknown
Sources:
Disc. AE: Eye disorders NEC...
AEs leading to
discontinuation/dose reduction:
Eye disorders NEC (23 patients)
Sources:
0.2 mg/mL 2 times / day multiple, intranasal
Recommended
Dose: 0.2 mg/mL, 2 times / day
Route: intranasal
Route: multiple
Dose: 0.2 mg/mL, 2 times / day
Sources:
unhealthy, mean 38.8 years
Health Status: unhealthy
Age Group: mean 38.8 years
Sex: M+F
Sources:
AEs

AEs

AESignificanceDosePopulation
Blepharoconjunctivitis 3 patients
Disc. AE
0.05 % 4 times / day multiple, ophthalmic
Recommended
Dose: 0.05 %, 4 times / day
Route: ophthalmic
Route: multiple
Dose: 0.05 %, 4 times / day
Sources:
unhealthy, 5 - 17 years
Health Status: unhealthy
Age Group: 5 - 17 years
Sex: M+F
Sources:
Headache 3 patients
Disc. AE
0.05 % 4 times / day multiple, ophthalmic
Recommended
Dose: 0.05 %, 4 times / day
Route: ophthalmic
Route: multiple
Dose: 0.05 %, 4 times / day
Sources:
unhealthy, 5 - 17 years
Health Status: unhealthy
Age Group: 5 - 17 years
Sex: M+F
Sources:
Eye disorders NEC 33 patients
0.5 mg/mL 2 times / day multiple, ophthalmic
Recommended
unhealthy, < 12 years
Eye disorders NEC 7 patients
0.5 mg/mL 2 times / day multiple, ophthalmic
Recommended
unhealthy, > 12 years
Eye disorders NEC 23 patients
Disc. AE
0.05 % 4 times / day multiple, ophthalmic
Recommended
Dose: 0.05 %, 4 times / day
Route: ophthalmic
Route: multiple
Dose: 0.05 %, 4 times / day
Sources:
unhealthy, adult
Health Status: unhealthy
Age Group: adult
Sex: unknown
Sources:
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG

OverviewOther

Other InhibitorOther SubstrateOther Inducer


Drug as perpetrator​

Drug as perpetrator​

TargetModalityActivityMetaboliteClinical evidence
no
unlikely (co-administration study)
Comment: the likelihood of systemic drug interactions with drugs affecting the cytochrome P-450 is minimal
Page: 1.0
Drug as victim

Drug as victim

TargetModalityActivityMetaboliteClinical evidence
no
unlikely (co-administration study)
Comment: the likelihood of systemic drug interactions with drugs affecting the cytochrome P-450 is minimal
Page: 1.0
PubMed

PubMed

TitleDatePubMed
Spinal NTS2 receptor activation reverses signs of neuropathic pain.
2013-09
Evaluation of histamine-induced conjunctival oedema in guinea pigs by means of image analysis.
2010-12
Clinical utility and patient adherence with ebastine for allergic rhinitis.
2010-10-14
Neurotensin is a regulator of insulin secretion in pancreatic beta-cells.
2010-10
Azelastine hydrochloride, a dual-acting anti-inflammatory ophthalmic solution, for treatment of allergic conjunctivitis.
2010-09-07
Levocabastine nasal spray significantly improves perennial allergic rhinitis: a single-blind placebo-controlled study.
2010-08
Relation between cooling sheet effect and tear histamine concenration in allergic conjunctivitis.
2010-07
Bepotastine besilate, a highly selective histamine H(1) receptor antagonist, suppresses vascular hyperpermeability and eosinophil recruitment in in vitro and in vivo experimental allergic conjunctivitis models.
2010-07
Treatment of allergic conjunctivitis: results of a 1-month, single-masked randomized study.
2010-04-13
Treatment of congestion in upper respiratory diseases.
2010-04-08
beta-Lactotensin derived from bovine beta-lactoglobulin suppresses food intake via the CRF system followed by the CGRP system in mice.
2009-12
Azelastine nasal spray for the treatment of allergic and nonallergic rhinitis.
2009-11
NT69L, a novel analgesic, shows synergy with morphine.
2009-10-19
[Effect of intra nasally applied fluticasone propionate and levocabastine on the expression of aquaporin 5 in nasal mucosa of rat with experimental allergic rhinitis].
2009-10
Evidence for a role of NTS2 receptors in the modulation of tonic pain sensitivity.
2009-07-06
Role of histamine H(4) receptor in allergic conjunctivitis in mice.
2009-04-17
The effect of levocabastine hydrochloride on human Tenon's capsule fibroblasts: inhibition of proliferation, suppression of DNA synthesis and induction of apoptosis.
2009
[Intra-annual and seasonal allergic conjunctivitis treatment: comparison of two therapeutic protocols].
2008-12
Drug use in children: cohort study in three European countries.
2008-11-24
Randomized double-blind placebo-controlled trial of sublingual immunotherapy in children with house dust mite allergy in primary care: study design and recruitment.
2008-10-20
Effectiveness of twice daily azelastine nasal spray in patients with seasonal allergic rhinitis.
2008-10
Contribution of alpha4beta1 integrin to the antiallergic effect of levocabastine.
2008-09-15
Treatment of allergic conjunctivitis with olopatadine hydrochloride eye drops.
2008-09
The effect of a combined therapy with a histamine H1 antagonist and a chemical mediator release inhibitor on allergic conjunctivitis.
2008
Neurotensin protects pancreatic beta cells from apoptosis.
2008
Clinical and biological efficacy of preservative-free NAAGA eye-drops versus levocabastine eye-drops in vernal keratoconjunctivitis patients.
2007-12
The effect of levocabastine and furosemide pretreatment on hyperreactive response after nasal provocation with hypotonic aerosol in subjects with allergic rhinitis.
2007-11
Inhibition of release of vasoactive and inflammatory mediators in airway and vascular tissues and macrophages by a chinese herbal medicine formula for allergic rhinitis.
2007-06
Seasonal allergic rhinitis in adolescents and adults.
2007-04-01
Review of azelastine nasal spray in the treatment of allergic and non-allergic rhinitis.
2007-04
Inhibition of release of inflammatory mediators in primary and cultured cells by a Chinese herbal medicine formula for allergic rhinitis.
2007-02-15
Interactions between NTS2 neurotensin and opioid receptors on two nociceptive responses assessed on the hot plate test in mice.
2006-12-15
Effect of antihistamine eye drops on the conjunctival provocation test with Japanese cedar pollen allergen.
2006-12
Effect of beta-lactotensin on acute stress and fear memory.
2006-12
The early efficacy of topical levocabastine in patients with allergic conjunctivitis.
2006-09
[Misleading advertisement on Opatanol].
2006-07-01
Effects of excitotoxic lesions of the medial prefrontal cortex on density of high affinity [125I-Tyr3]neurotensin binding sites within the ventral midbrain and striatum.
2006-06-13
Efficacy of levocabastine hydrochloride ophthalmic suspension in the conjunctival allergen challenge test in Japanese subjects with seasonal allergic conjunctivitis.
2006-06
Preferential inhibition of human phosphodiesterase 4 by ibudilast.
2006-05-01
The reliability, validity, and preliminary responsiveness of the Eye Allergy Patient Impact Questionnaire (EAPIQ).
2005-10-31
Potent spinal analgesia elicited through stimulation of NTS2 neurotensin receptors.
2005-09-07
Efficacy, cost-effectiveness, and tolerability of mometasone furoate, levocabastine, and disodium cromoglycate nasal sprays in the treatment of seasonal allergic rhinitis.
2005-09
[Comparison of three antiallergic eyedrops in a specific conjunctival provocation test: mequitazine, levocabastine and dexamethasone].
2005-03
Comparison of allergen immunotherapy and drug treatment in seasonal rhinoconjunctivitis: a 3-years study.
2005-02
Actual therapeutic management of allergic and hyperreactive nasal disorders.
2004
Stable expression of the mouse levocabastine-sensitive neurotensin receptor in HEK 293 cell line: binding properties, photoaffinity labeling, and internalization mechanism.
1998-02-13
Structure, functional expression, and cerebral localization of the levocabastine-sensitive neurotensin/neuromedin N receptor from mouse brain.
1996-09-15
Molecular cloning of a levocabastine-sensitive neurotensin binding site.
1996-05-20
Selective effect of levocabastine on histamine receptor and histamine release from human leukocytes and guinea pig isolated tissue.
1996-04
Evidence for a displaceable non-specific [3H]neurotensin binding site in rat brain.
1986-08
Patents

Sample Use Guides

The usual dose is one drop instilled in affected eyes four times per day.
Route of Administration: Other
Levocabastine binds the alpha(4)beta(1) integrin and prevents eosinophil adhesion to vascular cell adhesion molecule-1 (VCAM-1), FN or human umbilical vascular endothelial cells (HUVEC) in vitro
Substance Class Chemical
Created
by admin
on Mon Mar 31 18:50:43 GMT 2025
Edited
by admin
on Mon Mar 31 18:50:43 GMT 2025
Record UNII
COU3RRH769
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
(±)-TRANS-1-(CIS-4-CYANO-4-(P-FLUOROPHENYL)CYCLOHEXYL)-3-METHYL-4-PHENYLISONIPECOTIC ACID
Preferred Name English
CABASTINE
INN  
INN  
Official Name English
cabastine [INN]
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C29578
Created by admin on Mon Mar 31 18:50:43 GMT 2025 , Edited by admin on Mon Mar 31 18:50:43 GMT 2025
Code System Code Type Description
EVMPD
SUB06040MIG
Created by admin on Mon Mar 31 18:50:43 GMT 2025 , Edited by admin on Mon Mar 31 18:50:43 GMT 2025
PRIMARY
CAS
79449-98-2
Created by admin on Mon Mar 31 18:50:43 GMT 2025 , Edited by admin on Mon Mar 31 18:50:43 GMT 2025
PRIMARY
SMS_ID
100000081589
Created by admin on Mon Mar 31 18:50:43 GMT 2025 , Edited by admin on Mon Mar 31 18:50:43 GMT 2025
PRIMARY
NCI_THESAURUS
C79561
Created by admin on Mon Mar 31 18:50:43 GMT 2025 , Edited by admin on Mon Mar 31 18:50:43 GMT 2025
PRIMARY
ChEMBL
CHEMBL2218900
Created by admin on Mon Mar 31 18:50:43 GMT 2025 , Edited by admin on Mon Mar 31 18:50:43 GMT 2025
PRIMARY
INN
5392
Created by admin on Mon Mar 31 18:50:43 GMT 2025 , Edited by admin on Mon Mar 31 18:50:43 GMT 2025
PRIMARY
EPA CompTox
DTXSID001024637
Created by admin on Mon Mar 31 18:50:43 GMT 2025 , Edited by admin on Mon Mar 31 18:50:43 GMT 2025
PRIMARY
FDA UNII
COU3RRH769
Created by admin on Mon Mar 31 18:50:43 GMT 2025 , Edited by admin on Mon Mar 31 18:50:43 GMT 2025
PRIMARY
Related Record Type Details
ACTIVE MOIETY