Rupatadine

Rupatadine

Clinical data
Trade names	Rupafin, Alergoliber, Rinialer, Pafinur, Rupax, Ralif
AHFS/Drugs.com	International Drug Names
Routes of administration	Oral
ATC code	R06AX28 (WHO)
Legal status
Legal status	Prescription drug
Pharmacokinetic data
Protein binding	98–99%
Metabolism	Hepatic, CYP-mediated
Elimination half-life	5.9 hours
Excretion	34.6% 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	158876-82-5 N (free base) 182349-12-8 (fumarate)
PubChem CID	133017
ChemSpider	117388 Y
UNII	2AE8M83G3E
ChEMBL	ChEMBL91397 Y
E number	{{#property:P628}}
ECHA InfoCard	{{#property:P2566}}
Chemical and physical data
Formula	C26H26ClN3
Molar mass	415.958 g/mol
3D model (JSmol)	Interactive image
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)

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List of terms related to Rupatadine

Editor-In-Chief: C. Michael Gibson, M.S., M.D. [1]

Overview

Rupatadine is a second generation antihistamine and PAF antagonist used to treat allergies. It was discovered and developed by J. Uriach y Cia, S. A. and is marketed under several trade names such as Rupafin, Alergoliber, Rinialer, Pafinur, Rupax and Ralif.

Therapeutic indications approved

Rupatadine fumarate has been approved for the treatment of allergic rhinitis and chronic urticaria in adults and children over 12 years. The defined daily dose (DDD) is 10 mg orally.

Available form

Rupatadine is available as round, light salmon coloured tablets containing 10 mg of rupatadine (as fumarate) to be administered orally, once a day.

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.

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.

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 TNF in human mast cells and monocytes.

Pharmacokinetics

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

History

Rupatadine discovery, pre-clinical and clinical development was performed by J. Uriach y Cia, S. A., a Spanish pharmaceutical company. It was launched in 2003 in Spain by J. Uriach y Cia, S. A., with the brand name of Rupafin. The registration of the product is approved in 23 countries from the EU, 8 Central American countries, Brazil, Argentina, Chile, Turkey and 14 African countries.

Efficacy in humans

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.