Details of the Drug

General Information of Drug (ID: DMLPICK)

Drug Name
Quinidine
Synonyms
Quinact; Quinaglute; Quinalan; Quinatime; Quindine; Quinicardine; Quinidex; Quinidine sulfate; Quiniduran; Quinora; beta-Quinine; Cardioquin; Chinidin; Chinidine; Cin-Quin; Cinchonan-9-ol, 6'-methoxy-, (9S)-; Conchinin; Conchinine; Conquinine; Duraquin; ITX08688JL; Kinidin; Pitayine; chinidinum; quinidina; quinidine; (+)-Quinidine; (8R,9S)-Quinidine; (9S)-6'-Methoxycinchonan-9-ol; (S)-[(2R,4S,5R)-5-ethenyl-1-azabicyclo[2.2.2]octan-2-yl](6-methoxyquinolin-4-yl)methanol; 56-54-2; CHEBI:28593; CHEMBL1294; MFCD00135581; UNII-ITX08688JL
Affected Organisms
Humans and other mammals
ATC Code
C01BA01: Quinidine
C01BA: Antiarrhythmics, class Ia
C01B: ANTIARRHYTHMICS, CLASS I AND III
C01: CARDIAC THERAPY
C: CARDIOVASCULAR SYSTEM
Structure
3D MOL 2D MOL
#Ro5 Violations (Lipinski): 0 Molecular Weight (mw) 324.4
Logarithm of the Partition Coefficient (xlogp) 2.9
Rotatable Bond Count (rotbonds) 4
Hydrogen Bond Donor Count (hbonddonor) 1
Hydrogen Bond Acceptor Count (hbondacc) 4
ADMET Property
BDDCS Class
Biopharmaceutics Drug Disposition Classification System (BDDCS) Class 1: high solubility and high permeability [1]
Bioavailability
75% of drug becomes completely available to its intended biological destination(s) [2]
Clearance
The clearance of drug is 3C5 mL/min/kg in adults []
Elimination
18% of drug is excreted from urine in the unchanged form [1]
Half-life
The concentration or amount of drug in body reduced by one-half in 6 - 8 hours [3]
MRTD
The Maximum Recommended Therapeutic Dose (MRTD) of drug that ensured maximising efficacy and moderate side effect is 30.82362 micromolar/kg/day [4]
Unbound Fraction
The unbound fraction of drug in plasma is 0.26% [3]
Vd
The volume of distribution (Vd) of drug is 2-3 L/kg []
Water Solubility
The ability of drug to dissolve in water is measured as 11.1 mg/mL [1]
Adverse Drug Reaction (ADR)
ADR Term Variation Related DOT DOT ID REF
Sudden cardiac death Not Available SCN5A OTGYZWR6 [5]
Sudden cardiac death Not Available KCNE1 OTZNQUW9 [5]
Torsade de pointes Not Available MINK1 OTKB0RA8 [5]
Chemical Identifiers
Formula
C20H24N2O2
IUPAC Name
(S)-[(2R,4S,5R)-5-ethenyl-1-azabicyclo[2.2.2]octan-2-yl]-(6-methoxyquinolin-4-yl)methanol
Canonical SMILES
COC1=CC2=C(C=CN=C2C=C1)C(C3CC4CCN3CC4C=C)O
InChI
InChI=1S/C20H24N2O2/c1-3-13-12-22-9-7-14(13)10-19(22)20(23)16-6-8-21-18-5-4-15(24-2)11-17(16)18/h3-6,8,11,13-14,19-20,23H,1,7,9-10,12H2,2H3/t13-,14-,19+,20-/m0/s1
InChIKey
LOUPRKONTZGTKE-LHHVKLHASA-N
Cross-matching ID
PubChem CID
441074
ChEBI ID
CHEMBL1294
CAS Number
56-54-2
UNII
ITX08688JL
DrugBank ID
DB00908
INTEDE ID
DR1379
Drug-Molecule Activity Atlas (DMA)NEW Click to Jump to the Detailed DMA Information of This Drug
Drug Pharmacogenomic Perturbation (DPP)NEW Click to Jump to the Detailed DPP Information of This Drug
Drug ADMET Endpoint Profile (DAE)NEW Click to Jump to the Detailed DAE Information of This Drug
Combinatorial Drugs (CBD) Click to Jump to the Detailed CBD Information of This Drug

Molecular Interaction Atlas of This Drug


Drug-Metabolizing Enzyme (DME)
DME Name DME ID UniProt ID MOA REF
Cytochrome P450 3A4 (CYP3A4) DE4LYSA CP3A4_HUMAN Substrate [6]
Cytochrome P450 2E1 (CYP2E1) DEVDYN7 CP2E1_HUMAN Substrate [7]
Cytochrome P450 2D6 (CYP2D6) DECB0K3 CP2D6_HUMAN Substrate [8]
Cytochrome P450 2C9 (CYP2C9) DE5IED8 CP2C9_HUMAN Substrate [9]
Cytochrome P450 2C8 (CYP2C8) DES5XRU CP2C8_HUMAN Substrate [10]
Cytochrome P450 3A7 (CYP3A7) DERD86B CP3A7_HUMAN Substrate [11]

Drug Off-Target (DOT)
DOT Name DOT ID UniProt ID Interaction REF
Alpha-1A adrenergic receptor (ADRA1A) OTUIWCL5 ADA1A_HUMAN Protein Interaction/Cellular Processes [12]
Alpha-1B adrenergic receptor (ADRA1B) OTSAYAFD ADA1B_HUMAN Protein Interaction/Cellular Processes [12]
Alpha-1D adrenergic receptor (ADRA1D) OTW2CD1O ADA1D_HUMAN Protein Interaction/Cellular Processes [12]
ATP-dependent translocase ABCB1 (ABCB1) OTEJROBO MDR1_HUMAN Regulation of Drug Effects [13]
Cyclin-dependent kinase inhibitor 1 (CDKN1A) OTQWHCZE CDN1A_HUMAN Gene/Protein Processing [14]
Inhibin beta E chain (INHBE) OTOI2NYG INHBE_HUMAN Gene/Protein Processing [15]
Misshapen-like kinase 1 (MINK1) OTKB0RA8 MINK1_HUMAN Drug Response [5]
Multidrug and toxin extrusion protein 1 (SLC47A1) OTZX0U5Q S47A1_HUMAN Gene/Protein Processing [16]
Nuclear protein 1 (NUPR1) OT4FU8C0 NUPR1_HUMAN Gene/Protein Processing [17]
Potassium voltage-gated channel subfamily E member 1 (KCNE1) OTZNQUW9 KCNE1_HUMAN Drug Response [5]
Molecular Interaction Atlas (MIA) Jump to Detail Molecular Interaction Atlas of This Drug

References

1 BDDCS applied to over 900 drugs
2 Critical Evaluation of Human Oral Bioavailability for Pharmaceutical Drugs by Using Various Cheminformatics Approaches
3 Trend Analysis of a Database of Intravenous Pharmacokinetic Parameters in Humans for 1352 Drug Compounds
4 Estimating the safe starting dose in phase I clinical trials and no observed effect level based on QSAR modeling of the human maximum recommended daily dose
5 ADReCS-Target: target profiles for aiding drug safety research and application. Nucleic Acids Res. 2018 Jan 4;46(D1):D911-D917. doi: 10.1093/nar/gkx899.
6 10th North American ISSX meeting. October 24-28, 2000. Indianapolis, Indiana, USA. Abstracts. Drug Metab Rev. 2000;32 Suppl 2:137-340.
7 In vitro metabolism of quinidine: the (3S)-3-hydroxylation of quinidine is a specific marker reaction for cytochrome P-4503A4 activity in human liver microsomes. J Pharmacol Exp Ther. 1999 Apr;289(1):31-7.
8 Binding of quinidine radically increases the stability and decreases the flexibility of the cytochrome P450 2D6 active site. J Inorg Biochem. 2012 May;110:46-50.
9 Effect of diclofenac, disulfiram, itraconazole, grapefruit juice and erythromycin on the pharmacokinetics of quinidine. Br J Clin Pharmacol. 1999 Dec;48(6):829-38.
10 Role of cytochrome P450 2C8 in drug metabolism and interactions. Pharmacol Rev. 2016 Jan;68(1):168-241.
11 Drug Interactions Flockhart Table
12 Effects of quinidine and verapamil on human cardiovascular alpha1-adrenoceptors. Circulation. 1998 Apr 7;97(13):1227-30. doi: 10.1161/01.cir.97.13.1227.
13 Transport inhibition of digoxin using several common P-gp expressing cell lines is not necessarily reporting only on inhibitor binding to P-gp. PLoS One. 2013 Aug 16;8(8):e69394. doi: 10.1371/journal.pone.0069394. eCollection 2013.
14 Control of mammary tumor cell growth in vitro by novel cell differentiation and apoptosis agents. Breast Cancer Res Treat. 2002 Sep;75(2):107-17. doi: 10.1023/a:1019698807564.
15 A toxicogenomic approach to drug-induced phospholipidosis: analysis of its induction mechanism and establishment of a novel in vitro screening system. Toxicol Sci. 2005 Feb;83(2):282-92.
16 Molecular identification and functional characterization of rat multidrug and toxin extrusion type transporter 1 as an organic cation/H+ antiporter in the kidney. Drug Metab Dispos. 2006 Nov;34(11):1868-74. doi: 10.1124/dmd.106.010876. Epub 2006 Aug 23.
17 In vitro detection of drug-induced phospholipidosis using gene expression and fluorescent phospholipid based methodologies. Toxicol Sci. 2007 Sep;99(1):162-73.