Drug Details

General Information of the Drug (ID: DR8051)
Name
Quinidine
Synonyms
quinidine; 56-54-2; (+)-Quinidine; Conchinin; Chinidin; Pitayine; Quinidex; beta-Quinine; (8R,9S)-Quinidine; (9S)-6'-Methoxycinchonan-9-ol; Cin-Quin; Conquinine; Kinidin; Conchinine; chinidinum; quinidina; Quiniduran; Chinidine; Cinchonan-9-ol, 6'-methoxy-, (9S)-; UNII-ITX08688JL; Quinaglute; Auriquin; Quinidine sulfate; CHEBI:28593; (S)-[(2R,4S,5R)-5-ethenyl-1-azabicyclo[2.2.2]octan-2-yl](6-methoxyquinolin-4-yl)methanol; alpha-(6-Methoxy-4-quinolyl)-5-vinyl-2-quinuclidinemethanol; MFCD00135581; Quinicardine; CHEMBL1294; Cardioquin; Duraquin; Quinact; Quinalan; Quinatime; (1S)-(6-Methoxyquinolin-4-yl)((2R,4S,5R)-5-vinylquinuclidin-2-yl)methanol; Quinidine hydrochloride monohydrate; ITX08688JL; 6-Methoxy-alpha-(5-vinyl-2-quinuclidinyl)-4-quinolinemethanol; beta-Quinidine; (3'.alpha., 9S)-6'-Methoxycinchonan-9-ol; Quinidine, 98%, anhydrous; TCMDC-131239; NCI-C56246; (8R,9S)-6'-Methoxycinchonan-9-ol; (R)-(6-methoxyquinolin-4-yl)((3S,4R,7S)-3-vinylquinuclidin-7-yl)methanol; (S)-(6-methoxy-4-quinolyl)-[(2R,4S,5R)-5-vinylquinuclidin-2-yl]methanol; (S)-[(4S,5R,7R)-5-ethenyl-1-azabicyclo[2.2.2]octan-7-yl]-(6-methoxyquinolin-4-yl)methanol; Chinidin [German]; SMR000857275; Quinidine [BAN:NF]; (S)-[(2R,4S,5R)-5-ethenyl-1-azabicyclo[2.2.2]octan-2-yl]-(6-methoxyquinolin-4-yl)methanol; Quinindine; CCRIS 672; HSDB 225; (S)-(6-methoxyquinolin-4-yl)((2R,5R)-5-vinylquinuclidin-2-yl)methanol; (S)-(6-methoxyquinolin-4-yl)((1S,2R,4S,5R)-5-vinylquinuclidin-2-yl)methanol; (S)-(6-Methoxy-quinolin-4-yl)-((2R,5R)-5-vinyl-1-aza-bicyclo[2.2.2]oct-2-yl)-methanol; QDN; EINECS 200-279-0; Quinidine, anhydrous; PubChem7994; Prestwick3_000280; bmse000511; Epitope ID:141803; SCHEMBL15943; BSPBio_000160; MLS001335913; MLS001335914; MLS002548869; BPBio1_000176; GTPL2342; DTXSID4023549; SCHEMBL17537608; HMS2234L10; HMS3259O09; ACT09863; HY-B1751; ZINC3831405; (9S)-6-Methoxy-alpha-(5-vinyl-2-quinuclidinyl)-4-quinolinemethanol; alpha-(6-Methoxy-4-quinolyl)-5-vinyl-2-quinuclidinemethanol (9S)-; BDBM50121975; RW2069; AKOS015920101; CCG-256507; CS-7812; DB00908; MCULE-7178915526; NC00478; SDCCGMLS-0066600.P001; NCGC00091231-01; NCGC00091231-02; NCGC00091231-03; AS-30538; AB00514657; 6470-EP1441224A2; 6470-EP2272835A1; 6470-EP2272844A1; 6470-EP2272972A1; 6470-EP2272973A1; 6470-EP2275411A2; 6470-EP2277872A1; 6470-EP2305655A2; 6470-EP2314576A1; 6470-EP2314585A1; M-7594; AB01562940_01; Q412496; W-109256; BRD-K59632282-052-01-5; BRD-K59632282-052-02-3; BRD-K70799801-311-02-7; Quinidine, crystallized, >=98.0% (dried material, NT); 101143-86-6
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Molecular Type
Small molecule
Disease Supraventricular tachyarrhythmia [ICD-11: BC81] Approved [1]
Structure
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2D MOL

3D MOL

ADMET Property
BDDCS Class
Biopharmaceutics Drug Disposition Classification System (BDDCS) Class 1: high solubility and high permeability
Bioavailability
75% of drug becomes completely available to its intended biological destination(s)
Clearance
The clearance of drug is 3C5 mL/min/kg in adults
Elimination
18% of drug is excreted from urine in the unchanged form
Half-life
The concentration or amount of drug in body reduced by one-half in 6 - 8 hours
MRTD
The Maximum Recommended Therapeutic Dose (MRTD) of drug that ensured maximising efficacy and moderate side effect is 30.82362 micromolar/kg/day
Unbound Fraction
The unbound fraction of drug in plasma is 0.26%
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
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Formula
C20H24N2O2
PubChem CID
441074
Canonical SMILES
COC1=CC2=C(C=CN=C2C=C1)C(C3CC4CCN3CC4C=C)O
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
CAS Number
CAS 56-54-2
ChEBI ID
CHEBI:28593
DrugBank ID
DB00908
Combinatorial Therapeutic Effect(s) Validated Clinically or Experimentally
    α. A List of Natural Product(s) Able to Reverse the Resistance of This Drug
          Cinchonine      Cinchona calisaya     Click to Show/Hide the Molecular Data of This NP
                 Reversing Drug Resistance     Click to Show/Hide
                    Representative Experiment Reporting the Effect of This Combination [2]
                    Detail(s)  Combination Info  click to show the detail info of this combination
                    Molecule(s)
                    Regulation		 Down-regulation Expression ABCB1  Molecule Info 
Pathway MAP
Up-regulation Cleavage CASP3  Molecule Info 
Pathway MAP
Up-regulation Cleavage PARP1  Molecule Info 
Pathway MAP
                    In-vitro Model MES-SA CVCL_1404 Uterine corpus sarcoma Homo sapiens
MES-SA/Dx5 CVCL_2598 Uterine corpus sarcoma Homo sapiens
                    Experimental
                    Result(s)		 Hydrocinchonine exerted MDR reversal activity and synergistic apoptotic effect with TAX in MES-SA/DX5 cells almost comparable with quinidine and cinchonine as a potent MDR-reversal and combined therapy agent with TAX.
References
Reference 1 Drugs@FDA. U.S. Food and Drug Administration. U.S. Department of Health Human Services. 2001
Reference 2 Hydrocinchonine, cinchonine, and quinidine potentiate paclitaxel-induced cytotoxicity and apoptosis via multidrug resistance reversal in MES-SA/DX5 uterine sarcoma cells. Environ Toxicol. 2011 Aug;26(4):424-31.
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