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 312 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 2737
Platelet activating factor receptor 18 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 2737

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 8307	RUPAFIN Approved Use Symptomatic treatment of allergic rhinitis and urticaria Launch Date 1.04129279E12
Urticaria 38 Sources: https://www.ncbi.nlm.nih.gov/pubmed/17020424 https://www.ncbi.nlm.nih.gov/pubmed/27500993	Primary		Approved 8307	RUPAFIN Approved Use Symptomatic treatment of allergic rhinitis and urticaria Launch Date 1.04129279E12

PubMed

Title	Date	PubMed
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: pharmacological profile and its use in the treatment of allergic disorders.	2006 Oct	17020424
Rupatadine: a review of its use in the management of allergic disorders.	2007	17335300
Antihistaminic effects of rupatadine and PKPD modelling.	2008 Apr-Jun	18777946
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
Determination of rupatadine in pharmaceutical formulations by a validated stability-indicating MEKC method.	2008 Sep	18693320
Rupatadine: pharmacological profile and its use in the treatment of allergic rhinitis.	2009 Dec	23120659
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	19059745
Torsade de pointes associated with rupatadine.	2009 Mar	19268083
Futura study: evaluation of efficacy and safety of rupatadine fumarate in the treatment of persistent allergic rhinitis.	2009 Sep-Oct	19893935
Rupatadine improves nasal symptoms, airflow and inflammation in patients with persistent allergic rhinitis: a pilot study.	2010 Apr-Jun	20487631
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 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
[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 16 19:28:43 UTC 2022` Edited by `admin` on `Fri Dec 16 19:28:43 UTC 2022`
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