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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
MOL RATIO 1 MOL RATIO (average)
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 4 / 4
E/Z Centers 0
Optical Activity UNSPECIFIED

Description

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

Approval Year

Targets

Primary TargetPharmacologyConditionPotency

Conditions

ConditionModalityTargetsHighest PhaseProduct
Palliative
LIVOSTIN

Cmax

ValueDoseCo-administeredAnalytePopulation
7.4 ng/mL
0.5 mg single, oral
LEVOCABASTINE plasma
Homo sapiens
22.2 μg/L
2 mg single, oral
LEVOCABASTINE plasma
Homo sapiens
7.3 μg/L
0.5 mg single, oral
LEVOCABASTINE plasma
Homo sapiens
12.1 μg/L
1 mg single, oral
LEVOCABASTINE plasma
Homo sapiens

AUC

ValueDoseCo-administeredAnalytePopulation
319 ng × h/mL
0.5 mg single, oral
LEVOCABASTINE plasma
Homo sapiens
1142 μg × h/L
2 mg single, oral
LEVOCABASTINE plasma
Homo sapiens
337 μg × h/L
0.5 mg single, oral
LEVOCABASTINE plasma
Homo sapiens
580 μg × h/L
1 mg single, oral
LEVOCABASTINE plasma
Homo sapiens

T1/2

ValueDoseCo-administeredAnalytePopulation
35.7 h
0.5 mg single, oral
LEVOCABASTINE plasma
Homo sapiens
37.5 h
0.5 mg single, oral
LEVOCABASTINE plasma
Homo sapiens
37.5 h
1 mg single, oral
LEVOCABASTINE plasma
Homo sapiens

Funbound

ValueDoseCo-administeredAnalytePopulation
45%
2 mg single, oral
LEVOCABASTINE plasma
Homo sapiens
45%
0.5 mg single, oral
LEVOCABASTINE plasma
Homo sapiens
45%
1 mg single, oral
LEVOCABASTINE plasma
Homo sapiens

Doses

AEs

Overview

CYP3A4CYP2C9CYP2D6hERG

OverviewOther

Other InhibitorOther SubstrateOther Inducer


Drug as perpetrator​

Drug as victim

Sourcing

PubMed

Sample Use Guides

In Vivo Use Guide
The usual dose is one drop instilled in affected eyes four times per day.
Route of Administration: Other
In Vitro Use Guide
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
Record UNII
COU3RRH769
Record Status Validated (UNII)
Record Version