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
Structure for Rupatadine (DB11614)
- 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.
Reduce drug development failure ratesBuild, train, & validate machine-learning modelswith evidence-based and structured datasets.Build, train, & validate predictive machine-learning models with structured datasets.- Associated Conditions
Indication Type Indication Combined Product Details Approval Level Age Group Patient Characteristics Dose Form Symptomatic treatment of Allergic rhinitis •••••••••••• Symptomatic treatment of Hives •••••••••••• Symptomatic treatment of Pruritus •••••••••••• - Contraindications & Blackbox Warnings
Prevent Adverse Drug Events TodayTap into our Clinical API for life-saving information on contraindications & blackbox warnings, population restrictions, harmful risks, & more.Avoid life-threatening adverse drug events with our Clinical API- 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.
Target Actions Organism APlatelet-activating factor receptor antagonistHumans AHistamine H1 receptor antagonistHumans - 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
Improve decision support & research outcomesWith structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates. View sample adverse effects data in our new Data Library!Improve decision support & research outcomes with our structured adverse effects data.- Toxicity
Not Available
- Pathways
Pathway Category Rupatadine H1-Antihistamine Action Drug action - Pharmacogenomic Effects/ADRs Browse all" title="About SNP Mediated Effects/ADRs" id="snp-actions-info" class="drug-info-popup" href="javascript:void(0);">
- Not Available
Interactions
- Drug Interactions Learn More" title="About Drug Interactions" id="structured-interactions-info" class="drug-info-popup" href="javascript:void(0);">
- 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.
Drug Interaction Integrate drug-drug
interactions in your softwareAbametapir The serum concentration of Rupatadine can be increased when it is combined with Abametapir. Abatacept The metabolism of Rupatadine can be increased when combined with Abatacept. Abiraterone The metabolism of Rupatadine can be decreased when combined with Abiraterone. Abrocitinib The metabolism of Abrocitinib can be decreased when combined with Rupatadine. Acebutolol The metabolism of Rupatadine can be decreased when combined with Acebutolol. - Food Interactions
- Avoid grapefruit products. Grapefruit inhibits CYP3A metabolism, which may increase the serum concentration of rupatadine.
- Take with or without food.
Products
Drug product information from 10+ global regionsOur datasets provide approved product information including:dosage, form, labeller, route of administration, and marketing period.Access drug product information from over 10 global regions.- Product Ingredients
Ingredient UNII CAS InChI Key Rupatadine fumarate XJ6OT32M93 182349-12-8 JYBLCDXVHQWMSU-WLHGVMLRSA-N Rupatadine trihydrochloride G61C8NZY2T 156611-76-6 BQFOTHHRVVHLEW-UHFFFAOYSA-N - Brand Name Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Rupall Tablet 10 mg Oral Medexus Inc 2017-01-16 Not applicable Canada 
Rupall Solution 1 mg / mL Oral Medexus Inc 2017-01-20 Not applicable Canada
Categories
- ATC Codes
- R06AX28 — Rupatadine
- Drug Categories
- Antihistamines for Systemic Use
- Benzocycloheptenes
- Cytochrome P-450 CYP2C19 Substrates
- Cytochrome P-450 CYP2C9 Substrates
- Cytochrome P-450 CYP2D6 Substrates
- Cytochrome P-450 CYP3A Substrates
- Cytochrome P-450 CYP3A4 Substrates
- Cytochrome P-450 Substrates
- Dibenzocycloheptenes
- Histamine Antagonists
- Histamine H1 Antagonists
- Histamine H1 Antagonists, Non-Sedating
- Piperidines
- Platelet Activating Factor, antagonists & inhibitors
- Potential QTc-Prolonging Agents
- QTc Prolonging Agents
- 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
- 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]
- Alfaro V: Role of histamine and platelet-activating factor in allergic rhinitis. J Physiol Biochem. 2004 Jun;60(2):101-11. [Article]
- External Links
- 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 Learn More" title="About Clinical Trials" id="clinical-trials-info" class="drug-info-popup" href="javascript:void(0);">
Phase Status Purpose Conditions Count 4 Terminated Prevention Healthy Subjects (HS) 1 4 Unknown Status Prevention Allergic Reaction 1 4 Withdrawn Treatment Allergic Rhinitis (AR) 1 3 Recruiting Treatment Rheumatoid Arthritis 1 3 Terminated Treatment Chronic Urticaria 1
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage Forms
Form Route Strength Solution Oral 1 MG/ML Tablet Oral 10.000 mg Syrup Oral 100.00 mg Tablet Oral Solution Oral 1.00 mg/ml Solution Oral 100 mg Solution Oral 1 mg / mL Tablet Oral 10 mg - Prices
- Not Available
- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
Property Value Source melting point (°C) 194-201 FDA Label logP 0.8 FDA Label - Predicted Properties
Property Value Source Water Solubility 0.00544 mg/mL ALOGPS logP 4.82 ALOGPS logP 5.37 Chemaxon logS -4.9 ALOGPS pKa (Strongest Basic) 7.19 Chemaxon Physiological Charge 1 Chemaxon Hydrogen Acceptor Count 3 Chemaxon Hydrogen Donor Count 0 Chemaxon Polar Surface Area 29.02 Å2 Chemaxon Rotatable Bond Count 2 Chemaxon Refractivity 133.83 m3·mol-1 Chemaxon Polarizability 46.98 Å3 Chemaxon Number of Rings 5 Chemaxon Bioavailability 1 Chemaxon Rule of Five No Chemaxon Ghose Filter No Chemaxon Veber's Rule Yes Chemaxon MDDR-like Rule No Chemaxon - Predicted ADMET Features
- Not Available
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS splash10-014i-0000900000-2b04bac13ae72fd1a796 Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS splash10-03di-0000900000-f34b34975d461ecafd36 Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS splash10-03e9-6011900000-9ef8b4ad99714bd64edb Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS splash10-014i-0001900000-7f64dd6c57d151fc22fe Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS splash10-001u-9305100000-72f5fe43b9e8009034c8 Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS splash10-014r-1269200000-c248b482017c4821a1fc Predicted 1H NMR Spectrum 1D NMR Not Applicable Predicted 13C NMR Spectrum 1D NMR Not Applicable - Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 217.3808747 predictedDarkChem Lite v0.1.0 [M-H]- 201.2808 predictedDeepCCS 1.0 (2019) [M+H]+ 218.6638747 predictedDarkChem Lite v0.1.0 [M+H]+ 203.63881 predictedDeepCCS 1.0 (2019) [M+Na]+ 217.8231747 predictedDarkChem Lite v0.1.0 [M+Na]+ 210.51096 predictedDeepCCS 1.0 (2019)
Targets
Build, predict & validate machine-learning models
Use our structured and evidence-based datasets to unlock newinsights and accelerate drug research.
Use our structured and evidence-based datasets to unlock new insights and accelerate drug research.
- 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
- 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
- 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
- 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 at August 05, 2016 23:52 / Updated at February 08, 2023 20:46