RUPATADINE

Details

Stereochemistry	ACHIRAL
Molecular Formula	C26H26ClN3
Molecular Weight	415.958
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

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

InChI

InChIKey=WUZYKBABMWJHDL-UHFFFAOYSA-N

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

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 1.04129279E12
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 1.04129279E12

PubMed

Title	Date	PubMed
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
The proarrhythmic antihistaminic drug terfenadine increases spontaneous calcium release in human atrial myocytes.	2006 Dec 28	17078945
Evaluation of the cognitive, psychomotor and pharmacokinetic profiles of rupatadine, hydroxyzine and cetirizine, in combination with alcohol, in healthy volunteers.	2006 Jan	16389668
New antihistamines: a critical view.	2006 Nov	17136293
[Antihistamines in allergic rhinitis].	2007	18260244
[Protective effect of rupatadine against oleic acid-induced acute lung injury in rabbits].	2007 Mar	17520822
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
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
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
Paradoxical exacerbation of chronic urticaria by H1-antihistamines and montelukast.	2009 Dec	20128233
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
Pharmacological profile, efficacy and safety of rupatadine in allergic rhinitis.	2009 Jun	18695846
Treatment of acquired cold urticaria with rupatadine.	2009 Sep	19392988
Futura study: evaluation of efficacy and safety of rupatadine fumarate in the treatment of persistent allergic rhinitis.	2009 Sep-Oct	19893935
Structurally diverse metal coordination compounds, bearing imidodiphosphinate and diphosphinoamine ligands, as potential inhibitors of the platelet activating factor.	2010	20689709
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
Efficacy and tolerability of rupatadine at four times the recommended dose against histamine- and platelet-activating factor-induced flare responses and ex vivo platelet aggregation in healthy males.	2010 Dec	20819087
Stereoselective synthesis of desloratadine derivatives as antagonist of histamine.	2010 Feb 15	20110173
Rupatadine and its effects on symptom control, stimulation time, and temperature thresholds in patients with acquired cold urticaria.	2010 Jan	20143651
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

Official Name

English

RUPATADINE [MART.]

Common Name

English

rupatadine [INN]

Common Name

English

UR-12592

Code

English

RUPATADINE [MI]

Common Name

English

Rupatadine [WHO-DD]

Common Name

English

Classification Tree Code System Code

WHO-ATC

R06AX28