3-Hydroxyquinine (BioDeep_00000006479)

 

Secondary id: BioDeep_00001870233

human metabolite Endogenous blood metabolite natural product


代谢物信息卡片


(3S,4R,6S)-3-ethenyl-6-[(R)-hydroxy(6-methoxyquinolin-4-yl)methyl]-1-azabicyclo[2.2.2]octan-3-ol

化学式: C20H24N2O3 (340.17868339999995)
中文名称:
谱图信息: 最多检出来源 Homo sapiens(blood) 0.35%

分子结构信息

SMILES: C=CC1(O)CN2CCC1CC2C(O)c1ccnc2ccc(OC)cc12
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

描述信息

3-Hydroxyquinine is a major metabolite of quinine. The formation of 3-hydroxyquinine is catalysed by cytochrome P450 3A4. [HMDB]
3-Hydroxyquinine is a major metabolite of quinine. The formation of 3-hydroxyquinine is catalysed by cytochrome P450 3A4.

同义名列表

8 个代谢物同义名

(3S,4R,6S)-3-ethenyl-6-[(R)-hydroxy(6-methoxyquinolin-4-yl)methyl]-1-azabicyclo[2.2.2]octan-3-ol; 3-Hydroxyquinidine, (8alpha,9R)-isomer; 3-Hydroxyquinidine, (3alpha,9S)-isomer; 6-Methoxycinchonan-3,9-diol; (3R)-Hydroxyquinidine; 3-Hydroxyquinidine; 3-Hydroxyquinine; 3-Hydroxyquinine



数据库引用编号

18 个数据库交叉引用编号

分类词条

相关代谢途径

Reactome(0)

BioCyc(0)

PlantCyc(0)

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)

9 个相关的物种来源信息

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]
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  • 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]
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  • 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]
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  • 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]
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  • 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]
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  • 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]
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