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

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)

Hydrogen Bond Donor Count (hbonddonor)

Hydrogen Bond Acceptor Count (hbondacc)

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	KCNQ1	OT8SPJNX	[5]
Torsade de pointes	Not Available	MINK1	OTKB0RA8	[5]
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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: LOUPRKONTZGTKE-LHHVKLHASA-N
InChIKey: 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

Cross-matching ID

PubChem CID: 441074
ChEBI ID: CHEBI:28593
CAS Number: 56-54-2
DrugBank ID: DB00908
INTEDE ID: DR1379

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]

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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]
Angiotensin-converting enzyme 2 (ACE2)	OTTRZGU7	ACE2_HUMAN	Gene/Protein Processing	[13]
Asparagine synthetase (ASNS)	OT8R922G	ASNS_HUMAN	Gene/Protein Processing	[14]
ATP-dependent translocase ABCB1 (ABCB1)	OTEJROBO	MDR1_HUMAN	Regulation of Drug Effects	[15]
Cyclin-dependent kinase inhibitor 1 (CDKN1A)	OTQWHCZE	CDN1A_HUMAN	Gene/Protein Processing	[16]
Cytochrome P450 1A2 (CYP1A2)	OTLLBX48	CP1A2_HUMAN	Gene/Protein Processing	[17]
Cytochrome P450 2D6 (CYP2D6)	OTZJC802	CP2D6_HUMAN	Gene/Protein Processing	[18]
Fatty acid-binding protein, liver (FABP1)	OTR34ETM	FABPL_HUMAN	Gene/Protein Processing	[19]

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Molecular Interaction Atlas (MIA)

MIA Detail

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	Effect of common medications on the expression of SARS-CoV-2 entry receptors in liver tissue. Arch Toxicol. 2020 Dec;94(12):4037-4041. doi: 10.1007/s00204-020-02869-1. Epub 2020 Aug 17.
14	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.
15	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.
16	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.
17	Predictive three-dimensional quantitative structure-activity relationship of cytochrome P450 1A2 inhibitors. J Med Chem. 2005 Jun 2;48(11):3808-15.
18	Inhibition of cytochrome P4502D6 activity with paroxetine normalizes the ultrarapid metabolizer phenotype as measured by nortriptyline pharmacokinetics and the debrisoquin test. Clin Pharmacol Ther. 2001 Oct;70(4):327-35.
19	In vitro detection of drug-induced phospholipidosis using gene expression and fluorescent phospholipid based methodologies. Toxicol Sci. 2007 Sep;99(1):162-73.