Levocabastine

Levocabastine
Clinical data
Trade names	Livostin
AHFS/Drugs.com	Micromedex Detailed Consumer Information
Pregnancy; category	AU: B3; ;
Routes of; administration	Ophthalmic, intranasal
ATC code	R01AC02 (WHO) S01GX02 (WHO);
Legal status
Legal status	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 ;
PubChem CID	54385;
IUPHAR/BPS	1586;
DrugBank	DB01106 ;
ChemSpider	16736421 ;
UNII	H68BP06S81;
KEGG	D08117 ;
ChEMBL	ChEMBL1201312 ;
CompTox Dashboard (EPA)	DTXSID1048548 ;
Chemical and physical data
Formula	C26H29FN2O2
Molar mass	420.519 g/mol 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 ; Key:ZCGOMHNNNFPNMX-KYTRFIICSA-N ;
	(what is this?) (verify)

Levocabastine (trade name Livostin) is a selective second-generation H₁ receptor antagonist which was discovered at Janssen Pharmaceutica in 1979. It is used for allergic conjunctivitis.^[2]

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.^[3]^[4] This has made it a useful tool for the study of this receptor.^[5]^[6]^[7]^[8]^[9]

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.^[10]

References

^ "RxMed: Pharmaceutical Information - LIVOSTIN NASAL SPRAY". Retrieved 13 November 2005.
^ 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): 491–6. doi:10.1111/j.1398-9995.1985.tb00255.x. PMID 2866725.
^ 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): 400–5. doi:10.1007/BF00500016. PMID 3022160.
^ 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): 285–93. doi:10.1016/0014-2999(87)90285-8. PMID 2888670.
^ Chalon P, Vita N, Kaghad M, Guillemot M, Bonnin J, Delpech B, Le Fur G, Ferrara P, Caput D (May 1996). "Molecular cloning of a levocabastine-sensitive neurotensin binding site". FEBS Letters. 386 (2–3): 91–4. doi:10.1016/0014-5793(96)00397-3. PMID 8647296.
^ 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". Journal of Neuroscience. 16 (18): 5613–20. PMID 8795617.
^ Sarret P, Esdaile MJ, Perron A, Martinez J, Stroh T, Beaudet A (September 2005). "Potent spinal analgesia elicited through stimulation of NTS2 neurotensin receptors". Journal of Neuroscience. 25 (36): 8188–96. doi:10.1523/JNEUROSCI.0810-05.2005. PMID 16148226.
^ 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.
^ Yamauchi R, Wada E, Kamichi S, Yamada D, Maeno H, Delawary M, Nakazawa T, Yamamoto T, Wada K (September 2007). "Neurotensin type 2 receptor is involved in fear memory in mice". Journal of Neurochemistry. 102 (5): 1669–76. doi:10.1111/j.1471-4159.2007.04805.x. PMID 17697051.
^ "Levocabastine ophthalmic". http://www.vademecum.es/principios-activos-levocabastina+oftalmica-s01gx02. {{cite web}}: |access-date= requires |url= (help); External link in |website= (help); Missing or empty |url= (help)

External links

^[1]

Template:Neuropeptide agonists and antagonists

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^ "LIVOSTIN (levocabastine hydrochloride) Ophthalmic Suspension). Full Prescribing Information". DailyMed. Retrieved 4 January 2016.

[1] "RxMed: Pharmaceutical Information - LIVOSTIN NASAL SPRAY". Retrieved 13 November 2005.

[2] 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): 491–6. doi:10.1111/j.1398-9995.1985.tb00255.x. PMID 2866725.

[3] 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): 400–5. doi:10.1007/BF00500016. PMID 3022160.

[pmid2888670-4] 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): 285–93. doi:10.1016/0014-2999(87)90285-8. PMID 2888670.

[pmid8647296-5] Chalon P, Vita N, Kaghad M, Guillemot M, Bonnin J, Delpech B, Le Fur G, Ferrara P, Caput D (May 1996). "Molecular cloning of a levocabastine-sensitive neurotensin binding site". FEBS Letters. 386 (2–3): 91–4. doi:10.1016/0014-5793(96)00397-3. PMID 8647296.

[pmid8795617-6] 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". Journal of Neuroscience. 16 (18): 5613–20. PMID 8795617.

[pmid16148226-7] Sarret P, Esdaile MJ, Perron A, Martinez J, Stroh T, Beaudet A (September 2005). "Potent spinal analgesia elicited through stimulation of NTS2 neurotensin receptors". Journal of Neuroscience. 25 (36): 8188–96. doi:10.1523/JNEUROSCI.0810-05.2005. PMID 16148226.

[pmid17074405-8] 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.

[pmid17697051-9] Yamauchi R, Wada E, Kamichi S, Yamada D, Maeno H, Delawary M, Nakazawa T, Yamamoto T, Wada K (September 2007). "Neurotensin type 2 receptor is involved in fear memory in mice". Journal of Neurochemistry. 102 (5): 1669–76. doi:10.1111/j.1471-4159.2007.04805.x. PMID 17697051.

[10] "Levocabastine ophthalmic". http://www.vademecum.es/principios-activos-levocabastina+oftalmica-s01gx02. {{cite web}}: |access-date= requires |url= (help); External link in |website= (help); Missing or empty |url= (help)

[11] "LIVOSTIN (levocabastine hydrochloride) Ophthalmic Suspension). Full Prescribing Information". DailyMed. Retrieved 4 January 2016.

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