Rupatadine

Identification

Summary

Rupatadine is a selective histamine H1 receptor antagonist and platelet activating factor (PAF) antagonist used to treat allergic rhinitis.

Brand Names
Rupall
Generic Name
Rupatadine
DrugBank Accession Number
DB11614
Background

Rupatadine is a dual histamine H1 receptor and platelet activating factor receptor antagonist that is used for symptomatic relief in seasonal and perennial rhinitis as well as chronic spontaneous urticaria. It was approved for marketing in Canada under the tradename Rupall and comes in tablet formulation for adult use and liquid formulation for pediatric use.

Type
Small Molecule
Groups
Approved
Structure
Thumb
Weight
Average: 415.97
Monoisotopic: 415.1815255
Chemical Formula
C26H26ClN3
Synonyms
  • Rupatadina
  • Rupatadine
External IDs
  • UR-12592

Pharmacology

Indication

For the symptomatic relief of nasal and non-nasal symptoms of seasonal allergic rhinitis and perennial allergic rhinitis in patients 2 years of age and older Label. Also used for the symptomatic relief of chronic spontaneous urticaria in patients 2 years of age and older.

Pharmacology
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Associated Conditions
Contraindications & Blackbox Warnings
Contraindications
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Pharmacodynamics

Rupatadine is an anti allergenic and acts to reduce allergic symptoms like urticaria, rhinorrhea, sneezing and itching Label.

Mechanism of action

Rupatadine is a dual histamine H1 receptor and platelet activating (PAF) receptor antagonist 1 Label. During allergic response mast cells undergo degranulation, releasing histamine and other substances 2. Histamine acts on H1 receptors to produce symptoms of nasal blockage, rhinorhea, itching, and swelling. PAF is produced from phospholipids cleaved by phospholipase A2. It acts to produce vascular leakage which contributes to rhinorhea and nasal blockage. By blocking both the H1 receptor and PAF receptor, rupatidine prevents these mediators from exerting their effects and so reduces the severity of allergic symptoms.

TargetActionsOrganism
APlatelet-activating factor receptor
antagonist
Humans
AHistamine H1 receptor
antagonist
Humans
Absorption

Rupatidine is rapidly absorbed with a Tmax of 1 h Label. Administration with a high fat meal increases exposure by 23% and increases Tmax to 2 h.

Volume of distribution

The apparent volume of distribution is 9799 L Label.

Protein binding

Rupatidine is 98.5-99.0% bound to human plasma proteins Label.

Metabolism

Rupatadine is metabolized by oxidation mediated primarily by CYP3A4 Label. CYP2C9, CYP2C19, and CYP2D6 are also involved to a lesser extent. The metabolites desloratidine and hydroxylated forms of desloratidine retain some activity as H1 receptor antagonists.

Route of elimination

Not Available

Half-life

The half life of elimination is 15.9 h in children 2-5 years old, 12.3 h in children 6-11 years old, 5.9 h in adults, and 8.7 h in geriatric patients Label.

Clearance

Systemic clearance is 1556.2 L/h in young adults and 798.2 L/h in geriatric patients Label.

Adverse Effects
Adverseeffects
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Toxicity

Not Available

Pathways
PathwayCategory
Rupatadine H1-Antihistamine ActionDrug action
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
DrugInteraction
AbametapirThe serum concentration of Rupatadine can be increased when it is combined with Abametapir.
AbataceptThe metabolism of Rupatadine can be increased when combined with Abatacept.
AbirateroneThe metabolism of Rupatadine can be decreased when combined with Abiraterone.
AcebutololThe metabolism of Rupatadine can be decreased when combined with Acebutolol.
AcenocoumarolThe metabolism of Acenocoumarol can be decreased when combined with Rupatadine.
AcetaminophenThe metabolism of Rupatadine can be decreased when combined with Acetaminophen.
AcetohexamideThe metabolism of Rupatadine can be decreased when combined with Acetohexamide.
Acetyl sulfisoxazoleThe metabolism of Rupatadine can be decreased when combined with Acetyl sulfisoxazole.
Acetylsalicylic acidThe metabolism of Rupatadine can be decreased when combined with Acetylsalicylic acid.
AcrivastineThe risk or severity of QTc prolongation can be increased when Acrivastine is combined with Rupatadine.
Interactions
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Food Interactions
  • Avoid grapefruit products. Grapefruit inhibits CYP3A metabolism, which may increase the serum concentration of rupatadine.
  • Take with or without food.

Products

Products2
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Product Ingredients
IngredientUNIICASInChI Key
Rupatadine fumarateXJ6OT32M93182349-12-8JYBLCDXVHQWMSU-WLHGVMLRSA-N
Rupatadine trihydrochlorideG61C8NZY2T156611-76-6BQFOTHHRVVHLEW-UHFFFAOYSA-N
Brand Name Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
RupallTablet10 mgOralMedexus Pharmaceuticals Inc2017-01-16Not applicableCanada flag
RupallSolution1 mg / mLOralMedexus Pharmaceuticals Inc2017-01-20Not applicableCanada flag

Categories

ATC Codes
R06AX28 — Rupatadine
Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as benzocycloheptapyridines. These are aromatic compounds containing a benzene ring and a pyridine ring fused to a seven membered carbocycle.
Kingdom
Organic compounds
Super Class
Organoheterocyclic compounds
Class
Benzocycloheptapyridines
Sub Class
Not Available
Direct Parent
Benzocycloheptapyridines
Alternative Parents
Methylpyridines / Aralkylamines / Piperidines / Benzenoids / Aryl chlorides / Heteroaromatic compounds / Trialkylamines / Azacyclic compounds / Organopnictogen compounds / Organochlorides
show 1 more
Substituents
Amine / Aralkylamine / Aromatic heteropolycyclic compound / Aryl chloride / Aryl halide / Azacycle / Benzenoid / Benzocycloheptapyridine / Heteroaromatic compound / Hydrocarbon derivative
show 10 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
Not Available
Affected organisms
Not Available

Chemical Identifiers

UNII
2AE8M83G3E
CAS number
158876-82-5
InChI Key
WUZYKBABMWJHDL-UHFFFAOYSA-N
InChI
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
IUPAC Name
13-chloro-2-{1-[(5-methylpyridin-3-yl)methyl]piperidin-4-ylidene}-4-azatricyclo[9.4.0.0^{3,8}]pentadeca-1(15),3(8),4,6,11,13-hexaene
SMILES
CC1=CC(CN2CCC(CC2)=C2C3=CC=C(Cl)C=C3CCC3=C2N=CC=C3)=CN=C1

References

General References
  1. Merlos M, Giral M, Balsa D, Ferrando R, Queralt M, Puigdemont A, Garcia-Rafanell J, Forn J: 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. [Article]
  2. Alfaro V: Role of histamine and platelet-activating factor in allergic rhinitis. J Physiol Biochem. 2004 Jun;60(2):101-11. [Article]
Human Metabolome Database
HMDB0240234
PubChem Compound
133017
PubChem Substance
347828008
ChemSpider
117388
BindingDB
50036935
ChEBI
135673
ChEMBL
CHEMBL91397
ZINC
ZINC000000598829
PharmGKB
PA165107052
Wikipedia
Rupatadine
FDA label
Download (794 KB)
MSDS
Download (56.5 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
4Not Yet RecruitingTreatmentAllergic Rhinitis (Disorder)1
4TerminatedPreventionHealthy Subjects (HS)1
4Unknown StatusPreventionHypersensitivity1
3RecruitingTreatmentRheumatoid Arthritis1
3TerminatedTreatmentChronic Urticaria1
3TerminatedTreatmentUrticaria1
2CompletedTreatmentCold Contact Urticaria1
2TerminatedTreatmentUrticaria1
1CompletedTreatmentHuman Experimentation (Human Volunteers)1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage Forms
FormRouteStrength
SolutionOral1 MG/ML
SolutionOral
TabletOral
SolutionOral1.00 mg/ml
SolutionOral100 mg
SolutionOral1 mg / mL
TabletOral10 mg
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)194-201FDA Label
logP0.8FDA Label
Predicted Properties
PropertyValueSource
Water Solubility0.00544 mg/mLALOGPS
logP4.82ALOGPS
logP5.37ChemAxon
logS-4.9ALOGPS
pKa (Strongest Basic)7.19ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area29.02 Å2ChemAxon
Rotatable Bond Count2ChemAxon
Refractivity133.83 m3·mol-1ChemAxon
Polarizability46.98 Å3ChemAxon
Number of Rings5ChemAxon
Bioavailability1ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET Features
Not Available

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available

Targets

Drugtargets2
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Kind
Protein
Organism
Humans
Pharmacological action
Yes
Actions
Antagonist
General Function
Platelet activating factor receptor activity
Specific Function
Receptor for platelet activating factor, a chemotactic phospholipid mediator that possesses potent inflammatory, smooth-muscle contractile and hypotensive activity. Seems to mediate its action via ...
Gene Name
PTAFR
Uniprot ID
P25105
Uniprot Name
Platelet-activating factor receptor
Molecular Weight
39203.075 Da
References
  1. Merlos M, Giral M, Balsa D, Ferrando R, Queralt M, Puigdemont A, Garcia-Rafanell J, Forn J: 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. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Yes
Actions
Antagonist
General Function
Histamine receptor activity
Specific Function
In peripheral tissues, the H1 subclass of histamine receptors mediates the contraction of smooth muscles, increase in capillary permeability due to contraction of terminal venules, and catecholamin...
Gene Name
HRH1
Uniprot ID
P35367
Uniprot Name
Histamine H1 receptor
Molecular Weight
55783.61 Da
References
  1. Merlos M, Giral M, Balsa D, Ferrando R, Queralt M, Puigdemont A, Garcia-Rafanell J, Forn J: 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. [Article]

Enzymes

Kind
Protein
Organism
Humans
Pharmacological action
No
Actions
Substrate
General Function
Vitamin d3 25-hydroxylase activity
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation react...
Gene Name
CYP3A4
Uniprot ID
P08684
Uniprot Name
Cytochrome P450 3A4
Molecular Weight
57342.67 Da
Kind
Protein
Organism
Humans
Pharmacological action
No
Actions
Substrate
General Function
Steroid hydroxylase activity
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
Gene Name
CYP2C9
Uniprot ID
P11712
Uniprot Name
Cytochrome P450 2C9
Molecular Weight
55627.365 Da
References
  1. Rupatadine Canadian Prescribing Information [File]
Kind
Protein
Organism
Humans
Pharmacological action
No
Actions
Substrate
General Function
Steroid hydroxylase activity
Specific Function
Responsible for the metabolism of a number of therapeutic agents such as the anticonvulsant drug S-mephenytoin, omeprazole, proguanil, certain barbiturates, diazepam, propranolol, citalopram and im...
Gene Name
CYP2C19
Uniprot ID
P33261
Uniprot Name
Cytochrome P450 2C19
Molecular Weight
55930.545 Da
Kind
Protein
Organism
Humans
Pharmacological action
No
Actions
Substrate
General Function
Steroid hydroxylase activity
Specific Function
Responsible for the metabolism of many drugs and environmental chemicals that it oxidizes. It is involved in the metabolism of drugs such as antiarrhythmics, adrenoceptor antagonists, and tricyclic...
Gene Name
CYP2D6
Uniprot ID
P10635
Uniprot Name
Cytochrome P450 2D6
Molecular Weight
55768.94 Da

Drug created on August 05, 2016 23:52 / Updated on October 24, 2021 16:00