Levocabastine

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]

Levocabastine

Clinical data
Trade names	Livostin
AHFS/Drugs.com	Micromedex Detailed Consumer Information
Pregnancy category	AU: B3
Routes of administration	Ophthalmic, intranasal^[1]
ATC code	R01AC02 (WHO) S01GX02 (WHO)
Legal status
Legal status	US: ℞-only^[2] In general: ℞ (Prescription only)
Identifiers
IUPAC name (3S,4R)-1-[cis-4-cyano-4-(4-fluorophenyl)cyclohexyl]-3-methyl-4-phenyl-4-piperidinecarboxylic acid
CAS Number	79516-68-0^Y
PubChem CID	54385
IUPHAR/BPS	1586
DrugBank	DB01106^Y
ChemSpider	16736421^Y
UNII	H68BP06S81
KEGG	D08117^Y
ChEMBL	ChEMBL1201312^N
CompTox Dashboard (EPA)	DTXSID1048548
Chemical and physical data
Formula	C26H29FN2O2
Molar mass	420.528 g·mol^−1
3D model (JSmol)	Interactive image
SMILES Fc1ccc(cc1)[C@]2(CC[C@@H](CC2)N3CC[C@@]([C@H](C)C3)(c4ccccc4)C(O)=O)C#N
InChI 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^Y Key:ZCGOMHNNNFPNMX-KYTRFIICSA-N^Y
^NY (what is this?)  (verify)

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.^[11]

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.

External links

• "Levocabastine". Drug Information Portal. U.S. National Library of Medicine.
• "Levocabastine hydrochloride". Drug Information Portal. U.S. National Library of Medicine.