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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.
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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
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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
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Not Available
- Pathways
Pathway Category Rupatadine H1-Antihistamine Action Drug 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.
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 Solution 1 mg / mL Oral Medexus Pharmaceuticals Inc. 2017-01-20 Not applicable Canada 
Rupall Tablet 10 mg Oral Medexus Pharmaceuticals Inc. 2017-01-16 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
Clinical Trial & Rare Diseases Add-on Data Package
Explore 4,000+ rare diseases, orphan drugs & condition pairs, clinical trial why stopped data, & more. Preview package Phase Status Purpose Conditions Count Start Date Why Stopped 100+ additional columns Unlock 175K+ rows when you subscribe.View sample data4 Terminated Prevention Healthy Volunteers (HV) 1 somestatus stop reason just information to hide 4 Unknown Status Prevention Allergic Reaction 1 somestatus stop reason just information to hide 4 Withdrawn Treatment Allergic Rhinitis (AR) 1 somestatus stop reason just information to hide 3 Recruiting Treatment Rheumatoid Arthritis 1 somestatus stop reason just information to hide 3 Terminated Treatment Chronic Urticaria 1 somestatus stop reason just information to hide
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage Forms
Form Route Strength Tablet Oral 10.000 mg Syrup Oral 100.00 mg Tablet Oral Tablet Oral 12.8 mg Solution Oral 1 mg/ml 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
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- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Antagonist
- General 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 a G protein that activates a phosphatidylinositol-calcium second messenger system
- Specific Function
- G protein-coupled purinergic nucleotide receptor activity
- 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
- 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 catecholamine release from adrenal medulla, as well as mediating neurotransmission in the central nervous system
- Specific Function
- G protein-coupled serotonin receptor activity
- 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
- A cytochrome P450 monooxygenase involved in the metabolism of sterols, steroid hormones, retinoids and fatty acids (PubMed:10681376, PubMed:11093772, PubMed:11555828, PubMed:12865317, PubMed:14559847, PubMed:15373842, PubMed:15764715, PubMed:19965576, PubMed:20702771, PubMed:21490593, PubMed:21576599). Mechanistically, uses molecular oxygen inserting one oxygen atom into a substrate, and reducing the second into a water molecule, with two electrons provided by NADPH via cytochrome P450 reductase (NADPH--hemoprotein reductase). Catalyzes the hydroxylation of carbon-hydrogen bonds (PubMed:12865317, PubMed:14559847, PubMed:15373842, PubMed:15764715, PubMed:21490593, PubMed:21576599, PubMed:2732228). Exhibits high catalytic activity for the formation of hydroxyestrogens from estrone (E1) and 17beta-estradiol (E2), namely 2-hydroxy E1 and E2, as well as D-ring hydroxylated E1 and E2 at the C-16 position (PubMed:11555828, PubMed:12865317, PubMed:14559847). Plays a role in the metabolism of androgens, particularly in oxidative deactivation of testosterone (PubMed:15373842, PubMed:15764715, PubMed:22773874, PubMed:2732228). Metabolizes testosterone to less biologically active 2beta- and 6beta-hydroxytestosterones (PubMed:15373842, PubMed:15764715, PubMed:2732228). Contributes to the formation of hydroxycholesterols (oxysterols), particularly A-ring hydroxylated cholesterol at the C-4beta position, and side chain hydroxylated cholesterol at the C-25 position, likely contributing to cholesterol degradation and bile acid biosynthesis (PubMed:21576599). Catalyzes bisallylic hydroxylation of polyunsaturated fatty acids (PUFA) (PubMed:9435160). Catalyzes the epoxidation of double bonds of PUFA with a preference for the last double bond (PubMed:19965576). Metabolizes endocannabinoid arachidonoylethanolamide (anandamide) to 8,9-, 11,12-, and 14,15-epoxyeicosatrienoic acid ethanolamides (EpETrE-EAs), potentially modulating endocannabinoid system signaling (PubMed:20702771). Plays a role in the metabolism of retinoids. Displays high catalytic activity for oxidation of all-trans-retinol to all-trans-retinal, a rate-limiting step for the biosynthesis of all-trans-retinoic acid (atRA) (PubMed:10681376). Further metabolizes atRA toward 4-hydroxyretinoate and may play a role in hepatic atRA clearance (PubMed:11093772). Responsible for oxidative metabolism of xenobiotics. Acts as a 2-exo-monooxygenase for plant lipid 1,8-cineole (eucalyptol) (PubMed:11159812). Metabolizes the majority of the administered drugs. Catalyzes sulfoxidation of the anthelmintics albendazole and fenbendazole (PubMed:10759686). Hydroxylates antimalarial drug quinine (PubMed:8968357). Acts as a 1,4-cineole 2-exo-monooxygenase (PubMed:11695850). Also involved in vitamin D catabolism and calcium homeostasis. Catalyzes the inactivation of the active hormone calcitriol (1-alpha,25-dihydroxyvitamin D(3)) (PubMed:29461981)
- Specific Function
- 1,8-cineole 2-exo-monooxygenase activity
- 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
- A cytochrome P450 monooxygenase involved in the metabolism of various endogenous substrates, including fatty acids and steroids (PubMed:12865317, PubMed:15766564, PubMed:19965576, PubMed:21576599, PubMed:7574697, PubMed:9435160, PubMed:9866708). Mechanistically, uses molecular oxygen inserting one oxygen atom into a substrate, and reducing the second into a water molecule, with two electrons provided by NADPH via cytochrome P450 reductase (NADPH--hemoprotein reductase) (PubMed:12865317, PubMed:15766564, PubMed:19965576, PubMed:21576599, PubMed:7574697, PubMed:9435160, PubMed:9866708). Catalyzes the epoxidation of double bonds of polyunsaturated fatty acids (PUFA) (PubMed:15766564, PubMed:19965576, PubMed:7574697, PubMed:9866708). Catalyzes the hydroxylation of carbon-hydrogen bonds. Metabolizes cholesterol toward 25-hydroxycholesterol, a physiological regulator of cellular cholesterol homeostasis (PubMed:21576599). Exhibits low catalytic activity for the formation of catechol estrogens from 17beta-estradiol (E2) and estrone (E1), namely 2-hydroxy E1 and E2 (PubMed:12865317). Catalyzes bisallylic hydroxylation and hydroxylation with double-bond migration of polyunsaturated fatty acids (PUFA) (PubMed:9435160, PubMed:9866708). Also metabolizes plant monoterpenes such as limonene. Oxygenates (R)- and (S)-limonene to produce carveol and perillyl alcohol (PubMed:11950794). Contributes to the wide pharmacokinetics variability of the metabolism of drugs such as S-warfarin, diclofenac, phenytoin, tolbutamide and losartan (PubMed:25994031)
- Specific Function
- (r)-limonene 6-monooxygenase activity
- 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
- A cytochrome P450 monooxygenase involved in the metabolism of polyunsaturated fatty acids (PUFA) (PubMed:18577768, PubMed:19965576, PubMed:20972997). Mechanistically, uses molecular oxygen inserting one oxygen atom into a substrate, and reducing the second into a water molecule, with two electrons provided by NADPH via cytochrome P450 reductase (NADPH--hemoprotein reductase) (PubMed:18577768, PubMed:19965576, PubMed:20972997). Catalyzes the hydroxylation of carbon-hydrogen bonds. Hydroxylates PUFA specifically at the omega-1 position (PubMed:18577768). Catalyzes the epoxidation of double bonds of PUFA (PubMed:19965576, PubMed:20972997). Also metabolizes plant monoterpenes such as limonene. Oxygenates (R)- and (S)-limonene to produce carveol and perillyl alcohol (PubMed:11950794). 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 imipramine. Hydroxylates fenbendazole at the 4' position (PubMed:23959307)
- Specific Function
- (r)-limonene 6-monooxygenase activity
- Gene Name
- CYP2C19
- Uniprot ID
- P33261
- Uniprot Name
- Cytochrome P450 2C19
- Molecular Weight
- 55944.565 Da
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- No
- Actions
- Substrate
- General Function
- A cytochrome P450 monooxygenase involved in the metabolism of fatty acids, steroids and retinoids (PubMed:18698000, PubMed:19965576, PubMed:20972997, PubMed:21289075, PubMed:21576599). Mechanistically, uses molecular oxygen inserting one oxygen atom into a substrate, and reducing the second into a water molecule, with two electrons provided by NADPH via cytochrome P450 reductase (NADPH--hemoprotein reductase) (PubMed:18698000, PubMed:19965576, PubMed:20972997, PubMed:21289075, PubMed:21576599). Catalyzes the epoxidation of double bonds of polyunsaturated fatty acids (PUFA) (PubMed:19965576, PubMed:20972997). Metabolizes endocannabinoid arachidonoylethanolamide (anandamide) to 20-hydroxyeicosatetraenoic acid ethanolamide (20-HETE-EA) and 8,9-, 11,12-, and 14,15-epoxyeicosatrienoic acid ethanolamides (EpETrE-EAs), potentially modulating endocannabinoid system signaling (PubMed:18698000, PubMed:21289075). Catalyzes the hydroxylation of carbon-hydrogen bonds. Metabolizes cholesterol toward 25-hydroxycholesterol, a physiological regulator of cellular cholesterol homeostasis (PubMed:21576599). Catalyzes the oxidative transformations of all-trans retinol to all-trans retinal, a precursor for the active form all-trans-retinoic acid (PubMed:10681376). Also involved in the oxidative metabolism of drugs such as antiarrhythmics, adrenoceptor antagonists, and tricyclic antidepressants
- Specific Function
- Anandamide 11,12 epoxidase activity
- 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