Alpha-hydroxyalprazolam (BioDeep_00000018243)

   

human metabolite Endogenous blood metabolite


代谢物信息卡片


{12-chloro-9-phenyl-2,4,5,8-tetraazatricyclo[8.4.0.0²,⁶]tetradeca-1(10),3,5,8,11,13-hexaen-3-yl}methanol

化学式: C17H13ClN4O (324.0778)
中文名称: Alpha-羟基阿普唑仑
谱图信息: 最多检出来源 Homo sapiens(blood) 43.18%

分子结构信息

SMILES: C1C2=NN=C(N2C3=C(C=C(C=C3)Cl)C(=N1)C4=CC=CC=C4)CO
InChI: InChI=1S/C17H13ClN4O/c18-12-6-7-14-13(8-12)17(11-4-2-1-3-5-11)19-9-15-20-21-16(10-23)22(14)15/h1-8,23H,9-10H2

描述信息

Alpha-hydroxyalprazolam is a metabolite of both alprazolam and adinazolam. Alprazolam (trade name Xanax, available among other generic names) is a short-acting anxiolytic of the benzodiazepine class of psychoactive drugs. Alprazolam, like other benzodiazepines, binds to specific sites on the GABAA gamma-amino-butyric acid receptor. Adinazolam (marketed under the brand name Deracyn) is a benzodiazepine derivative. It possesses anxiolytic, anticonvulsant, sedative, and antidepressant properties. Adinazolam was developed by Dr. Jackson B. Hester, who was seeking to enhance the antidepressant properties of alprazolam, which he also developed. (Wikipedia) Alpha-hydroxyalprazolam belongs to the family of Benzodiazepines. These are organic compounds containing a benzene ring fused to either isomers of diazepine(unsaturated seven-member heterocycle with two nitrogen atoms replacing two carbon atoms).

同义名列表

4 个代谢物同义名

{12-chloro-9-phenyl-2,4,5,8-tetraazatricyclo[8.4.0.0²,⁶]tetradeca-1(10),3,5,8,11,13-hexaen-3-yl}methanol; alpha-Hydroxyalprazolam; Α-hydroxyalprazolam; a-Hydroxyalprazolam



数据库引用编号

7 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)

1 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。

亚细胞结构定位 关联基因列表


文献列表

  • Szabolcs Sofalvi, Eric S Lavins, Claire K Kaspar, Haley M Michel, Christie L Mitchell-Mata, Marilyn A Huestis, Luigino G Apollonio. Development and Validation of an LC-MS-MS Method for the Detection of 40 Benzodiazepines and Three Z-Drugs in Blood and Urine by Solid-Phase Extraction. Journal of analytical toxicology. 2020 Oct; 44(7):708-717. doi: 10.1093/jat/bkaa072. [PMID: 32808043]
  • Yu-Dong Jeong, Min Kyung Kim, Sung Ill Suh, Moon Kyo In, Jin Young Kim, Ki-Jung Paeng. Rapid determination of benzodiazepines, zolpidem and their metabolites in urine using direct injection liquid chromatography-tandem mass spectrometry. Forensic science international. 2015 Dec; 257(?):84-92. doi: 10.1016/j.forsciint.2015.07.043. [PMID: 26282513]
  • D M Wong, J L Davis, C J Alcott, K L Hepworth-Warren, N L Galow-Kersh, S Rice, J F Coetzee. Pharmacokinetics and physiologic effects of alprazolam after a single oral dose in healthy mares. Journal of veterinary pharmacology and therapeutics. 2015 Jun; 38(3):301-4. doi: 10.1111/jvp.12192. [PMID: 25427652]
  • Elisabetta Bertol, Francesco Mari, Rafael Boscolo Berto, Guido Mannaioni, Fabio Vaiano, Donata Favretto. A mixed MDPV and benzodiazepine intoxication in a chronic drug abuser: determination of MDPV metabolites by LC-HRMS and discussion of the case. Forensic science international. 2014 Oct; 243(?):149-55. doi: 10.1016/j.forsciint.2014.08.002. [PMID: 25199615]
  • Eleni Kalogria, Constantinos Pistos, Irene Panderi. Hydrophilic interaction liquid chromatography/positive ion electrospray ionization mass spectrometry method for the quantification of alprazolam and α-hydroxy-alprazolam in human plasma. Journal of chromatography. B, Analytical technologies in the biomedical and life sciences. 2013 Dec; 942-943(?):158-64. doi: 10.1016/j.jchromb.2013.10.040. [PMID: 24269910]
  • Hadi Molanaei, Peter Stenvinkel, Abdul Rashid Qureshi, Juan Jesús Carrero, Olof Heimbürger, Bengt Lindholm, Ulf Diczfalusy, Ingegerd Odar-Cederlöf, Leif Bertilsson. Metabolism of alprazolam (a marker of CYP3A4) in hemodialysis patients with persistent inflammation. European journal of clinical pharmacology. 2012 May; 68(5):571-7. doi: 10.1007/s00228-011-1163-8. [PMID: 22159869]
  • Stephanie J Marin, Gwendolyn A McMillin. LC-MS/MS analysis of 13 benzodiazepines and metabolites in urine, serum, plasma, and meconium. Methods in molecular biology (Clifton, N.J.). 2010; 603(?):89-105. doi: 10.1007/978-1-60761-459-3_9. [PMID: 20077062]
  • Bruce A Goldberger, Chris W Chronister, Michele L Merves. Quantitation of benzodiazepines in blood and urine using gas chromatography-mass spectrometry (GC-MS). Methods in molecular biology (Clifton, N.J.). 2010; 603(?):75-87. doi: 10.1007/978-1-60761-459-3_8. [PMID: 20077061]
  • Agneta Wennerholm, Annika Allqvist, Jan-Olof Svensson, Lars L Gustafsson, Rajaa A Mirghani, Leif Bertilsson. Alprazolam as a probe for CYP3A using a single blood sample: pharmacokinetics of parent drug, and of alpha- and 4-hydroxy metabolites in healthy subjects. European journal of clinical pharmacology. 2005 Apr; 61(2):113-8. doi: 10.1007/s00228-004-0861-x. [PMID: 15806426]
  • Annika Allqvist, Agneta Wennerholm, Jan-Olof Svensson, Rajaa A Mirghani. Simultaneous quantification of alprazolam, 4- and alpha-hydroxyalprazolam in plasma samples using liquid chromatography mass spectrometry. Journal of chromatography. B, Analytical technologies in the biomedical and life sciences. 2005 Jan; 814(1):127-31. doi: 10.1016/j.jchromb.2004.10.012. [PMID: 15607716]
  • Zhaolin Jiang, Yu Zhu, Jiayi Tan, Limei Xing, Lijuan Yao, Qing Zhang, Guoying Tao. [Determination of alpha-hydroxytrizolam and alpha hydroxyaplrazolam from urine by acetylation derivatization using gas chromatography electron capture detection]. Se pu = Chinese journal of chromatography. 2004 Nov; 22(6):664. doi: NULL. [PMID: 15807132]
  • D J Crouch, D E Rollins, D V Canfield, D M Andrenyak, J E Schulties. Quantitation of alprazolam and alpha-hydroxyalprazolam in human plasma using liquid chromatography electrospray ionization MS-MS. Journal of analytical toxicology. 1999 Oct; 23(6):479-85. doi: 10.1093/jat/23.6.479. [PMID: 10517554]
  • A J Jenkins, B Levine, J L Locke, J E Smialek. A fatality due to alprazolam intoxication. Journal of analytical toxicology. 1997 May; 21(3):218-20. doi: 10.1093/jat/21.3.218. [PMID: 9171206]
  • K M Höld, D J Crouch, D E Rollins, D G Wilkins, D V Canfield, R A Maes. Determination of alprazolam and alpha-hydroxyalprazolam in human plasma by gas chromatography/negative-ion chemical ionization mass spectrometry. Journal of mass spectrometry : JMS. 1996 Sep; 31(9):1033-8. doi: 10.1002/(sici)1096-9888(199609)31:9<1033::aid-jms391>3.0.co;2-h. [PMID: 8831153]
  • A D Fraser, A F Isner, W Bryan. Urinary screening for adinazolam and its major metabolites by the Emit d.a.u. and FPIA benzodiazepine assays with confirmation by HPLC. Journal of analytical toxicology. 1993 Nov; 17(7):427-31. doi: 10.1093/jat/17.7.427. [PMID: 8309217]
  • P H Dickson, W Markus, J McKernan, H C Nipper. Urinalysis of alpha-hydroxyalprazolam, alpha-hydroxytriazolam, and other benzodiazepine compounds by GC/EIMS. Journal of analytical toxicology. 1992 Mar; 16(2):67-71. doi: 10.1093/jat/16.2.67. [PMID: 1501466]
  • V D Schmith, B Piraino, R B Smith, P D Kroboth. Alprazolam in end-stage renal disease: I. Pharmacokinetics. Journal of clinical pharmacology. 1991 Jun; 31(6):571-9. doi: 10.1002/j.1552-4604.1991.tb03740.x. [PMID: 1880224]
  • R L Miller, C L DeVane. Alprazolam, alpha-hydroxy- and 4-hydroxyalprazolam analysis in plasma by high-performance liquid chromatography. Journal of chromatography. 1988 Aug; 430(1):180-6. doi: 10.1016/s0378-4347(00)83150-3. [PMID: 3215955]