Details
| Stereochemistry | ABSOLUTE |
| Molecular Formula | C26H29FN2O2.ClH |
| Molecular Weight | 456.98 |
| Optical Activity | UNSPECIFIED |
| Defined Stereocenters | 4 / 4 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
Cl.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=OICFWWJHIMKBCD-VALQNVSPSA-N
InChI=1S/C26H29FN2O2.ClH/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);1H/t19-,23-,25-,26-;/m1./s1
| 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 |
| Molecular Formula | ClH |
| Molecular Weight | 36.461 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ACHIRAL |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Optical Activity | NONE |
DescriptionSources: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=420b3f66-87f0-47d8-947c-541e84eb594aCurator's Comment: description was created based on several sources, including
http://www.rxlist.com/livostin-side-effects-drug-center.htm
Sources: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=420b3f66-87f0-47d8-947c-541e84eb594a
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
Sources: http://adisinsight.springer.com/drugs/800009368
Curator's Comment: # Janssen Pharmaceutical
Approval Year
Targets
| Primary Target | Pharmacology | Condition | Potency |
|---|---|---|---|
Target ID: CHEMBL231 Sources: https://www.ncbi.nlm.nih.gov/pubmed/11915520 |
|||
Target ID: O95665 Gene ID: 23620.0 Gene Symbol: NTSR2 Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/8647296 |
Conditions
| Condition | Modality | Targets | Highest Phase | Product |
|---|---|---|---|---|
| Palliative | LIVOSTIN Approved UseLIVOSTIN™ 0.05% (levocabastine hydrochloride ophthalmic suspension) is indicated for the temporary relief of the signs and symptoms of seasonal allergic conjunctivitis. Launch Date1993 |
Cmax
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
7.4 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/7907347/ |
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
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
319 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/7907347/ |
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
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
35.7 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/7907347/ |
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
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
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
| Dose | Population | Adverse 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) Sources: Blepharoconjunctivitis (3 patients) |
0.5 mg/mL 2 times / day multiple, ophthalmic Recommended Dose: 0.5 mg/mL, 2 times / day Route: ophthalmic Route: multiple Dose: 0.5 mg/mL, 2 times / day Sources: |
unhealthy, < 12 years Health Status: unhealthy Age Group: < 12 years Sex: M+F Sources: |
Other AEs: Eye disorders NEC... Other AEs: Eye disorders NEC (33 patients) Sources: |
0.5 mg/mL 2 times / day multiple, ophthalmic Recommended Dose: 0.5 mg/mL, 2 times / day Route: ophthalmic Route: multiple Dose: 0.5 mg/mL, 2 times / day Sources: |
unhealthy, > 12 years Health Status: unhealthy Age Group: > 12 years Sex: M+F Sources: |
Other AEs: Eye disorders NEC... Other AEs: Eye disorders NEC (7 patients) Sources: |
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
| AE | Significance | Dose | Population |
|---|---|---|---|
| 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 Dose: 0.5 mg/mL, 2 times / day Route: ophthalmic Route: multiple Dose: 0.5 mg/mL, 2 times / day Sources: |
unhealthy, < 12 years Health Status: unhealthy Age Group: < 12 years Sex: M+F Sources: |
| Eye disorders NEC | 7 patients | 0.5 mg/mL 2 times / day multiple, ophthalmic Recommended Dose: 0.5 mg/mL, 2 times / day Route: ophthalmic Route: multiple Dose: 0.5 mg/mL, 2 times / day Sources: |
unhealthy, > 12 years Health Status: unhealthy Age Group: > 12 years Sex: M+F Sources: |
| 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
| CYP3A4 | CYP2C9 | CYP2D6 | hERG |
|---|---|---|---|
Drug as perpetrator
| Target | Modality | Activity | Metabolite | Clinical evidence |
|---|---|---|---|---|
Page: 1.0 |
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
| Target | Modality | Activity | Metabolite | Clinical evidence |
|---|---|---|---|---|
Page: 1.0 |
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
| Title | Date | PubMed |
|---|---|---|
| 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 |
Sample Use Guides
The usual dose is one drop instilled in affected eyes four times per day.
Route of Administration:
Other
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/18680729
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
Edited
Mon Mar 31 18:06:53 GMT 2025
by
admin
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| Record UNII |
124XMA6YEI
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Validated (UNII)
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NCI_THESAURUS |
C29578
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FDA ORPHAN DRUG |
24787
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T-35
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C47582
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CHEMBL1615438
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124XMA6YEI
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1294532
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DTXSID9045508
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PARENT -> SALT/SOLVATE |
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
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IMPURITY -> PARENT |
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ACTIVE MOIETY |