Rupatadine

Rupatadine is a second generation antihistamine and platelet-activating factor antagonist used to treat allergies. It was discovered and developed by Uriach[2] and is marketed as Rupafin and under several other trade names.

Rupatadine
Clinical data
Trade namesRupafin, others
AHFS/Drugs.comInternational Drug Names
Routes of
administration		Oral
ATC code
Legal status
Legal status
  • EU: Rx-only [1]
  • In general: ℞ (Prescription only)
Pharmacokinetic data
Protein binding98–99%
MetabolismLiver, CYP-mediated
Elimination half-life5.9 hours
Excretion34.6% urine, 60.9% faeces
Identifiers
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
CAS Number
PubChem CID
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.260.389
Chemical and physical data
FormulaC26H26ClN3
Molar mass415.97 g·mol−1
3D model (JSmol)
SMILES
  • Clc1cc5c(cc1)\C(=C3/CCN(Cc2cncc(c2)C)CC3)c4ncccc4CC5
InChI
  • InChI=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 Y
  • Key:WUZYKBABMWJHDL-UHFFFAOYSA-N Y
 NY (what is this?)  (verify)

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]

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]

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.[7]

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]

Pharmacokinetics

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

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]

Brand names

Brand names include Rupafin, Rupall,[10] Rinialer, Pafinur, Rupax, Urtimed, Wystamm and Ralif, among others.[11]

References
  1. https://www.ema.europa.eu/documents/psusa/rupatadine-list-nationally-authorised-medicinal-products-psusa/00002673/202012_en.pdf
  2. Patents: EP 577957, US 5407941, US 5476856
  3. UK package leaflet for Rupafin.
  4. Picado C (October 2006). "Rupatadine: pharmacological profile and its use in the treatment of allergic disorders". Expert Opinion on Pharmacotherapy. 7 (14): 1989–2001. doi:10.1517/14656566.7.14.1989. PMID 17020424. S2CID 38337440.
  5. Keam SJ, Plosker GL (2007). "Rupatadine: a review of its use in the management of allergic disorders". Drugs. 67 (3): 457–74. doi:10.2165/00003495-200767030-00008. PMID 17335300.
  6. Mullol J, Bousquet J, Bachert C, Canonica WG, Gimenez-Arnau A, Kowalski ML, et al. (April 2008). "Rupatadine in allergic rhinitis and chronic urticaria". Allergy. 63 Suppl 87: 5–28. doi:10.1111/j.1398-9995.2008.01640.x. PMID 18339040.
  7. Merlos M, Giral M, Balsa D, Ferrando R, Queralt M, Puigdemont A, et al. (January 1997). "Rupatadine, a new potent, orally active dual antagonist of histamine and platelet-activating factor (PAF)". The Journal of Pharmacology and Experimental Therapeutics. 280 (1): 114–21. PMID 8996188.
  8. Solans A, Carbó ML, Peña J, Nadal T, Izquierdo I, Merlos M (May 2007). "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. 29 (5): 900–908. doi:10.1016/j.clinthera.2007.05.004. PMID 17697908.
  9. Kapoor, Yagyesh; Kumar, Kapil (2020-01-01). "Structural and clinical impact of anti-allergy agents: An overview". Bioorganic Chemistry. 94: 103351. doi:10.1016/j.bioorg.2019.103351. ISSN 0045-2068. PMID 31668464. S2CID 204968012.
  10. "Pediapharm Announces the Commercial Launch of Rupall (rupatadine) in Canada". Pediapharm. January 25, 2017.
  11. International Drug Names: Rupatadine.
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