Levocabastine

    WARNING: This product is for research use only, not for human or veterinary use.

MedKoo CAT#: 318097

CAS#: 79516-68-0

Description: Levocabastine is a selective second-generation H1 receptor antagonists. It is used for allergic conjunctivitis. As well as acting as an antihistamine, levocabastine has also subsequently been found to act as a potent and selective antagonist for the neurotensin receptor NTS2, and was the first drug used to characterise the different neurotensin subtypes. This has made it a useful tool for the study of this receptor.

Chemical Structure

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Levocabastine
CAS# 79516-68-0
Product data Instruction

Theoretical Analysis

MedKoo Cat#: 318097
Name: Levocabastine
CAS#: 79516-68-0
Chemical Formula: C26H29FN2O2
Exact Mass: 420.22
Molecular Weight: 420.519
Elemental Analysis: C, 74.26; H, 6.95; F, 4.52; N, 6.66; O, 7.61

Price and Availability

This product is not in stock, which may be available by custom synthesis. For cost-effective reason, minimum order is 1g (price is usually high, lead time is 2~3 months, depending on the technical challenge). Quote less than 1g will not be provided. To request quote, please email to sales @medkoo.com or click below button.
Note: Price will be listed if it is available in the future.

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Synonym: Levocabastine, Livostin, Bilina

IUPAC/Chemical Name: (3S,4R)-1-[4-cyano-4-(4-fluorophenyl)cyclohexyl]-3-methyl-4-phenylpiperidine-4-carboxylic acid

InChi Key: ZCGOMHNNNFPNMX-YHYDXASRSA-N

InChi Code: 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

SMILES Code: O=C([C@@]1(C2=CC=CC=C2)[C@H](C)CN(C3CCC(C4=CC=C(F)C=C4)(C#N)CC3)CC1)O

Appearance: Solid powder

Purity: >98% (or refer to the Certificate of Analysis)

Shipping Condition: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility: Soluble in DMSO, not in water

Shelf Life: >2 years if stored properly

Drug Formulation: This drug may be formulated in DMSO

Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code: 2934.99.9001

More Info:

Product Data:
Product Data
Instruction:
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Biological target: Levocabastine is a selective second-generation H1 receptor antagonists.
In vitro activity: Levocabastine hydrochloride (10(-4) M), ketotifen fumarate (3 x 10(-5) M) and tranilast (10(-4) M) significantly inhibited proliferation of fibroblasts. Levocabastine hydrochloride (10(-4) M), ketotifen fumarate (10(-4) M) and tranilast (10(-3) M) inhibited DNA synthesis and induced apoptosis. Reference: Cutan Ocul Toxicol. 2009;28(2):83-9. https://pubmed.ncbi.nlm.nih.gov/19473114/
In vivo activity: Male Wistar rats received a single (i.p.) dose of levocabastine (50 μg/kg) or saline solution (controls) and were decapitated 18 h later. After levocabastine treatment, protein expression of PSD-95, GluN2B and β-actin decreased 97, 45 and 55%, respectively, whereas that of iNOS enhanced 3.5-fold versus controls. Results suggested that levocabastine administration induces alterations in synaptic proteins of the protein complex PSD-95/NMDA receptor/nNOS and in neuron cytoskeleton. Reference: Neurochem Int. 2021 Sep;148:105100. https://pubmed.ncbi.nlm.nih.gov/34139299/

Preparing Stock Solutions

The following data is based on the product molecular weight 420.52 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
Formulation protocol: 1. Asaoka R, Nakagamil T, Zhu H, Liu Y, Hotta Y. The effect of levocabastine hydrochloride on human Tenon's capsule fibroblasts: inhibition of proliferation, suppression of DNA synthesis and induction of apoptosis. Cutan Ocul Toxicol. 2009;28(2):83-9. doi: 10.1080/15569520902937901. PMID: 19473114. 2. Qasem AR, Bucolo C, Baiula M, Spartà A, Govoni P, Bedini A, Fascì D, Spampinato S. Contribution of alpha4beta1 integrin to the antiallergic effect of levocabastine. Biochem Pharmacol. 2008 Sep 15;76(6):751-62. doi: 10.1016/j.bcp.2008.07.007. Epub 2008 Jul 15. PMID: 18680729. 3. Lores-Arnaiz S, Karadayian AG, Gutnisky A, Miranda J, Rodríguez de Lores Arnaiz G. Changes in synaptic proteins of the complex PSD-95/NMDA receptor/nNOS and mitochondrial dysfunction after levocabastine treatment. Neurochem Int. 2021 Sep;148:105100. doi: 10.1016/j.neuint.2021.105100. Epub 2021 Jun 15. PMID: 34139299. 4. Gutnisky A, López Ordieres MG, Rodríguez de Lores Arnaiz G. The Administration of Levocabastine, a NTS2 Receptor Antagonist, Modifies Na(+), K(+)-ATPase Properties. Neurochem Res. 2016 Jun;41(6):1274-80. doi: 10.1007/s11064-015-1823-7. Epub 2016 Jan 7. PMID: 26738992.
In vitro protocol: 1. Asaoka R, Nakagamil T, Zhu H, Liu Y, Hotta Y. The effect of levocabastine hydrochloride on human Tenon's capsule fibroblasts: inhibition of proliferation, suppression of DNA synthesis and induction of apoptosis. Cutan Ocul Toxicol. 2009;28(2):83-9. doi: 10.1080/15569520902937901. PMID: 19473114. 2. Qasem AR, Bucolo C, Baiula M, Spartà A, Govoni P, Bedini A, Fascì D, Spampinato S. Contribution of alpha4beta1 integrin to the antiallergic effect of levocabastine. Biochem Pharmacol. 2008 Sep 15;76(6):751-62. doi: 10.1016/j.bcp.2008.07.007. Epub 2008 Jul 15. PMID: 18680729.
In vivo protocol: 1. Lores-Arnaiz S, Karadayian AG, Gutnisky A, Miranda J, Rodríguez de Lores Arnaiz G. Changes in synaptic proteins of the complex PSD-95/NMDA receptor/nNOS and mitochondrial dysfunction after levocabastine treatment. Neurochem Int. 2021 Sep;148:105100. doi: 10.1016/j.neuint.2021.105100. Epub 2021 Jun 15. PMID: 34139299. 2. Gutnisky A, López Ordieres MG, Rodríguez de Lores Arnaiz G. The Administration of Levocabastine, a NTS2 Receptor Antagonist, Modifies Na(+), K(+)-ATPase Properties. Neurochem Res. 2016 Jun;41(6):1274-80. doi: 10.1007/s11064-015-1823-7. Epub 2016 Jan 7. PMID: 26738992.

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1: 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. Review. Japanese. PubMed PMID: 11915520.

2: Noble S, McTavish D. Levocabastine. An update of its pharmacology, clinical efficacy and tolerability in the topical treatment of allergic rhinitis and conjunctivitis. Drugs. 1995 Dec;50(6):1032-49. Review. PubMed PMID: 8612470.

3: Heykants J, Van Peer A, Van de Velde V, Snoeck E, Meuldermans W, Woestenborghs R. The pharmacokinetic properties of topical levocabastine. A review. Clin Pharmacokinet. 1995 Oct;29(4):221-30. Review. PubMed PMID: 8549024.

4: Bahmer FA. Topical levocabastine--an effective alternative to oral antihistamines in seasonal allergic rhinoconjunctivitis. Clin Exp Allergy. 1995 Mar;25(3):220-7. Review. PubMed PMID: 7788568.

5: Knight A. The role of levocabastine in the treatment of allergic rhinoconjunctivitis. Br J Clin Pract. 1994 May-Jun;48(3):139-43. Review. PubMed PMID: 7913336.

6: Janssens MM, Vanden Bussche G. Levocabastine: an effective topical treatment of allergic rhinoconjunctivitis. Clin Exp Allergy. 1991 May;21 Suppl 2:29-36. Review. PubMed PMID: 1680536.

7: Dechant KL, Goa KL. Levocabastine. A review of its pharmacological properties and therapeutic potential as a topical antihistamine in allergic rhinitis and conjunctivitis. Drugs. 1991 Feb;41(2):202-24. Review. PubMed PMID: 1709851.

8: Abelson MB, Weintraub D. Levocabastine eye drops: a new approach for the treatment of acute allergic conjunctivitis. Eur J Ophthalmol. 1994 Apr-Jun;4(2):91-101. Review. PubMed PMID: 7950341.

9: Janssens MM. Levocabastine: a new topical approach for the treatment of paediatric allergic rhinoconjunctivitis. Rhinol Suppl. 1992 Sep;13:39-49. Review. PubMed PMID: 1358140.

10: Janssens M. Efficacy of levocabastine in conjunctival provocation studies. Doc Ophthalmol. 1992;82(4):341-51. Review. PubMed PMID: 1363980.