Rupatadine

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

Cat No.:V2041 Purity: ≥98%

COA Product Data Instructions for use SDS

Rupatadine (also known as UR-12592) is a potent inhibitor of PAFR and histamine (H1) receptor with Ki of 550 nM and 102 nM, respectively.

Rupatadine Chemical Structure CAS No.: 158876-82-5
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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Nature 2021, 597(7874):119-125.

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J Am Chem Soc 2022,144:21831-21836.

Cell 2020,183:1202-1218.e25.

Science Adv 2022:8,eabm9427.

Nature 2021,597(7874):119-125.

Cell 2020,183:1202-1218.e25.

PNAS Nexus 2022,1(3):pgac063.

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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

Rupatadine (also known as UR-12592) is a potent inhibitor of PAFR and histamine (H1) receptor with Ki of 550 nM and 102 nM, respectively. Rupatadine inhibits the effects of platelet-activating factor (PAF) and histamine (H1) by interacting with specific receptors. Rupatadine competitively suppresses histamine-induced guinea pig ileum contraction (pA2 = 9.29 ± 0.06) without affecting contraction induced by ACh, serotonin, or leukotriene D4 (LTD4). 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.

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 does not alter contractions induced by ACh, serotonin, or leukotriene D4 (LTD4), but it competitively inhibits histamine-induced guinea pig ileum contraction (pA2=9.29)[1].
Rupatadine does not affect platelet aggregation induced by arachidonic acid or ADP, but it competitively inhibits PAF-induced platelet aggregation in washed rabbit platelets (WRP) (pA2=6.68) and in human platelet-rich plasma (HPRP) (IC50=0.68 μM)[1].
Rupatadine has a concentration-dependent effect on TNF-α secretion, with maximum values of 92.5% when used at concentrations of 0.1-30 μM[2].

ln Vivo

border-color: rgb(238, 238, 238); text-align: justify;" width="80%">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)[1].
Rupatadine 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)[1].
Rupatadine (6 mg/kg) reduces lung density and facilitates the absorption of lesions[3].

Enzyme Assay

In 0.5 ml of 50 mM PBS, pH 7.5, antagonists are incubated for 30 minutes at 25 °C with guinea pig cerebellum membranes (0.6 mg/ml) and [3H]-pyrilamine (1.2 nM). The incubation is ended by the addition of 5 ml of ice-cold PBS containing 2 μM pyrilamine and the collection of membranes on Whatman GF/B filters. After being cleaned with 3 × 5 ml of ice-cold PBS and 2 μM pyrilamine, the filters are placed in counting vials. Using 3 ml of HiSafe 3, liquid scintillation counting is used to determine the amount of radioactivity retained by each filter. The determination of specific binding is based on the variation in the amount of [3H]-pyrilamine bound when unlabeled promethazine (10 μM) is present compared to when it is not.

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]. Rupatadine, a new potent, orally active dual antagonist of histamine and platelet-activating factor (PAF). J Pharmacol Exp Ther. 1997 Jan;280(1):114-21.

[2]. In vitro inhibitory effect of rupatadine on histamine and TNF-alpha release from dispersed canine skin mast cells and the human mast cell line HMC-1. Inflamm Res. 2000 Jul;49(7):355-60.

[3]. Rupatadine protects against pulmonary fibrosis by attenuating PAF-mediated senescence in rodents. PLoS One. 2013 Jul 15;8(7):e68631.

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

Physicochemical Properties

Molecular Formula

C26H26CLN3

Molecular Weight

415.96

Exact Mass

415.18

Elemental Analysis

C, 75.08; H, 6.30; Cl, 8.52; N, 10.10

CAS #

158876-82-5

Related CAS #

Rupatadine Fumarate; 182349-12-8; 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

InChi Key

WUZYKBABMWJHDL-UHFFFAOYSA-N

InChi Code

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

Chemical Name

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; UR-12592; UR 12592; UR12592; 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

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 mg/mL (~16.9 mM)

Water: <1 mg/mL

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

Solubility (In Vivo)

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	2.4041 mL	12.0204 mL	24.0408 mL
	5 mM	0.4808 mL	2.4041 mL	4.8082 mL
	10 mM	0.2404 mL	1.2020 mL	2.4041 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

Mass

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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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See Example

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?

Enter 350.26 in the Molecular Weight (MW) box
Enter 10 in the Concentration box and choose the correct unit (mM)
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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)
Enter 25 into the Concentration (End) box and select the correct unit (mM)
Enter 25 into the Volume (End) box and choose the correct unit (mL)
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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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g/mol

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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.

Enter the mass of the reagent and the desired reconstitution concentration as well as the correct units
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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)

Dosage mg/kg

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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 — 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.