Mechlorethamine (BioDeep_00000006426)

human metabolite blood metabolite Chemicals and Drugs Volatile Flavor Compounds

代谢物信息卡片

Merck frosst brand OF mechlorethamine hydrochloride

化学式: C5H11Cl2N (155.02685060000002)
中文名称: 氮芥
谱图信息: 最多检出来源 Danio rerio(blood) 19.59%

分子结构信息

SMILES: CN(CCCl)CCCl
InChI: InChI=1S/C5H11Cl2N/c1-8(4-2-6)5-3-7/h2-5H2,1H3

描述信息

Mechlorethamine is only found in individuals that have used or taken this drug. It is a vesicant and necrotizing irritant destructive to mucous membranes. It was formerly used as a war gas. The hydrochloride is used as an antineoplastic in Hodgkins disease and lymphomas. It causes severe gastrointestinal and bone marrow damage. [PubChem]Alkylating agents work by three different mechanisms: 1) attachment of alkyl groups to DNA bases, resulting in the DNA being fragmented by repair enzymes in their attempts to replace the alkylated bases, preventing DNA synthesis and RNA transcription from the affected DNA, 2) DNA damage via the formation of cross-links (bonds between atoms in the DNA) which prevents DNA from being separated for synthesis or transcription, and 3) the induction of mispairing of the nucleotides leading to mutations. Mechlorethamine is cell cycle phase-nonspecific.
L - Antineoplastic and immunomodulating agents > L01 - Antineoplastic agents > L01A - Alkylating agents > L01AA - Nitrogen mustard analogues
D000970 - Antineoplastic Agents > D018906 - Antineoplastic Agents, Alkylating > D009588 - Nitrogen Mustard Compounds
C274 - Antineoplastic Agent > C186664 - Cytotoxic Chemotherapeutic Agent > C2842 - DNA Binding Agent
D009676 - Noxae > D011042 - Poisons > D002619 - Chemical Warfare Agents
D009676 - Noxae > D000477 - Alkylating Agents
D009676 - Noxae > D007509 - Irritants

同义名列表

52 个代谢物同义名

Merck frosst brand OF mechlorethamine hydrochloride; Merck brand OF mechlorethamine hydrochloride; beta,Beta-dichlorodiethyl-N-methylamine; Hydrochloride N-oxide, mechlorethamine; N-Oxide, mechlorethamine hydrochloride; Mechlorethamine hydrochloride N oxide; Mechlorethamine hydrochloride N-oxide; b,Beta-dichlorodiethyl-N-methylamine; Β,beta-dichlorodiethyl-N-methylamine; N-Methyl-bis(beta-chloroethyl)amine; 2,2-Dichloro-N-methyldiethylamine; N-Methyl-bis(b-chloroethyl)amine; Methylbis(beta-chloroethyl)amine; N-Methyl-bis(2-chloroethyl)amine; Bis(beta-chloroethyl)methylamine; N-Methyl-bis(β-chloroethyl)amine; bis(2-chloroethyl)(methyl)amine; Hydrochloride, mechlorethamine; Methylbis(b-chloroethyl)amine; Bis(2-chloroethyl)methylamine; Methylbis(β-chloroethyl)amine; Mechlorethamine hydrochloride; Bis(β-chloroethyl)methylamine; Bis(b-chloroethyl)methylamine; Methylbis(2-chloroethyl)amine; N-Oxide, nitrogen mustard; Nitrogen mustard N-oxide; Nitrogen mustard N oxide; Mechlorethamine N-oxide; Mechlorethamine N oxide; Mechlorethamine oxide; Methylchlorethamine; Mechloroethamine; Nitrogen mustard; Nitrogranulogen; mechlorethamine; Chlorethazine; Mecloretamina; Chlormethine; Caryolysine; Mustargen; Nitromin; Cloramin; Embichin; NSC-762; Mustine; Mitomen; NSC 762; HN2; MBA; Nitrogen mustard; Mechlorethamine

数据库引用编号

17 个数据库交叉引用编号

ChEBI: CHEBI:28925
KEGG: C07115
KEGGdrug: D07671
PubChem: 4033
HMDB: HMDB0015025
Metlin: METLIN43236
DrugBank: DB00888
ChEMBL: CHEMBL427
Wikipedia: Mechlorethamine
MeSH: Mechlorethamine
chemspider: 3893
CAS: 51-75-2
PMhub: MS000019463
PubChem: 9326
NIKKAJI: J2.305A
RefMet: Mechlorethamine
KNApSAcK: 28925

分类词条

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

9606 - Homo sapiens: -

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

Haichang Li, Zhongguang Li, Xiuchun Li, Chuanxi Cai, Serena Li Zhao, Robert E Merritt, Xinyu Zhou, Tao Tan, Valerie Bergdall, Jianjie Ma. MG53 Mitigates Nitrogen Mustard-Induced Skin Injury. Cells. 2023 07; 12(14):. doi: 10.3390/cells12141915. [PMID: 37508578]
Jaclynn A Meshanni, Jordan M Lee, Kinal N Vayas, Rachel Sun, Chenghui Jiang, Grace L Guo, Andrew J Gow, Jeffrey D Laskin, Debra L Laskin. Suppression of lung oxidative stress, inflammation and fibrosis following nitrogen mustard exposure by the selective farnesoid X receptor agonist obeticholic acid. The Journal of pharmacology and experimental therapeutics. 2023 May; ?(?):. doi: 10.1124/jpet.123.001557. [PMID: 37188530]
Alexa Murray, Tanvi Banota, Grace L Guo, Ley Cody Smith, Jaclynn A Meshanni, Jordan Lee, Bo Kong, Elena V Abramova, Michael Goedken, Andrew J Gow, Jeffrey D Laskin, Debra L Laskin. Farnesoid X receptor regulates lung macrophage activation and injury following nitrogen mustard exposure. Toxicology and applied pharmacology. 2022 11; 454(?):116208. doi: 10.1016/j.taap.2022.116208. [PMID: 35998709]
Benediktus N Hapsianto, Naoshi Kojima, Ryoji Kurita, Hitoshi Yamagata, Hiroyuki Fujita, Teruo Fujii, Soo Hyeon Kim. Direct Capture and Amplification of Small Fragmented DNAs Using Nitrogen-Mustard-Coated Microbeads. Analytical chemistry. 2022 05; 94(21):7594-7600. doi: 10.1021/acs.analchem.2c00531. [PMID: 35578745]
Angela Cruz-Hernandez, Ryan P Mendoza, Kathleen Nguyen, Anna Harder, Christopher M Evans, Alison K Bauer, Neera Tewari-Singh, Jared M Brown. Mast Cells Promote Nitrogen Mustard-Mediated Toxicity in the Lung Associated With Proinflammatory Cytokine and Bioactive Lipid Mediator Production. Toxicological sciences : an official journal of the Society of Toxicology. 2021 10; 184(1):127-141. doi: 10.1093/toxsci/kfab107. [PMID: 34453837]
Andrea DeSantis-Rodrigues, Rita A Hahn, Peihong Zhou, Michael Babin, Kathy K H Svoboda, Yoke-Chen Chang, Donald R Gerecke, Marion K Gordon. SM1997 downregulates mustard-induced enzymes that disrupt corneal epithelial attachment. Anatomical record (Hoboken, N.J. : 2007). 2021 09; 304(9):1974-1983. doi: 10.1002/ar.24597. [PMID: 33554453]
Alessandro Venosa, L Cody Smith, Andrew J Gow, Helmut Zarbl, Jeffrey D Laskin, Debra L Laskin. Macrophage activation in the lung during the progression of nitrogen mustard induced injury is associated with histone modifications and altered miRNA expression. Toxicology and applied pharmacology. 2021 07; 423(?):115569. doi: 10.1016/j.taap.2021.115569. [PMID: 33971176]
Mark J Henderson, Kathleen A Trychta, Shyh-Ming Yang, Susanne Bäck, Adam Yasgar, Emily S Wires, Carina Danchik, Xiaokang Yan, Hideaki Yano, Lei Shi, Kuo-Jen Wu, Amy Q Wang, Dingyin Tao, Gergely Zahoránszky-Kőhalmi, Xin Hu, Xin Xu, David Maloney, Alexey V Zakharov, Ganesha Rai, Fumihiko Urano, Mikko Airavaara, Oksana Gavrilova, Ajit Jadhav, Yun Wang, Anton Simeonov, Brandon K Harvey. A target-agnostic screen identifies approved drugs to stabilize the endoplasmic reticulum-resident proteome. Cell reports. 2021 04; 35(4):109040. doi: 10.1016/j.celrep.2021.109040. [PMID: 33910017]
Haley Clark, Barbara Pereira Vera, Zijing Zhang, Lynae M Brayboy. MDR-1 function protects oocyte mitochondria against the transgenerational effects of nitrogen mustard exposure. Reproductive toxicology (Elmsford, N.Y.). 2020 12; 98(?):252-259. doi: 10.1016/j.reprotox.2020.10.010. [PMID: 33164761]
Buddhadeb Chandra, Kanchan Sinha Roy, Mahabul Shaik, Chandrakant Waghmare, RamaRao Golime, Meehir Palit. Gas chromatography-tandem mass spectrometry-based detection of half nitrogen mustards in plasma as a new biomarker of nitrogen mustard exposure. Analytical methods : advancing methods and applications. 2020 09; 12(36):4447-4456. doi: 10.1039/d0ay00916d. [PMID: 32856667]
Mai Otsuka, Hajime Miyaguchi, Masanobu Uchiyama. Analysis of nitrogen mustard degradation products via post-pentafluorobenzoylation liquid chromatography-tandem mass spectrometry. Journal of chromatography. A. 2020 Aug; 1625(?):461306. doi: 10.1016/j.chroma.2020.461306. [PMID: 32709349]
Yi-Hua Jan, Diane E Heck, Debra L Laskin, Jeffrey D Laskin. DNA damage signaling in the cellular responses to mustard vesicants. Toxicology letters. 2020 Jun; 326(?):78-82. doi: 10.1016/j.toxlet.2020.03.008. [PMID: 32173488]
Buddhadeb Chandra, Kanchan Sinha Roy, Mahabul Shaik, Chandrakant Waghmare, Meehir Palit. Mass spectral studies of silyl derivatives of partially hydrolyzed products of nitrogen mustards: Important markers of nitrogen mustard exposure. Rapid communications in mass spectrometry : RCM. 2020 Feb; 34(3):e8586. doi: 10.1002/rcm.8586. [PMID: 31509283]
Yulia Kaluzhny, Miriam W Kinuthia, Allison M Lapointe, Thoa Truong, Mitchell Klausner, Patrick Hayden. Oxidative stress in corneal injuries of different origin: Utilization of 3D human corneal epithelial tissue model. Experimental eye research. 2020 01; 190(?):107867. doi: 10.1016/j.exer.2019.107867. [PMID: 31705899]
Alessandro Venosa, Ley Cody Smith, Alexa Murray, Tanvi Banota, Andrew J Gow, Jeffrey D Laskin, Debra L Laskin. Regulation of Macrophage Foam Cell Formation During Nitrogen Mustard (NM)-Induced Pulmonary Fibrosis by Lung Lipids. Toxicological sciences : an official journal of the Society of Toxicology. 2019 12; 172(2):344-358. doi: 10.1093/toxsci/kfz187. [PMID: 31428777]
Tobie D Lee, Olivia W Lee, Kyle R Brimacombe, Lu Chen, Rajarshi Guha, Sabrina Lusvarghi, Bethilehem G Tebase, Carleen Klumpp-Thomas, Robert W Robey, Suresh V Ambudkar, Min Shen, Michael M Gottesman, Matthew D Hall. A High-Throughput Screen of a Library of Therapeutics Identifies Cytotoxic Substrates of P-glycoprotein. Molecular pharmacology. 2019 11; 96(5):629-640. doi: 10.1124/mol.119.115964. [PMID: 31515284]
Mai Otsuka, Hajime Miyaguchi, Masanobu Uchiyama. Analysis of degradation products of nitrogen mustards via hydrophilic interaction liquid chromatography-tandem mass spectrometry. Journal of chromatography. A. 2019 Sep; 1602(?):199-205. doi: 10.1016/j.chroma.2019.05.015. [PMID: 31109745]
Georgia Charkoftaki, James V Jester, David C Thompson, Vasilis Vasiliou. Nitrogen mustard-induced corneal injury involves the sphingomyelin-ceramide pathway. The ocular surface. 2018 01; 16(1):154-162. doi: 10.1016/j.jtos.2017.11.004. [PMID: 29129753]
Yuan Yang, Li Zhao, Li Xiao, Yumei Liang, Chang Wang, Xiao Fu, Xuejing Zhu, Shuguang Yuan, Jianling Zhu, Xiaoping Zhu, Yinghong Liu, Jun Li, Jian Luo, Fuyou Liu, Lin Sun. Chlormethine Hydrochloride is Not Inferior to Tacrolimus in Treating Steroid-Resistant Nephrotic Syndrome. Kidney & blood pressure research. 2018; 43(1):68-79. doi: 10.1159/000486911. [PMID: 29402844]
Irene Ojini, Alison Gammie. Rapid Identification of Chemoresistance Mechanisms Using Yeast DNA Mismatch Repair Mutants. G3 (Bethesda, Md.). 2015 Jul; 5(9):1925-35. doi: 10.1534/g3.115.020560. [PMID: 26199284]
Dileep Kumar, Neera Tewari-Singh, Chapla Agarwal, Anil K Jain, Swetha Inturi, Rama Kant, Carl W White, Rajesh Agarwal. Nitrogen mustard exposure of murine skin induces DNA damage, oxidative stress and activation of MAPK/Akt-AP1 pathway leading to induction of inflammatory and proteolytic mediators. Toxicology letters. 2015 Jun; 235(3):161-71. doi: 10.1016/j.toxlet.2015.04.006. [PMID: 25891025]
Dinesh G Goswami, Dileep Kumar, Neera Tewari-Singh, David J Orlicky, Anil K Jain, Rama Kant, Raymond C Rancourt, Deepanshi Dhar, Swetha Inturi, Chapla Agarwal, Carl W White, Rajesh Agarwal. Topical nitrogen mustard exposure causes systemic toxic effects in mice. Experimental and toxicologic pathology : official journal of the Gesellschaft fur Toxikologische Pathologie. 2015 Feb; 67(2):161-70. doi: 10.1016/j.etp.2014.11.006. [PMID: 25481215]
Maria A Pino, Magdalena Pietka-Ottlik, Blase Billack. Selected ebselen analogs reduce mechlorethamine toxicity in vitro. Cutaneous and ocular toxicology. 2014 Mar; 33(1):32-41. doi: 10.3109/15569527.2013.794818. [PMID: 23734969]
Erlong Zhang, Shenglin Luo, Xu Tan, Chunmeng Shi. Mechanistic study of IR-780 dye as a potential tumor targeting and drug delivery agent. Biomaterials. 2014 Jan; 35(2):771-8. doi: 10.1016/j.biomaterials.2013.10.033. [PMID: 24148240]
Ruijin Zheng, Iris Po, Vladimir Mishin, Adrienne T Black, Diane E Heck, Debra L Laskin, Patrick J Sinko, Donald R Gerecke, Marion K Gordon, Jeffrey D Laskin. The generation of 4-hydroxynonenal, an electrophilic lipid peroxidation end product, in rabbit cornea organ cultures treated with UVB light and nitrogen mustard. Toxicology and applied pharmacology. 2013 Oct; 272(2):345-55. doi: 10.1016/j.taap.2013.06.025. [PMID: 23845594]
Jennifer A Kanakry, Hailun Li, Lan L Gellert, M Victor Lemas, Wen-son Hsieh, Fangxin Hong, King L Tan, Randy D Gascoyne, Leo I Gordon, Richard I Fisher, Nancy L Bartlett, Patrick Stiff, Bruce D Cheson, Ranjana Advani, Thomas P Miller, Brad S Kahl, Sandra J Horning, Richard F Ambinder. Plasma Epstein-Barr virus DNA predicts outcome in advanced Hodgkin lymphoma: correlative analysis from a large North American cooperative group trial. Blood. 2013 May; 121(18):3547-53. doi: 10.1182/blood-2012-09-454694. [PMID: 23386127]
Anne-Charlotte Dubbelman, Robert S Jansen, Hilde Rosing, Mona Darwish, Edward Hellriegel, Philmore Robertson, Jan H M Schellens, Jos H Beijnen. Metabolite profiling of bendamustine in urine of cancer patients after administration of [14C]bendamustine. Drug metabolism and disposition: the biological fate of chemicals. 2012 Jul; 40(7):1297-307. doi: 10.1124/dmd.112.045229. [PMID: 22492615]
Zeki Ilker Kunak, Enis Macit, Hakan Yaren, Halil Yaman, Erdinc Cakir, Ibrahim Aydin, Turker Turker, Yasemin Gulcan Kurt, Ayhan Ozcan, Bulent Uysal, Salim Isbilir, Emin Ozgur Akgul, Tuncer Cayci, Ahmet Korkmaz, Levent Kenar. Protective effects of melatonin and S-methylisothiourea on mechlorethamine induced nephrotoxicity. The Journal of surgical research. 2012 Jun; 175(1):e17-23. doi: 10.1016/j.jss.2011.11.002. [PMID: 22261582]
Colleen M O'Connor, Sabina Sheppard, Cassie A Hartline, Helen Huls, Mark Johnson, Shana L Palla, Sourindra Maiti, Wencai Ma, R Eric Davis, Suzanne Craig, Dean A Lee, Richard Champlin, Heather Wilson, Laurence J N Cooper. Adoptive T-cell therapy improves treatment of canine non-Hodgkin lymphoma post chemotherapy. Scientific reports. 2012; 2(?):249. doi: 10.1038/srep00249. [PMID: 22355761]
Muntha K Reddy, Grier Mills, Christopher Nixon, Shane A Wyatt, Timothy R Croley. High-throughput sample preparation and simultaneous column regeneration liquid chromatography-tandem mass spectrometry method for determination of nitrogen mustard metabolites in human urine. Journal of chromatography. B, Analytical technologies in the biomedical and life sciences. 2011 Aug; 879(24):2383-8. doi: 10.1016/j.jchromb.2011.06.029. [PMID: 21764395]
Yasuto Kido, Pär Matsson, Kathleen M Giacomini. Profiling of a prescription drug library for potential renal drug-drug interactions mediated by the organic cation transporter 2. Journal of medicinal chemistry. 2011 Jul; 54(13):4548-58. doi: 10.1021/jm2001629. [PMID: 21599003]
Levent Kenar, Orkun Alp. Determination of nitrogen mustard hydrolysis products in rat urine samples using GC-MS. Journal of chromatographic science. 2011 May; 49(5):361-4. doi: 10.1093/chromsci/49.5.361. [PMID: 21549026]
Lisa Schulmeister. Extravasation management: clinical update. Seminars in oncology nursing. 2011 Feb; 27(1):82-90. doi: 10.1016/j.soncn.2010.11.010. [PMID: 21255716]
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De-Ying Zhang, Da-Wei He, Guang-Hui Wei, Xing Liu, Tao Lin, Xu-Liang Li. [Phyllanthus urinaria extract promotes N-cadherin expression in nitrogen mustard-disrupted testicular tissues in vivo]. Zhonghua nan ke xue = National journal of andrology. 2008 May; 14(5):396-400. doi: ". [PMID: 18572855]
Maria A Pino, Blase Billack. Reduction of vesicant toxicity by butylated hydroxyanisole in A-431 skin cells. Cutaneous and ocular toxicology. 2008; 27(3):161-72. doi: 10.1080/15569520802092070. [PMID: 18988086]
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Emmanuel Laffitte, Jean-Pierre Venetz, John-David Aubert, Michel A Duchosal, Renato G Panizzon, Manuel Pascual. Mycosis fungoides in a lung transplant recipient with advanced ciclosporin nephropathy: management with mechlorethamine and subsequent renal transplantation. Dermatology (Basel, Switzerland). 2008; 217(1):87-8. doi: 10.1159/000128283. [PMID: 18446031]
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