Cycloserine (BioDeep_00000014653)

 

Secondary id: BioDeep_00000407608

human metabolite blood metabolite Chemicals and Drugs Antibiotics Volatile Flavor Compounds natural product


代谢物信息卡片


(4R)-4-amino-1,2-oxazolidin-3-one

化学式: C3H6N2O2 (102.04292559999999)
中文名称: 环丝氨酸, D-环丝氨酸
谱图信息: 最多检出来源 Homo sapiens(blood) 12.16%

分子结构信息

SMILES: C1C(C(=O)NO1)N
InChI: InChI=1S/C3H6N2O2/c4-2-1-7-5-3(2)6/h2H,1,4H2,(H,5,6)/t2-/m1/s1

描述信息

Cycloserine is only found in individuals that have used or taken this drug. It is an antibiotic substance produced by Streptomyces garyphalus. [PubChem]Cycloserine is an analog of the amino acid D-alanine. It interferes with an early step in bacterial cell wall synthesis in the cytoplasm by competitive inhibition of two enzymes, L-alanine racemase, which forms D-alanine from L-alanine, and D-alanylalanine synthetase, which incorporates D-alanine into the pentapeptide necessary for peptidoglycan formation and bacterial cell wall synthesis.
J - Antiinfectives for systemic use > J04 - Antimycobacterials > J04A - Drugs for treatment of tuberculosis > J04AB - Antibiotics
D000890 - Anti-Infective Agents > D000900 - Anti-Bacterial Agents > D000995 - Antitubercular Agents
C254 - Anti-Infective Agent > C52588 - Antibacterial Agent > C280 - Antitubercular Agent
D000890 - Anti-Infective Agents > D023303 - Oxazolidinones
D009676 - Noxae > D000963 - Antimetabolites
D-Cycloserine is an antibiotic which targets sequential bacterial cell wall peptidoglycan biosynthesis enzymes. D-Cycloserine is a partial NMDA agonist that can improve cognitive functions. D-Cycloserine can be used for multidrug-resistant tuberculosis research[1][2].
D-Cycloserine is an antibiotic which targets sequential bacterial cell wall peptidoglycan biosynthesis enzymes. D-Cycloserine is a partial NMDA agonist that can improve cognitive functions. D-Cycloserine can be used for multidrug-resistant tuberculosis research[1][2].

同义名列表

32 个代谢物同义名

(4R)-4-amino-1,2-oxazolidin-3-one; (R)-4-AMINO-isoxazolidin-3-one; (+)-4-Amino-3-isoxazolidinone; D-4-Amino-3-isoxazolidinone; R-4-Amino-3-isoxazolidinone; D-Cycloserine synth. BP 88; D-4-Amino-3-isoxazolidone; D-Cycloserine, synthetic; alpha-Cycloserine; D-(+)-Cycloserine; (+)-Cycloserine; Cyclo-D-serine; DL-Cycloserine; D-Cycloserine; a-Cycloserine; Α-cycloserine; ABBR DCS; L-Cycloserine; Orientomycin; Cycloserinum; D-Oxamicina; Cycloserine; Cicloserina; D-Oxamycin; Ro-1-9213; Seromycin; PA-94; PA 94; D-CS; DCS; Cycloserine; Cycloserine



数据库引用编号

20 个数据库交叉引用编号

分类词条

相关代谢途径

Reactome(0)

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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)

22 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

  • Tingting Zhang, Xia Yu, Shu'an Wen, Yi Xue, Hua Xiao, Ruyan Ren, Fen Wang, Lingling Dong, Shibing Qin, Hairong Huang. Bone Penetration of Cycloserine in Osteoarticular Tuberculosis Patients of China. Antimicrobial agents and chemotherapy. 2022 05; 66(5):e0222421. doi: 10.1128/aac.02224-21. [PMID: 35400177]
  • Xiaocui Wu, Guangkun Tan, Wei Sha, Haican Liu, Jinghui Yang, Yinjuan Guo, Xin Shen, Zheyuan Wu, Hongbo Shen, Fangyou Yu. Use of Whole-Genome Sequencing to Predict Mycobacterium tuberculosis Complex Drug Resistance from Early Positive Liquid Cultures. Microbiology spectrum. 2022 04; 10(2):e0251621. doi: 10.1128/spectrum.02516-21. [PMID: 35311541]
  • Wing-Kee Lee, Michelle Maaß, Amy Quach, Nataliya Poscic, Holly Prangley, Erin-Claire Pallott, Jiyoon L Kim, Jason S Pierce, Besim Ogretmen, Anthony H Futerman, Frank Thévenod. Dependence of ABCB1 transporter expression and function on distinct sphingolipids generated by ceramide synthases-2 and -6 in chemoresistant renal cancer. The Journal of biological chemistry. 2022 02; 298(2):101492. doi: 10.1016/j.jbc.2021.101492. [PMID: 34915026]
  • Xuyen H Le, Chun-Pong Lee, A Harvey Millar. The mitochondrial pyruvate carrier (MPC) complex mediates one of three pyruvate-supplying pathways that sustain Arabidopsis respiratory metabolism. The Plant cell. 2021 08; 33(8):2776-2793. doi: 10.1093/plcell/koab148. [PMID: 34137858]
  • 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]
  • Richard Court, Chad M Centner, Maxwell Chirehwa, Lubbe Wiesner, Paolo Denti, Nihal de Vries, Joseph Harding, Tawanda Gumbo, Gary Maartens, Helen McIlleron. Neuropsychiatric toxicity and cycloserine concentrations during treatment for multidrug-resistant tuberculosis. International journal of infectious diseases : IJID : official publication of the International Society for Infectious Diseases. 2021 Apr; 105(?):688-694. doi: 10.1016/j.ijid.2021.03.001. [PMID: 33684562]
  • Md Ajijur Rahman, Frank Kaiser, Shirin Jamshidi, Marta Freitas Monteiro, Khondaker Miraz Rahman, Peter Mullany, Adam P Roberts. Integron gene cassettes harboring novel variants of D-alanine-D-alanine ligase confer high-level resistance to D-cycloserine. Scientific reports. 2020 11; 10(1):20709. doi: 10.1038/s41598-020-77377-4. [PMID: 33244063]
  • Maxwell T Chirehwa, Richard Court, Mariana de Kock, Lubbe Wiesner, Nihal de Vries, Joseph Harding, Tawanda Gumbo, Gary Maartens, Rob Warren, Paolo Denti, Helen McIlleron. Population Pharmacokinetics of Cycloserine and Pharmacokinetic/Pharmacodynamic Target Attainment in Multidrug-Resistant Tuberculosis Patients Dosed with Terizidone. Antimicrobial agents and chemotherapy. 2020 10; 64(11):. doi: 10.1128/aac.01381-20. [PMID: 32816738]
  • Ruben van der Galiën, Natasha Van't Boveneind-Vrubleuskaya, Charles Peloquin, Alena Skrahina, Daan J Touw, Jan-Willem C Alffenaar. Pharmacokinetic Modeling, Simulation, and Development of a Limited Sampling Strategy of Cycloserine in Patients with Multidrug-/Extensively Drug-Resistant Tuberculosis. Clinical pharmacokinetics. 2020 07; 59(7):899-910. doi: 10.1007/s40262-020-00860-8. [PMID: 31981103]
  • Stefanie Malan-Müller, Vladimir B C de Souza, Willie M U Daniels, Soraya Seedat, Mark D Robinson, Sîan M J Hemmings. Shedding Light on the Transcriptomic Dark Matter in Biological Psychiatry: Role of Long Noncoding RNAs in D-cycloserine-Induced Fear Extinction in Posttraumatic Stress Disorder. Omics : a journal of integrative biology. 2020 06; 24(6):352-369. doi: 10.1089/omi.2020.0031. [PMID: 32453623]
  • Matthew W Johnson, Natalie R Bruner, Patrick S Johnson, Kenneth Silverman, Meredith S Berry. Randomized controlled trial of d-cycloserine in cocaine dependence: Effects on contingency management and cue-induced cocaine craving in a naturalistic setting. Experimental and clinical psychopharmacology. 2020 Apr; 28(2):157-168. doi: 10.1037/pha0000306. [PMID: 31368770]
  • Halina Baran, Carina Kronsteiner, Berthold Kepplinger. Kynurenine Aminotransferases I, II and III Are Present in Saliva. Neuro-Signals. 2020 03; 28(1):1-13. doi: 10.33594/000000217. [PMID: 32153151]
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  • Lulu Yao, Zongliang Wang, Di Deng, Rongzhen Yan, Jun Ju, Qiang Zhou. The impact of D-cycloserine and sarcosine on in vivo frontal neural activity in a schizophrenia-like model. BMC psychiatry. 2019 10; 19(1):314. doi: 10.1186/s12888-019-2306-1. [PMID: 31653237]
  • Mwila Mulubwa, Pierre Mugabo. Steady-state population pharmacokinetics of terizidone and its metabolite cycloserine in patients with drug-resistant tuberculosis. British journal of clinical pharmacology. 2019 09; 85(9):1946-1956. doi: 10.1111/bcp.13975. [PMID: 31046167]
  • Sireesha Dodda, Ajitha Makula, Raj Narayana Kandhagatla. Development and validation of bioanalytical method for quantification of cycloserine in human plasma by liquid chromatography-tandem mass spectrometry: Application to pharmacokinetic study. Biomedical chromatography : BMC. 2019 Aug; 33(8):e4548. doi: 10.1002/bmc.4548. [PMID: 30945752]
  • Mwila Mulubwa, Pierre Mugabo. Sensitive Ultra-performance Liquid Chromatography Tandem Mass Spectrometry Method for Determination of Cycloserine in Plasma for a Pharmacokinetics Study. Journal of chromatographic science. 2019 Jul; 57(6):560-564. doi: 10.1093/chromsci/bmz028. [PMID: 30927010]
  • Rajeev Ranjan, Ashish Srivastava, Reena Bharti, Trisha Roy, Sonia Verma, Lipika Ray, Amit Misra. Preclinical Development of Inhalable d-Cycloserine and Ethionamide To Overcome Pharmacokinetic Interaction and Enhance Efficacy against Mycobacterium tuberculosis. Antimicrobial agents and chemotherapy. 2019 06; 63(6):. doi: 10.1128/aac.00099-19. [PMID: 30962335]
  • M Alizadeh Asfestani, E Braganza, J Schwidetzky, J Santiago, S Soekadar, J Born, G B Feld. Overnight memory consolidation facilitates rather than interferes with new learning of similar materials-a study probing NMDA receptors. Neuropsychopharmacology : official publication of the American College of Neuropsychopharmacology. 2018 10; 43(11):2292-2298. doi: 10.1038/s41386-018-0139-0. [PMID: 30046156]
  • H Zhu, S-C Guo, Z-Q Liu, B Wang, L Fu, N-H Chu, Y Lu. Therapeutic drug monitoring of cycloserine and linezolid during anti-tuberculosis treatment in Beijing, China. The international journal of tuberculosis and lung disease : the official journal of the International Union against Tuberculosis and Lung Disease. 2018 08; 22(8):931-936. doi: 10.5588/ijtld.17.0648. [PMID: 29991404]
  • Agibothu Kupparam Hemanth Kumar, Alok Kumar, Thiruvengadam Kannan, Rakesh Bhatia, Dipti Agarwal, Santosh Kumar, Rajeshwar Dayal, Sheo Pratap Singh, Geetha Ramachandran. Pharmacokinetics of Second-Line Antituberculosis Drugs in Children with Multidrug-Resistant Tuberculosis in India. Antimicrobial agents and chemotherapy. 2018 05; 62(5):. doi: 10.1128/aac.02410-17. [PMID: 29463539]
  • A K Hemanth Kumar, Arun Kumar Polisetty, V Sudha, A Vijayakumar, Geetha Ramachandran. A selective and sensitive high performance liquid chromatography assay for the determination of cycloserine in human plasma. The Indian journal of tuberculosis. 2018 Apr; 65(2):118-123. doi: 10.1016/j.ijtb.2017.08.034. [PMID: 29579424]
  • Y-M Fan, S-P Ding, Z-J Bao, L-M Wu, L-B Zhen, Q Xia, M Zhu. Prognostic factors for treatment success in patients with multidrug-resistant tuberculosis in China. The international journal of tuberculosis and lung disease : the official journal of the International Union against Tuberculosis and Lung Disease. 2018 03; 22(3):300-305. doi: 10.5588/ijtld.17.0183. [PMID: 29471908]
  • Xia Yu, Xiling Zeng, Wenhui Shi, Yanjie Hu, Wenjuan Nie, Naihui Chu, Hairong Huang. Validation of Cycloserine Efficacy in Treatment of Multidrug-Resistant and Extensively Drug-Resistant Tuberculosis in Beijing, China. Antimicrobial agents and chemotherapy. 2018 03; 62(3):. doi: 10.1128/aac.01824-17. [PMID: 29311073]
  • R Court, L Wiesner, A Stewart, N de Vries, J Harding, G Maartens, T Gumbo, H McIlleron. Steady state pharmacokinetics of cycloserine in patients on terizidone for multidrug-resistant tuberculosis. The international journal of tuberculosis and lung disease : the official journal of the International Union against Tuberculosis and Lung Disease. 2018 01; 22(1):30-33. doi: 10.5588/ijtld.17.0475. [PMID: 29297422]
  • Peter Karel, Francesca Calabrese, Marco Riva, Paola Brivio, Bas Van der Veen, Liesbeth Reneman, Michel Verheij, Judith Homberg. d-Cycloserine enhanced extinction of cocaine-induced conditioned place preference is attenuated in serotonin transporter knockout rats. Addiction biology. 2018 01; 23(1):120-129. doi: 10.1111/adb.12483. [PMID: 27957784]
  • Jiazhen Chen, Shuo Zhang, Peng Cui, Wanliang Shi, Wenhong Zhang, Ying Zhang. Identification of novel mutations associated with cycloserine resistance in Mycobacterium tuberculosis. The Journal of antimicrobial chemotherapy. 2017 Dec; 72(12):3272-3276. doi: 10.1093/jac/dkx316. [PMID: 28961957]
  • Zhengsheng Mao, Xin Wang, Bingxin Li, Jing Jin, Ming Xu, Youping Liu, Xin Di. A simplified LC-MS/MS method for rapid determination of cycloserine in small-volume human plasma using protein precipitation coupled with dilution techniques to overcome matrix effects and its application to a pharmacokinetic study. Analytical and bioanalytical chemistry. 2017 Apr; 409(11):3025-3032. doi: 10.1007/s00216-017-0249-2. [PMID: 28224247]
  • M R Kapolowicz, L T Thompson. Acute high-intensity noise induces rapid Arc protein expression but fails to rapidly change GAD expression in amygdala and hippocampus of rats: Effects of treatment with D-cycloserine. Hearing research. 2016 12; 342(?):69-79. doi: 10.1016/j.heares.2016.09.010. [PMID: 27702572]
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  • Sang-In Park, Jaeseong Oh, Kyungho Jang, Jangsoo Yoon, Seol Ju Moon, Jong Sun Park, Jae Ho Lee, Junghan Song, In-Jin Jang, Kyung-Sang Yu, Jae-Yong Chung. Pharmacokinetics of Second-Line Antituberculosis Drugs after Multiple Administrations in Healthy Volunteers. Antimicrobial agents and chemotherapy. 2015 Aug; 59(8):4429-35. doi: 10.1128/aac.00354-15. [PMID: 25987620]
  • Seung Heon Lee, Kyung-Ah Seo, Young Min Lee, Hyun-Kyung Lee, Je Hyeong Kim, Chol Shin, Jong-Ryul Ghim, Jae-Gook Shin, Dong Hyun Kim. Low Serum Concentrations of Moxifloxacin, Prothionamide, and Cycloserine on Sputum Conversion in Multi-Drug Resistant TB. Yonsei medical journal. 2015 Jul; 56(4):961-7. doi: 10.3349/ymj.2015.56.4.961. [PMID: 26069117]
  • Huili Zhou, Guolan Wu, Xingjiang Hu, Meixiang Zhu, You Zhai, Jian Liu, Jianzhong Shentu, Lihua Wu. Pharmacokinetic Properties and Tolerability of Cycloserine Following Oral Administration in Healthy Chinese Volunteers: A Randomized, Open-Label, Single- and Multiple-Dose 3-Way Crossover Study. Clinical therapeutics. 2015 Jun; 37(6):1292-300. doi: 10.1016/j.clinthera.2015.03.015. [PMID: 25869627]
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  • Kerry C Carson, Lusiana V Boseiwaqa, Sara K Thean, Niki F Foster, Thomas V Riley. Isolation of Clostridium difficile from faecal specimens--a comparison of chromID C. difficile agar and cycloserine-cefoxitin-fructose agar. Journal of medical microbiology. 2013 Sep; 62(Pt 9):1423-1427. doi: 10.1099/jmm.0.056515-0. [PMID: 23579394]
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