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
Antihistamines in late-phase clinical development for allergic disease.	2002 Feb	11829715
The proarrhythmic antihistaminic drug terfenadine increases spontaneous calcium release in human atrial myocytes.	2006 Dec 28	17078945
Effects of rupatadine vs placebo on allergen-induced symptoms in patients exposed to aeroallergens in the Vienna Challenge Chamber.	2006 Jan	16440531
[Antihistamines in allergic rhinitis].	2007	18260244
Rupatadine: a review of its use in the management of allergic disorders.	2007	17335300
Determination of rupatadine in pharmaceutical formulations by a validated stability-indicating MEKC method.	2008 Sep	18693320
Reduction of nasal volume after allergen-induced rhinitis in patients treated with rupatadine: a randomized, cross-over, double-blind, placebo-controlled study.	2009	20128424
Unsuspected polymorphic metabolism of rupatadine via its primary metabolite, desloratadine.	2009 Jun	19172210
No cardiac effects of therapeutic and supratherapeutic doses of rupatadine: results from a 'thorough QT/QTc study' performed according to ICH guidelines.	2010 Apr	20406224
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
Rupatadine and its effects on symptom control, stimulation time, and temperature thresholds in patients with acquired cold urticaria.	2010 Jan	20143651
Rupatadine and heart rhythm disturbances.	2010 Jan	19727070

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