RUPATADINE FUMARATE

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 Search

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
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
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
Central and peripheral evaluation of rupatadine, a new antihistamine/platelet-activating factor antagonist, at different doses in healthy volunteers.	2004	15539863
Rupatadine 10 mg and ebastine 10 mg in seasonal allergic rhinitis: a comparison study.	2004 Jul	15180765
Rupatadine 10 mg and cetirizine 10 mg in seasonal allergic rhinitis: a randomised, double-blind parallel study.	2005	15864879
New antihistamines: a critical view.	2006 Nov	17136293
Rupatadine in the treatment of chronic idiopathic urticaria: a double-blind, randomized, placebo-controlled multicentre study.	2007 May	17441794
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
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
Reduction of nasal volume after allergen-induced rhinitis in patients treated with rupatadine: a randomized, cross-over, double-blind, placebo-controlled study.	2009	20128424
Ebastine in the light of CONGA recommendations for the development of third-generation antihistamines.	2009 Aug 31	21437146
Stereoselective synthesis of desloratadine derivatives as antagonist of histamine.	2010 Feb 15	20110173
[Rupatadine, oral Rupatall].	2010 Mar	20429393

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 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

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