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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

1.04129279E12
Primary
RUPAFIN

Approved Use

Symptomatic treatment of allergic rhinitis and urticaria

Launch Date

1.04129279E12
PubMed

PubMed

TitleDatePubMed
Central and peripheral evaluation of rupatadine, a new antihistamine/platelet-activating factor antagonist, at different doses in healthy volunteers.
2004
Rupatadine 10 mg and ebastine 10 mg in seasonal allergic rhinitis: a comparison study.
2004 Jul
Rupatadine: pharmacological profile and its use in the treatment of allergic disorders.
2006 Oct
Rupatadine: a review of its use in the management of allergic disorders.
2007
Antihistaminic effects of rupatadine and PKPD modelling.
2008 Apr-Jun
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
[Torsades de pointes associated with rupatadine].
2008 Mar
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
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
Rupatadine: pharmacological profile and its use in the treatment of allergic rhinitis.
2009 Dec
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
Torsade de pointes associated with rupatadine.
2009 Mar
Futura study: evaluation of efficacy and safety of rupatadine fumarate in the treatment of persistent allergic rhinitis.
2009 Sep-Oct
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
Stereoselective synthesis of desloratadine derivatives as antagonist of histamine.
2010 Feb 15
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
[Rupatadine, oral Rupatall].
2010 Mar
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 16 19:28:43 UTC 2022
Edited
by admin
on Fri Dec 16 19:28:43 UTC 2022
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 16 19:28:43 UTC 2022 , Edited by admin on Fri Dec 16 19:28:43 UTC 2022
WHO-VATC QR06AX28
Created by admin on Fri Dec 16 19:28:43 UTC 2022 , Edited by admin on Fri Dec 16 19:28:43 UTC 2022
NCI_THESAURUS C29578
Created by admin on Fri Dec 16 19:28:43 UTC 2022 , Edited by admin on Fri Dec 16 19:28:43 UTC 2022
Code System Code Type Description
WIKIPEDIA
RUPATADINE
Created by admin on Fri Dec 16 19:28:43 UTC 2022 , Edited by admin on Fri Dec 16 19:28:43 UTC 2022
PRIMARY
INN
7443
Created by admin on Fri Dec 16 19:28:43 UTC 2022 , Edited by admin on Fri Dec 16 19:28:43 UTC 2022
PRIMARY
EPA CompTox
DTXSID00166534
Created by admin on Fri Dec 16 19:28:43 UTC 2022 , Edited by admin on Fri Dec 16 19:28:43 UTC 2022
PRIMARY
ChEMBL
CHEMBL91397
Created by admin on Fri Dec 16 19:28:43 UTC 2022 , Edited by admin on Fri Dec 16 19:28:43 UTC 2022
PRIMARY
DRUG BANK
DB11614
Created by admin on Fri Dec 16 19:28:43 UTC 2022 , Edited by admin on Fri Dec 16 19:28:43 UTC 2022
PRIMARY
EVMPD
SUB10406MIG
Created by admin on Fri Dec 16 19:28:43 UTC 2022 , Edited by admin on Fri Dec 16 19:28:43 UTC 2022
PRIMARY
NCI_THESAURUS
C73055
Created by admin on Fri Dec 16 19:28:43 UTC 2022 , Edited by admin on Fri Dec 16 19:28:43 UTC 2022
PRIMARY
FDA UNII
2AE8M83G3E
Created by admin on Fri Dec 16 19:28:43 UTC 2022 , Edited by admin on Fri Dec 16 19:28:43 UTC 2022
PRIMARY
PUBCHEM
133017
Created by admin on Fri Dec 16 19:28:43 UTC 2022 , Edited by admin on Fri Dec 16 19:28:43 UTC 2022
PRIMARY
MESH
C103639
Created by admin on Fri Dec 16 19:28:43 UTC 2022 , Edited by admin on Fri Dec 16 19:28:43 UTC 2022
PRIMARY
CAS
158876-82-5
Created by admin on Fri Dec 16 19:28:43 UTC 2022 , Edited by admin on Fri Dec 16 19:28:43 UTC 2022
PRIMARY
DRUG CENTRAL
2413
Created by admin on Fri Dec 16 19:28:43 UTC 2022 , Edited by admin on Fri Dec 16 19:28:43 UTC 2022
PRIMARY
MERCK INDEX
M9700
Created by admin on Fri Dec 16 19:28:43 UTC 2022 , Edited by admin on Fri Dec 16 19:28:43 UTC 2022
PRIMARY Merck Index
Related Record Type Details
TARGET -> INHIBITOR
SALT/SOLVATE -> PARENT
Related Record Type Details
ACTIVE MOIETY