RUPATADINE

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 Search

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
Sources: https://www.tga.gov.au/auspar/auspar-rupatadine
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

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Histamine H1 receptor 315 Target ID: CHEMBL231 Sources: https://www.ncbi.nlm.nih.gov/pubmed/8996188 \| https://www.ncbi.nlm.nih.gov/pubmed/27500993 \| https://www.tga.gov.au/auspar/auspar-rupatadine	Antagonist 2778
Platelet activating factor receptor 20 Target ID: CHEMBL250 Sources: https://www.ncbi.nlm.nih.gov/pubmed/8996188 \| https://www.ncbi.nlm.nih.gov/pubmed/27500993 \| https://www.tga.gov.au/auspar/auspar-rupatadine	Antagonist 2778

Conditions

Condition	Modality	Targets	Highest Phase	Product
Allergic rhinitis 100 Sources: https://www.ncbi.nlm.nih.gov/pubmed/17020424 https://www.ncbi.nlm.nih.gov/pubmed/27500993	Primary		Approved 8429	RUPAFIN Approved Use Symptomatic treatment of allergic rhinitis and urticaria Launch Date 2002
Urticaria 39 Sources: https://www.ncbi.nlm.nih.gov/pubmed/17020424 https://www.ncbi.nlm.nih.gov/pubmed/27500993	Primary		Approved 8429	RUPAFIN Approved Use Symptomatic treatment of allergic rhinitis and urticaria Launch Date 2002

PubMed

Title	Date	PubMed
Antihistamines in late-phase clinical development for allergic disease.	2002 Feb	11829715
Rupatadine: a new selective histamine H1 receptor and platelet-activating factor (PAF) antagonist. A review of pharmacological profile and clinical management of allergic rhinitis.	2003 Jun	12944997
Rupatadine 10 mg and ebastine 10 mg in seasonal allergic rhinitis: a comparison study.	2004 Jul	15180765
New antihistamines: a critical view.	2006 Nov	17136293
[Protective effect of rupatadine against oleic acid-induced acute lung injury in rabbits].	2007 Mar	17520822
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	17697908
Rupatadine in allergic rhinitis and chronic urticaria.	2008 Apr	18339040
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	18588560
[Torsades de pointes associated with rupatadine].	2008 Mar	18361911
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	18840369
Herbex-kid Inhibits Immediate Hypersensitivity Reactions in Mice and Rats.	2008 Sep	18830458
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	19132803
Paradoxical exacerbation of chronic urticaria by H1-antihistamines and montelukast.	2009 Dec	20128233
Torsade de pointes associated with rupatadine.	2009 Mar	19268083
Treatment of acquired cold urticaria with rupatadine.	2009 Sep	19392988
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	20819087
Stereoselective synthesis of desloratadine derivatives as antagonist of histamine.	2010 Feb 15	20110173
Rupatadine does not potentiate the CNS depressant effects of lorazepam: randomized, double-blind, crossover, repeated dose, placebo-controlled study.	2010 Jun	20565458

Patents

Sample Use Guides

In Vivo Use Guide

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

In Vitro Use Guide

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

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Name

Type

Language

RUPATADINE

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