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
SMILES
[H][C@]1(C[C@@H]2CC[N@]1C[C@]2(O)C=C)[C@H](O)C3=C4C=C(OC)C=CC4=NC=C3
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
| 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
| Title | Date | PubMed |
|---|---|---|
| Quinine 3-hydroxylation as a biomarker reaction for the activity of CYP3A4 in man. | 2003 May |
|
| 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 |
|
| Simultaneous liquid chromatographic analysis of ritonavir, quinine and 3-hydroxyquinine in human plasma. | 2009 Feb 1 |
|
| 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 |
| Substance Class |
Chemical
Created
by
admin
on
Edited
Sat Dec 16 07:32:37 GMT 2023
by
admin
on
Sat Dec 16 07:32:37 GMT 2023
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| Record UNII |
4D7695509M
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| Record Status |
Validated (UNII)
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| Record Version |
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DTXSID901316798
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4D7695509M
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78549-61-8
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| Related Record | Type | Details | ||
|---|---|---|---|---|
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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.
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