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Details

Stereochemistry ACHIRAL
Molecular Formula C26H26ClN3.3ClH
Molecular Weight 525.341
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of RUPATADINE TRIHYDROCHLORIDE

SMILES

Cl.Cl.Cl.CC1=CN=CC(CN2CCC(CC2)=C3C4=CC=C(Cl)C=C4CCC5=CC=CN=C35)=C1

InChI

InChIKey=BQFOTHHRVVHLEW-UHFFFAOYSA-N
InChI=1S/C26H26ClN3.3ClH/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;3*1H

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

Molecular Formula ClH
Molecular Weight 36.461
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
The proarrhythmic antihistaminic drug terfenadine increases spontaneous calcium release in human atrial myocytes.
2006 Dec 28
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
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
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
[Torsades de pointes associated with rupatadine].
2008 Mar
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
Successful treatment of chronic drug-resistant urticaria with alprazolam.
2009 Feb
Torsade de pointes associated with rupatadine.
2009 Mar
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
Structurally diverse metal coordination compounds, bearing imidodiphosphinate and diphosphinoamine ligands, as potential inhibitors of the platelet activating factor.
2010
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
Rupatadine does not potentiate the CNS depressant effects of lorazepam: randomized, double-blind, crossover, repeated dose, placebo-controlled study.
2010 Jun
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 Dec 16 03:21:15 GMT 2023
Edited
by admin
on Sat Dec 16 03:21:15 GMT 2023
Record UNII
G61C8NZY2T
Record Status Validated (UNII)
Record Version
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Name Type Language
RUPATADINE TRIHYDROCHLORIDE
MI  
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)-, TRIHYDROCHLORIDE
Common Name English
RUPATADINE TRIHYDROCHLORIDE [MI]
Common Name English
8-CHLORO-6,11-DIHYDRO-11-(1-((5-METHYL-3-PYRIDINYL)METHYL)-4-PIPERIDINYLIDENE)-5H-BENZO(5,6)CYCLOHEPTA(1,2-B)PYRIDINE TRIHYDROCHLORIDE
Systematic 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)-, HYDROCHLORIDE (1:3)
Systematic Name English
Code System Code Type Description
PUBCHEM
133016
Created by admin on Sat Dec 16 03:21:15 GMT 2023 , Edited by admin on Sat Dec 16 03:21:15 GMT 2023
PRIMARY
DRUG BANK
DBSALT001923
Created by admin on Sat Dec 16 03:21:15 GMT 2023 , Edited by admin on Sat Dec 16 03:21:15 GMT 2023
PRIMARY
MERCK INDEX
m9700
Created by admin on Sat Dec 16 03:21:15 GMT 2023 , Edited by admin on Sat Dec 16 03:21:15 GMT 2023
PRIMARY Merck Index
FDA UNII
G61C8NZY2T
Created by admin on Sat Dec 16 03:21:15 GMT 2023 , Edited by admin on Sat Dec 16 03:21:15 GMT 2023
PRIMARY
CAS
156611-76-6
Created by admin on Sat Dec 16 03:21:15 GMT 2023 , Edited by admin on Sat Dec 16 03:21:15 GMT 2023
PRIMARY
EPA CompTox
DTXSID90166109
Created by admin on Sat Dec 16 03:21:15 GMT 2023 , Edited by admin on Sat Dec 16 03:21:15 GMT 2023
PRIMARY
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