Details of the Drug Metabolized by Drug-Metabolizing Enzyme (DME)

General Information of Drug (ID: DR1385)
Drug Name
Quinine sulfate
Synonyms
Quinine bisulfate; Quinine bisulfate [NF]; Quinine hydrogen sulfate; Quinine hydrogen sulphate; Quinine, sulfate (1:1) (salt); Qualaquin; Quinine; Quinine HCl; Quinine anhydrous; Quinine sulphate; Quinine, Anhydrous; Quinine, tannate; Quinineanhydrous; Quinoline alkaloid; UNII-A7V27PHC7A; chininum; quinina; quinine bisulphate; (-)-Quinine; (8S,9R)-Quinine; (R)-(-)-quinine; 130-95-0; 6'-Methoxycinchonan-9-ol; 6'-Methoxycinchonidine; 6'-Methoxycinchonine; 6-Methoxycinchonine; A7V27PHC7A; Aflukin; CHEBI:15854; Chinin; Chinin [German]; Chinine; Cinchonan-9-ol, 6'-methoxy-, (8a,9R)-; Coco-Quinine; LOUPRKONTZGTKE-WZBLMQSHSA-N; MFCD00198096; NSC 192949; SCHEMBL29712; UNII-M201HC068W; (-)-Quinine Sulfate Dihydrate; (R)-(6-Methoxyquinolin-4-yl)((1S,2S,4S,5R)-5-vinylquinuclidin-2-yl)methanol sulfate; 549-56-4; 6119-70-6; 804-63-7; 8alpha,9R-6'-Methoxycinchonan-9-ol, sulfate (1:1) salt; CHEMBL1201100; EC 208-970-9; EINECS 208-970-9; FEMA No. 2975; GNF-Pf-506; M201HC068W; QUININE SULFATE DIHYDRATE
Indication Malaria [ICD11: 1F40] Approved [1]
Structure
3D MOL is unavailable 2D MOL
Pharmaceutical Properties Molecular Weight 422.5 Topological Polar Surface Area 129
Heavy Atom Count 29 Rotatable Bond Count 4
Hydrogen Bond Donor Count 3 Hydrogen Bond Acceptor Count 8
Cross-matching ID
PubChem CID
11949689
CAS Number
549-56-4
TTD Drug ID
D03DDR
Formula
C20H26N2O6S
Canonical SMILES
COC1=CC2=C(C=CN=C2C=C1)C(C3CC4CCN3CC4C=C)O.OS(=O)(=O)O
InChI
1S/C20H24N2O2.H2O4S/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;1-5(2,3)4/h3-6,8,11,13-14,19-20,23H,1,7,9-10,12H2,2H3;(H2,1,2,3,4)/t13-,14-,19-,20+;/m0./s1
InChIKey
AKYHKWQPZHDOBW-DSXUQNDKSA-N
The Metabolic Roadmap of This Drug
The Full List of Drug Metabolites (DM) of This Drug
DM Name DM ID PubChem ID Reaction DM Level REF
10, 11-Dihydroxydihydroquinine DM015874
14589195
Unclear - Unclear 1 [9]
2'-oxoquininone DM018116 N. A. Unclear - Unclear 1 [10]
3-hydroxyquinine DM015981
21120296
Unclear - Unclear 1 [10] , [11] , [12]
N-oxidequinine DM018115 N. A. Unclear - Unclear 1 [10]
Quinine sulfate Metabolite M1 DM018113 N. A. Oxidation - Hydroxylation 1 [13]
Quinine sulfate Metabolite M2 DM018114 N. A. Multi-steps Reaction - DemethylationHydroxylation 1 [13]
Quinine sulfate Metabolite M3 DM015983
21153009
Oxidation - Demethylation 1 [13]
Quinine sulfate Metabolite M2 DM018114 N. A. Unclear - Unclear 2 [13]
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR010016 Quinine sulfate Quinine sulfate Metabolite M1 Oxidation - Hydroxylation CYP3A4 ... [13]
MR010018 Quinine sulfate Quinine sulfate Metabolite M3 Oxidation - Demethylation CYP3A4 ... [13]
MR010020 Quinine sulfate Quinine sulfate Metabolite M2 Multi-steps Reaction - DemethylationHydroxylation CYP3A4 [13]
MR010021 Quinine sulfate 3-hydroxyquinine Unclear - Unclear CYP3A4 [10], [11], [12]
MR010022 Quinine sulfate N-oxidequinine Unclear - Unclear Unclear [10]
MR010023 Quinine sulfate 2'-oxoquininone Unclear - Unclear Unclear [10]
MR010024 Quinine sulfate 10, 11-Dihydroxydihydroquinine Unclear - Unclear Unclear [9]
MR010017 Quinine sulfate Metabolite M1 Quinine sulfate Metabolite M2 Unclear - Unclear Unclear [13]
MR010019 Quinine sulfate Metabolite M3 Quinine sulfate Metabolite M2 Unclear - Unclear Unclear [13]
⏷ Show the Full List of 9 MR(s)
Drug-Metabolizing Enzyme(s) (DME) Metabolizing This Drug
DME Name DME Info Species Uniprot ID EC Number REF
Cytochrome P450 1A2 (CYP1A2) DME0003 Homo sapiens
CP1A2_HUMAN
1.14.14.1
[2]
Cytochrome P450 2C8 (CYP2C8) DME0018 Homo sapiens
CP2C8_HUMAN
1.14.14.1
[3]
Cytochrome P450 2C9 (CYP2C9) DME0019 Homo sapiens
CP2C9_HUMAN
1.14.14.1
[4]
Cytochrome P450 2D6 (CYP2D6) DME0009 Homo sapiens
CP2D6_HUMAN
1.14.14.1
[5]
Cytochrome P450 3A4 (CYP3A4) DME0001 Homo sapiens
CP3A4_HUMAN
1.14.14.55
[6]
Cytochrome P450 3A5 (CYP3A5) DME0012 Homo sapiens
CP3A5_HUMAN
1.14.14.1
[7]
Cytochrome P450 3A7 (CYP3A7) DME0015 Homo sapiens
CP3A7_HUMAN
1.14.14.1
[7]
Mephenytoin 4-hydroxylase (CYP2C19) DME0021 Homo sapiens
CP2CJ_HUMAN
1.14.14.1
[8]
⏷ Show the Full List of 8  DME(s)
References
1 Quinine Sulfate was approved by FDA. The 2020 official website of the U.S. Food and Drug Administration.
2 The roles of cytochrome P450 3A4 and 1A2 in the 3-hydroxylation of quinine in vivo. Clin Pharmacol Ther. 1999 Nov;66(5):454-60.
3 Role of cytochrome P450 2C8 in drug metabolism and interactions. Pharmacol Rev. 2016 Jan;68(1):168-241.
4 Identification of human cytochrome P450 isoforms involved in the 3-hydroxylation of quinine by human live microsomes and nine recombinant human cytochromes P450. J Pharmacol Exp Ther. 1996 Dec;279(3):1327-34.
5 Inhibition of cytochrome P450 2D6: structure-activity studies using a series of quinidine and quinine analogues. Chem Res Toxicol. 2003 Apr;16(4):450-9.
6 Quinine induced simvastatin toxicity through cytochrome inhibition - a case report. BMC Geriatr. 2016 Oct 1;16(1):168.
7 Drug Interactions Flockhart Table
8 Organic anion-transporting polypeptide B (OATP-B) and its functional comparison with three other OATPs of human liver. Gastroenterology. 2001 Feb;120(2):525-33.
9 Alteration of the Disposition of Quinine in Healthy Volunteers After Concurrent Ciprofloxacin Administration
10 Metabolism of quinine in man: identification of a major metabolite, and effects of smoking and rifampicin pretreatment
11 Effects of Plasmodium falciparum infection on the pharmacokinetics of quinine and its metabolites in pregnant and non-pregnant Sudanese women
12 Rapid quantification of quinine and its major metabolite (3S)-3-hydroxyquinine in diluted urine by UPLC-MS/MS
13 CYP450 phenotyping and metabolite identification of quinine by accurate mass UPLC-MS analysis: a possible metabolic link to blackwater fever

If you find any error in data or bug in web service, please kindly report it to Dr. Yin and Dr. Li.