Basic information
- CAS
158876-82-5- Standard SMILES
Cc1cncc(CN2CCC(=C3c4ccc(Cl)cc4CCc4cccnc43)CC2)c1- InChIKey
WUZYKBABMWJHDL-UHFFFAOYSA-N- Molecular formula
- C26H26ClN3
- Average molar mass
- 416 g/mol
- Monoisotopic mass
- 415.1815255
Overview
Rupatadine is a benzocycloheptapyridine.
Names & identifiers
- Preferred name
- Rupatadine
- IUPAC
- 13-chloro-2-[1-[(5-methyl-3-pyridinyl)methyl]piperidin-4-ylidene]-4-azatricyclo[9.4.0.03,8]pentadeca-1(11),3(8),4,6,12,14-hexaene
- English name
- Rupatadine
- Molecular formula
- C26H26ClN3
- Molecular weight
- 415.96
Names & synonyms
Rupatadine158876-82-5RinialerRupatadina2AE8M83G3EUR-12592DTXSID00166534rupatadinumRefChem:883977DTXCID9089025R06AX2813-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
Show more names
RupatidineRupafiRupafinROPATADINE
8-Chloro-6,11-dihydro-11-(1-((5-methyl-3-pyridinyl)methyl)-4-piperidinylidene)-5H-benzo(5,6)cyclohepta(1,2-b)pyridinePafinurAlergoliberRupax8-Chloro-11-(1-((5-methylpyridin-3-yl)methyl)piperidin-4-ylidene)-6,11-dihydro-5H-benzo[5,6]cyclohepta[1,2-b]pyridineRupatadine [INN]UNII-2AE8M83G3ECHEMBL91397
Database identifiers
- CAS
158876-82-5- PubChem CID
- 133017
- DTXSID
DTXSID00166534- ChEMBL
CHEMBL91397- ChEBI
CHEBI:135673
Properties
Computed structural properties
- XLogP
- 5.8
- Topological polar surface area
- 29 Ų
- Hydrogen bond donors
- 0
- Hydrogen bond acceptors
- 3
- Rotatable bonds
- 2
- Heavy atoms
- 30
- Formal charge
- 0
- Complexity
- 609
Experimental & physicochemical properties
Drugs
Pharmaceuticals
Pharmaceuticals -> Listed in ZINC15
Human DrugsBreast Feeding; Lactation; Milk, Human; Antihistamines; Nonsedating Antihistamines; Histamine Antagonists; Platelet Activating Factor Antagonists
Melting Point194-201
Physicochemical properties
- Melting point
- 58 · 58-61°C
- Boiling point
- 586.4 · 586.4±50.0 °C(Predicted)
- Density
- 1.233 · 1.233±0.06 g/cm3(Predicted)
- storage temp.
- -20 °C · Store at -20°C
- solubility
- Dichloromethane; Ethyl Acetate
- form
- Oil
- pka
- 6.95 · 6.95±0.20(Predicted)
- 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
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
GHS classification
GHS Classification
Warning
H302 (50%): Harmful if swallowed [Warning Acute toxicity, oral]
P261, P264, P264+P265, P270, P271, P273, P280, P301+P317, P302+P352, P304+P340, P305+P351+P338, P319, P321, P330, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 2 reports by companies from 2 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Hazard information
Hazard Classes and CategoriesAcute Tox. 4 (50%)
Toxicology
Effects During Pregnancy and Lactation◉ Summary of Use during Lactation
Safety data
- wgk
- WGK 3
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- Storage Class
- 11 - Combustible Solids
- Hazard statements
- H302-H413
- Hazard Classifications
- Acute Tox. 4 OralAquatic Chronic 4
- Precautionary statements
- P301+P312+P330
Chemistry & industry
Pharmacology
ATC Code
R06AX28
R - Respiratory system
QR - Respiratory system
Protein BindingRupatidine is 98.5-99.0% bound to human plasma proteins.
PharmacodynamicsRupatadine is an anti allergenic and acts to reduce allergic symptoms like urticaria, rhinorrhea, sneezing and itching.
Mechanism of Action
Rupatadine is a dual histamine H1 receptor and platelet activating (PAF) receptor antagonist. During allergic response mast cells undergo degranulation, releasing histamine and other substances. 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.
Biological Half-LifeThe 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.
Metabolism/Metabolites
Rupatadine is metabolized by oxidation mediated primarily by CYP3A4. 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.
Rupatadine has known human metabolites that include Desloratadine.
Absorption, Distribution and Excretion
Rupatidine is rapidly absorbed with a Tmax of 1 h. Administration with a high fat meal increases exposure by 23% and increases Tmax to 2 h.
The apparent volume of distribution is 9799 L.
Systemic clearance is 1556.2 L/h in young adults and 798.2 L/h in geriatric patients.
Related reactions
1 records
Compound notes
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