Details of the Drug

General Information of Drug (ID: DMBPN7T)

Drug Name
RUPATADINE
Synonyms
Rupatadine trihydrochloride; UNII-G61C8NZY2T; G61C8NZY2T; 156611-76-6; Rupatadine HCl; Rupatadine hydrochloride; UR 12592; AC1L320L; DTXSID90166109; BQFOTHHRVVHLEW-UHFFFAOYSA-N; 8-Chloro-6,11-dihydro-11-(1-((5-methyl-3-pyridinyl)methyl)-4-piperidinylidene)-5H-benzo(5,6)cyclohepta(1,2-b)pyridine trihydrochloride; 5H-Benzo(5,6)cyclohepta(1,2-b)pyridine, 8-chloro-6,11-dihydro-11-(1-((5-methyl-3-pyridinyl)methyl)-4-piperidinylidene)-, trihydrochloride
Drug Type
Small molecular drug
Structure
3D MOL 2D MOL
#Ro5 Violations (Lipinski): 1 Molecular Weight (mw) 416
Logarithm of the Partition Coefficient (xlogp) 5.8
Rotatable Bond Count (rotbonds) 2
Hydrogen Bond Donor Count (hbonddonor) 0
Hydrogen Bond Acceptor Count (hbondacc) 3
ADMET Property
Absorption
The drug is rapidly absorbed and reaches peak plasma concentration in 1 hours []
Clearance
The sytemic clearance of drug is 1556.2 L/h []
Half-life
The concentration or amount of drug in body reduced by one-half in 15.9 hours (in children 2 - 5 years old), 12.3 hours (in children 6 - 11 years old), 5.9 hours (in adults), and 8.7 hours (in geriatric patients) []
Metabolism
The drug is metabolized via oxidation mediated primarily by CYP3A4 []
Vd
The volume of distribution (Vd) of drug is 9799 L []
Chemical Identifiers
Formula
C26H26ClN3
IUPAC Name
13-chloro-2-[1-[(5-methylpyridin-3-yl)methyl]piperidin-4-ylidene]-4-azatricyclo[9.4.0.03,8]pentadeca-1(11),3(8),4,6,12,14-hexaene
Canonical SMILES
CC1=CC(=CN=C1)CN2CCC(=C3C4=C(CCC5=C3N=CC=C5)C=C(C=C4)Cl)CC2
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
InChIKey
WUZYKBABMWJHDL-UHFFFAOYSA-N
Cross-matching ID
PubChem CID
133017
ChEBI ID
CHEBI:135673
CAS Number
158876-82-5
DrugBank ID
DB11614
TTD ID
D0S1CQ
INTEDE ID
DR1451

Molecular Interaction Atlas of This Drug


Drug Therapeutic Target (DTT)
DTT Name DTT ID UniProt ID MOA REF
Histamine H1 receptor (H1R) TTTIBOJ HRH1_HUMAN Inhibitor [1]
Platelet-activating factor receptor (PTAFR) TTQL5VC PTAFR_HUMAN Inhibitor [1]

Drug-Metabolizing Enzyme (DME)
DME Name DME ID UniProt ID MOA REF
Cytochrome P450 3A4 (CYP3A4) DE4LYSA CP3A4_HUMAN Substrate [2]
Cytochrome P450 2C9 (CYP2C9) DE5IED8 CP2C9_HUMAN Substrate [3]
Cytochrome P450 3A5 (CYP3A5) DEIBDNY CP3A5_HUMAN Substrate [4]
Molecular Interaction Atlas (MIA) Jump to Detail Molecular Interaction Atlas of This Drug

Molecular Expression Atlas of This Drug

Molecule Name Molecule Type Gene Name p-value Fold-Change Z-score
Histamine H1 receptor (H1R) DTT HRH1 6.86E-09 0.3 0.55
Platelet-activating factor receptor (PTAFR) DTT PTAFR 3.75E-05 0.25 0.35
Cytochrome P450 3A5 (CYP3A5) DME CYP3A5 3.85E-05 8.08E-01 6.07E-01
Cytochrome P450 2C9 (CYP2C9) DME CYP2C9 2.25E-03 -4.98E-01 -6.49E-01
Cytochrome P450 3A4 (CYP3A4) DME CYP3A4 6.90E-01 2.35E-02 7.88E-02
Molecular Expression Atlas (MEA) Jump to Detail Molecular Expression Atlas of This Drug

References

1 Designed multiple ligands. An emerging drug discovery paradigm. J Med Chem. 2005 Oct 20;48(21):6523-43.
2 Rupatadine: pharmacological profile and its use in the treatment of allergic disorders. Expert Opin Pharmacother. 2006 Oct;7(14):1989-2001.
3 Product Monograph of Xtandi Rupatadine (as rupatadine fumarate).
4 CYP3A5*3 and MDR1 C3435T are influencing factors of inter-subject variability in rupatadine pharmacokinetics in healthy Chinese volunteers. Eur J Drug Metab Pharmacokinet. 2016 Apr;41(2):117-24.