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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 of RUPATADINE

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

Molecular Formula C26H26ClN3
Molecular Weight 415.958
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

2002
Primary
RUPAFIN

Approved Use

Symptomatic treatment of allergic rhinitis and urticaria

Launch Date

2002
PubMed

PubMed

TitleDatePubMed
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
Influence of food on the oral bioavailability of rupatadine tablets in healthy volunteers: a single-dose, randomized, open-label, two-way crossover study.
2007 May
Rupatadine in the treatment of chronic idiopathic urticaria: a double-blind, randomized, placebo-controlled multicentre study.
2007 May
[Torsades de pointes associated with rupatadine].
2008 Mar
Reduction of nasal volume after allergen-induced rhinitis in patients treated with rupatadine: a randomized, cross-over, double-blind, placebo-controlled study.
2009
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
Successful treatment of chronic drug-resistant urticaria with alprazolam.
2009 Feb
Unsuspected polymorphic metabolism of rupatadine via its primary metabolite, desloratadine.
2009 Jun
Rupatadine inhibits proinflammatory mediator secretion from human mast cells triggered by different stimuli.
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 and levocetirizine for seasonal allergic rhinitis: a comparative study of efficacy and safety.
2010 Aug
Rupatadine and its effects on symptom control, stimulation time, and temperature thresholds in patients with acquired cold urticaria.
2010 Jan
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 Fri Dec 15 16:11:15 GMT 2023
Edited
by admin
on Fri Dec 15 16:11:15 GMT 2023
Record UNII
2AE8M83G3E
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
RUPATADINE
INN   MART.   MI   WHO-DD  
INN  
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
Created by admin on Fri Dec 15 16:11:15 GMT 2023 , Edited by admin on Fri Dec 15 16:11:15 GMT 2023
WHO-VATC QR06AX28
Created by admin on Fri Dec 15 16:11:15 GMT 2023 , Edited by admin on Fri Dec 15 16:11:15 GMT 2023
NCI_THESAURUS C29578
Created by admin on Fri Dec 15 16:11:15 GMT 2023 , Edited by admin on Fri Dec 15 16:11:15 GMT 2023
Code System Code Type Description
WIKIPEDIA
RUPATADINE
Created by admin on Fri Dec 15 16:11:15 GMT 2023 , Edited by admin on Fri Dec 15 16:11:15 GMT 2023
PRIMARY
INN
7443
Created by admin on Fri Dec 15 16:11:15 GMT 2023 , Edited by admin on Fri Dec 15 16:11:15 GMT 2023
PRIMARY
EPA CompTox
DTXSID00166534
Created by admin on Fri Dec 15 16:11:15 GMT 2023 , Edited by admin on Fri Dec 15 16:11:15 GMT 2023
PRIMARY
ChEMBL
CHEMBL91397
Created by admin on Fri Dec 15 16:11:15 GMT 2023 , Edited by admin on Fri Dec 15 16:11:15 GMT 2023
PRIMARY
DRUG BANK
DB11614
Created by admin on Fri Dec 15 16:11:15 GMT 2023 , Edited by admin on Fri Dec 15 16:11:15 GMT 2023
PRIMARY
EVMPD
SUB10406MIG
Created by admin on Fri Dec 15 16:11:15 GMT 2023 , Edited by admin on Fri Dec 15 16:11:15 GMT 2023
PRIMARY
NCI_THESAURUS
C73055
Created by admin on Fri Dec 15 16:11:15 GMT 2023 , Edited by admin on Fri Dec 15 16:11:15 GMT 2023
PRIMARY
FDA UNII
2AE8M83G3E
Created by admin on Fri Dec 15 16:11:15 GMT 2023 , Edited by admin on Fri Dec 15 16:11:15 GMT 2023
PRIMARY
PUBCHEM
133017
Created by admin on Fri Dec 15 16:11:15 GMT 2023 , Edited by admin on Fri Dec 15 16:11:15 GMT 2023
PRIMARY
MESH
C103639
Created by admin on Fri Dec 15 16:11:15 GMT 2023 , Edited by admin on Fri Dec 15 16:11:15 GMT 2023
PRIMARY
CAS
158876-82-5
Created by admin on Fri Dec 15 16:11:15 GMT 2023 , Edited by admin on Fri Dec 15 16:11:15 GMT 2023
PRIMARY
SMS_ID
100000084369
Created by admin on Fri Dec 15 16:11:15 GMT 2023 , Edited by admin on Fri Dec 15 16:11:15 GMT 2023
PRIMARY
DRUG CENTRAL
2413
Created by admin on Fri Dec 15 16:11:15 GMT 2023 , Edited by admin on Fri Dec 15 16:11:15 GMT 2023
PRIMARY
MERCK INDEX
m9700
Created by admin on Fri Dec 15 16:11:15 GMT 2023 , Edited by admin on Fri Dec 15 16:11:15 GMT 2023
PRIMARY Merck Index
Related Record Type Details
SALT/SOLVATE -> PARENT
TARGET -> INHIBITOR
SALT/SOLVATE -> PARENT
Related Record Type Details
ACTIVE MOIETY