Levocabastine

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Levocabastine
Levocabastine.svg
Levocabastine 3D.png
Above: levocabastine molecular structure Below: 3D representation of levocabastine molecule
Clinical data
Trade names Livostin
AHFS/Drugs.com Micromedex Detailed Consumer Information
Pregnancy
category
  • AU:B3
Routes of
administration 		Ophthalmic, intranasal [1]
ATC code
Legal status
Legal status
Identifiers
  • (3S,4R)-1-[cis-4-cyano-4-(4-fluorophenyl)cyclohexyl]-3-methyl-4-phenyl-4-piperidinecarboxylic acid
CAS Number
PubChem CID
IUPHAR/BPS
DrugBank
ChemSpider
UNII
KEGG
ChEMBL
CompTox Dashboard (EPA)
Chemical and physical data
Formula C26H29FN2O2
Molar mass 420.528 g·mol−1
3D model (JSmol)
  • Fc1ccc(cc1)[C@]2(CC[C@@H](CC2)N3CC[C@@]([C@H](C)C3)(c4ccccc4)C(O)=O)C#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 Yes check.svgY
  • Key:ZCGOMHNNNFPNMX-KYTRFIICSA-N Yes check.svgY
 X mark.svgNYes check.svgY  (what is this?)    (verify)

Levocabastine (trade name Livostin or Livocab, depending on the region) is a selective second-generation H1 receptor antagonist which was discovered at Janssen Pharmaceutica in 1979. It is used for allergic conjunctivitis. [3]

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. [4] [5] This has made it a useful tool for the study of this receptor. [6] [7] [8] [9] [10]

The pharmaceutical drug Bilina is a combination of Levocabastine, benzalkonium chloride, and other components and is typically used in a 0.5 mg/ml suspension as eye-drops, dispensed in 4ml bottles for the treatment of allergic conjunctivitis or similar allergic ocular conditions. Another formulation is available as a nasal spray for the management of allergic rhinitis. [11] [12]

References

  1. ↑ "Livostin Nasal Spray". RxMed: Pharmaceutical Information. Retrieved 13 November 2005.
  2. ↑ "Livostin - levocabastine hydrochloride suspension". DailyMed. U.S. National Library of Medicine. Retrieved 4 January 2016.
  3. ↑ Pipkorn U, Bende M, Hedner J, Hedner T (October 1985). "A double-blind evaluation of topical levocabastine, a new specific H1 antagonist in patients with allergic conjunctivitis". Allergy. 40 (7): 491–496. doi:10.1111/j.1398-9995.1985.tb00255.x. PMID   2866725. S2CID   8681108.
  4. ↑ Schotte A, Leysen JE, Laduron PM (August 1986). "Evidence for a displaceable non-specific [3H]neurotensin binding site in rat brain". Naunyn-Schmiedeberg's Archives of Pharmacology. 333 (4): 400–405. doi:10.1007/BF00500016. PMID   3022160. S2CID   23692347.
  5. ↑ Kitabgi P, Rostène W, Dussaillant M, Schotte A, Laduron PM, Vincent JP (August 1987). "Two populations of neurotensin binding sites in murine brain: discrimination by the antihistamine levocabastine reveals markedly different radioautographic distribution". European Journal of Pharmacology. 140 (3): 285–293. doi:10.1016/0014-2999(87)90285-8. PMID   2888670.
  6. ↑ Chalon P, Vita N, Kaghad M, Guillemot M, Bonnin J, Delpech B, et al. (May 1996). "Molecular cloning of a levocabastine-sensitive neurotensin binding site". FEBS Letters. 386 (2–3): 91–94. doi: 10.1016/0014-5793(96)00397-3 . PMID   8647296. S2CID   5802578.
  7. ↑ Mazella J, Botto JM, Guillemare E, Coppola T, Sarret P, Vincent JP (September 1996). "Structure, functional expression, and cerebral localization of the levocabastine-sensitive neurotensin/neuromedin N receptor from mouse brain". The Journal of Neuroscience. 16 (18): 5613–5620. doi: 10.1523/JNEUROSCI.16-18-05613.1996 . PMC   6578974 . PMID   8795617.
  8. ↑ Sarret P, Esdaile MJ, Perron A, Martinez J, Stroh T, Beaudet A (September 2005). "Potent spinal analgesia elicited through stimulation of NTS2 neurotensin receptors". The Journal of Neuroscience. 25 (36): 8188–8196. doi: 10.1523/JNEUROSCI.0810-05.2005 . PMC   6725526 . PMID   16148226.
  9. ↑ Bredeloux P, Costentin J, Dubuc I (December 2006). "Interactions between NTS2 neurotensin and opioid receptors on two nociceptive responses assessed on the hot plate test in mice". Behavioural Brain Research. 175 (2): 399–407. doi:10.1016/j.bbr.2006.09.016. PMID   17074405. S2CID   24790151.
  10. ↑ Yamauchi R, Wada E, Kamichi S, Yamada D, Maeno H, Delawary M, et al. (September 2007). "Neurotensin type 2 receptor is involved in fear memory in mice". Journal of Neurochemistry. 102 (5): 1669–1676. doi: 10.1111/j.1471-4159.2007.04805.x . PMID   17697051. S2CID   19774998.
  11. ↑ "Levocabastine ophthalmic". vademecum.es. Retrieved 11 September 2014.
  12. ↑ "★ Levocabastina 🥇". www.vademecum.es. Retrieved 2024-09-16.
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