RUPATADINE FUMARATE

Details

Stereochemistry	ACHIRAL
Molecular Formula	C26H26ClN3.C4H4O4
Molecular Weight	532.03
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	1
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

OC(=O)\C=C\C(O)=O.CC1=CN=CC(CN2CCC(CC2)=C3C4=CC=C(Cl)C=C4CCC5=CC=CN=C35)=C1

InChI

InChIKey=JYBLCDXVHQWMSU-WLHGVMLRSA-N

InChI=1S/C26H26ClN3.C4H4O4/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;5-3(6)1-2-4(7)8/h2-3,6-7,10,13-16H,4-5,8-9,11-12,17H2,1H3;1-2H,(H,5,6)(H,7,8)/b;2-1+

HIDE SMILES / InChI

Description
Sources: https://www.tga.gov.au/auspar/auspar-rupatadine
Curator's Comment: Description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/8996188 | https://www.ncbi.nlm.nih.gov/pubmed/27500993

Rupatadine is characterised as a non-sedating H1 anti-histamine and platelet-activating factor (PAF) receptor antagonist. Rupatadine is indicated for the treatment of allergic rhinitis and urticaria. Rupatadine is a safe and well tolerated drug in patients over 2 years old, with no central nervous system or cardiovascular effects and it can be taken with or without foods.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Histamine H1 receptor 315 Target ID: CHEMBL231 Sources: https://www.ncbi.nlm.nih.gov/pubmed/8996188 \| https://www.ncbi.nlm.nih.gov/pubmed/27500993 \| https://www.tga.gov.au/auspar/auspar-rupatadine	Antagonist 2778
Platelet activating factor receptor 20 Target ID: CHEMBL250 Sources: https://www.ncbi.nlm.nih.gov/pubmed/8996188 \| https://www.ncbi.nlm.nih.gov/pubmed/27500993 \| https://www.tga.gov.au/auspar/auspar-rupatadine	Antagonist 2778

Conditions

Condition	Modality	Targets	Highest Phase	Product
Allergic rhinitis 100 Sources: https://www.ncbi.nlm.nih.gov/pubmed/17020424 https://www.ncbi.nlm.nih.gov/pubmed/27500993	Primary		Approved 8429	RUPAFIN Approved Use Symptomatic treatment of allergic rhinitis and urticaria Launch Date 2002
Urticaria 39 Sources: https://www.ncbi.nlm.nih.gov/pubmed/17020424 https://www.ncbi.nlm.nih.gov/pubmed/27500993	Primary		Approved 8429	RUPAFIN Approved Use Symptomatic treatment of allergic rhinitis and urticaria Launch Date 2002

PubMed

Title	Date	PubMed
Antihistamines in late-phase clinical development for allergic disease.	2002 Feb	11829715
Rupatadine: a new selective histamine H1 receptor and platelet-activating factor (PAF) antagonist. A review of pharmacological profile and clinical management of allergic rhinitis.	2003 Jun	12944997
Central and peripheral evaluation of rupatadine, a new antihistamine/platelet-activating factor antagonist, at different doses in healthy volunteers.	2004	15539863
A randomized, double-blind, parallel-group study, comparing the efficacy and safety of rupatadine (20 and 10 mg), a new PAF and H1 receptor-specific histamine antagonist, to loratadine 10 mg in the treatment of seasonal allergic rhinitis.	2004	15160440
Rupatadine 10 mg and ebastine 10 mg in seasonal allergic rhinitis: a comparison study.	2004 Jul	15180765
Rupatadine 10 mg and cetirizine 10 mg in seasonal allergic rhinitis: a randomised, double-blind parallel study.	2005	15864879
Rupatadine: pharmacological profile and its use in the treatment of allergic disorders.	2006 Oct	17020424
Lack of effects between rupatadine 10 mg and placebo on actual driving performance of healthy volunteers.	2007 Jul	17599335
Once-daily rupatadine improves the symptoms of chronic idiopathic urticaria: a randomised, double-blind, placebo-controlled study.	2007 May-Jun	17478385
Rupatadine in allergic rhinitis and chronic urticaria.	2008 Apr	18339040
Antihistaminic effects of rupatadine and PKPD modelling.	2008 Apr-Jun	18777946
High performance liquid chromatography-tandem mass spectrometric determination of rupatadine in human plasma and its pharmacokinetics.	2008 Aug 5	18472381
A 12-week placebo-controlled study of rupatadine 10 mg once daily compared with cetirizine 10 mg once daily, in the treatment of persistent allergic rhinitis.	2008 Jul	18588560
[Torsades de pointes associated with rupatadine].	2008 Mar	18361911
Pharmacokinetic and safety profile of rupatadine when coadministered with azithromycin at steady-state levels: a randomized, open-label, two-way, crossover, Phase I study.	2008 Sep	18840369
Herbex-kid Inhibits Immediate Hypersensitivity Reactions in Mice and Rats.	2008 Sep	18830458
Determination of rupatadine in pharmaceutical formulations by a validated stability-indicating MEKC method.	2008 Sep	18693320
Reduction of nasal volume after allergen-induced rhinitis in patients treated with rupatadine: a randomized, cross-over, double-blind, placebo-controlled study.	2009	20128424
Safety of rupatadine administered over a period of 1 year in the treatment of persistent allergic rhinitis: a multicentre, open-label study in Spain.	2009	19132803
Ebastine in the light of CONGA recommendations for the development of third-generation antihistamines.	2009 Aug 31	21437146
Rupatadine: pharmacological profile and its use in the treatment of allergic rhinitis.	2009 Dec	23120659
Successful treatment of chronic drug-resistant urticaria with alprazolam.	2009 Feb	19203665
Simultaneous determination of rupatadine and its metabolite desloratadine in human plasma by a sensitive LC-MS/MS method: application to the pharmacokinetic study in healthy Chinese volunteers.	2009 Feb 20	19059745
Unsuspected polymorphic metabolism of rupatadine via its primary metabolite, desloratadine.	2009 Jun	19172210
Pharmacological profile, efficacy and safety of rupatadine in allergic rhinitis.	2009 Jun	18695846
Heart rhythm disturbances associated with rupatadine: a case series from the Spanish and Portuguese pharmacovigilance systems.	2009 May	19225450
Futura study: evaluation of efficacy and safety of rupatadine fumarate in the treatment of persistent allergic rhinitis.	2009 Sep-Oct	19893935
Rupatadine inhibits proinflammatory mediator secretion from human mast cells triggered by different stimuli.	2010	19672095
No cardiac effects of therapeutic and supratherapeutic doses of rupatadine: results from a 'thorough QT/QTc study' performed according to ICH guidelines.	2010 Apr	20406224
Rupatadine improves nasal symptoms, airflow and inflammation in patients with persistent allergic rhinitis: a pilot study.	2010 Apr-Jun	20487631
Rupatadine and levocetirizine for seasonal allergic rhinitis: a comparative study of efficacy and safety.	2010 Aug	20713756
Rupatadine does not potentiate the CNS depressant effects of lorazepam: randomized, double-blind, crossover, repeated dose, placebo-controlled study.	2010 Jun	20565458
[Rupatadine, oral Rupatall].	2010 Mar	20429393

Patents

Sample Use Guides

In Vivo Use Guide

Adults and adolescents (over 12 years of age): The recommended dose is 10 mg (one tablet) once a day, with or without food. Paediatric patients: Rupatadine 10 mg Tablets is not recommended for use in children below age 12. In children aged 2 to 11 years, the administration of rupatadine 1 mg/ml oral solution is recommended.

Route of Administration: Oral

In Vitro Use Guide

platelet-activating factor stimulated a statistically significant release of histamine, interleukin-8, and tumor necrosis factor (0.001-0.1 μmol/L). Pretreatment with rupatadine (25 μmol/L) for 10 minutes inhibited this effect.

Name

Type

Language

RUPATADINE FUMARATE

Common Name

English

RUPATADINE FUMARATE [MI]

Common Name

English

Rupatadine fumarate [WHO-DD]

Common Name

English

RUPATADINE FUMARATE [JAN]

Common Name

English

5H-BENZO(5,6)CYCLOHEPTA(1,2-B)PYRIDINE, 8-CHLORO-6,11-DIHYDRO-11-(1-((5-METHYL-3-PYRIDINYL)METHYL)-4-PIPERIDINYLIDENE)-, (2E)-2-BUTENEDIOATE (1:1)

Systematic Name

English

RUPAFIN

Brand Name

English

RUPATADINE FUMARATE [EP MONOGRAPH]

Common Name

English

Code System Code Type Description

DRUG BANK

DBSALT001922