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Details

Stereochemistry ABSOLUTE
Molecular Formula C20H24N2O3
Molecular Weight 340.4162
Optical Activity UNSPECIFIED
Defined Stereocenters 5 / 5
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of 3-HYDROXYQUININE

SMILES

COC1=CC2=C(C=CN=C2C=C1)[C@@H](O)[C@@H]3C[C@@H]4CC[N@]3C[C@]4(O)C=C

InChI

InChIKey=BSRUJCFCZKMFMB-YGHPHNMRSA-N
InChI=1S/C20H24N2O3/c1-3-20(24)12-22-9-7-13(20)10-18(22)19(23)15-6-8-21-17-5-4-14(25-2)11-16(15)17/h3-6,8,11,13,18-19,23-24H,1,7,9-10,12H2,2H3/t13-,18-,19+,20+/m0/s1

HIDE SMILES / InChI

Molecular Formula C20H24N2O3
Molecular Weight 340.4162
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 4 / 4
E/Z Centers 0
Optical Activity UNSPECIFIED

Approval Year

PubMed

PubMed

TitleDatePubMed
Effects of Plasmodium falciparum infection on the pharmacokinetics of quinine and its metabolites in pregnant and non-pregnant Sudanese women.
2010-12
Genetic variations in ABCB1 and CYP3A5 as well as sex influence quinine disposition among Ugandans.
2010-06
Pharmacokinetic interactions between ritonavir and quinine in healthy volunteers following concurrent administration.
2010-03
Simultaneous liquid chromatographic analysis of ritonavir, quinine and 3-hydroxyquinine in human plasma.
2009-02-01
Variable inhibitory effect of different brands of commercial herbal supplements on human cytochrome P-450 CYP3A4.
2009
Pharmacokinetics and clinical efficacy of midazolam in children with severe malaria and convulsions.
2008-10
Inhibition of CYP3A4 and CYP3A5 catalyzed metabolism of alprazolam and quinine by ketoconazole as racemate and four different enantiomers.
2007-02
Quinine distribution in pregnant mice with Plasmodium berghei malaria.
2006-07
Ketoconazole increases plasma concentrations of antimalarial mefloquine in healthy human volunteers.
2005-06
High-performance liquid chromatographic method for the determination of quinine and 3-hydroxyquinine in blood samples dried on filter paper.
2003-09-25
Metabolism and elimination of quinine in healthy volunteers.
2003-09
Quinine 3-hydroxylation as a biomarker reaction for the activity of CYP3A4 in man.
2003-05
Is quinine a suitable probe to assess the hepatic drug-metabolizing enzyme CYP3A4?
2002-12
Quinine pharmacokinetics in chronic haemodialysis patients.
2002-12
Enzyme kinetics for the formation of 3-hydroxyquinine and three new metabolites of quinine in vitro; 3-hydroxylation by CYP3A4 is indeed the major metabolic pathway.
2002-12
Effects of cigarette smoking on quinine pharmacokinetics in malaria.
2002-08
Substance Class Chemical
Created
by admin
on Mon Mar 31 21:41:46 GMT 2025
Edited
by admin
on Mon Mar 31 21:41:46 GMT 2025
Record UNII
4D7695509M
Record Status Validated (UNII)
Record Version
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Name Type Language
3-HYDROXYQUININE
Common Name English
(-)-(3S)-3-HYDROXYQUININE
Preferred Name English
3-HYDROXYQUININE, (-)-
Common Name English
CINCHONAN-3,9-DIOL, 6'-METHOXY-, (8.ALPHA.,9R)-
Systematic Name English
Code System Code Type Description
CHEBI
17685
Created by admin on Mon Mar 31 21:41:46 GMT 2025 , Edited by admin on Mon Mar 31 21:41:46 GMT 2025
PRIMARY
PUBCHEM
157225
Created by admin on Mon Mar 31 21:41:46 GMT 2025 , Edited by admin on Mon Mar 31 21:41:46 GMT 2025
PRIMARY
EPA CompTox
DTXSID901316798
Created by admin on Mon Mar 31 21:41:46 GMT 2025 , Edited by admin on Mon Mar 31 21:41:46 GMT 2025
PRIMARY
FDA UNII
4D7695509M
Created by admin on Mon Mar 31 21:41:46 GMT 2025 , Edited by admin on Mon Mar 31 21:41:46 GMT 2025
PRIMARY
CHEBI
58234
Created by admin on Mon Mar 31 21:41:46 GMT 2025 , Edited by admin on Mon Mar 31 21:41:46 GMT 2025
PRIMARY
CAS
78549-61-8
Created by admin on Mon Mar 31 21:41:46 GMT 2025 , Edited by admin on Mon Mar 31 21:41:46 GMT 2025
PRIMARY
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