Rupatadine

Overview

Rupatadine is a second generation antihistamine and platelet-activating factor antagonist used to treat allergies. It was discovered and developed by and is marketed as Rupafin and under several other trade names.[1][2] WP⚠ Part of this sentence could not be copied from the source. Open the source to read it in full.

Uses, dosage and effects

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.[3] WP

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.[4][5][6] WP

Risks and side effects

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. WP

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.[7] WP

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.[4] WP

Pharmacokinetics

Rupatadine has several active metabolites such as desloratadine, 3-hydroxydesloratadine, 5-hydroxydesloratadine and 6-hydroxydesloratadine.[8][9] WP

History

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.[10] WP

Chemistry

Formula

C26H26ClN3 PC

CAS number

158876-82-5 PC

Molar mass (g/mol)

416.0 PC

IUPAC name (computed by PubChem)

13-chloro-2-[1-[(5-methyl-3-pyridinyl)methyl]piperidin-4-ylidene]-4-azatricyclo[9.4.0.03,8]pentadeca-1(11),3(8),4,6,12,14-hexaene PC

SMILES

CC1=CC(=CN=C1)CN2CCC(=C3C4=C(CCC5=C3N=CC=C5)C=C(C=C4)Cl)CC2 PC

InChIKey

WUZYKBABMWJHDL-UHFFFAOYSA-N PC

PubChem CID

133017

Harm reduction information

No harm reduction data is on file for this compound yet. That means no dose, timing or combination data from PsychonautWiki or TripSit. Please don't guess a dose from similar compounds. If you have taken it and feel unwell, contact emergency services or a poison control center.

User reports

Pop culture

No references added yet.

Sources

1. Other 8-chloro-11-[1-[(5-methyl-3-pyridyl)methyl]-4-piperidyliden]-6,11-dihydro-5H-benzo[5,6]cyclohepta[1,2-b]pyridine
2. Other Treatment of PAF and histamine-mediated diseases with 8-chloro-11-[1-[(5-methyl-3-pyridyl)methyl]-4-piperidyliden]-6,11-dihydro-5H-benzo[5,6]cyclohepta[1,2-b]pyridine
3. Other UK package leaflet for Rupafin. link 2
4. Journal / agency Picado C. Rupatadine: pharmacological profile and its use in the treatment of allergic disorders. Expert Opinion on Pharmacotherapy. October 2006. doi:10.1517/14656566.7.14.1989 · PMID 17020424
5. Journal / agency Keam SJ, Plosker GL. Rupatadine: a review of its use in the management of allergic disorders. Drugs. 2007. doi:10.2165/00003495-200767030-00008 · PMID 17335300
6. Journal / agency 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. Rupatadine in allergic rhinitis and chronic urticaria. Allergy. April 2008. doi:10.1111/j.1398-9995.2008.01640.x · PMID 18339040
7. Journal / agency Merlos M, Giral M, Balsa D, Ferrando R, Queralt M, Puigdemont A, García-Rafanell J, Forn J. Rupatadine, a new potent, orally active dual antagonist of histamine and platelet-activating factor (PAF). The Journal of Pharmacology and Experimental Therapeutics. January 1997. doi:10.1016/S0022-3565(24)36413-4 · PMID 8996188
8. Journal / agency Solans A, Carbó ML, Peña J, Nadal T, Izquierdo I, Merlos M. Influence of food on the oral bioavailability of rupatadine tablets in healthy volunteers: a single-dose, randomized, open-label, two-way crossover study. Clinical Therapeutics. May 2007. doi:10.1016/j.clinthera.2007.05.004 · PMID 17697908
9. Journal / agency Kapoor Y, Kumar K. Structural and clinical impact of anti-allergy agents: An overview. Bioorganic Chemistry. January 2020. doi:10.1016/j.bioorg.2019.103351 · PMID 31668464
10. Other Pediapharm Announces the Commercial Launch of Rupall (rupatadine) in Canada. January 25, 2017

Text and values on this page are quoted from Wikipedia (CC BY-SA 4.0), PubChem (public domain). Each value links to the exact revision it came from.