Rupatadine
{{Short description|Second generation H1-antihistamine}}
{{Drugbox
| Verifiedfields = changed
| Watchedfields = changed
| verifiedrevid = 464384578
| image = Rupatadine.svg
| alt =
| image2 = Rupatadine ball and stick structure.png
| tradename = Rupafin, others
| Drugs.com = {{drugs.com|international|rupatadine}}
| pregnancy_AU =
| pregnancy_category =
| routes_of_administration = By mouth
| ATC_prefix = R06
| ATC_suffix = AX28
| legal_AU =
| legal_AU_comment =
| legal_BR =
| legal_BR_comment =
| legal_CA = Rx-only
| legal_CA_comment = {{cite web | title=Health Canada New Drug Authorizations: 2016 Highlights | website=Health Canada | date=14 March 2017 | url=https://www.canada.ca/en/health-canada/services/publications/drugs-health-products/health-canada-new-drug-authorizations-2016-highlights.html | access-date=7 April 2024}}
| legal_DE =
| legal_DE_comment =
| legal_NZ =
| legal_NZ_comment =
| legal_UK =
| legal_UK_comment =
| legal_US =
| legal_US_comment =
| legal_EU = Rx-only
| legal_UN =
| legal_UN_comment =
| legal_status = Rx-only
| bioavailability =
| protein_bound = 98–99%
| metabolism = Liver, CYP-mediated
| elimination_half-life = 5.9 hours
| excretion = 34.6% urine, 60.9% faeces
| CAS_number_Ref = {{cascite|changed|??}}
| CAS_number = 158876-82-5
| CAS_supplemental = (free base)
{{CAS|182349-12-8}} (fumarate)
| PubChem = 133017
| DrugBank_Ref = {{drugbankcite|changed|drugbank}}
| DrugBank = DB11614
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 117388
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = 2AE8M83G3E
| ChEBI = 135673
| ChEMBL_Ref = {{ebicite|correct|EBI}}
| ChEMBL = 91397
| KEGG_Ref = {{keggcite|changed|kegg}}
| KEGG = D07407
| IUPAC_name = 8-Chloro-6,11-dihydro-11-[1-[(5-methyl-3-pyridinyl)methyl]-4-piperidinylidene]-5H-benzo[5,6]cyclohepta[1,2-b]pyridine fumarate
| C=26 | H=26 | Cl=1 | N=3
| smiles = Clc1cc5c(cc1)\C(=C3/CCN(Cc2cncc(c2)C)CC3)c4ncccc4CC5
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 1S/C26H26ClN3/c1-18-13-19(16-28-15-18)17-30-11-8-20(9-12-30)25-24-7-6-23(27)14-22(24)5-4-21-3-2-10-29-26(21)25/h2-3,6-7,10,13-16H,4-5,8-9,11-12,17H2,1H3
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = WUZYKBABMWJHDL-UHFFFAOYSA-N
}}
Rupatadine is a second generation antihistamine and platelet-activating factor antagonist used to treat allergies. It was discovered and developed by {{Interlanguage link|Grupo Uriach|lt=Uriach|es}}Patents: {{Patent|EP|577957}}, {{Patent|US|5407941}}, {{Patent|US|5476856}} and is marketed as Rupafin and under several other trade names.
Medical uses
Rupatadine fumarate has been approved for the treatment of allergic rhinitis and chronic urticaria in adults and children over 12 years. It is available as round, light salmon coloured tablets containing 10 mg of rupatadine (as fumarate) to be administered orally, once a day.[https://www.drugs.com/uk/pdf/leaflet/841244.pdf?download=1 UK package leaflet for Rupafin] {{Webarchive|url=https://web.archive.org/web/20180210003154/https://www.drugs.com/uk/pdf/leaflet/841244.pdf?download=1 |date=2018-02-10 }}.
The efficacy of rupatadine as treatment for allergic rhinitis (AR) and chronic idiopathic urticaria (CIU) has been investigated in adults and adolescents (aged over 12 years) in several controlled studies, showing a rapid onset of action and a good safety profile even in prolonged treatment periods of a year.{{cite journal | vauthors = Keam SJ, Plosker GL | title = Rupatadine: a review of its use in the management of allergic disorders | journal = Drugs | volume = 67 | issue = 3 | pages = 457–474 | year = 2007 | pmid = 17335300 | doi = 10.2165/00003495-200767030-00008 | s2cid = 195691512 }}{{cite journal | vauthors = Mullol J, Bousquet J, Bachert C, Canonica WG, Gimenez-Arnau A, Kowalski ML, Martí-Guadaño E, Maurer M, Picado C, Scadding G, Van Cauwenberge P | display-authors = 6 | title = Rupatadine in allergic rhinitis and chronic urticaria | journal = Allergy | volume = 63 | issue = Suppl 87 | pages = 5–28 | date = April 2008 | pmid = 18339040 | doi = 10.1111/j.1398-9995.2008.01640.x | doi-access = free }}
Side effects
Rupatadine is a non-sedating antihistamine. However, as in other non sedating second-generation antihistamines, the most common side effects in controlled clinical studies were somnolence, headaches and fatigue.
Pharmacology
= Mechanism of action =
Rupatadine is a second generation, non-sedating, long-acting histamine antagonist with selective peripheral H1 receptor antagonist activity. It further blocks the receptors of the platelet-activating factor (PAF) according to in vitro and in vivo studies.{{cite journal | vauthors = Merlos M, Giral M, Balsa D, Ferrando R, Queralt M, Puigdemont A, García-Rafanell J, Forn J | display-authors = 6 | title = Rupatadine, a new potent, orally active dual antagonist of histamine and platelet-activating factor (PAF) | journal = The Journal of Pharmacology and Experimental Therapeutics | volume = 280 | issue = 1 | pages = 114–121 | date = January 1997 | doi = 10.1016/S0022-3565(24)36413-4 | pmid = 8996188 }}
Rupatadine possesses anti-allergic properties such as the inhibition of the degranulation of mast cells induced by immunological and non-immunological stimuli, and inhibition of the release of cytokines, particularly of the tumor necrosis factors (TNF) in human mast cells and monocytes.{{cite journal | vauthors = Picado C | title = Rupatadine: pharmacological profile and its use in the treatment of allergic disorders | journal = Expert Opinion on Pharmacotherapy | volume = 7 | issue = 14 | pages = 1989–2001 | date = October 2006 | pmid = 17020424 | doi = 10.1517/14656566.7.14.1989 | s2cid = 38337440 }}
= Pharmacokinetics =
Rupatadine has several active metabolites such as desloratadine, 3-hydroxydesloratadine,{{cite journal | vauthors = Solans A, Carbó ML, Peña J, Nadal T, Izquierdo I, Merlos M | title = Influence of food on the oral bioavailability of rupatadine tablets in healthy volunteers: a single-dose, randomized, open-label, two-way crossover study | journal = Clinical Therapeutics | volume = 29 | issue = 5 | pages = 900–908 | date = May 2007 | pmid = 17697908 | doi = 10.1016/j.clinthera.2007.05.004 }} 5-hydroxydesloratadine and 6-hydroxydesloratadine.{{cite journal | vauthors = Kapoor Y, Kumar K | title = Structural and clinical impact of anti-allergy agents: An overview | journal = Bioorganic Chemistry | volume = 94 | pages = 103351 | date = January 2020 | pmid = 31668464 | doi = 10.1016/j.bioorg.2019.103351 | s2cid = 204968012 }}
History
Rupatadine discovery, pre-clinical and clinical development was performed by Uriach, a Spanish pharmaceutical company. It was launched in 2003 in Spain under the brand name of Rupafin. It was launched in Canada under the name Rupall.{{cite web | title = Pediapharm Announces the Commercial Launch of Rupall (rupatadine) in Canada | url = http://www.pedia-pharm.com/en/press-releases/pediapharm-announces-the-commercial-launch-of-rupall-rupatadine-in-canada/ | archive-url = https://web.archive.org/web/20191028165951/http://www.pedia-pharm.com/en/press-releases/pediapharm-announces-the-commercial-launch-of-rupall-rupatadine-in-canada/ | archive-date = 28 October 2019| publisher = Pediapharm | date = January 25, 2017 }}
Brand names
Brand names include Rupafin, Rupall, Rupanase, Rinialer, Pafinur, Rupax, Urtimed, Wystamm and Ralif, Rupita (EURO Pharma Ltd.)among others.{{drugs.com|international|rupatadine}}: Rupatadine.
References
{{Reflist}}
{{Antihistamines}}
{{Histaminergics}}
{{PAF signaling}}
{{Tricyclics}}
{{Portal bar | Medicine}}
Category:H1 receptor antagonists