QDN

Quinidine

Created:	2014-10-15
Last modified:	2021-03-01

Find Related PDB Entry
3 entries where QDN is found as a standalone ligand

Help Find related ligands:
Similar Ligands (Stereospecific) Similar Ligands (including Stereoisomers) Similar Ligands (Quick Screen) Similar Ligands (Substructure Stereospecific) Similar Ligands (Substructure including Stereoisomers)

Help

Find related ligands:

Similar Ligands (Stereospecific) Similar Ligands (including Stereoisomers) Similar Ligands (Quick Screen) Similar Ligands (Substructure Stereospecific) Similar Ligands (Substructure including Stereoisomers)

Chemical Details
Formal Charge	0
Atom Count	48
Chiral Atom Count	5
Bond Count	51
Aromatic Bond Count	11

Toggle Hydrogen Toggle Labels

Chemical Component Summary
Name	Quinidine
Synonyms	(9S)-6'-methoxycinchonan-9-ol
Systematic Name (OpenEye OEToolkits)	(S)-[(1S,2R,4S,5R)-5-ethenyl-1-azabicyclo[2.2.2]octan-2-yl]-(6-methoxyquinolin-4-yl)methanol
Formula	C₂₀ H₂₄ N₂ O₂
Molecular Weight	324.417
Type	NON-POLYMER

Chemical Descriptors
Type	Program	Version	Descriptor
SMILES	ACDLabs	12.01	O(c4cc1c(nccc1C(O)C2N3CCC(C2)C(/C=C)C3)cc4)C
SMILES	CACTVS	3.385	COc1ccc2nccc([CH](O)[CH]3C[CH]4CC[N]3C[CH]4C=C)c2c1
SMILES	OpenEye OEToolkits	1.9.2	COc1ccc2c(c1)c(ccn2)C(C3CC4CCN3CC4C=C)O
Canonical SMILES	CACTVS	3.385	COc1ccc2nccc([C@H](O)[C@H]3C[C@@H]4CC[N@]3C[C@@H]4C=C)c2c1
Canonical SMILES	OpenEye OEToolkits	1.9.2	COc1ccc2c(c1)c(ccn2)[C@@H]([C@H]3C[C@@H]4CC[N@]3C[C@@H]4C=C)O
InChI	InChI	1.03	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	InChI	1.03	LOUPRKONTZGTKE-LHHVKLHASA-N

Drug Info: DrugBank

DrugBank ID	DB00908
Name	Quinidine
Groups	approved investigational
Description	Quinidine is a D-isomer of [quinine] present in the bark of the Cinchona tree and similar plant species. This alkaloid was first described in 1848 and has a long history as an antiarrhythmic medication.[A38016,A250050] Quinidine is considered the first antiarrhythmic drug (class Ia) and is moderately efficacious in the acute conversion of atrial fibrillation to normal sinus rhythm.[A38016] It prolongs cellular action potential by blocking sodium and potassium currents. A phenomenon known as “quinidine syncope” was first described in the 1950s, characterized by syncopal attacks and ventricular fibrillation in patients treated with this drug.[A38016] Due to its side effects and increased risk of mortality, the use of quinidine was reduced over the next few decades. However, it continues to be used in the treatment of Brugada syndrome, short QT syndrome and idiopathic ventricular fibrillation.[A250050]
Synonyms	Conquinine (S)-(6-Methoxyquinolin-4-yl)((2R,5R)-5-vinylquinuclidin-2-yl)methanol (R)-(6-Methoxyquinolin-4-yl)((3S,4R,7S)-3-vinylquinuclidin-7-yl)methanol beta-Quinine Pitayine (8R,9S)-Quinidine Chinidinum Conchinin α-(6-methoxy-4-quinolyl)-5-vinyl-2-quinuclidinemethanol Chinidin Quinidine hydrochloride 6-methoxy-α-(5-vinyl-2-quinuclidinyl)-4-quinolinemethanol Quinidine Quinidine polygalacturonate Quinidina (S)-(6-Methoxy-quinolin-4-yl)-((2R,5R)-5-vinyl-1-aza-bicyclo[2.2.2]oct-2-yl)-methanol CIN-QUIN (+)-quinidine Quinidine gluconate Quinidine sulfate β-quinine
Brand Names	Cardioquin Tablets Quinidine Sulfate Quinidine gluconate Quinate Tab 325mg Quinidine Gluconate Quinidine Sulfate Injection 190mg/ml Quinidine Sulfate Tab 200mg Nuedexta Quinidine Sulfate 200mg Apo Quinidine Tab 200mg Quinidex Extentabs Srt 300mg Quinidine 200 Tab Apo-quin-G Tab 325mg Quinidine Gluconate for Inj 80mg/ml USP Novo-quinidin 200mg
Indication	Quinidine is indicated for the management and prophylactic therapy of atrial fibrillation/flutter, as well as the suppression of recurrent documented ventricular arrhythmias.[L42420,L3719] It is also used in the treatment of Brugada syndrome, short QT syndrome and idiopathic ventricular fibrillation.[A250050,A250055].
Categories	Adrenergic Agents Adrenergic alpha-1 Receptor Antagonists Adrenergic alpha-Antagonists Adrenergic Antagonists Agents producing tachycardia Agents that produce hypertension Agents that produce neuromuscular block (indirect) Agents that reduce seizure threshold Alkaloids Anti-Infective Agents Antiarrhythmic agents Antiarrhythmics, Class I Antiarrhythmics, Class Ia Anticholinergic Agents Antimalarials Antiparasitic Agents Antiprotozoals Biological Products Biopolymers BSEP/ABCB11 Inhibitors Carbohydrates Cardiac Therapy Cardiovascular Agents Cholinergic Agents Cinchona Alkaloids Complex Mixtures Compounds used in a research, industrial, or household setting Cytochrome P-450 CYP1A2 Inhibitors Cytochrome P-450 CYP1A2 Inhibitors (strong) Cytochrome P-450 CYP2B6 Inhibitors Cytochrome P-450 CYP2B6 Inhibitors (strength unknown) Cytochrome P-450 CYP2C8 Inducers Cytochrome P-450 CYP2C8 Inducers (weak) Cytochrome P-450 CYP2C8 Inhibitors Cytochrome P-450 CYP2C8 Inhibitors (weak) Cytochrome P-450 CYP2C9 Inhibitors Cytochrome P-450 CYP2C9 Inhibitors (moderate) Cytochrome P-450 CYP2C9 Substrates Cytochrome P-450 CYP2C9 Substrates with a Narrow Therapeutic Index Cytochrome P-450 CYP2D6 Inhibitors Cytochrome P-450 CYP2D6 Inhibitors (strong) Cytochrome P-450 CYP2E1 Substrates Cytochrome P-450 CYP2E1 Substrates with a Narrow Therapeutic Index Cytochrome P-450 CYP3A Inhibitors Cytochrome P-450 CYP3A Substrates Cytochrome P-450 CYP3A4 Inhibitors Cytochrome P-450 CYP3A4 Inhibitors (weak) Cytochrome P-450 CYP3A4 Substrates Cytochrome P-450 CYP3A4 Substrates with a Narrow Therapeutic Index Cytochrome P-450 CYP3A7 Substrates Cytochrome P-450 CYP3A7 Substrates with a Narrow Therapeutic Index Cytochrome P-450 Enzyme Inducers Cytochrome P-450 Enzyme Inhibitors Cytochrome P-450 Substrates Drugs causing inadvertant photosensitivity Drugs that are Mainly Renally Excreted Drugs that are Mainly Renally Excreted with a Narrow Therapeutic Index Enzyme Inhibitors Heterocyclic Compounds, Fused-Ring Highest Risk QTc-Prolonging Agents Macromolecular Substances Membrane Transport Modulators Muscarinic Antagonists Narrow Therapeutic Index Drugs Negative Inotrope Neurotransmitter Agents OAT3/SLC22A8 Inhibitors OATP1B1/SLCO1B1 Inhibitors OCT1 inhibitors OCT2 Inhibitors P-glycoprotein inhibitors P-glycoprotein substrates P-glycoprotein substrates with a Narrow Therapeutic Index Pharmaceutical Preparations Photosensitizing Agents Plant Extracts Plant Preparations Polymers Polysaccharides QTc Prolonging Agents Quinolines Quinuclidines Sodium Channel Blockers Voltage-Gated Sodium Channel Blockers
ATC-Code	C01BA01 C01BA51 C01BA71
CAS number	56-54-2

Drug Targets

Name	Target Sequence	Pharmacological Action	Actions
Sodium channel protein type 5 subunit alpha	MANFLLPRGTSSFRRFTRESLAAIEKRMAEKQARGSTTLQESREGLPEEE...	unknown	inhibitor
Potassium channel subfamily K member 1	MLQSLAGSSCVRLVERHRSAWCFGFLVLGYLLYLVFGAVVFSSVELPYED...	unknown	inhibitor
Potassium channel subfamily K member 6	MRRGALLAGALAAYAAYLVLGALLVARLEGPHEARLRAELETLRAQLLQR...	unknown	inhibitor
Potassium voltage-gated channel subfamily H member 2	MPVRRGHVAPQNTFLDTIIRKFEGQSRKFIIANARVENCAVIYCNDGFCE...	unknown	inhibitor
Alpha-1A adrenergic receptor	MVFLSGNASDSSNCTQPPAPVNISKAILLGVILGGLILFGVLGNILVILS...	unknown	antagonist
Alpha-1B adrenergic receptor	MNPDLDTGHNTSAPAHWGELKNANFTGPNQTSSNSTLPQLDITRAISVGL...	unknown	antagonist
Alpha-1D adrenergic receptor	MTFRDLLSVSFEGPRPDSSAGGSSAGGGGGSAGGAAPSEGPAVGGVPGGA...	unknown	antagonist
Cytochrome P450 3A4	MALIPDLAMETWLLLAVSLVLLYLYGTHSHGLFKKLGIPGPTPLPFLGNI...	unknown	substrate,inhibitor
Cytochrome P450 3A7	MDLIPNLAVETWLLLAVSLILLYLYGTRTHGLFKKLGIPGPTPLPFLGNA...	unknown	substrate
Cytochrome P450 2D6	MGLEALVPLAVIVAIFLLLVDLMHRRQRWAARYPPGPLPLPGLGNLLHVD...	unknown	inhibitor
Cytochrome P450 1A2	MALSQSVPFSATELLLASAIFCLVFWVLKGLRPRVPKGLKSPPEPWGWPL...	unknown	inhibitor
Cytochrome P450 2E1	MSALGVTVALLVWAAFLLLVSMWRQVHSSWNLPPGPFPLPIIGNLFQLEL...	unknown	substrate
Cytochrome P450 1A1	MLFPISMSATEFLLASVIFCLVFWVIRASRPQVPKGLKNPPGPWGWPLIG...	unknown	inhibitor
Cytochrome P450 2B6	MELSVLLFLALLTGLLLLLVQRHPNTHDRLPPGPRPLPLLGNLLQMDRRG...	unknown	inhibitor
Cytochrome P450 2C9	MDSLVVLVLCLSCLLLLSLWRQSSGRGKLPPGPTPLPVIGNILQIGIKDI...	unknown	substrate,inhibitor
Cytochrome P450 2C8	MEPFVVLVLCLSFMLLFSLWRQSCRRRKLPPGPTPLPIIGNMLQIDVKDI...	unknown	inhibitor
Serum albumin	MKWVTFISLLFLFSSAYSRGVFRRDAHKSEVAHRFKDLGEENFKALVLIA...	unknown	binder
Alpha-1-acid glycoprotein 1	MALSWVLTVLSLLPLLEAQIPLCANLVPVPITNATLDQITGKWFYIASAF...	unknown	binder
Solute carrier family 22 member 2	MPTTVDDVLEHGGEFHFFQKQMFFLLALLSATFAPIYVGIVFLGFTPDHR...	unknown	inhibitor
Solute carrier family 22 member 1	MPTVDDILEQVGESGWFQKQAFLILCLLSAAFAPICVGIVFLGFTPDHHC...	unknown	inhibitor
Solute carrier family 22 member 5	MRDYDEVTAFLGEWGPFQRLIFFLLSASIIPNGFTGLSSVFLIATPEHRC...	unknown	inhibitor
P-glycoprotein 1	MDLEGDRNGGAKKKNFFKLNNKSEKDKKEKKPTVSVFSMFRYSNWLDKLY...	unknown	substrate,inhibitor
Solute carrier organic anion transporter family member 1A2	MGETEKRIETHRIRCLSKLKMFLLAITCAFVSKTLSGSYMNSMLTQIERQ...	unknown	inhibitor
Solute carrier family 22 member 8	MTFSEILDRVGSMGHFQFLHVAILGLPILNMANHNLLQIFTAATPVHHCR...	unknown	inhibitor
Canalicular multispecific organic anion transporter 1	MLEKFCNSTFWNSSFLDSPEADLPLCFEQTVLVWIPLGYLWLLAPWQLLH...	unknown	inhibitor
Solute carrier family 22 member 4	MRDYDEVIAFLGEWGPFQRLIFFLLSASIIPNGFNGMSVVFLAGTPEHRC...	unknown	inhibitor
Solute carrier organic anion transporter family member 1B1	MDQNQHLNKTAEAQPSENKKTRYCNGLKMFLAALSLSFIAKTLGAIIMKS...	unknown	inhibitor
Bile salt export pump	MSDSVILRSIKKFGEENDGFESDKSYNNDKKSRLQDEKKGDGVRVGFFQL...	unknown	inhibitor
View More

Drug Info/Drug Targets: DrugBank 3.0: a comprehensive resource for 'omics' research on drugs. Knox C, Law V, Jewison T, Liu P, Ly S, Frolkis A, Pon A, Banco K, Mak C, Neveu V, Djoumbou Y, Eisner R, Guo AC, Wishart DS. Nucleic Acids Res. 2011 Jan; 39 (Database issue):D1035-41. | PMID:21059682