Levocabastine

{{Short description|Chemical compound}}

{{Drugbox

| Verifiedfields = changed

| Watchedfields = changed

| verifiedrevid = 462090822

| image = Levocabastine.svg

| width = 260

| caption = Above: levocabastine molecular structure

Below: 3D representation of levocabastine molecule

| image2 = Levocabastine 3D.png

| tradename = Livostin

| Drugs.com = {{drugs.com|CONS|levocabastine}}

| pregnancy_AU = B3

| pregnancy_US = C

| legal_US = Rx-only

| legal_US_comment = {{cite web|title=Livostin - levocabastine hydrochloride suspension |url=http://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=420b3f66-87f0-47d8-947c-541e84eb594a| work = DailyMed | publisher = U.S. National Library of Medicine |access-date=4 January 2016}}

| legal_status = Rx-only

| routes_of_administration = Ophthalmic, intranasal{{cite web | url = http://www.rxmed.com/b.main/b2.pharmaceutical/b2.1.monographs/CPS-%20Monographs/CPS-%20(General%20Monographs-%20L)/LIVOSTIN%20NASAL%20SPRAY.html | work = RxMed: Pharmaceutical Information | title = Livostin Nasal Spray | access-date = 13 November 2005}}

| ATC_prefix = R01

| ATC_suffix = AC02

| ATC_supplemental = {{ATC|S01|GX02}}

| bioavailability =

| protein_bound =

| metabolism =

| elimination_half-life =

| CAS_number_Ref = {{cascite|correct|??}}

| CAS_number = 79516-68-0

| PubChem = 54385

| IUPHAR_ligand = 1586

| DrugBank_Ref = {{drugbankcite|correct|drugbank}}

| DrugBank = DB01106

| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}

| ChemSpiderID = 16736421

| UNII_Ref = {{fdacite|correct|FDA}}

| UNII = H68BP06S81

| KEGG_Ref = {{keggcite|correct|kegg}}

| KEGG = D08117

| ChEMBL_Ref = {{ebicite|changed|EBI}}

| ChEMBL = 1201312

| IUPAC_name = (3S,4R)-1-[cis-4-cyano-4-(4-fluorophenyl)cyclohexyl]-3-methyl-4-phenyl-4-piperidinecarboxylic acid

| C = 26

| H = 29

| F = 1

| N = 2

| O = 2

| smiles = Fc1ccc(cc1)[C@]2(CC[C@@H](CC2)N3CC[C@@]([C@H](C)C3)(c4ccccc4)C(O)=O)C#N

| StdInChI_Ref = {{stdinchicite|correct|chemspider}}

| StdInChI = 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

| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}

| StdInChIKey = ZCGOMHNNNFPNMX-KYTRFIICSA-N

}}

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.{{cite journal | vauthors = Pipkorn U, Bende M, Hedner J, Hedner T | title = A double-blind evaluation of topical levocabastine, a new specific H1 antagonist in patients with allergic conjunctivitis | journal = Allergy | volume = 40 | issue = 7 | pages = 491–496 | date = October 1985 | pmid = 2866725 | doi = 10.1111/j.1398-9995.1985.tb00255.x | s2cid = 8681108 }}

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.{{cite journal | vauthors = Schotte A, Leysen JE, Laduron PM | title = Evidence for a displaceable non-specific [3H]neurotensin binding site in rat brain | journal = Naunyn-Schmiedeberg's Archives of Pharmacology | volume = 333 | issue = 4 | pages = 400–405 | date = August 1986 | pmid = 3022160 | doi = 10.1007/BF00500016 | s2cid = 23692347 }}{{cite journal | vauthors = Kitabgi P, Rostène W, Dussaillant M, Schotte A, Laduron PM, Vincent JP | title = Two populations of neurotensin binding sites in murine brain: discrimination by the antihistamine levocabastine reveals markedly different radioautographic distribution | journal = European Journal of Pharmacology | volume = 140 | issue = 3 | pages = 285–293 | date = August 1987 | pmid = 2888670 | doi = 10.1016/0014-2999(87)90285-8 }} This has made it a useful tool for the study of this receptor.{{cite journal | vauthors = Chalon P, Vita N, Kaghad M, Guillemot M, Bonnin J, Delpech B, Le Fur G, Ferrara P, Caput D | display-authors = 6 | title = Molecular cloning of a levocabastine-sensitive neurotensin binding site | journal = FEBS Letters | volume = 386 | issue = 2–3 | pages = 91–94 | date = May 1996 | pmid = 8647296 | doi = 10.1016/0014-5793(96)00397-3 | s2cid = 5802578 | doi-access = free }}{{cite journal | vauthors = Mazella J, Botto JM, Guillemare E, Coppola T, Sarret P, Vincent JP | title = Structure, functional expression, and cerebral localization of the levocabastine-sensitive neurotensin/neuromedin N receptor from mouse brain | journal = The Journal of Neuroscience | volume = 16 | issue = 18 | pages = 5613–5620 | date = September 1996 | pmid = 8795617 | pmc = 6578974 | doi = 10.1523/JNEUROSCI.16-18-05613.1996 | doi-access = free }}{{cite journal | vauthors = Sarret P, Esdaile MJ, Perron A, Martinez J, Stroh T, Beaudet A | title = Potent spinal analgesia elicited through stimulation of NTS2 neurotensin receptors | journal = The Journal of Neuroscience | volume = 25 | issue = 36 | pages = 8188–8196 | date = September 2005 | pmid = 16148226 | pmc = 6725526 | doi = 10.1523/JNEUROSCI.0810-05.2005 | doi-access = free }}{{cite journal | vauthors = Bredeloux P, Costentin J, Dubuc I | title = Interactions between NTS2 neurotensin and opioid receptors on two nociceptive responses assessed on the hot plate test in mice | journal = Behavioural Brain Research | volume = 175 | issue = 2 | pages = 399–407 | date = December 2006 | pmid = 17074405 | doi = 10.1016/j.bbr.2006.09.016 | s2cid = 24790151 }}{{cite journal | vauthors = Yamauchi R, Wada E, Kamichi S, Yamada D, Maeno H, Delawary M, Nakazawa T, Yamamoto T, Wada K | display-authors = 6 | title = Neurotensin type 2 receptor is involved in fear memory in mice | journal = Journal of Neurochemistry | volume = 102 | issue = 5 | pages = 1669–1676 | date = September 2007 | pmid = 17697051 | doi = 10.1111/j.1471-4159.2007.04805.x | s2cid = 19774998 | doi-access = free }}

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.{{cite web|title=Levocabastine ophthalmic|website=vademecum.es |url=http://www.vademecum.es/principios-activos-levocabastina+oftalmica-s01gx02|access-date=11 September 2014}}{{Cite web |title=★ Levocabastina 🥇 |url=https://www.vademecum.es/principios-activos-levocabastina-r01ac02-es |access-date=2024-09-16 |website=www.vademecum.es}}