3-Hydroxyquinine (BioDeep_00001870233)
Main id: BioDeep_00000006479
代谢物信息卡片
3-Hydroxyquinine
化学式: C20H24N2O3 (340.17868339999995)
中文名称:
谱图信息:
最多检出来源 () 0%
分子结构信息
SMILES: C=C[C@]1(CN2CC[C@@H]1C[C@H]2[C@@H](c1ccnc2ccc(cc12)OC)O)O
InChI: 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
数据库引用编号
8 个数据库交叉引用编号
- ChEBI: CHEBI:17685
- KEGG: C07344
- PubChem: 157225
- CAS: 78549-61-8
- MetaboLights: MTBLC17685
- PubChem: 9551
- NIKKAJI: J410.729B
- RefMet: 3-Hydroxyquinine
分类词条
相关代谢途径
Reactome(0)
BioCyc(0)
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代谢反应
0 个相关的代谢反应过程信息。
Reactome(0)
BioCyc(0)
WikiPathways(0)
Plant Reactome(0)
INOH(0)
PlantCyc(0)
COVID-19 Disease Map(0)
PathBank(0)
PharmGKB(0)
2 个相关的物种来源信息
- 7461 Apis cerana: 10.1371/JOURNAL.PONE.0175573
- 7461 Apis cerana: 10.1371/JOURNAL.PONE.0175573
在这里通过桑基图来展示出与当前的这个代谢物在我们的BioDeep知识库中具有相关联信息的其他代谢物。在这里进行关联的信息来源主要有：
- PubMed: 来源于PubMed文献库中的文献信息，我们通过自然语言数据挖掘得到的在同一篇文献中被同时提及的相关代谢物列表，这个列表按照代谢物同时出现的文献数量降序排序，取前10个代谢物作为相关研究中关联性很高的代谢物集合展示在桑基图中。
- NCBI Taxonomy: 通过文献数据挖掘，得到的代谢物物种来源信息关联。这个关联信息同样按照出现的次数降序排序，取前10个代谢物作为高关联度的代谢物集合展示在桑吉图上。
- Chemical Taxonomy: 在物质分类上处于同一个分类集合中的其他代谢物
- Chemical Reaction: 在化学反应过程中，存在为当前代谢物相关联的生化反应过程中的反应底物或者反应产物的关联代谢物信息。
点击图上的相关代谢物的名称，可以跳转到相关代谢物的信息页面。
文献列表
- Adebanjo J Adegbola, Julius O Soyinka, Babatunde A Adeagbo, Sharon I Igbinoba, Thomas I Nathaniel. Alteration of the Disposition of Quinine in Healthy Volunteers After Concurrent Ciprofloxacin Administration.
American journal of therapeutics.
2016 Mar; 23(2):e398-404. doi:
10.1097/mjt.0000000000000087. [PMID: 25406952] - Sharon I Igbinoba, Cyprian O Onyeji, Moses A Akanmu, Julius O Soyinka, Srirama Sarma V V Pullela, James M Cook, Thomas I Nathaniel. Effect of dehusked Garcinia kola seeds on the overall pharmacokinetics of quinine in healthy Nigerian volunteers.
Journal of clinical pharmacology.
2015 Mar; 55(3):348-54. doi:
10.1002/jcph.414. [PMID: 25328082] - Kassoum Kayentao, Etienne A Guirou, Ogobara K Doumbo, Meera Venkatesan, Christopher V Plowe, Teresa L Parsons, Craig W Hendrix, Myaing M Nyunt. Preliminary study of quinine pharmacokinetics in pregnant women with malaria-HIV co-infection.
The American journal of tropical medicine and hygiene.
2014 Mar; 90(3):530-534. doi:
10.4269/ajtmh.13-0655. [PMID: 24420779] - Linda Björkhem-Bergman, Tobias Bäckström, Hanna Nylén, Yuko Rönquist-Nii, Eva Bredberg, Tommy B Andersson, Leif Bertilsson, Ulf Diczfalusy. Quinine compared to 4β-hydroxycholesterol and midazolam as markers for CYP3A induction by rifampicin.
Drug metabolism and pharmacokinetics.
2014; 29(4):352-5. doi:
10.2133/dmpk.dmpk-13-sh-138. [PMID: 24522201] - Nilufer Rahmioglu, James Heaton, Gail Clement, Raj Gill, Gabriela Surdulescu, Karolina Zlobecka, Dylan Hodgkiss, Norman W Smith, Kourosh R Ahmadi. Genome-wide association study reveals a complex genetic architecture underpinning-induced CYP3A4 enzyme activity.
European journal of drug metabolism and pharmacokinetics.
2013 Mar; 38(1):63-7. doi:
10.1007/s13318-012-0103-z. [PMID: 22945461] - Nilufer Rahmioglu, James Heaton, Gail Clement, Raj Gill, Gabriela Surdulescu, Karolina Zlobecka, Dylan Hodgkiss, Yongmin Ma, Robert C Hider, Norman W Smith, Kourosh R Ahmadi. Genetic epidemiology of induced CYP3A4 activity.
Pharmacogenetics and genomics.
2011 Oct; 21(10):642-51. doi:
10.1097/fpc.0b013e3283498ecf. [PMID: 21750469] - Nilufer Rahmioglu, Gwénaëlle Le Gall, James Heaton, Kristine L Kay, Norman W Smith, Ian J Colquhoun, Kourosh R Ahmadi, E Kate Kemsley. Prediction of variability in CYP3A4 induction using a combined 1H NMR metabonomics and targeted UPLC-MS approach.
Journal of proteome research.
2011 Jun; 10(6):2807-16. doi:
10.1021/pr200077n. [PMID: 21491888] - James Heaton, Nilufer Rahmioglu, Kourosh R Ahmadi, Cristina Legido-Quigley, Norman W Smith. Rapid quantification of quinine and its major metabolite (3S)-3-hydroxyquinine in diluted urine by UPLC-MS/MS.
Journal of pharmaceutical and biomedical analysis.
2011 Jun; 55(3):494-9. doi:
10.1016/j.jpba.2011.02.004. [PMID: 21377309] - Rajaa A Mirghani, Ishraga Elagib, Gehad Elghazali, Urban Hellgren, Lars L Gustafsson. Effects of Plasmodium falciparum infection on the pharmacokinetics of quinine and its metabolites in pregnant and non-pregnant Sudanese women.
European journal of clinical pharmacology.
2010 Dec; 66(12):1229-34. doi:
10.1007/s00228-010-0877-3. [PMID: 20717655] - Jackson K Mukonzo, Paul Waako, Jasper Ogwal-Okeng, Lars L Gustafsson, Eleni Aklillu. Genetic variations in ABCB1 and CYP3A5 as well as sex influence quinine disposition among Ugandans.
Therapeutic drug monitoring.
2010 Jun; 32(3):346-52. doi:
10.1097/ftd.0b013e3181da79d6. [PMID: 20357698] - Julius O Soyinka, Cyprian O Onyeji, Sharon I Omoruyi. Simultaneous liquid chromatographic analysis of ritonavir, quinine and 3-hydroxyquinine in human plasma.
Journal of chromatography. B, Analytical technologies in the biomedical and life sciences.
2009 Feb; 877(4):441-5. doi:
10.1016/j.jchromb.2008.12.045. [PMID: 19147413] - Sompon Wanwimolruk, Keldon Wong, Preeya Wanwimolruk. Variable inhibitory effect of different brands of commercial herbal supplements on human cytochrome P-450 CYP3A4.
Drug metabolism and drug interactions.
2009; 24(1):17-35. doi:
10.1515/dmdi.2009.24.1.17. [PMID: 19353999] - Simon N Muchohi, Gilbert O Kokwaro, Bernhards R Ogutu, Geoffrey Edwards, Steve A Ward, Charles R J C Newton. Pharmacokinetics and clinical efficacy of midazolam in children with severe malaria and convulsions.
British journal of clinical pharmacology.
2008 Oct; 66(4):529-38. doi:
10.1111/j.1365-2125.2008.03239.x. [PMID: 18662297] - I I Abdelrahim, I Adam, G Elghazali, L L Gustafsson, M I Elbashir, R A Mirghani. Pharmacokinetics of quinine and its metabolites in pregnant Sudanese women with uncomplicated Plasmodium falciparum malaria.
Journal of clinical pharmacy and therapeutics.
2007 Feb; 32(1):15-9. doi:
10.1111/j.1365-2710.2007.00788.x. [PMID: 17286785] - Frédéric Lirussi, Eric Pussard. Quinine distribution in pregnant mice with Plasmodium berghei malaria.
European journal of pharmaceutical sciences : official journal of the European Federation for Pharmaceutical Sciences.
2006 Jul; 28(4):284-90. doi:
10.1016/j.ejps.2006.03.004. [PMID: 16716571] - W Ridtitid, M Wongnawa, W Mahatthanatrakul, N Raungsri, M Sunbhanich. Ketoconazole increases plasma concentrations of antimalarial mefloquine in healthy human volunteers.
Journal of clinical pharmacy and therapeutics.
2005 Jun; 30(3):285-90. doi:
10.1111/j.1365-2710.2005.00651.x. [PMID: 15896247] - Tanja Busk Bidstrup, Nicolaj Stilling, Per Damkier, Birgitte Scharling, Mikael Søndergård Thomsen, Kim Brøsen. Rifampicin seems to act as both an inducer and an inhibitor of the metabolism of repaglinide.
European journal of clinical pharmacology.
2004 Apr; 60(2):109-14. doi:
10.1007/s00228-004-0746-z. [PMID: 15034704] - Rajaa A Mirghani, Urban Hellgren, Leif Bertilsson, Lars L Gustafsson, Orjan Ericsson. Metabolism and elimination of quinine in healthy volunteers.
European journal of clinical pharmacology.
2003 Sep; 59(5-6):423-7. doi:
10.1007/s00228-003-0637-8. [PMID: 12920491] - Rajaa A Mirghani, Orjan Ericsson, Gunnel Tybring, Lars L Gustafsson, Leif Bertilsson. Quinine 3-hydroxylation as a biomarker reaction for the activity of CYP3A4 in man.
European journal of clinical pharmacology.
2003 May; 59(1):23-8. doi:
10.1007/s00228-003-0575-5. [PMID: 12743670] - Louise Roy, Pierre Bannon, Jean-Pierre Villeneuve. Quinine pharmacokinetics in chronic haemodialysis patients.
British journal of clinical pharmacology.
2002 Dec; 54(6):604-9. doi:
10.1046/j.1365-2125.2002.01680.x. [PMID: 12492607] - Sompon Wanwimolruk, Mary F Paine, Susan N Pusek, Paul B Watkins. Is quinine a suitable probe to assess the hepatic drug-metabolizing enzyme CYP3A4?.
British journal of clinical pharmacology.
2002 Dec; 54(6):643-51. doi:
10.1046/j.1365-2125.2002.01687.x. [PMID: 12492613] - S Pukrittayakamee, P Pitisuttithum, H Zhang, A Jantra, S Wanwimolruk, N J White. Effects of cigarette smoking on quinine pharmacokinetics in malaria.
European journal of clinical pharmacology.
2002 Aug; 58(5):315-9. doi:
10.1007/s00228-002-0447-4. [PMID: 12185554] - R A Mirghani, O Ericsson, J Cook, P Yu, L L Gustafsson. Simultaneous determination of quinine and four metabolites in plasma and urine by high-performance liquid chromatography.
Journal of chromatography. B, Biomedical sciences and applications.
2001 Apr; 754(1):57-64. doi:
10.1016/s0378-4347(00)00577-6. [PMID: 11318427] - P Damkier, K Brøsen. Quinidine as a probe for CYP3A4 activity: intrasubject variability and lack of correlation with probe-based assays for CYP1A2, CYP2C9, CYP2C19, and CYP2D6.
Clinical pharmacology and therapeutics.
2000 Aug; 68(2):199-209. doi:
10.1067/mcp.2000.108532. [PMID: 10976551] - R E Benton, M Sale, D A Flockhart, R L Woosley. Greater quinidine-induced QTc interval prolongation in women.
Clinical pharmacology and therapeutics.
2000 Apr; 67(4):413-8. doi:
10.1067/mcp.2000.105761. [PMID: 10801251] - R A Mirghani, U Hellgren, P A Westerberg, O Ericsson, L Bertilsson, L L Gustafsson. The roles of cytochrome P450 3A4 and 1A2 in the 3-hydroxylation of quinine in vivo.
Clinical pharmacology and therapeutics.
1999 Nov; 66(5):454-60. doi:
10.1016/s0009-9236(99)70008-1. [PMID: 10579472] - P C Ho, S C Chalcroft, P F Coville, S Wanwimolruk. Grapefruit juice has no effect on quinine pharmacokinetics.
European journal of clinical pharmacology.
1999 Jul; 55(5):393-8. doi:
10.1007/s002280050646. [PMID: 10456490] - P Newton, D Keeratithakul, P Teja-Isavadharm, S Pukrittayakamee, D Kyle, N White. Pharmacokinetics of quinine and 3-hydroxyquinine in severe falciparum malaria with acute renal failure.
Transactions of the Royal Society of Tropical Medicine and Hygiene.
1999 Jan; 93(1):69-72. doi:
10.1016/s0035-9203(99)90184-0. [PMID: 10492795] - R A Mirghani, O Ericsson, L L Gustafsson. High-performance liquid chromatographic method for the determination of the major quinine metabolite, 3-hydroxyquinine, in plasma and urine.
Journal of chromatography. B, Biomedical sciences and applications.
1998 Apr; 708(1-2):209-16. doi:
10.1016/s0378-4347(97)00629-4. [PMID: 9653964] - S Wanwimolruk, S M Wong, H Zhang, P F Coville, R J Walker. Metabolism of quinine in man: identification of a major metabolite, and effects of smoking and rifampicin pretreatment.
The Journal of pharmacy and pharmacology.
1995 Nov; 47(11):957-63. doi:
10.1111/j.2042-7158.1995.tb03277.x. [PMID: 8708992] - F Nielsen, K K Nielsen, K Brøsen. Determination of quinidine, dihydroquinidine, (3S)-3-hydroxyquinidine and quinidine N-oxide in plasma and urine by high-performance liquid chromatography.
Journal of chromatography. B, Biomedical applications.
1994 Oct; 660(1):103-10. doi:
10.1016/0378-4347(94)00259-2. [PMID: 7858702] - C P Babalola, O O Bolaji, P A Dixon, F A Ogunbona. Column liquid chromatographic analysis of quinine in human plasma, saliva and urine.
Journal of chromatography.
1993 Jun; 616(1):151-4. doi:
10.1016/0378-4347(93)80482-j. [PMID: 8376486] - C O Onyeji, P A Dixon, N C Ugwu. Disposition of quinine in rats with induced renal failure.
Pharmaceutisch weekblad. Scientific edition.
1992 Aug; 14(4):185-90. doi:
10.1007/bf01962536. [PMID: 1437497] - G L Hoyer, D C Clawson, L A Brookshier, P E Nolan, F I Marcus. High-performance liquid chromatographic method for the quantitation of quinidine and selected quinidine metabolites.
Journal of chromatography.
1991 Dec; 572(1-2):159-69. doi:
10.1016/0378-4347(91)80480-z. [PMID: 1818051] - O O Bolaji, C P Babalola, P A Dixon. Characterization of the principal metabolite of quinine in human urine by 1H-n.m.r. spectroscopy.
Xenobiotica; the fate of foreign compounds in biological systems.
1991 Apr; 21(4):447-50. doi:
10.3109/00498259109039484. [PMID: 1897244] - R Leroyer, O Varoquaux, C Advenier, M Pays. Quinidine oxidative metabolism. Identification and biosynthesis of quinidine 10,11-dihydrodiol stereoisomers.
Biomedical chromatography : BMC.
1990 Mar; 4(2):61-4. doi:
10.1002/bmc.1130040205. [PMID: 2350599] - K Brøsen, F Davidsen, L F Gram. Quinidine kinetics after a single oral dose in relation to the sparteine oxidation polymorphism in man.
British journal of clinical pharmacology.
1990 Feb; 29(2):248-53. doi:
10.1111/j.1365-2125.1990.tb03628.x. [PMID: 2306418] - B H Ackerman, K M Olsen, E E Kennedy, E H Taylor, B H Chen, D Jordan, D J Ackerman. Disposition of 3-hydroxyquinidine in patients receiving initial intravenous quinidine gluconate for electrophysiology testing of ventricular tachycardia.
DICP : the annals of pharmacotherapy.
1989 May; 23(5):375-8. doi:
10.1177/106002808902300504. [PMID: 2728524] - R A Wooding-Scott, J Smalley, J Visco, R L Slaughter. The pharmacokinetics and pharmacodynamics of quinidine and 3-hydroxyquinidine.
British journal of clinical pharmacology.
1988 Oct; 26(4):415-21. doi:
10.1111/j.1365-2125.1988.tb03400.x. [PMID: 3190991] - A A Killeen, L D Bowers. Fetal supraventricular tachycardia treated with high-dose quinidine: toxicity associated with marked elevation of the metabolite, 3(S)-3-hydroxyquinidine.
Obstetrics and gynecology.
1987 Sep; 70(3 Pt 2):445-9. doi:
NULL. [PMID: 3627599] - D J Edwards, J E Axelson, J P Visco, S vanEvery, R L Slaughter, D Lalka. Lack of effect of smoking on the metabolism and pharmacokinetics of quinidine in patients.
British journal of clinical pharmacology.
1987 Mar; 23(3):351-4. doi:
10.1111/j.1365-2125.1987.tb03057.x. [PMID: 3567051] - S Vozeh, M Bindschedler, H R Ha, G Kaufmann, T W Guentert, F Follath. Pharmacodynamics of 3-hydroxyquinidine alone and in combination with quinidine in healthy persons.
The American journal of cardiology.
1987 Mar; 59(6):681-4. doi:
10.1016/0002-9149(87)91192-1. [PMID: 3825912] - S Vozeh, T Uematsu, T W Guentert, H R Ha, F Follath. Kinetics and electrocardiographic changes after oral 3-OH-quinidine in healthy subjects.
Clinical pharmacology and therapeutics.
1985 May; 37(5):575-81. doi:
10.1038/clpt.1985.90. [PMID: 3987181] - R Camsonne, M A Moulin, P Charbonneau, C Bazin. Elimination kinetic of high polar metabolites pool of quinidine from human serum.
International journal of clinical pharmacology, therapy, and toxicology.
1985 Feb; 23(2):74-5. doi:
NULL. [PMID: 3988396] - R Leroyer, C Jarreau, M Pays, O Varoquaux, C Advenier. Reverse-phase liquid chromatography and pharmacokinetic study of two hydroxylated analogues of quinidine in dogs.
Journal of pharmaceutical sciences.
1984 Jun; 73(6):844-6. doi:
10.1002/jps.2600730640. [PMID: 6547483] - R Leroyer, C Jarreau, M Pays. [Quinidine and enzyme induction. Erroneous interpretation of the plasma levels of 3-hydroxyquinidine and O-demethylquinidine].
Therapie.
1984 Jan; 39(1):57-9. doi:
NULL. [PMID: 6463946] - J M St-Onge, G Sirois, M A Gagnon. Urinary excretion kinetics of intact quinidine and 3-OH-quinidine after oral administration of a single oral dose of quinidine gluconate in the fasting and non-fasting state.
European journal of drug metabolism and pharmacokinetics.
1983 Oct; 8(4):363-72. doi:
10.1007/bf03188768. [PMID: 6673973] - J M Juliard, J Heckle, P Jaillon, J M Poirier, J P Aubry, G Cheymol, F X Jarreau. [Comparison of the cardiac electrophysiologic effects of quinidine, 3-hydroxyquinidine and 3-hydroxyhydroquinidine in the anesthesized dog. Study of plasma dose response relations].
Archives des maladies du coeur et des vaisseaux.
1983 Jun; 76(6):670-8. doi:
NULL. [PMID: 6414408] - R Camsonne, M A Moulin, J P Ryckelynck, P Mignot, F Albessard, M Perault, M C Bigot, O Richard. [Chronic renal insufficiency. Elevated levels of the active metabolite (3-hydroxyquinidine) of quinidine].
La Nouvelle presse medicale.
1982 Oct; 11(41):3062-3. doi:
NULL. [PMID: 7145692] - C Liddle, G G Graham, R K Christopher, S Bhuwapathanapun, A M Duffield. Identification of new urinary metabolites in man of quinine using methane chemical ionization gas chromatography-mass spectrometry.
Xenobiotica; the fate of foreign compounds in biological systems.
1981 Feb; 11(2):81-7. doi:
10.3109/00498258109045277. [PMID: 7233970] - P A Reece, M Peikert. Simple and selective high-performance liquid chromatographic method for estimating plasma quinidine levels.
Journal of chromatography.
1980 Feb; 181(2):207-17. doi:
10.1016/s0378-4347(00)81606-0. [PMID: 7372754]