Details
Stereochemistry | ABSOLUTE |
Molecular Formula | C26H29FN2O2 |
Molecular Weight | 420.5191 |
Optical Activity | UNSPECIFIED |
Defined Stereocenters | 4 / 4 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
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
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 |
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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 |
|
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 |
|
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 |
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 |
|
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 |
|
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 |
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% |
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 |
|
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 |
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: Page: 12 |
unhealthy, 5 - 17 years n = 24 Health Status: unhealthy Condition: paralimbic keratitis of immuno-allergic type Age Group: 5 - 17 years Sex: M+F Population Size: 24 Sources: Page: 12 |
Disc. AE: Headache, Blepharoconjunctivitis... AEs leading to discontinuation/dose reduction: Headache (3 patients) Sources: Page: 12Blepharoconjunctivitis (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 Co-administed with:: sodium cromoglycate nasal spray(20 mg/ml) Sources: |
unhealthy, < 12 years n = 177 Health Status: unhealthy Condition: allergic conjunctivitis Age Group: < 12 years Sex: M+F Population Size: 177 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 Co-administed with:: sodium cromoglycate nasal spray(20 mg/ml) Sources: |
unhealthy, > 12 years n = 56 Health Status: unhealthy Condition: allergic conjunctivitis Age Group: > 12 years Sex: M+F Population Size: 56 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: Page: 11 |
unhealthy, adult n = 148 Health Status: unhealthy Condition: allergic conjunctivitis Age Group: adult Sex: unknown Population Size: 148 Sources: Page: 11 |
Disc. AE: Eye disorders NEC... AEs leading to discontinuation/dose reduction: Eye disorders NEC (23 patients) Sources: Page: 11 |
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 n = 137 Health Status: unhealthy Condition: seasonal allergic rhinitis Age Group: mean 38.8 years Sex: M+F Population Size: 137 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: Page: 12 |
unhealthy, 5 - 17 years n = 24 Health Status: unhealthy Condition: paralimbic keratitis of immuno-allergic type Age Group: 5 - 17 years Sex: M+F Population Size: 24 Sources: Page: 12 |
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: Page: 12 |
unhealthy, 5 - 17 years n = 24 Health Status: unhealthy Condition: paralimbic keratitis of immuno-allergic type Age Group: 5 - 17 years Sex: M+F Population Size: 24 Sources: Page: 12 |
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 Co-administed with:: sodium cromoglycate nasal spray(20 mg/ml) Sources: |
unhealthy, < 12 years n = 177 Health Status: unhealthy Condition: allergic conjunctivitis Age Group: < 12 years Sex: M+F Population Size: 177 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 Co-administed with:: sodium cromoglycate nasal spray(20 mg/ml) Sources: |
unhealthy, > 12 years n = 56 Health Status: unhealthy Condition: allergic conjunctivitis Age Group: > 12 years Sex: M+F Population Size: 56 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: Page: 11 |
unhealthy, adult n = 148 Health Status: unhealthy Condition: allergic conjunctivitis Age Group: adult Sex: unknown Population Size: 148 Sources: Page: 11 |
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 |
---|---|---|
Evidence for a displaceable non-specific [3H]neurotensin binding site in rat brain. | 1986 Aug |
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Selective effect of levocabastine on histamine receptor and histamine release from human leukocytes and guinea pig isolated tissue. | 1996 Apr |
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Molecular cloning of a levocabastine-sensitive neurotensin binding site. | 1996 May 20 |
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Structure, functional expression, and cerebral localization of the levocabastine-sensitive neurotensin/neuromedin N receptor from mouse brain. | 1996 Sep 15 |
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Stable expression of the mouse levocabastine-sensitive neurotensin receptor in HEK 293 cell line: binding properties, photoaffinity labeling, and internalization mechanism. | 1998 Feb 13 |
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Actual therapeutic management of allergic and hyperreactive nasal disorders. | 2004 |
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Comparison of allergen immunotherapy and drug treatment in seasonal rhinoconjunctivitis: a 3-years study. | 2005 Feb |
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[Comparison of three antiallergic eyedrops in a specific conjunctival provocation test: mequitazine, levocabastine and dexamethasone]. | 2005 Mar |
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The reliability, validity, and preliminary responsiveness of the Eye Allergy Patient Impact Questionnaire (EAPIQ). | 2005 Oct 31 |
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Efficacy, cost-effectiveness, and tolerability of mometasone furoate, levocabastine, and disodium cromoglycate nasal sprays in the treatment of seasonal allergic rhinitis. | 2005 Sep |
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Potent spinal analgesia elicited through stimulation of NTS2 neurotensin receptors. | 2005 Sep 7 |
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Effect of antihistamine eye drops on the conjunctival provocation test with Japanese cedar pollen allergen. | 2006 Dec |
|
Effect of beta-lactotensin on acute stress and fear memory. | 2006 Dec |
|
Interactions between NTS2 neurotensin and opioid receptors on two nociceptive responses assessed on the hot plate test in mice. | 2006 Dec 15 |
|
[Misleading advertisement on Opatanol]. | 2006 Jul 1 |
|
Efficacy of levocabastine hydrochloride ophthalmic suspension in the conjunctival allergen challenge test in Japanese subjects with seasonal allergic conjunctivitis. | 2006 Jun |
|
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 Jun 13 |
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Preferential inhibition of human phosphodiesterase 4 by ibudilast. | 2006 May 1 |
|
The early efficacy of topical levocabastine in patients with allergic conjunctivitis. | 2006 Sep |
|
Review of azelastine nasal spray in the treatment of allergic and non-allergic rhinitis. | 2007 Apr |
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Seasonal allergic rhinitis in adolescents and adults. | 2007 Apr 1 |
|
Clinical and biological efficacy of preservative-free NAAGA eye-drops versus levocabastine eye-drops in vernal keratoconjunctivitis patients. | 2007 Dec |
|
Inhibition of release of inflammatory mediators in primary and cultured cells by a Chinese herbal medicine formula for allergic rhinitis. | 2007 Feb 15 |
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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 Jun |
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The effect of levocabastine and furosemide pretreatment on hyperreactive response after nasal provocation with hypotonic aerosol in subjects with allergic rhinitis. | 2007 Nov |
|
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 |
|
[Intra-annual and seasonal allergic conjunctivitis treatment: comparison of two therapeutic protocols]. | 2008 Dec |
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Drug use in children: cohort study in three European countries. | 2008 Nov 24 |
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Effectiveness of twice daily azelastine nasal spray in patients with seasonal allergic rhinitis. | 2008 Oct |
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Randomized double-blind placebo-controlled trial of sublingual immunotherapy in children with house dust mite allergy in primary care: study design and recruitment. | 2008 Oct 20 |
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Treatment of allergic conjunctivitis with olopatadine hydrochloride eye drops. | 2008 Sep |
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Contribution of alpha4beta1 integrin to the antiallergic effect of levocabastine. | 2008 Sep 15 |
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The effect of levocabastine hydrochloride on human Tenon's capsule fibroblasts: inhibition of proliferation, suppression of DNA synthesis and induction of apoptosis. | 2009 |
|
Role of histamine H(4) receptor in allergic conjunctivitis in mice. | 2009 Apr 17 |
|
beta-Lactotensin derived from bovine beta-lactoglobulin suppresses food intake via the CRF system followed by the CGRP system in mice. | 2009 Dec |
|
Evidence for a role of NTS2 receptors in the modulation of tonic pain sensitivity. | 2009 Jul 6 |
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Azelastine nasal spray for the treatment of allergic and nonallergic rhinitis. | 2009 Nov |
|
[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 Oct |
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NT69L, a novel analgesic, shows synergy with morphine. | 2009 Oct 19 |
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Treatment of congestion in upper respiratory diseases. | 2010 Apr 8 |
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Levocabastine nasal spray significantly improves perennial allergic rhinitis: a single-blind placebo-controlled study. | 2010 Aug |
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Evaluation of histamine-induced conjunctival oedema in guinea pigs by means of image analysis. | 2010 Dec |
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Relation between cooling sheet effect and tear histamine concenration in allergic conjunctivitis. | 2010 Jul |
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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 Jul |
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Neurotensin is a regulator of insulin secretion in pancreatic beta-cells. | 2010 Oct |
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Clinical utility and patient adherence with ebastine for allergic rhinitis. | 2010 Oct 14 |
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Azelastine hydrochloride, a dual-acting anti-inflammatory ophthalmic solution, for treatment of allergic conjunctivitis. | 2010 Sep 7 |
|
Treatment of allergic conjunctivitis: results of a 1-month, single-masked randomized study. | 2010 Sep-Oct |
|
Spinal NTS2 receptor activation reverses signs of neuropathic pain. | 2013 Sep |
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
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Classification Tree | Code System | Code | ||
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NCI_THESAURUS |
C29578
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WHO-VATC |
QR01AC02
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WHO-VATC |
QS01GX02
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WHO-ATC |
R01AC02
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WHO-ATC |
S01GX02
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LEVOCABASTINE
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SUB08465MIG
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C61806
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H68BP06S81
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79516-68-0
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1564
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1586
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Levocabastine
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C047340
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DTXSID1048548
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H68BP06S81
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CHEMBL1615438
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DB01106
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100000082806
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28627
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m6785
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5393
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ACTIVE MOIETY
SALT/SOLVATE (PARENT)