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Details

Stereochemistry ABSOLUTE
Molecular Formula C20H24N2O3
Molecular Weight 340.4169
Optical Activity UNSPECIFIED
Defined Stereocenters 5 / 5
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of 3-HYDROXYQUININE

SMILES

C=C[C@]1(CN2CC[C@@]1([H])C[C@@]2([H])[C@@]([H])(c3ccnc4ccc(cc34)OC)O)O

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 340.4169
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 4 / 4
E/Z Centers 0
Optical Activity UNSPECIFIED

Approval Year

PubMed

PubMed

TitleDatePubMed
Is quinine a suitable probe to assess the hepatic drug-metabolizing enzyme CYP3A4?
2002 Dec
Quinine 3-hydroxylation as a biomarker reaction for the activity of CYP3A4 in man.
2003 May
Metabolism and elimination of quinine in healthy volunteers.
2003 Sep
High-performance liquid chromatographic method for the determination of quinine and 3-hydroxyquinine in blood samples dried on filter paper.
2003 Sep 25
Ketoconazole increases plasma concentrations of antimalarial mefloquine in healthy human volunteers.
2005 Jun
Quinine distribution in pregnant mice with Plasmodium berghei malaria.
2006 Jul
Inhibition of CYP3A4 and CYP3A5 catalyzed metabolism of alprazolam and quinine by ketoconazole as racemate and four different enantiomers.
2007 Feb
Pharmacokinetics and clinical efficacy of midazolam in children with severe malaria and convulsions.
2008 Oct
Variable inhibitory effect of different brands of commercial herbal supplements on human cytochrome P-450 CYP3A4.
2009
Effects of Plasmodium falciparum infection on the pharmacokinetics of quinine and its metabolites in pregnant and non-pregnant Sudanese women.
2010 Dec
Genetic variations in ABCB1 and CYP3A5 as well as sex influence quinine disposition among Ugandans.
2010 Jun
Pharmacokinetic interactions between ritonavir and quinine in healthy volunteers following concurrent administration.
2010 Mar
Substance Class Chemical
Created
by admin
on Sat Jun 26 15:24:58 UTC 2021
Edited
by admin
on Sat Jun 26 15:24:58 UTC 2021
Record UNII
4D7695509M
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
3-HYDROXYQUININE
Common Name English
(-)-(3S)-3-HYDROXYQUININE
Common Name English
3-HYDROXYQUININE, (-)-
Common Name English
CINCHONAN-3,9-DIOL, 6'-METHOXY-, (8.ALPHA.,9R)-
Systematic Name English
Code System Code Type Description
PUBCHEM
157225
Created by admin on Sat Jun 26 15:24:58 UTC 2021 , Edited by admin on Sat Jun 26 15:24:58 UTC 2021
PRIMARY
FDA UNII
4D7695509M
Created by admin on Sat Jun 26 15:24:58 UTC 2021 , Edited by admin on Sat Jun 26 15:24:58 UTC 2021
PRIMARY
CAS
78549-61-8
Created by admin on Sat Jun 26 15:24:58 UTC 2021 , Edited by admin on Sat Jun 26 15:24:58 UTC 2021
PRIMARY
Related Record Type Details
PARENT -> METABOLITE LESS ACTIVE
Quinine is metabolized almost exclusively via hepatic oxidative cytochrome P450 (CYP) pathways. In vitro studies using human liver microsomes and recombinant P450 enzymes have shown that quinine is metabolized mainly by CYP3A4. Depending on the in vitro experimental conditions, other enzymes, including CYP1A2, CYP2C8, CYP2C9, CYP2C19, CYP2D6, and CYP2E1 were shown to have some role in the metabolism of quinine.