Rupatadine Fumarate (UR-12592)

Alias: Rupatadine Fumarate; UR-12592 Fumarate; UR 12592 Fumarate; UR12592 Fumarate; Pafinur; Rupax; Rupafin; Alergoliber; Rinialer; Ralif

Cat No.:V1245 Purity: ≥98%

COA Product Data Instructions for use SDS

Rupatadine Fumarate (UR-12592; UR12592; Pafinur; Rupax; Rupafin; Alergoliber; Rinialer; Ralif), the fumarate salt of Rupatadine, is a potent inhibitor of PAFR and antagonist of histamine (H1) receptor used to treat allergies.

Rupatadine Fumarate (UR-12592) Chemical Structure CAS No.: 182349-12-8
Product category: Histamine Receptor

This product is for research use only, not for human use. We do not sell to patients.

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Purity & Quality Control Documentation

Current batch：

Purity: ≥98%

COA

MSDS

NMR

Instructions

Product Description
Bioactivity & Protocols
Physicochemical Properties
Solubility Data
Calculators
Clinical Trial Information
Biological Data

Product Description

Biological Activity I Assay Protocols (From Reference)

Targets

H₁ Receptor ( Ki = 0.1 μM ); PAF ( Ki = 0.55 μM )

ln Vitro

In vitro activity: Rupatadine interacts with certain receptors to block the effects of histamine (H1) and platelet-activating factor (PAF). Without influencing contraction caused by ACh, serotonin, or leukotriene D4 (LTD4), rupatadine competitively inhibits histamine-induced guinea pig ileum contraction (pA2 = 9.29 ± 0.06). Additionally, it selectively prevents platelet aggregation caused by PAF in washed rabbit platelets (WRP) (pA2 = 6.68 ± 0.08) and in human platelet-rich plasma (HPRP) (IC50 = 0.68 μM), but not in platelet aggregation caused by arachidonic acid or ADP.[1] Another study reports that SR-27417A only shows inhibitory effect against TNF-α, while rupatadine and loratadine show similar inhibitory effect on histamine and TNF-α release.[2]

ln Vivo

Rupatadine inhibits the effects of histamine and PAF in vivo, including bronchoconstriction in guinea pigs (ID50 = 113 and 9.6 μg/kg i.v.) and hypotension in rats (ID50 = 1.4 and 0.44 mg/kg i.v., respectively). Additionally, it significantly reduces endotoxin-induced mortality in mice and rats (ID50 = 1.6 and 0.66 mg/kg i.v.) as well as PAF-induced mortality in mice (ID50 = 0.31 and 3.0 mg/kg i.v. and p.o., respectively). The histamine- and PAF-induced increase in vascular permeability test in dogs indicates that rupatadine has a long half-life (42% and 34% inhibition at 26 hours after 1 mg/kg p.o.). Rupatadine at 100 mg/kg p.o. does not alter spontaneous motor activity in mice or increase the amount of time they spend sleeping on barbiturates, indicating that it has no sedative effects.[1]

Enzyme Assay

For 30 minutes at 25 °C, antagonists are incubated with guinea pig cerebellum membranes (0.6 mg/ml) and [3H]-pyrilamine (1.2 nM) in 0.5 ml of 50 mM PBS. The membranes are collected on Whatman GF/B filters and 5 ml of ice-cold PBS containing 2 μM pyrilamine is added to end the incubation. After that, the filters are placed in counting vials after being cleaned with 3 x 5 ml of ice-cold PBS plus 2 μM pyrilamine. Liquid scintillation counting in 3 ml of HiSafe 3 is used to determine the amount of radioactivity retained by each filter. The difference between the [3H]-pyrilamine bound in the absence and in the presence of a large molar excess (10 μM) of unlabeled promethazine allows for the determination of specific binding.

Cell Assay

C18-PAF is used to induce platelet aggregation, which is then measured with a dual-channel aggregometer Chrono-log 560. Platelet aggregation is measured both with and without the test compounds (5-min incubation). The inhibitors' activity is represented by their IC50 values. Rupatadine is tested in WRP against other aggregating agents, such as arachidonic acid (1 mM) and ADP (5 μM), in order to determine its selectivity. Rupatadine is present at different concentrations (3 × 10^-7–3 × 10^-5 M) and in the absence to obtain dose-response curves for PAF-induced aggregation in WRP.

Animal Protocol

Dissolved in saline; 1 mg/kg; i.v. injection

PAF- and histamine-induced hypotension in normotensive rats

References

[1]. J Pharmacol Exp Ther . 1997 Jan;280(1):114-21.

[2]. Inflamm Res . 2000 Jul;49(7):355-60.

[3]. Neuropsychobiology . 2004;50(4):311-21.

[4]. Indian J Otolaryngol Head Neck Surg . 2009 Dec;61(4):320-32.

These protocols are for reference only. InvivoChem does not independently validate these methods.

Physicochemical Properties

Molecular Formula

C30H30CLN3O4

Molecular Weight

532.03

Exact Mass

531.19

Elemental Analysis

C, 67.73; H, 5.68; Cl, 6.66; N, 7.90; O, 12.03

CAS #

182349-12-8

Related CAS #

Rupatadine; 158876-82-5; Rupatadine-d4 fumarate; 1795153-63-7

Appearance

Solid powder

SMILES

CC1=CC(=CN=C1)CN2CCC(=C3C4=C(CCC5=C3N=CC=C5)C=C(C=C4)Cl)CC2.C(=C/C(=O)O)\C(=O)O

InChi Key

JYBLCDXVHQWMSU-WLHGVMLRSA-N

InChi Code

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+

Chemical Name

(E)-but-2-enedioic acid;13-chloro-2-[1-[(5-methylpyridin-3-yl)methyl]piperidin-4-ylidene]-4-azatricyclo[9.4.0.03,8]pentadeca-1(11),3(8),4,6,12,14-hexaene

Synonyms

Rupatadine Fumarate; UR-12592 Fumarate; UR 12592 Fumarate; UR12592 Fumarate; Pafinur; Rupax; Rupafin; Alergoliber; Rinialer; Ralif

HS Tariff Code

2934.99.9001

Storage

Powder -20°C 3 years

4°C 2 years

In solvent -80°C 6 months

-20°C 1 month

Note: Please store this product in a sealed and protected environment, avoid exposure to moisture.

Shipping Condition

Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)

Solubility Data

Solubility (In Vitro)

DMSO: 9~30 mg/mL (16.9~56.4 mM)

Water: <1 mg/mL

Ethanol: ~13 mg/mL (~24.4 mM)

Solubility (In Vivo)

Solubility in Formulation 1: ≥ 2.08 mg/mL (3.91 mM) (saturation unknown) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 20.8 mg/mL clear DMSO stock solution to 400 μL PEG300 and mix evenly; then add 50 μL Tween-80 to the above solution and mix evenly; then add 450 μL normal saline to adjust the volume to 1 mL.
Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution.

Solubility in Formulation 2: ≥ 2.08 mg/mL (3.91 mM) (saturation unknown) in 10% DMSO + 90% (20% SBE-β-CD in Saline) (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 20.8 mg/mL clear DMSO stock solution to 900 μL of 20% SBE-β-CD physiological saline solution and mix evenly.
Preparation of 20% SBE-β-CD in Saline (4°C，1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution.

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Solubility in Formulation 3: ≥ 2.08 mg/mL (3.91 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 20.8 mg/mL clear DMSO stock solution to 900 μL of corn oil and mix evenly.

Solubility in Formulation 4: 30% Propylene glycol , 5% Tween 80 , 65% D5W: 30 mg/mL

(Please use freshly prepared in vivo formulations for optimal results.)

Preparing Stock Solutions		1 mg	5 mg	10 mg
	1 mM	1.8796 mL	9.3980 mL	18.7959 mL
	5 mM	0.3759 mL	1.8796 mL	3.7592 mL
	10 mM	0.1880 mL	0.9398 mL	1.8796 mL

*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.

Calculator

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Molarity Calculator allows you to calculate the mass, volume, and/or concentration required for a solution, as detailed below:

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An example of molarity calculation using the molarity calculator is shown below:
What is the mass of compound required to make a 10 mM stock solution in 5 ml of DMSO given that the molecular weight of the compound is 350.26 g/mol?

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The answer of 17.513 mg appears in the Mass box. In a similar way, you may calculate the volume and concentration.

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Dilution Calculator allows you to calculate how to dilute a stock solution of known concentrations. For example, you may Enter C1, C2 & V2 to calculate V1, as detailed below:

What volume of a given 10 mM stock solution is required to make 25 ml of a 25 μM solution?
Using the equation C1V1 = C2V2, where C1=10 mM, C2=25 μM, V2=25 ml and V1 is the unknown:

Enter 10 into the Concentration (Start) box and choose the correct unit (mM)
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The answer of 62.5 μL (0.1 ml) appears in the Volume (Start) box

Molecular formula

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Molecular Weight Calculator allows you to calculate the molar mass and elemental composition of a compound, as detailed below:

Note: Chemical formula is case sensitive: C12H18N3O4 c12h18n3o4
Instructions to calculate molar mass (molecular weight) of a chemical compound:

To calculate molar mass of a chemical compound, please enter the chemical/molecular formula and click the “Calculate’ button.

Definitions of molecular mass, molecular weight, molar mass and molar weight:

Molecular mass (or molecular weight) is the mass of one molecule of a substance and is expressed in the unified atomic mass units (u). (1 u is equal to 1/12 the mass of one atom of carbon-12)
Molar mass (molar weight) is the mass of one mole of a substance and is expressed in g/mol.

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Reconstitution Calculator allows you to calculate the volume of solvent required to reconstitute your vial.

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The answer appears in the Volume (to add to vial) box

In vivo Formulation Calculator (Clear solution)

Step 1: Enter information below (Recommended: An additional animal to make allowance for loss during the experiment)

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Step 2: Enter in vivo formulation (This is only a calculator, not the exact formulation for a specific product. Please contact us first if there is no in vivo formulation in the solubility section.)

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Calculation results

Working concentration： mg/mL；

Method for preparing DMSO stock solution： mg drug pre-dissolved in μL DMSO (stock solution concentration mg/mL). Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug.

Method for preparing in vivo formulation:：Take μL DMSO stock solution, next add μL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH₂O，mix and clarify.

Note： (1) Please be sure that the solution is clear before the addition of next solvent. Dissolution methods like vortex, ultrasound or warming and heat may be used to aid dissolving.
(2) Be sure to add the solvent(s) in order.

Clinical Trial Information

NCT Number	Recruitment	interventions	Conditions	Sponsor/Collaborators	Start Date	Phases
NCT03770923	Recruiting	Drug: Rupatadine Drug: Montelukast	Rheumatoid Arthritis	Sherief Abd-Elsalam	October 1, 2018	Phase 3
NCT01481909	Completed	Drug: Rupatadin	Mastocytosis	Marcus Maurer	September 2010	Phase 2 Phase 3
NCT05356143	Completed	Drug: Rupatadine	Healthy	J. Uriach and Company	December 2, 2021	Phase 1
NCT01605487	Completed	Drug: Rupatadine	Cold Contact Urticaria	Charite University, Berlin, Germany	June 2012	Phase 2
NCT01481909	Completed	Drug: Rupatadin	Mastocytosis	Marcus Maurer	September 2010	Phase 2 Phase 3

Biological Data

Dose-response curves of PAF-induced aggregation in washed rabbit platelets were obtained in the absence (○) or presence of 3 × 10−7 (), 10−6 (▵), 3 × 10−6 (▴), 10−5 (□) and 3 × 10−5 (•) M rupatadine.J Pharmacol Exp Ther.1997 Jan;280(1):114-21.

Rupatadine Fumarate — Dose-response curves for histamine-induced contraction of guinea pig ileum were obtained in the absence of (○) or presence of 10−9 (), 3 × 10−8(▵), 10−8 (▴) and 3 × 10−8 (□) M rupatadine.J Pharmacol Exp Ther.1997 Jan;280(1):114-21.