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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2017-11-21 17:40:04 UTC
Update Date2019-07-23 14:38:54 UTC
HMDB IDHMDB0240234
Secondary Accession NumbersNone
Metabolite Identification
Common NameRupatadine
DescriptionRupatadine 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. It is available as round, light salmon coloured tablets containing 10 mg of rupatadine (as fumarate) to be administered orally, once a day. Rupatadine is a drug which is used 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 [fda label]. also used for the symptomatic relief of chronic spontaneous urticaria in patients 2 years of age and older. Rupatadine is a non-sedating antihistamine. Rupatadine possesses anti-allergic properties such as the inhibition of the degranulation of mast cells induced by immunological and non-immunological stimuli, and inhibition of the release of cytokines, particularly of the tumor necrosis factors (TNF) in human mast cells and monocytes. Rupatadine is a very strong basic compound (based on its pKa). In humans, rupatadine is involved in rupatadine h1-antihistamine action. The efficacy of rupatadine as treatment for allergic rhinitis (AR) and chronic idiopathic urticaria (CIU) has been investigated in adults and adolescents (aged over 12 years) in several controlled studies, showing a rapid onset of action and a good safety profile even in prolonged treatment periods of a year. However, as in other non sedating second-generation antihistamines, the most common side effects in controlled clinical studies were somnolence, headaches and fatigue. Rupatadine has several active metabolites such as desloratadine, 3-hydroxydesloratadine, 6-hydroxydesloratadine and 5-hydroxydesloratadine. Rupatadine is a second generation antihistamine and PAF antagonist used to treat allergies. It was launched in Canada under the name Rupall and has been mocked in the media for the similarity to the name of the famous gay drag queen RuPaul specifically parodied as a pill to turn anyone into RuPaul and stated to have the option to take anally Brand names include Rupafin, Rupall, Rinialer, Pafinur, Rupax, Urtimed and Ralif, among others. Rupatadine fumarate has been approved for the treatment of allergic rhinitis and chronic urticaria in adults and children over 12 years. It further blocks the receptors of the platelet-activating factor (PAF) according to in vitro and in vivo studies. It was launched in 2003 in Spain under the brand name of Rupafin.
Structure
Data?1563892734
Synonyms
ValueSource
AlergoliberHMDB
PafinurHMDB
RinialerHMDB
RupafinHMDB
RupaxHMDB
RupatadineHMDB
8-chloro-6,11-dihydro-11-(1-((5-Methyl-3-pyridinyl)methyl)-4-piperidinylidene)-5H-benzo(5,6)cyclohepta(1,2-b)pyridineMeSH, HMDB
Chemical FormulaC26H26ClN3
Average Molecular Weight415.97
Monoisotopic Molecular Weight415.1815255
IUPAC Name13-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
Traditional Name13-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
CAS Registry Number158876-82-5
SMILES
CC1=CC(CN2CCC(CC2)=C2C3=CC=C(Cl)C=C3CCC3=C2N=CC=C3)=CN=C1
InChI Identifier
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
InChI KeyWUZYKBABMWJHDL-UHFFFAOYSA-N
Chemical Taxonomy
Description 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.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassBenzocycloheptapyridines
Sub ClassNot Available
Direct ParentBenzocycloheptapyridines
Alternative Parents
Substituents
  • Benzocycloheptapyridine
  • Methylpyridine
  • Aralkylamine
  • Aryl chloride
  • Aryl halide
  • Piperidine
  • Benzenoid
  • Pyridine
  • Heteroaromatic compound
  • Tertiary aliphatic amine
  • Tertiary amine
  • Azacycle
  • Organonitrogen compound
  • Organochloride
  • Organohalogen compound
  • Hydrocarbon derivative
  • Organopnictogen compound
  • Organic nitrogen compound
  • Amine
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Process

Naturally occurring process:

Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP4.82ALOGPS
logP5.37ChemAxon
logS-4.9ALOGPS
pKa (Strongest Basic)7.19ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area29.02 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity133.83 m³·mol⁻¹ChemAxon
Polarizability46.98 ųChemAxon
Number of Rings5ChemAxon
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-0001900000-50ad6856523ebb65d61cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014r-1459800000-b77f7dd4eb9730e8a3f9Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9122100000-8b1654433eb949efa7e2Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-0000900000-049e64830c3bc2a7ceb9Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03di-0112900000-355dcca35f8056d1382dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9104000000-16b70b4af0fce61811cfSpectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB11614
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkRupatadine
METLIN IDNot Available
PubChem Compound133017
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Picado C: Rupatadine: pharmacological profile and its use in the treatment of allergic disorders. Expert Opin Pharmacother. 2006 Oct;7(14):1989-2001. [PubMed:17020424 ]