CHEBI:28593 - quinidine

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ChEBI Name quinidine
ChEBI ID CHEBI:28593
Definition A cinchona alkaloid consisting of cinchonine with the hydrogen at the 6-position of the quinoline ring substituted by methoxy.
Stars This entity has been manually annotated by the ChEBI Team.
Secondary ChEBI IDs CHEBI:127150, CHEBI:355477, CHEBI:8719, CHEBI:597286, CHEBI:604323, CHEBI:595841, CHEBI:26494, CHEBI:529982
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Formula C20H24N2O2
Net Charge 0
Average Mass 324.41680
Monoisotopic Mass 324.184
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
SMILES [H][C@@]1(C[C@@H]2CC[N@]1C[C@@H]2C=C)[C@@H](O)c1ccnc2ccc(OC)cc12
Roles Classification
Biological Role(s): muscarinic antagonist
A drug that binds to but does not activate muscarinic cholinergic receptors, thereby blocking the actions of endogenous acetylcholine or exogenous agonists.
EC 1.14.13.181 (13-deoxydaunorubicin hydroxylase) inhibitor
An EC 1.14.13.* (oxidoreductase acting on paired donors, incorporating 1 atom of oxygen, with NADH or NADPH as one donor) inhibitor that interferes with the action of 13-deoxydaunorubicin hydroxylase (EC 1.14.13.181).
EC 3.6.3.44 (xenobiotic-transporting ATPase) inhibitor
An EC 3.6.3.* (acid anhydride hydrolase catalysing transmembrane movement of substances) inhibitor that interferes with the action of xenobiotic-transporting ATPase (EC 3.6.3.44).
potassium channel blocker
An agent that inhibits cell membrane glycoproteins that are selectively permeable to potassium ions.
P450 inhibitor
An enzyme inhibitor that interferes with the activity of cytochrome P450 involved in catalysis of organic substances.
sodium channel blocker
An agent that inhibits sodium influx through cell membranes.
alpha-adrenergic antagonist
An agent that binds to but does not activate alpha-adrenergic receptors thereby blocking the actions of endogenous or exogenous alpha-adrenergic agonists. alpha-Adrenergic antagonists are used in the treatment of hypertension, vasospasm, peripheral vascular disease, shock, and pheochromocytoma.
antimalarial
A drug used in the treatment of malaria. Antimalarials are usually classified on the basis of their action against Plasmodia at different stages in their life cycle in the human.
metabolite
Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
(via alkaloid )
Application(s): muscarinic antagonist
A drug that binds to but does not activate muscarinic cholinergic receptors, thereby blocking the actions of endogenous acetylcholine or exogenous agonists.
anti-arrhythmia drug
A drug used for the treatment or prevention of cardiac arrhythmias. Anti-arrhythmia drugs may affect the polarisation-repolarisation phase of the action potential, its excitability or refractoriness, or impulse conduction or membrane responsiveness within cardiac fibres.
alpha-adrenergic antagonist
An agent that binds to but does not activate alpha-adrenergic receptors thereby blocking the actions of endogenous or exogenous alpha-adrenergic agonists. alpha-Adrenergic antagonists are used in the treatment of hypertension, vasospasm, peripheral vascular disease, shock, and pheochromocytoma.
antimalarial
A drug used in the treatment of malaria. Antimalarials are usually classified on the basis of their action against Plasmodia at different stages in their life cycle in the human.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing quinidine (CHEBI:28593) has parent hydride cinchonan (CHEBI:35933)
quinidine (CHEBI:28593) has role α-adrenergic antagonist (CHEBI:37890)
quinidine (CHEBI:28593) has role anti-arrhythmia drug (CHEBI:38070)
quinidine (CHEBI:28593) has role antimalarial (CHEBI:38068)
quinidine (CHEBI:28593) has role EC 1.14.13.181 (13-deoxydaunorubicin hydroxylase) inhibitor (CHEBI:77781)
quinidine (CHEBI:28593) has role EC 3.6.3.44 (xenobiotic-transporting ATPase) inhibitor (CHEBI:77748)
quinidine (CHEBI:28593) has role muscarinic antagonist (CHEBI:48876)
quinidine (CHEBI:28593) has role P450 inhibitor (CHEBI:50183)
quinidine (CHEBI:28593) has role potassium channel blocker (CHEBI:50509)
quinidine (CHEBI:28593) has role sodium channel blocker (CHEBI:38633)
quinidine (CHEBI:28593) is a cinchona alkaloid (CHEBI:51323)
Incoming quinidine D-gluconate (CHEBI:27502) has functional parent quinidine (CHEBI:28593)
quinidine sulfate (CHEBI:28482) has functional parent quinidine (CHEBI:28593)
IUPAC Name
(9S)-6'-methoxycinchonan-9-ol
Synonyms Sources
(+)-quinidine ChemIDplus
(+)-Quinidine KEGG COMPOUND
(8R,9S)-quinidine ChemIDplus
(R)-(6-methoxyquinolin-4-yl)((3S,4R,7S)-3-vinylquinuclidin-7-yl)methanol ChEMBL
(S)-(6-Methoxy-quinolin-4-yl)-((2R,5R)-5-vinyl-1-aza-bicyclo[2.2.2]oct-2-yl)-methanol ChEMBL
(S)-(6-methoxyquinolin-4-yl)((2R,5R)-5-vinylquinuclidin-2-yl)methanol ChEMBL
6-methoxy-α-(5-vinyl-2-quinuclidinyl)-4-quinolinemethanol NIST Chemistry WebBook
α-(6-methoxy-4-quinolyl)-5-vinyl-2-quinuclidinemethanol NIST Chemistry WebBook
β-quinine NIST Chemistry WebBook
Chinidin ChemIDplus
chinidinum ChEBI
CIN-QUIN ChEMBL
Conchinin ChemIDplus
conquinine ChemIDplus
pitayine ChemIDplus
quinidina ChEBI
quinidine ChEMBL
Quinidine KEGG COMPOUND
Brand Name Source
Kinidin KEGG DRUG
Database Links Databases
2346 DrugCentral
C06527 KEGG COMPOUND
D08458 KEGG DRUG
DB00908 DrugBank
LSM-3325 LINCS
View more database links
Registry Numbers Types Sources
56-54-2 CAS Registry Number KEGG COMPOUND
56-54-2 CAS Registry Number ChemIDplus
56-54-2 CAS Registry Number NIST Chemistry WebBook
91866 Beilstein Registry Number Beilstein
91866 Reaxys Registry Number Reaxys
Citations Waiting for Citations Types Sources
12477351 PubMed citation ChEMBL
12699389 PubMed citation ChEMBL
14971904 PubMed citation ChEMBL
14973303 PubMed citation Europe PMC
15089813 PubMed citation Europe PMC
15225721 PubMed citation ChEMBL
15270556 PubMed citation ChEMBL
15328252 PubMed citation Europe PMC
16570918 PubMed citation ChEMBL
17132069 PubMed citation ChEMBL
17228875 PubMed citation ChEMBL
17249648 PubMed citation Europe PMC
17870541 PubMed citation ChEMBL
18324762 PubMed citation ChEMBL
18395298 PubMed citation ChEMBL
18788725 PubMed citation ChEMBL
23861085 PubMed citation Europe PMC
24130427 PubMed citation Europe PMC
445303 PubMed citation Europe PMC
8337232 PubMed citation Europe PMC
9864343 PubMed citation Europe PMC
Last Modified
26 June 2017
General Comment
2011-02-08 Occurring in the bark of Cinchona species, it is the (8R,9S)-diastereoisomer of quinine and is a class I anti-arrhythmic agent. It is also frequently used for directing chirality in asymmetric synthesis.