Cilastatin (BioDeep_00000002152)

 

Secondary id: BioDeep_00000397743

human metabolite blood metabolite Chemicals and Drugs


代谢物信息卡片


(Z)-7-((R)-2-Amino-2-carboxy-ethylsulphanyl)-2-[((S)-2,2-dimethyl-cyclopropanecarbonyl)-amino]-hept-2-enoic acid

化学式: C16H26N2O5S (358.1562346)
中文名称: 西司他丁
谱图信息: 最多检出来源 Viridiplantae(plant) 2.84%

分子结构信息

SMILES: CC1(C)CC1C(=O)NC(=CCCCCSCC(N)C(=O)O)C(=O)O
InChI: InChI=1S/C16H26N2O5S/c1-16(2)8-10(16)13(19)18-12(15(22)23)6-4-3-5-7-24-9-11(17)14(20)21/h6,10-11H,3-5,7-9,17H2,1-2H3,(H,18,19)(H,20,21)(H,22,23)/b12-6-/t10-,11+/m1/s1

描述信息

A renal dehydropeptidase-I and leukotriene D4 dipeptidase inhibitor. Since the antibiotic, imipenem, is hydrolyzed by dehydropeptidase-I, which resides in the brush border of the renal tubule, cilastatin is administered with imipenem to increase its effectiveness. The drug also inhibits the metabolism of leukotriene D4 to leukotriene E4. [PubChem]
D004791 - Enzyme Inhibitors > D011480 - Protease Inhibitors
C471 - Enzyme Inhibitor > C783 - Protease Inhibitor
CONFIDENCE standard compound; INTERNAL_ID 2129

同义名列表

20 个代谢物同义名

(Z)-7-((R)-2-Amino-2-carboxy-ethylsulphanyl)-2-[((S)-2,2-dimethyl-cyclopropanecarbonyl)-amino]-hept-2-enoic acid; (Z)-7-((R)-2-Amino-2-carboxy-ethylsulfanyl)-2-[((S)-2,2-dimethyl-cyclopropanecarbonyl)-amino]-hept-2-enoic acid; (Z)-7-((R)-2-Amino-2-carboxy-ethylsulphanyl)-2-[((S)-2,2-dimethyl-cyclopropanecarbonyl)-amino]-hept-2-enoate; (2Z)-7-{[(2R)-2-amino-2-carboxyethyl]sulfanyl}-2-{[(1S)-2,2-dimethylcyclopropyl]formamido}hept-2-enoic acid; (Z)-7-((R)-2-Amino-2-carboxy-ethylsulfanyl)-2-[((S)-2,2-dimethyl-cyclopropanecarbonyl)-amino]-hept-2-enoate; (L)-7-(2-Amino-2-carboxy-ethylsulphanyl)-2-[(2,2-dimethyl-cyclopropanecarbonyl)-amino]-hept-2-enoic acid; (L)-7-(2-Amino-2-carboxy-ethylsulfanyl)-2-[(2,2-dimethyl-cyclopropanecarbonyl)-amino]-hept-2-enoic acid; (L)-7-(2-Amino-2-carboxy-ethylsulphanyl)-2-[(2,2-dimethyl-cyclopropanecarbonyl)-amino]-hept-2-enoate; (L)-7-(2-Amino-2-carboxy-ethylsulfanyl)-2-[(2,2-dimethyl-cyclopropanecarbonyl)-amino]-hept-2-enoate; (Z)-(S)-6-Carboxy-6-[(S)-2,2-dimethylcyclopropanecarboxamido]hex-5-enyl-L-cysteine; Monosodium salt, cilastatin; Salt, cilastatin monosodium; Cilastatin monosodium salt; Sodium, cilastatin; Cilastatin Sodium; Cilastatinum; Cilastatina; Cilastatine; Cilastatin; MK0791



数据库引用编号

29 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)

3 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

  • Fan Wu, Ting Zhao, Yu Zhang, Yan Wang, Guoxin Liao, Baojing Zhang, Chao Wang, Xiangge Tian, Lei Feng, Bangjiang Fang, Xiaokui Huo, Xiaochi Ma. Beneficial herb-drug interaction of rhein in Jinhongtang and Imipenem/Cilastatin mediated by organic anion transporters. Journal of ethnopharmacology. 2023 Apr; ?(?):116449. doi: 10.1016/j.jep.2023.116449. [PMID: 37023835]
  • Rebeca González-Fernández, María Ángeles González-Nicolás, Manuel Morales, Julio Ávila, Alberto Lázaro, Pablo Martín-Vasallo. FKBP51, AmotL2 and IQGAP1 Involvement in Cilastatin Prevention of Cisplatin-Induced Tubular Nephrotoxicity in Rats. Cells. 2022 05; 11(9):. doi: 10.3390/cells11091585. [PMID: 35563891]
  • Estefanía Moreno-Gordaliza, Maria Dolores Marazuela, Óscar Pastor, Alberto Lázaro, María Milagros Gómez-Gómez. Lipidomics Reveals Cisplatin-Induced Renal Lipid Alterations during Acute Kidney Injury and Their Attenuation by Cilastatin. International journal of molecular sciences. 2021 Nov; 22(22):. doi: 10.3390/ijms222212521. [PMID: 34830406]
  • Katsuyuki Matsushita, Kiyoshi Mori, Turgay Saritas, Mahaba B Eiwaz, Yoshio Funahashi, Megan N Nickerson, Jessica F Hebert, Adam C Munhall, James A McCormick, Motoko Yanagita, Michael P Hutchens. Cilastatin Ameliorates Rhabdomyolysis-induced AKI in Mice. Journal of the American Society of Nephrology : JASN. 2021 10; 32(10):2579-2594. doi: 10.1681/asn.2020030263. [PMID: 34341182]
  • T Becerir, O Tokgün, S Yuksel. The therapeutic effect of Cilastatin on drug-induced nephrotoxicity: a new perspective. European review for medical and pharmacological sciences. 2021 Sep; 25(17):5436-5447. doi: 10.26355/eurrev_202109_26651. [PMID: 34533819]
  • Samuel Martinez-Erro, Francisco Navas, Eva Romaní-Cubells, Paloma Fernández-García, Victoria Morales, Raul Sanz, Rafael A García-Muñoz. Kidney-Protector Lipidic Cilastatin Derivatives as Structure-Directing Agents for the Synthesis of Mesoporous Silica Nanoparticles for Drug Delivery. International journal of molecular sciences. 2021 Jul; 22(15):. doi: 10.3390/ijms22157968. [PMID: 34360733]
  • Ci Han, Nana Guo, Yue Bu, Yahui Peng, Xueting Li, Xiaohui Ma, Mengyuan Yang, Xiaonan Jia, Jin Zhang, Xiaowei Liu, Kaijiang Yu, Changsong Wang. Intestinal microbiota and antibiotic-associated acute gastrointestinal injury in sepsis mice. Aging. 2021 03; 13(7):10099-10111. doi: 10.18632/aging.202768. [PMID: 33818419]
  • Matilde Zaballos, Mercedes Power, María Iluminada Canal-Alonso, María Ángeles González-Nicolás, Wenceslao Vasquez-Jimenez, Pablo Lozano-Lominchar, Pilar Cabrerizo-Torrente, Natividad Palencia-García, Susana Gago-Quiroga, María Dolores Ginel-Feito, Consuelo Jiménez, Alberto Lázaro, Luis González-Bayón. Effect of Cilastatin on Cisplatin-Induced Nephrotoxicity in Patients Undergoing Hyperthermic Intraperitoneal Chemotherapy. International journal of molecular sciences. 2021 Jan; 22(3):. doi: 10.3390/ijms22031239. [PMID: 33513824]
  • Masashi Arita, Satoshi Watanabe, Nobumasa Aoki, Shoji Kuwahara, Ryo Suzuki, Sawako Goto, Yuko Abe, Miho Takahashi, Miyuki Sato, Satoshi Hokari, Aya Ohtsubo, Satoshi Shoji, Koichiro Nozaki, Kosuke Ichikawa, Rie Kondo, Masachika Hayashi, Yasuyoshi Ohshima, Hideyuki Kabasawa, Michihiro Hosojima, Toshiyuki Koya, Akihiko Saito, Toshiaki Kikuchi. Combination therapy of cisplatin with cilastatin enables an increased dose of cisplatin, enhancing its antitumor effect by suppression of nephrotoxicity. Scientific reports. 2021 01; 11(1):750. doi: 10.1038/s41598-020-80853-6. [PMID: 33437029]
  • Iris H Chen, David P Nicolau, Joseph L Kuti. Imipenem/Cilastatin/Relebactam Alone and in Combination against Pseudomonas aeruginosa in the In Vitro Pharmacodynamic Model. Antimicrobial agents and chemotherapy. 2020 11; 64(12):. doi: 10.1128/aac.01764-20. [PMID: 33139283]
  • Mersedeh Shayan, Sepideh Elyasi. Cilastatin as a protective agent against drug-induced nephrotoxicity: a literature review. Expert opinion on drug safety. 2020 Aug; 19(8):999-1010. doi: 10.1080/14740338.2020.1796967. [PMID: 32666842]
  • Zhi Rao, Zi-Long Dang, Bin Li, Lei Zhu, Hong-Yan Qin, Xin-An Wu, Yu-Hui Wei. Determination of Total and Unbound Meropenem, Imipenem/Cilastatin, and Cefoperazone/Sulbactam in Human Plasma: Application for Therapeutic Drug Monitoring in Critically Ill Patients. Therapeutic drug monitoring. 2020 08; 42(4):578-587. doi: 10.1097/ftd.0000000000000736. [PMID: 32049891]
  • Yu Ah Hong, So Young Jung, Keum Jin Yang, Dai Sig Im, Kyung Hwan Jeong, Cheol Whee Park, Hyeon Seok Hwang. Cilastatin Preconditioning Attenuates Renal Ischemia-Reperfusion Injury via Hypoxia Inducible Factor-1α Activation. International journal of molecular sciences. 2020 May; 21(10):. doi: 10.3390/ijms21103583. [PMID: 32438631]
  • Pratik Bhagunde, Francheska Colon-Gonzalez, Yang Liu, Jin Wu, Shiyao Sherrie Xu, Graigory Garrett, Patricia Jumes, Kenneth Lasseter, Thomas Marbury, Matthew L Rizk, Mallika Lala, Elizabeth G Rhee, Joan R Butterton, Keith Boundy. Impact of renal impairment and human organic anion transporter inhibition on pharmacokinetics, safety and tolerability of relebactam combined with imipenem and cilastatin. British journal of clinical pharmacology. 2020 05; 86(5):944-957. doi: 10.1111/bcp.14204. [PMID: 31856304]
  • Xiaokui Huo, Qiang Meng, Changyuan Wang, Jingjing Wu, Chong Wang, Yanna Zhu, Xiaodong Ma, Huijun Sun, Kexin Liu. Protective effect of cilastatin against diclofenac-induced nephrotoxicity through interaction with diclofenac acyl glucuronide via organic anion transporters. British journal of pharmacology. 2020 05; 177(9):1933-1948. doi: 10.1111/bph.14957. [PMID: 32000294]
  • Kang Luo, Sun Woo Lim, Jian Jin, Long Jin, Hyo Wook Gil, Dai Sig Im, Hyeon Seok Hwang, Chul Woo Yang. Cilastatin protects against tacrolimus-induced nephrotoxicity via anti-oxidative and anti-apoptotic properties. BMC nephrology. 2019 06; 20(1):221. doi: 10.1186/s12882-019-1399-6. [PMID: 31200653]
  • Estefanía Moreno-Gordaliza, Diego Esteban-Fernández, Alberto Lázaro, Sarah Aboulmagd, Blanca Humanes, Alberto Tejedor, Michael W Linscheid, M Milagros Gómez-Gómez. Lipid imaging for visualizing cilastatin amelioration of cisplatin-induced nephrotoxicity. Journal of lipid research. 2018 09; 59(9):1561-1574. doi: 10.1194/jlr.m080465. [PMID: 30049708]
  • Weihong Shi, Mingyang Duan, Ligang Jie, Weifeng Sun. A successful treatment of severe systemic lupus erythematosus caused by occult pulmonary infection-associated with hemophagocytic syndrome: A case report. Medicine. 2018 May; 97(19):e0595. doi: 10.1097/md.0000000000010595. [PMID: 29742693]
  • Matthew L Rizk, Elizabeth G Rhee, Patricia A Jumes, Mark H Gotfried, Tian Zhao, Eric Mangin, Sheng Bi, Cynthia M Chavez-Eng, Zufei Zhang, Joan R Butterton. Intrapulmonary Pharmacokinetics of Relebactam, a Novel β-Lactamase Inhibitor, Dosed in Combination with Imipenem-Cilastatin in Healthy Subjects. Antimicrobial agents and chemotherapy. 2018 03; 62(3):. doi: 10.1128/aac.01411-17. [PMID: 29311084]
  • Gabriel Hundeshagen, David N Herndon, Karel D Capek, Ludwik K Branski, Charles D Voigt, Elizabeth A Killion, Janos Cambiaso-Daniel, Michaela Sljivich, Andrew De Crescenzo, Ronald P Mlcak, Michael P Kinsky, Celeste C Finnerty, William B Norbury. Co-administration of vancomycin and piperacillin-tazobactam is associated with increased renal dysfunction in adult and pediatric burn patients. Critical care (London, England). 2017 12; 21(1):318. doi: 10.1186/s13054-017-1899-3. [PMID: 29262848]
  • Amal Tahri, Kamilia Ksouda, Rim Kallel, Salima Daoud, Tahia Boudawara, Khaled Mounir Zeghal, Zouheir Sahnoun. A carbapenem antibiotic imipenem/cilastatin induces an oxidative stress-status and gonadotoxic effects in « wistar » rats. Biomedicine & pharmacotherapy = Biomedecine & pharmacotherapie. 2017 Nov; 95(?):308-316. doi: 10.1016/j.biopha.2017.08.039. [PMID: 28858728]
  • Blanca Humanes, Sonia Camaño, Jose Manuel Lara, Venkatta Sabbisetti, María Ángeles González-Nicolás, Joseph V Bonventre, Alberto Tejedor, Alberto Lázaro. Cisplatin-induced renal inflammation is ameliorated by cilastatin nephroprotection. Nephrology, dialysis, transplantation : official publication of the European Dialysis and Transplant Association - European Renal Association. 2017 Oct; 32(10):1645-1655. doi: 10.1093/ndt/gfx005. [PMID: 28340076]
  • Dai Sig Im, Hye Jin Shin, Keum Jin Yang, So Young Jung, Ho Yeon Song, Hyeon Seok Hwang, Hyo-Wook Gil. Cilastatin attenuates vancomycin-induced nephrotoxicity via P-glycoprotein. Toxicology letters. 2017 Aug; 277(?):9-17. doi: 10.1016/j.toxlet.2017.05.023. [PMID: 28549670]
  • Yoshihisa Hori, Nobumasa Aoki, Shoji Kuwahara, Michihiro Hosojima, Ryohei Kaseda, Sawako Goto, Tomomichi Iida, Shankhajit De, Hideyuki Kabasawa, Reika Kaneko, Hiroyuki Aoki, Yoshinari Tanabe, Hiroshi Kagamu, Ichiei Narita, Toshiaki Kikuchi, Akihiko Saito. Megalin Blockade with Cilastatin Suppresses Drug-Induced Nephrotoxicity. Journal of the American Society of Nephrology : JASN. 2017 Jun; 28(6):1783-1791. doi: 10.1681/asn.2016060606. [PMID: 28052987]
  • Mario Martínez-Florensa, Marta Consuegra-Fernández, Fernando Aranda, Noelia Armiger-Borràs, Marianna Di Scala, Esther Carrasco, Jerónimo Pachón, Jordi Vila, Gloria González-Aseguinolaza, Francisco Lozano. Protective Effects of Human and Mouse Soluble Scavenger-Like CD6 Lymphocyte Receptor in a Lethal Model of Polymicrobial Sepsis. Antimicrobial agents and chemotherapy. 2017 01; 61(1):. doi: 10.1128/aac.01391-16. [PMID: 27895015]
  • Bradley A Boucher, Joanna Q Hudson, David M Hill, Joseph M Swanson, G Christopher Wood, S Casey Laizure, Angela Arnold-Ross, Zhe-Yi Hu, William L Hickerson. Pharmacokinetics of Imipenem/Cilastatin Burn Intensive Care Unit Patients Undergoing High-Dose Continuous Venovenous Hemofiltration. Pharmacotherapy. 2016 12; 36(12):1229-1237. doi: 10.1002/phar.1866. [PMID: 27862103]
  • Chien-Chih Wu, Tsung-Yu Pai, Fei-Yuan Hsiao, Li-Jiuan Shen, Fe-Lin Lin Wu. The Effect of Different Carbapenem Antibiotics (Ertapenem, Imipenem/Cilastatin, and Meropenem) on Serum Valproic Acid Concentrations. Therapeutic drug monitoring. 2016 10; 38(5):587-92. doi: 10.1097/ftd.0000000000000316. [PMID: 27322166]
  • L Y Deng, Z C Yang, Y L Gong, G T Huang, S P Yin, B Jiang, Y Z Peng. [Therapeutic effect of phages on extensively drug-resistant Acinetobacter baumannii-induced sepsis in mice]. Zhonghua shao shang za zhi = Zhonghua shaoshang zazhi = Chinese journal of burns. 2016 Sep; 32(9):523-8. doi: 10.3760/cma.j.issn.1009-2587.2016.09.003. [PMID: 27647067]
  • Naoki Kuroshima, Takayuki Tanaka, Tamotsu Kuroki, Amane Kitasato, Tomohiko Adachi, Shinichiro Ono, Hajime Matsushima, Takanori Hirayama, Akihiko Soyama, Masaaki Hidaka, Mitsuhisa Takatsuki, Susumu Eguchi. Triple-drug therapy to prevent pancreatic fistula after pancreatectomy in a rat model. Pancreatology : official journal of the International Association of Pancreatology (IAP) ... [et al.]. 2016 Sep; 16(5):917-21. doi: 10.1016/j.pan.2016.06.011. [PMID: 27396917]
  • P Wilkowski, M Ciszek, K Dobrzaniecka, J Sańko-Resmer, A Łabuś, K Grygiel, T Grochowiecki, G Młynarczyk, L Pączek. Successful Treatment of Urinary Tract Infection in Kidney Transplant Recipients Caused by Multiresistant Klebsiella pneumoniae Producing New Delhi Metallo-Beta-Lactamase (NDM-1) With Strains Genotyping. Transplantation proceedings. 2016 Jun; 48(5):1576-9. doi: 10.1016/j.transproceed.2016.01.060. [PMID: 27496450]
  • Yusuke Shono, Melissa D Docampo, Jonathan U Peled, Suelen M Perobelli, Enrico Velardi, Jennifer J Tsai, Ann E Slingerland, Odette M Smith, Lauren F Young, Jyotsna Gupta, Sophia R Lieberman, Hillary V Jay, Katya F Ahr, Kori A Porosnicu Rodriguez, Ke Xu, Marco Calarfiore, Hendrik Poeck, Silvia Caballero, Sean M Devlin, Franck Rapaport, Jarrod A Dudakov, Alan M Hanash, Boglarka Gyurkocza, George F Murphy, Camilla Gomes, Chen Liu, Eli L Moss, Shannon B Falconer, Ami S Bhatt, Ying Taur, Eric G Pamer, Marcel R M van den Brink, Robert R Jenq. Increased GVHD-related mortality with broad-spectrum antibiotic use after allogeneic hematopoietic stem cell transplantation in human patients and mice. Science translational medicine. 2016 05; 8(339):339ra71. doi: 10.1126/scitranslmed.aaf2311. [PMID: 27194729]
  • Anne Fournier, Philippe Eggimann, Jean-Luc Pagani, Jean-Pierre Revelly, Laurent A Decosterd, Oscar Marchetti, André Pannatier, Pierre Voirol, Yok-Ai Que. Impact of the introduction of real-time therapeutic drug monitoring on empirical doses of carbapenems in critically ill burn patients. Burns : journal of the International Society for Burn Injuries. 2015 Aug; 41(5):956-68. doi: 10.1016/j.burns.2015.01.001. [PMID: 25678084]
  • Richard D Moulton, Kenneth J Ruterbories, David W Bedwell, Michael A Mohutsky. In vitro characterization of the bioconversion of pomaglumetad methionil, a novel metabotropic glutamate 2/3 receptor agonist peptide prodrug. Drug metabolism and disposition: the biological fate of chemicals. 2015 May; 43(5):756-61. doi: 10.1124/dmd.114.062893. [PMID: 25755052]
  • Blanca Humanes, Juan Carlos Jado, Sonia Camaño, Virginia López-Parra, Ana María Torres, Luís Antonio Álvarez-Sala, Emilia Cercenado, Alberto Tejedor, Alberto Lázaro. Protective Effects of Cilastatin against Vancomycin-Induced Nephrotoxicity. BioMed research international. 2015; 2015(?):704382. doi: 10.1155/2015/704382. [PMID: 26504822]
  • Kyung-Mee Park, Hyun-Suk Nam, Heung-Myong Woo. Successful management of multidrug-resistant Pseudomonas aeruginosa pneumonia after kidney transplantation in a dog. The Journal of veterinary medical science. 2013 Nov; 75(11):1529-33. doi: 10.1292/jvms.13-0194. [PMID: 23842146]
  • Zhe-Yi Hu, Bradley A Boucher, S Casey Laizure, Vanessa L Herring, Robert B Parker, William L Hickerson. Nonvolatile salt-free stabilizer for the quantification of polar imipenem and cilastatin in human plasma using hydrophilic interaction chromatography/quadrupole mass spectrometry with contamination sensitive off-axis electrospray. Journal of mass spectrometry : JMS. 2013 Aug; 48(8):945-50. doi: 10.1002/jms.3240. [PMID: 23893642]
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  • Gabriela A Albarellos, Graciela A Denamiel, Laura Montoya, Pamela C Quaine, Martín P Lupi, María F Landoni. Pharmacokinetics of imipenem after intravenous, intramuscular and subcutaneous administration to cats. Journal of feline medicine and surgery. 2013 Jun; 15(6):483-7. doi: 10.1177/1098612x12471526. [PMID: 23253883]
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  • Hai-yan Yin, Xiao-ling Ye, Rui Zhang, You-feng Zhu. [Domestic imipenem cilastatin sodium for the treatment of severe aspiration pneumonia, a curative effect observation]. Zhongguo wei zhong bing ji jiu yi xue = Chinese critical care medicine = Zhongguo weizhongbing jijiuyixue. 2012 Oct; 24(10):628-31. doi: NULL. [PMID: 23040783]
  • Blanca Humanes, Alberto Lazaro, Sonia Camano, Estefanía Moreno-Gordaliza, Jose A Lazaro, Montserrat Blanco-Codesido, Jose M Lara, Alberto Ortiz, Maria M Gomez-Gomez, Pablo Martín-Vasallo, Alberto Tejedor. Cilastatin protects against cisplatin-induced nephrotoxicity without compromising its anticancer efficiency in rats. Kidney international. 2012 Sep; 82(6):652-63. doi: 10.1038/ki.2012.199. [PMID: 22718191]
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