quinidine Indications/Contra | FAERs-F | FAERs-M | Orange Bk | BioActivity |

Stem definitionDrug idCAS RN
2346 56-54-2

Description:

MoleculeDescription

Molfile Inchi Smiles

Synonyms:

  • quincardine
  • quinidine polygalacturonate
  • quinidine sulfate dihydrate
  • quinidine
  • quinidine sulfate
  • quinidine gluconate
  • chinidin
  • conchinin
  • conchinine
  • conquinine
  • quindine
  • pitayine
  • beta-Quinidine
  • quinidine hydrochloride monohydrate
  • quinidine hydrochloride
  • quinidine HCl
An optical isomer of quinine, extracted from the bark of the CHINCHONA tree and similar plant species. This alkaloid dampens the excitability of cardiac and skeletal muscles by blocking sodium and potassium currents across cellular membranes. It prolongs cellular ACTION POTENTIALS, and decreases automaticity. Quinidine also blocks muscarinic and alpha-adrenergic neurotransmission.
  • Molecular weight: 324.42
  • Formula: C20H24N2O2
  • CLOGP: 2.79
  • LIPINSKI: 0
  • HAC: 4
  • HDO: 1
  • TPSA: 45.59
  • ALOGS: -2.99
  • ROTB: 4

  • Status: OFP

  • Legend:
    OFP - off patent
    OFM - off market
    ONP - on patent

Drug dosage:

DoseUnitRoute
1.20 g O

ADMET properties:

PropertyValueReference
BDDCS (Biopharmaceutical Drug Disposition Classification System) 1 Benet LZ, Broccatelli F, Oprea TI
S (Water solubility) 11.10 mg/mL Benet LZ, Broccatelli F, Oprea TI
EoM (Fraction excreted unchanged in urine) 18 % Benet LZ, Broccatelli F, Oprea TI
MRTD (Maximum Recommended Therapeutic Daily Dose) 30.82 ┬ÁM/kg/day Contrera JF, Matthews EJ, Kruhlak NL, Benz RD
BA (Bioavailability) 75 % Kim MT, Sedykh A, Chakravarti SK, Saiakhov RD, Zhu H
Vd (Volume of distribution) 2.90 L/kg Lombardo F, Berellini G, Obach RS
CL (Clearance) 4 mL/min/kg Lombardo F, Berellini G, Obach RS
fu (Fraction unbound in plasma) 0.26 % Lombardo F, Berellini G, Obach RS
t_half (Half-life) 6.60 hours Lombardo F, Berellini G, Obach RS

Approvals:

DateAgencyCompanyOrphan
July 12, 1950 FDA LILLY

FDA Adverse Event Reporting System (Female)

MedDRA adverse event termLikelihood ratioLikelihood ratio thresholdPatients taking drug having adverse eventPatients taking drug not having adverse eventPatients not taking drug having adverse eventPatients not taking drug not having adverse event
Death 76.20 25.68 76 1628 335472 46348886
Inability to afford medication 44.58 25.68 10 1694 1166 46683192
Lethargy 34.25 25.68 22 1682 51149 46633209
Drug effective for unapproved indication 26.83 25.68 7 1697 1535 46682823

FDA Adverse Event Reporting System (Male)

MedDRA adverse event termLikelihood ratioLikelihood ratio thresholdPatients taking drug having adverse eventPatients taking drug not having adverse eventPatients not taking drug having adverse eventPatients not taking drug not having adverse event
Drug ineffective 44.21 35.50 53 873 340334 29611218

Pharmacologic Action:

SourceCodeDescription
ATC C01BA01 CARDIOVASCULAR SYSTEM
CARDIAC THERAPY
ANTIARRHYTHMICS, CLASS I AND III
Antiarrhythmics, class Ia
ATC C01BA51 CARDIOVASCULAR SYSTEM
CARDIAC THERAPY
ANTIARRHYTHMICS, CLASS I AND III
Antiarrhythmics, class Ia
ATC C01BA71 CARDIOVASCULAR SYSTEM
CARDIAC THERAPY
ANTIARRHYTHMICS, CLASS I AND III
Antiarrhythmics, class Ia
FDA EPC N0000175426 Antiarrhythmic
MeSH PA D018663 Adrenergic Agents
MeSH PA D000317 Adrenergic alpha-Antagonists
MeSH PA D018674 Adrenergic Antagonists
MeSH PA D000889 Anti-Arrhythmia Agents
MeSH PA D000890 Anti-Infective Agents
MeSH PA D000962 Antimalarials
MeSH PA D000977 Antiparasitic Agents
MeSH PA D000981 Antiprotozoal Agents
MeSH PA D002317 Cardiovascular Agents
MeSH PA D018678 Cholinergic Agents
MeSH PA D018680 Cholinergic Antagonists
MeSH PA D065690 Cytochrome P-450 CYP2D6 Inhibitors
MeSH PA D065607 Cytochrome P-450 Enzyme Inhibitors
MeSH PA D004791 Enzyme Inhibitors
MeSH PA D049990 Membrane Transport Modulators
MeSH PA D065606 Metabolic Side Effects of Drugs and Substances
MeSH PA D018727 Muscarinic Antagonists
MeSH PA D018377 Neurotransmitter Agents
MeSH PA D026941 Sodium Channel Blockers
MeSH PA D061567 Voltage-Gated Sodium Channel Blockers
FDA EPC N0000182135 Cytochrome P450 2D6 Inhibitor
FDA MoA N0000182137 Cytochrome P450 2D6 Inhibitors
CHEBI has role CHEBI:37890 alpha-adrenoceptor antagonists
CHEBI has role CHEBI:38068 antimalarials
CHEBI has role CHEBI:38070 antiarrhythmic agent
CHEBI has role CHEBI:38633 sodium channel blockers
CHEBI has role CHEBI:48876 antimuskarinika
CHEBI has role CHEBI:50183 cytochrome p450 inhibitor
CHEBI has role CHEBI:77748 steroid-transporting atpase inhibitors
CHEBI has role CHEBI:77781 13-deoxydaunorubicin hydroxylase inhibitor
CHEBI has role CHEBI:88188 allergenic drug

Drug Use (View source of the data)

DiseaseRelationSNOMED_IDDOID
Atrial fibrillation indication 49436004 DOID:0060224
Malaria indication 61462000 DOID:12365
Pseudobulbar affect indication 432776007
Life-Threatening Ventricular Tachycardia indication
Cardioversion of Atrial Fibrillation indication
Psoriasis contraindication 9014002 DOID:8893
Poisoning by digitalis glycoside contraindication 12876009
Complete atrioventricular block contraindication 27885002
Torsades de pointes contraindication 31722008
Hypokalemia contraindication 43339004
Low blood pressure contraindication 45007003
Chronic heart failure contraindication 48447003
Bradycardia contraindication 48867003
Left ventricular hypertrophy contraindication 55827005
Poisoning by quinidine contraindication 59826007
Left bundle branch block contraindication 63467002
Left heart failure contraindication 85232009
Pulmonary emphysema contraindication 87433001
Kidney disease contraindication 90708001 DOID:557
Myasthenia gravis contraindication 91637004 DOID:437
Anemia due to enzyme deficiency contraindication 111577008
Prolonged QT interval contraindication 111975006
Hypomagnesemia contraindication 190855004
Partial atrioventricular block contraindication 195039008
Disease of liver contraindication 235856003 DOID:409
Esophageal dysmotility contraindication 266434009 DOID:9192
Thrombocytopenic disorder contraindication 302215000 DOID:1588
Congenital long QT syndrome contraindication 442917000
Non-specific intraventricular conduction delay contraindication 698252002
Digitalis Toxicity with AV Conduction Defects contraindication

Acid dissociation constants calculated using MoKa v3.0.0

Dissociation levelDissociation constantType (acidic/basic)
pKa1 12.44 acidic
pKa2 8.02 Basic
pKa3 4.1 Basic

Orange Book patent data (new drug applications)

None

Orange Book exclusivity data (new drug applications)

None

Bioactivity Summary:

TargetClassPharosUniProtActionTypeActivity value
(-log[M])
Mechanism
action
Bioact sourceMoA source
Sodium channel protein type 5 subunit alpha Ion channel BLOCKER IC50 5.16 CHEMBL CHEMBL
Cytochrome P450 2D6 Enzyme INHIBITOR Ki 7.92 SCIENTIFIC LITERATURE DRUG LABEL
Sodium channel alpha subunits; brain (Types I, II, III) Ion channel BLOCKER IC50 5.49 CHEMBL CHEMBL
Solute carrier family 22 member 2 Transporter IC50 4.06 WOMBAT-PK
Potassium/sodium hyperpolarization-activated cyclic nucleotide-gated channel 4 Ion channel IC50 4.11 WOMBAT-PK
Sodium channel subunit beta-4 Ion channel WOMBAT-PK
Sodium channel subunit beta-3 Ion channel WOMBAT-PK
Sodium channel subunit beta-2 Ion channel WOMBAT-PK
Sodium channel subunit beta-1 Ion channel WOMBAT-PK
Multidrug resistance protein 1 Transporter Ki 5.59 CHEMBL
Potassium voltage-gated channel subfamily H member 2 Ion channel IC50 6.49 CHEMBL
Multidrug and toxin extrusion protein 1 Transporter IC50 4.95 CHEMBL
Cholinesterase Enzyme IC50 5.91 CHEMBL
Equilibrative nucleoside transporter 4 Transporter INHIBITOR Ki 4.60 IUPHAR
Potassium voltage-gated channel subfamily A member 5 Ion channel BLOCKER Kd 5.20 IUPHAR
Muscarinic acetylcholine receptor M2 GPCR Ki 8.12 PDSP
Potassium voltage-gated channel subfamily H member 1 Ion channel BLOCKER IC50 5.80 IUPHAR
Potassium voltage-gated channel subfamily A member 7 Ion channel BLOCKER Kd 4.80 IUPHAR
Potassium voltage-gated channel subfamily D member 2 Unclassified IC50 5.66 CHEMBL
Cholinesterase Enzyme IC50 5.13 CHEMBL
Potassium channel subfamily T member 1 Unclassified BLOCKER IC50 4 IUPHAR
Sodium channel protein type 5 subunit alpha Unclassified BLOCKER IC50 5 IUPHAR

External reference:

IDSource
4017419 VUID
N0000179295 NUI
D00642 KEGG_DRUG
7054-25-3 SECONDARY_CAS_RN
4017417 VANDF
4017418 VANDF
4017419 VANDF
4019925 VANDF
C0034414 UMLSCUI
CHEBI:28593 CHEBI
QDN PDB_CHEM_ID
CHEMBL21578 ChEMBL_ID
DB00908 DRUGBANK_ID
CHEMBL1294 ChEMBL_ID
CHEMBL1200437 ChEMBL_ID
CHEMBL2165709 ChEMBL_ID
CHEMBL1201486 ChEMBL_ID
CHEMBL3707183 ChEMBL_ID
D011802 MESH_DESCRIPTOR_UI
441074 PUBCHEM_CID
2342 IUPHAR_LIGAND_ID
C016713 MESH_SUPPLEMENTAL_RECORD_UI
C047144 MESH_SUPPLEMENTAL_RECORD_UI
ITX08688JL UNII
35220 RXNORM
2389 MMSL
2395 MMSL
5402 MMSL
5403 MMSL
5404 MMSL
72295 MMSL
d00020 MMSL
000618 NDDF
000619 NDDF
000620 NDDF
000621 NDDF
004377 NDDF
31306009 SNOMEDCT_US
372697008 SNOMEDCT_US
5907009 SNOMEDCT_US
77632008 SNOMEDCT_US
82230005 SNOMEDCT_US

Pharmaceutical products:

ProductCategoryIngredientsNDCFormQuantityRouteMarketingLabel
Quinidine Sulfate HUMAN PRESCRIPTION DRUG LABEL 1 0185-1047 TABLET 300 mg ORAL ANDA 18 sections
Quinidine Sulfate HUMAN PRESCRIPTION DRUG LABEL 1 0185-4346 TABLET 200 mg ORAL ANDA 18 sections
Quinidine Gluconate HUMAN PRESCRIPTION DRUG LABEL 1 51407-288 TABLET, EXTENDED RELEASE 324 mg ORAL ANDA 26 sections
Quinidine Gluconate HUMAN PRESCRIPTION DRUG LABEL 1 53489-141 TABLET, EXTENDED RELEASE 324 mg ORAL ANDA 26 sections
Quinidine Gluconate HUMAN PRESCRIPTION DRUG LABEL 1 54738-901 TABLET, EXTENDED RELEASE 324 mg ORAL ANDA 25 sections
NUEDEXTA HUMAN PRESCRIPTION DRUG LABEL 2 64597-301 CAPSULE, GELATIN COATED 10 mg ORAL NDA 27 sections
Quinidine Sulfate HUMAN PRESCRIPTION DRUG LABEL 1 68151-1991 TABLET 200 mg ORAL ANDA 13 sections
Quinidine Gluconate HUMAN PRESCRIPTION DRUG LABEL 1 68151-2701 TABLET, EXTENDED RELEASE 324 mg ORAL ANDA 25 sections