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MedKoo Cat#: 598722 | Name: Levocabastine HCl

Description:

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

Levocabastine HCl is an antihistaminic agent.

Chemical Structure

Levocabastine HCl
CAS#79547-78-7

Theoretical Analysis

MedKoo Cat#: 598722

Name: Levocabastine HCl

CAS#: 79547-78-7

Chemical Formula: C26H30ClFN2O2

Exact Mass:

Molecular Weight: 456.99

Elemental Analysis: C, 68.34; H, 6.62; Cl, 7.76; F, 4.16; N, 6.13; O, 7.00

Price and Availability

This product is currently not in stock but may be available through custom synthesis. To ensure cost efficiency, the minimum order quantity is 1 gram. The estimated lead time is 2 to 4 months, with pricing dependent on the complexity of the synthesis (typically high for intricate chemistries). Quotes for quantities below 1 gram will not be provided. To request a quote, please click the button below. Note: If this product becomes available in stock in the future, pricing will be listed accordingly.
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Related CAS #
79516-68-0 (free base) 79547-78-7 (HCl)
Synonym
Levocabastine hydrochloride; Levocabastine HCl; Livostin; R 50,547; R-50,547; R50,547;
IUPAC/Chemical Name
(3S,4R)-1-((1s,4R)-4-cyano-4-(4-fluorophenyl)cyclohexyl)-3-methyl-4-phenylpiperidine-4-carboxylic acid hydrochloride
InChi Key
OICFWWJHIMKBCD-VALQNVSPSA-N
InChi Code
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
SMILES Code
C[C@H]1[C@@](C(O)=O)(c2ccccc2)CCN([C@H]3CC[C@@](c4ccc(F)cc4)(C#N)CC3)C1.Cl
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
Shelf Life
>3 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
2934.99.03.00
More Info
Product Data
Product Data
Instruction
View handling instruction
Biological target:
Levocabastine (R 50547) hydrochloride is a potent and selective histamine H1-receptor antagonist.
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/
Solvent mg/mL mM comments
Solubility
PBS (pH 7.2) 0.3 0.72
Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 456.99 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.
1: 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. PubMed PMID: 26738992. 2: Murdoch RD, Bareille P, Ignar D, Mark S, Miller SR, Gupta A, Salapatek AM, Patel P. Once-daily dosing of levocabastine has comparable efficacy to twice-daily dosing in the treatment of allergic rhinitis assessed in an allergen challenge chamber. Int J Clin Pharmacol Ther. 2015 Oct;53(10):811-8. doi: 10.5414/CP202389. PubMed PMID: 26249767. 3: Murdoch RD, Bareille P, Ignar D, Miller SR, Gupta A, Boardley R, Zieglmayer P, Zieglmayer R, Lemel P, Horak F. The improved efficacy of a fixed-dose combination of fluticasone furoate and levocabastine relative to the individual components in the treatment of allergic rhinitis. Clin Exp Allergy. 2015 Aug;45(8):1346-55. doi: 10.1111/cea.12556. PubMed PMID: 25900517. 4: Allaire C, Siou-Mermet R, Bassols A. [Safety and efficacy of a new preservative-free levocabastine ophthalmic solution (Levofree®) using the conjunctival provocation test]. J Fr Ophtalmol. 2012 Sep;35(7):491-8. doi: 10.1016/j.jfo.2011.08.016. Epub 2012 Apr 10. French. PubMed PMID: 22498504. 5: Allen A, Murdoch RD, Bareille P, Burns O, Hughes S, Gupta A, Miller SR. Pharmacokinetics, Safety, and Tolerability of Once-Daily Intranasal Fluticasone Furoate and Levocabastine Administered Alone or Simultaneously as fluticasone Furoate/Levocabastine Fixed-Dose Combination. Clin Pharmacol Drug Dev. 2016 May;5(3):225-31. doi: 10.1002/cpdd.218. Epub 2015 Dec 4. PubMed PMID: 27163502. 6: Bahmer FA, Ruprecht KW. Safety and efficacy of topical levocabastine compared with oral terfenadine. Ann Allergy. 1994 May;72(5):429-34. PubMed PMID: 7909999. 7: 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. 8: 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. 9: 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. 10: Okubo K, Uchida E, Nogami S. Levocabastine nasal spray significantly improves perennial allergic rhinitis: a single-blind placebo-controlled study. Auris Nasus Larynx. 2010 Aug;37(4):436-42. doi: 10.1016/j.anl.2009.11.014. Epub 2010 Feb 6. PubMed PMID: 20138720. 11: Schata M, Jorde W, Richarz-Barthauer U. Levocabastine nasal spray better than sodium cromoglycate and placebo in the topical treatment of seasonal allergic rhinitis. J Allergy Clin Immunol. 1991 Apr;87(4):873-8. PubMed PMID: 1672878. 12: Hampel FC Jr, Martin BG, Dolen J, Travers S, Karcher K, Holton D. Efficacy and safety of levocabastine nasal spray for seasonal allergic rhinitis. Am J Rhinol. 1999 Jan-Feb;13(1):55-62. PubMed PMID: 10088031. 13: Stokes TC, Feinberg G. Rapid onset of action of levocabastine eye-drops in histamine-induced conjunctivitis. Clin Exp Allergy. 1993 Sep;23(9):791-4. PubMed PMID: 10779311. 14: Søhoel P, Freng BA, Kramer J, Poppe S, Rebo R, Korsrud FR, Garud O, Woxen OJ, Olsen AK. Topical levocabastine compared with orally administered terfenadine for the prophylaxis and treatment of seasonal rhinoconjunctivitis. J Allergy Clin Immunol. 1993 Jul;92(1 Pt 1):73-81. PubMed PMID: 8101534. 15: Bende M, Pipkorn U. Topical levocabastine, a selective H1 antagonist, in seasonal allergic rhinoconjunctivitis. Allergy. 1987 Oct;42(7):512-5. PubMed PMID: 2891316. 16: Fujishima H, Fukagawa K, Takano Y, Okamoto S, Nakagawa Y, Uchio E, Yokoi N, Fukushima A, Takamura E. The early efficacy of topical levocabastine in patients with allergic conjunctivitis. Allergol Int. 2006 Sep;55(3):301-3. PubMed PMID: 17075271. 17: 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. 18: Minami K, Hossen MA, Kamei C. Increasing effect by simultaneous use of levocabastine and pemirolast on experimental allergic conjunctivitis in rats. Biol Pharm Bull. 2005 Mar;28(3):473-6. PubMed PMID: 15744071. 19: Azevedo M, Castel-Branco MG, Oliveira JF, Ramos E, Delgado L, Almeida J. Double-blind comparison of levocabastine eye drops with sodium cromoglycate and placebo in the treatment of seasonal allergic conjunctivitis. Clin Exp Allergy. 1991 Nov;21(6):689-94. PubMed PMID: 1685691. 20: Frostad AB, Olsen AK. A comparison of topical levocabastine and sodium cromoglycate in the treatment of pollen-provoked allergic conjunctivitis. Clin Exp Allergy. 1993 May;23(5):406-9. PubMed PMID: 8101467.