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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 of RUPATADINE FUMARATE

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

Molecular Formula C4H4O4
Molecular Weight 116.0722
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 1
Optical Activity NONE

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
Antihistamines in late-phase clinical development for allergic disease.
2002 Feb
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
[Antihistamines in allergic rhinitis].
2007
Lack of effects between rupatadine 10 mg and placebo on actual driving performance of healthy volunteers.
2007 Jul
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 allergic rhinitis and chronic urticaria.
2008 Apr
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
Reduction of nasal volume after allergen-induced rhinitis in patients treated with rupatadine: a randomized, cross-over, double-blind, placebo-controlled study.
2009
Paradoxical exacerbation of chronic urticaria by H1-antihistamines and montelukast.
2009 Dec
Pharmacological profile, efficacy and safety of rupatadine in allergic rhinitis.
2009 Jun
Torsade de pointes associated with rupatadine.
2009 Mar
Structurally diverse metal coordination compounds, bearing imidodiphosphinate and diphosphinoamine ligands, as potential inhibitors of the platelet activating factor.
2010
Rupatadine improves nasal symptoms, airflow and inflammation in patients with persistent allergic rhinitis: a pilot study.
2010 Apr-Jun
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 Thu Jul 06 01:27:19 UTC 2023
Edited
by admin
on Thu Jul 06 01:27:19 UTC 2023
Record UNII
XJ6OT32M93
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
RUPATADINE FUMARATE
MI   WHO-DD  
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
Created by admin on Thu Jul 06 01:27:20 UTC 2023 , Edited by admin on Thu Jul 06 01:27:20 UTC 2023
PRIMARY
EVMPD
SUB22090
Created by admin on Thu Jul 06 01:27:20 UTC 2023 , Edited by admin on Thu Jul 06 01:27:20 UTC 2023
PRIMARY
MERCK INDEX
M9700
Created by admin on Thu Jul 06 01:27:20 UTC 2023 , Edited by admin on Thu Jul 06 01:27:20 UTC 2023
PRIMARY Merck Index
SMS_ID
100000085399
Created by admin on Thu Jul 06 01:27:20 UTC 2023 , Edited by admin on Thu Jul 06 01:27:20 UTC 2023
PRIMARY
FDA UNII
XJ6OT32M93
Created by admin on Thu Jul 06 01:27:20 UTC 2023 , Edited by admin on Thu Jul 06 01:27:20 UTC 2023
PRIMARY
CAS
182349-12-8
Created by admin on Thu Jul 06 01:27:20 UTC 2023 , Edited by admin on Thu Jul 06 01:27:20 UTC 2023
PRIMARY
PUBCHEM
6449107
Created by admin on Thu Jul 06 01:27:20 UTC 2023 , Edited by admin on Thu Jul 06 01:27:20 UTC 2023
PRIMARY
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IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
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IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
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ACTIVE MOIETY