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Details

Stereochemistry ACHIRAL
Molecular Formula C26H26ClN3
Molecular Weight 415.9586
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of RUPATADINE

SMILES

Cc1cc(cnc1)CN2CCC(=C3c4ccc(cc4CCc5cccnc53)Cl)CC2

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

Molecular Formula C26H26ClN3
Molecular Weight 415.9586
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description
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

Curator's Comment:: Rupatadine poorly crosses the blood-brain barrier, however rupatidine fumarate displays psychomotor impairment activity only at the highest dose (80 mg), while therapeutically relevant lower doses (10 and 20 mg) were similar to placebo. https://www.ncbi.nlm.nih.gov/pubmed/15539863

Approval Year

TargetsConditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
RUPAFIN

Approved Use

Symptomatic treatment of allergic rhinitis and urticaria

Launch Date

1.04129279E12
Primary
RUPAFIN

Approved Use

Symptomatic treatment of allergic rhinitis and urticaria

Launch Date

1.04129279E12
PubMed

PubMed

TitleDatePubMed
Antihistamines in late-phase clinical development for allergic disease.
2002 Feb
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
Central and peripheral evaluation of rupatadine, a new antihistamine/platelet-activating factor antagonist, at different doses in healthy volunteers.
2004
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
Rupatadine 10 mg and ebastine 10 mg in seasonal allergic rhinitis: a comparison study.
2004 Jul
Rupatadine 10 mg and cetirizine 10 mg in seasonal allergic rhinitis: a randomised, double-blind parallel study.
2005
Rupatadine: pharmacological profile and its use in the treatment of allergic disorders.
2006 Oct
Characterization of the de novo biosynthetic enzyme of platelet activating factor, DDT-insensitive cholinephosphotransferase, of human mesangial cells.
2007
Lack of effects between rupatadine 10 mg and placebo on actual driving performance of healthy volunteers.
2007 Jul
[Protective effect of rupatadine against oleic acid-induced acute lung injury in rabbits].
2007 Mar
Rupatadine in the treatment of chronic idiopathic urticaria: a double-blind, randomized, placebo-controlled multicentre study.
2007 May
Once-daily rupatadine improves the symptoms of chronic idiopathic urticaria: a randomised, double-blind, placebo-controlled study.
2007 May-Jun
Rupatadine in allergic rhinitis and chronic urticaria.
2008 Apr
Antihistaminic effects of rupatadine and PKPD modelling.
2008 Apr-Jun
High performance liquid chromatography-tandem mass spectrometric determination of rupatadine in human plasma and its pharmacokinetics.
2008 Aug 5
[Torsades de pointes associated with rupatadine].
2008 Mar
Herbex-kid Inhibits Immediate Hypersensitivity Reactions in Mice and Rats.
2008 Sep
Determination of rupatadine in pharmaceutical formulations by a validated stability-indicating MEKC method.
2008 Sep
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
Ebastine in the light of CONGA recommendations for the development of third-generation antihistamines.
2009 Aug 31
Rupatadine: pharmacological profile and its use in the treatment of allergic rhinitis.
2009 Dec
Paradoxical exacerbation of chronic urticaria by H1-antihistamines and montelukast.
2009 Dec
Successful treatment of chronic drug-resistant urticaria with alprazolam.
2009 Feb
Unsuspected polymorphic metabolism of rupatadine via its primary metabolite, desloratadine.
2009 Jun
Pharmacological profile, efficacy and safety of rupatadine in allergic rhinitis.
2009 Jun
Heart rhythm disturbances associated with rupatadine: a case series from the Spanish and Portuguese pharmacovigilance systems.
2009 May
The use of a responder analysis to identify clinically meaningful differences in chronic urticaria patients following placebo- controlled treatment with rupatadine 10 and 20 mg.
2009 Sep
Futura study: evaluation of efficacy and safety of rupatadine fumarate in the treatment of persistent allergic rhinitis.
2009 Sep-Oct
Structurally diverse metal coordination compounds, bearing imidodiphosphinate and diphosphinoamine ligands, as potential inhibitors of the platelet activating factor.
2010
No cardiac effects of therapeutic and supratherapeutic doses of rupatadine: results from a 'thorough QT/QTc study' performed according to ICH guidelines.
2010 Apr
Rupatadine improves nasal symptoms, airflow and inflammation in patients with persistent allergic rhinitis: a pilot study.
2010 Apr-Jun
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
Rupatadine and heart rhythm disturbances.
2010 Jan
Patents

Sample Use Guides

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
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.
Substance Class Chemical
Created
by admin
on Sat Jun 26 00:32:49 UTC 2021
Edited
by admin
on Sat Jun 26 00:32:49 UTC 2021
Record UNII
2AE8M83G3E
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
RUPATADINE
INN   MART.   MI   WHO-DD  
INN  
Official Name English
RUPATADINE [WHO-DD]
Common Name English
RUPATADINE [MART.]
Common Name English
RUPATADINE [INN]
Common Name English
UR-12592
Code English
RUPATADINE [MI]
Common Name English
Classification Tree Code System Code
WHO-ATC R06AX28
Created by admin on Sat Jun 26 00:32:49 UTC 2021 , Edited by admin on Sat Jun 26 00:32:49 UTC 2021
WHO-VATC QR06AX28
Created by admin on Sat Jun 26 00:32:49 UTC 2021 , Edited by admin on Sat Jun 26 00:32:49 UTC 2021
NCI_THESAURUS C29578
Created by admin on Sat Jun 26 00:32:49 UTC 2021 , Edited by admin on Sat Jun 26 00:32:49 UTC 2021
Code System Code Type Description
WIKIPEDIA
RUPATADINE
Created by admin on Sat Jun 26 00:32:49 UTC 2021 , Edited by admin on Sat Jun 26 00:32:49 UTC 2021
PRIMARY
INN
7443
Created by admin on Sat Jun 26 00:32:49 UTC 2021 , Edited by admin on Sat Jun 26 00:32:49 UTC 2021
PRIMARY
EPA CompTox
158876-82-5
Created by admin on Sat Jun 26 00:32:49 UTC 2021 , Edited by admin on Sat Jun 26 00:32:49 UTC 2021
PRIMARY
ChEMBL
CHEMBL91397
Created by admin on Sat Jun 26 00:32:49 UTC 2021 , Edited by admin on Sat Jun 26 00:32:49 UTC 2021
PRIMARY
DRUG BANK
DB11614
Created by admin on Sat Jun 26 00:32:49 UTC 2021 , Edited by admin on Sat Jun 26 00:32:49 UTC 2021
PRIMARY
EVMPD
SUB10406MIG
Created by admin on Sat Jun 26 00:32:49 UTC 2021 , Edited by admin on Sat Jun 26 00:32:49 UTC 2021
PRIMARY
NCI_THESAURUS
C73055
Created by admin on Sat Jun 26 00:32:49 UTC 2021 , Edited by admin on Sat Jun 26 00:32:49 UTC 2021
PRIMARY
FDA UNII
2AE8M83G3E
Created by admin on Sat Jun 26 00:32:49 UTC 2021 , Edited by admin on Sat Jun 26 00:32:49 UTC 2021
PRIMARY
PUBCHEM
133017
Created by admin on Sat Jun 26 00:32:49 UTC 2021 , Edited by admin on Sat Jun 26 00:32:49 UTC 2021
PRIMARY
MESH
C103639
Created by admin on Sat Jun 26 00:32:49 UTC 2021 , Edited by admin on Sat Jun 26 00:32:49 UTC 2021
PRIMARY
CAS
158876-82-5
Created by admin on Sat Jun 26 00:32:49 UTC 2021 , Edited by admin on Sat Jun 26 00:32:49 UTC 2021
PRIMARY
DRUG CENTRAL
2413
Created by admin on Sat Jun 26 00:32:49 UTC 2021 , Edited by admin on Sat Jun 26 00:32:49 UTC 2021
PRIMARY
MERCK INDEX
M9700
Created by admin on Sat Jun 26 00:32:49 UTC 2021 , Edited by admin on Sat Jun 26 00:32:49 UTC 2021
PRIMARY Merck Index
Related Record Type Details
TARGET -> INHIBITOR
SALT/SOLVATE -> PARENT
Related Record Type Details
ACTIVE MOIETY