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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

2002
Primary
RUPAFIN

Approved Use

Symptomatic treatment of allergic rhinitis and urticaria

Launch Date

2002
PubMed

PubMed

TitleDatePubMed
Rupatadine 10 mg and ebastine 10 mg in seasonal allergic rhinitis: a comparison study.
2004 Jul
Effects of rupatadine vs placebo on allergen-induced symptoms in patients exposed to aeroallergens in the Vienna Challenge Chamber.
2006 Jan
Evaluation of the cognitive, psychomotor and pharmacokinetic profiles of rupatadine, hydroxyzine and cetirizine, in combination with alcohol, in healthy volunteers.
2006 Jan
New antihistamines: a critical view.
2006 Nov
[Antihistamines in allergic rhinitis].
2007
Characterization of the de novo biosynthetic enzyme of platelet activating factor, DDT-insensitive cholinephosphotransferase, of human mesangial cells.
2007
Rupatadine: a review of its use in the management of allergic disorders.
2007
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
Antihistaminic effects of rupatadine and PKPD modelling.
2008 Apr-Jun
[Torsades de pointes associated with rupatadine].
2008 Mar
Herbex-kid Inhibits Immediate Hypersensitivity Reactions in Mice and Rats.
2008 Sep
Reduction of nasal volume after allergen-induced rhinitis in patients treated with rupatadine: a randomized, cross-over, double-blind, placebo-controlled study.
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
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
Heart rhythm disturbances associated with rupatadine: a case series from the Spanish and Portuguese pharmacovigilance systems.
2009 May
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
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 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
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 does not potentiate the CNS depressant effects of lorazepam: randomized, double-blind, crossover, repeated dose, placebo-controlled study.
2010 Jun
[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 15 18:11:48 GMT 2023
Edited
by admin
on Fri Dec 15 18:11:48 GMT 2023
Record UNII
XJ6OT32M93
Record Status Validated (UNII)
Record Version
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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 Fri Dec 15 18:11:49 GMT 2023 , Edited by admin on Fri Dec 15 18:11:49 GMT 2023
PRIMARY
EVMPD
SUB22090
Created by admin on Fri Dec 15 18:11:49 GMT 2023 , Edited by admin on Fri Dec 15 18:11:49 GMT 2023
PRIMARY
MERCK INDEX
m9700
Created by admin on Fri Dec 15 18:11:49 GMT 2023 , Edited by admin on Fri Dec 15 18:11:49 GMT 2023
PRIMARY Merck Index
SMS_ID
100000085399
Created by admin on Fri Dec 15 18:11:49 GMT 2023 , Edited by admin on Fri Dec 15 18:11:49 GMT 2023
PRIMARY
FDA UNII
XJ6OT32M93
Created by admin on Fri Dec 15 18:11:49 GMT 2023 , Edited by admin on Fri Dec 15 18:11:49 GMT 2023
PRIMARY
CAS
182349-12-8
Created by admin on Fri Dec 15 18:11:49 GMT 2023 , Edited by admin on Fri Dec 15 18:11:49 GMT 2023
PRIMARY
PUBCHEM
6449107
Created by admin on Fri Dec 15 18:11:49 GMT 2023 , Edited by admin on Fri Dec 15 18:11:49 GMT 2023
PRIMARY
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