Cilazapril (BioDeep_00000017964)

   

human metabolite blood metabolite Chemicals and Drugs


代谢物信息卡片


(1S,9S)-9-{[(2S)-1-ethoxy-1-oxo-4-phenylbutan-2-yl]amino}-10-oxo-octahydro-1H-pyridazino[1,2-a][1,2]diazepine-1-carboxylic acid

化学式: C22H31N3O5 (417.2263596)
中文名称: 西拉普利
谱图信息: 最多检出来源 Homo sapiens(blood) 2.31%

分子结构信息

SMILES: CCOC(=O)C(CCC1=CC=CC=C1)NC2CCCN3CCCC(N3C2=O)C(=O)O
InChI: InChI=1S/C22H31N3O5/c1-2-30-22(29)18(13-12-16-8-4-3-5-9-16)23-17-10-6-14-24-15-7-11-19(21(27)28)25(24)20(17)26/h3-5,8-9,17-19,23H,2,6-7,10-15H2,1H3,(H,27,28)/t17-,18-,19-/m0/s1

描述信息

Cilazapril is only found in individuals that have used or taken this drug. It is one of the angiotensin-converting enzyme inhibitors (ACE inhibitors) used for hypertension. It is a prodrug that is hydrolyzed after absorption to its main metabolite cilazaprilat. [PubChem]Cilazapri, as a pyridazine ACE inhibitor, competes with angiotensin I for binding at the angiotensin-converting enzyme, blocking the conversion of angiotensin I to angiotensin II. As angiotensin II is a vasoconstrictor and a negative feedback mediator for renin activity, lower angiotensin II levels results in a decrease in blood pressure, an increase in renin activity, and stimulation of baroreceptor reflex mechanisms. Kininase II, an enzyme which degrades the vasodilator bradykinin, is identical to ACE and may also be inhibited.
C - Cardiovascular system > C09 - Agents acting on the renin-angiotensin system > C09A - Ace inhibitors, plain > C09AA - Ace inhibitors, plain
D004791 - Enzyme Inhibitors > D011480 - Protease Inhibitors > D000806 - Angiotensin-Converting Enzyme Inhibitors
C78274 - Agent Affecting Cardiovascular System > C270 - Antihypertensive Agent
C471 - Enzyme Inhibitor > C783 - Protease Inhibitor > C247 - ACE Inhibitor
D002317 - Cardiovascular Agents > D000959 - Antihypertensive Agents

同义名列表

19 个代谢物同义名

(1S,9S)-9-{[(2S)-1-ethoxy-1-oxo-4-phenylbutan-2-yl]amino}-10-oxo-octahydro-1H-pyridazino[1,2-a][1,2]diazepine-1-carboxylic acid; Monohydrobromide, cilazapril; Cilazapril monohydrobromide; Monohydrate, cilazapril; Cilazapril, (s*)-isomer; Cilazapril Monohydrate; Anhydrous, cilazapril; Cilazapril, anhydrous; Cilazapril anhydrous; Hydrate, cilazapril; Cilazapril hydrate; Cilazaprilum; Ro 31-2848; Ro 34-2848; Cilazapril; Inhibace; Vascace; Vascase; Dynorm



数据库引用编号

11 个数据库交叉引用编号

分类词条

相关代谢途径

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代谢反应

0 个相关的代谢反应过程信息。

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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。



文献列表

  • 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]
  • Krzysztof Łukawski, Tomasz Jakubus, Agnieszka Janowska, Grzegorz Raszewski, Stanisław J Czuczwar. Enalapril enhances the anticonvulsant activity of lamotrigine in the test of maximal electroshock. Pharmacological reports : PR. 2013; 65(4):1012-7. doi: 10.1016/s1734-1140(13)71083-1. [PMID: 24145096]
  • Krzysztof Łukawski, Tomasz Jakubus, Agnieszka Janowska, Stanisław J Czuczwar. Interactions between ACE inhibitors and classical antiepileptic drugs in the mouse maximal electroshock seizures. Pharmacology, biochemistry, and behavior. 2011 Nov; 100(1):152-6. doi: 10.1016/j.pbb.2011.06.030. [PMID: 21741989]
  • Filomila Kolocouri, Yannis Dotsikas, Constantinos Apostolou, Constantinos Kousoulos, Georgios-Stefanos Soumelas, Yannis L Loukas. Advantages of automation in plasma sample preparation prior to HPLC/MS/MS quantification: application to the determination of cilazapril and cilazaprilat in a bioequivalence study. Journal of AOAC International. 2011 May; 94(3):758-64. doi: . [PMID: 21797003]
  • Jae Il Shin, Beom Jin Lim, Pyung Kil Kim, Jae Seung Lee, Hyeon Joo Jeong, Ji Hong Kim. Effects of cyclosporin A therapy combined with steroids and angiotensin converting enzyme inhibitors on childhood IgA nephropathy. Journal of Korean medical science. 2010 May; 25(5):723-7. doi: 10.3346/jkms.2010.25.5.723. [PMID: 20436708]
  • Fs Tian, R Luo, Zq Zhao, Y Wu, Dj Ban. Blockade of the RAS increases plasma adiponectin in subjects with metabolic syndrome and enhances differentiation and adiponectin expression of human preadipocytes. Experimental and clinical endocrinology & diabetes : official journal, German Society of Endocrinology [and] German Diabetes Association. 2010 Apr; 118(4):258-65. doi: 10.1055/s-0029-1237706. [PMID: 19856251]
  • Aleksander Skoczylas, Marcin Adamczak, Jerzy Chudek, Andrzej Wiecek. Cilazapril increases plasma ghrelin concentration in obese patients with arterial hypertension. Endokrynologia Polska. 2010 Jan; 61(1):21-7. doi: NULL. [PMID: 20205100]
  • Shao-Sung Huang, Tao-Cheng Wu, Shing-Jong Lin, Jaw-Wen Chen. Combination of an ACE inhibitor and indapamide improves blood pressure control, but attenuates the beneficial effects of ACE inhibition on plasma adiponectin in patients with essential hypertension. Circulation journal : official journal of the Japanese Circulation Society. 2009 Dec; 73(12):2282-7. doi: 10.1253/circj.cj-09-0387. [PMID: 19789415]
  • Marcin Renke, Leszek Tylicki, Narcyz Knap, Przemyslaw Rutkowski, Alexander Neuwelt, Andriy Petranyuk, Wojciech Larczynski, Michał Wozniak, Boleslaw Rutkowski. High-dose angiotensin-converting enzyme inhibitor attenuates oxidative stress in patients with chronic kidney disease. Nephrology, dialysis, transplantation : official publication of the European Dialysis and Transplant Association - European Renal Association. 2009 Feb; 24(2):689-90. doi: 10.1093/ndt/gfn665. [PMID: 19054799]
  • Jicheng Lv, Hong Zhang, Yuqing Chen, Guangtao Li, Lei Jiang, Ajay K Singh, Haiyan Wang. Combination therapy of prednisone and ACE inhibitor versus ACE-inhibitor therapy alone in patients with IgA nephropathy: a randomized controlled trial. American journal of kidney diseases : the official journal of the National Kidney Foundation. 2009 Jan; 53(1):26-32. doi: 10.1053/j.ajkd.2008.07.029. [PMID: 18930568]
  • Giovanni F M Strippoli, Ausilia Maione, Francesco P Schena, G Tognoni, Jonathan C Craig. IgA nephropathy: a disease in search of a large-scale clinical trial to reliably inform practice. American journal of kidney diseases : the official journal of the National Kidney Foundation. 2009 Jan; 53(1):5-8. doi: 10.1053/j.ajkd.2008.10.035. [PMID: 19101396]
  • Marcin Renke, Leszek Tylicki, Narcyz Knap, Przemyslaw Rutkowski, Alexander Neuwelt, Wojciech Larczynski, Michal Wozniak, Boleslaw Rutkowski. Spironolactone attenuates oxidative stress in patients with chronic kidney disease. Hypertension (Dallas, Tex. : 1979). 2008 Nov; 52(5):e132-3; author reply e134. doi: 10.1161/hypertensionaha.108.120568. [PMID: 18824658]
  • Ilka Knütter, Claudia Wollesky, Gabor Kottra, Martin G Hahn, Wiebke Fischer, Katja Zebisch, Reinhard H H Neubert, Hannelore Daniel, Matthias Brandsch. Transport of angiotensin-converting enzyme inhibitors by H+/peptide transporters revisited. The Journal of pharmacology and experimental therapeutics. 2008 Nov; 327(2):432-41. doi: 10.1124/jpet.108.143339. [PMID: 18713951]
  • Nikola Radović, Snjezan Cuzić, Mladen Knotek. Effect of unilateral ureteral obstruction and anti-angiotensin II treatment on renal tubule and interstitial cell apoptosis in rats. Croatian medical journal. 2008 Oct; 49(5):600-7. doi: 10.3325/cmj.2008.5.600. [PMID: 18925693]
  • Leszek Tylicki, Przemysław Rutkowski, Marcin Renke, Wojciech Larczyński, Ewa Aleksandrowicz, Wiesława Lysiak-Szydlowska, Bolesław Rutkowski. Triple pharmacological blockade of the renin-angiotensin-aldosterone system in nondiabetic CKD: an open-label crossover randomized controlled trial. American journal of kidney diseases : the official journal of the National Kidney Foundation. 2008 Sep; 52(3):486-93. doi: 10.1053/j.ajkd.2008.02.297. [PMID: 18423812]
  • Shih-Hsien Sung, Tao-Cheng Wu, Shing-Jong Lin, Jaw-Wen Chen. Efficacy of a very-low-dose combination of perindopril and indapamide--preterax compared with cilazapril monotherapy in patients with inadequate blood pressure control--a randomized, double-blind, add-on study. Journal of the Chinese Medical Association : JCMA. 2008 May; 71(5):247-53. doi: 10.1016/s1726-4901(08)70115-1. [PMID: 18490229]
  • Alper Sonmez, Mahmut Ilker Yilmaz, Ahmet Korkmaz, Turgut Topal, Kayser Caglar, Ayper Kaya, Tayfun Eyileten, Mujdat Yenicesu, Yusuf Oguz, Seref Basal, Osman Metin Ipcioglu, Abdulgaffar Vural. Hyperbaric oxygen treatment augments the efficacy of cilazapril and simvastatin regimens in an experimental nephrotic syndrome model. Clinical and experimental nephrology. 2008 Apr; 12(2):110-118. doi: 10.1007/s10157-007-0017-2. [PMID: 18175058]
  • Eduardo Cantoni Rosa, Maria Tereza Zanella, Nárcia Elisa Bellucci Kohlmann, Sandra Roberta Gouveia Ferreira, Frida Liane Plavnik, Artur Beltrame Ribeiro, Osvaldo Kohlmann. Blood pressure and cardiorenal responses to antihypertensive therapy in obese women. Arquivos brasileiros de endocrinologia e metabologia. 2008 Feb; 52(1):65-75. doi: 10.1590/s0004-27302008000100010. [PMID: 18345398]
  • Seetha U Monrad, Paul D Killen, Marc R Anderson, Amanda Bradke, Mariana J Kaplan. The role of aldosterone blockade in murine lupus nephritis. Arthritis research & therapy. 2008; 10(1):R5. doi: 10.1186/ar2353. [PMID: 18197980]
  • Leszek Tylicki, Marcin Renke, Przemysław Rutkowski, Wojciech Larczyński, Ewa Aleksandrowicz, Wiesława Lysiak-Szydlowska, Bolesław Rutkowski. Dual blockade of the renin-angiotensin-aldosterone system with high-dose angiotensin-converting enzyme inhibitor for nephroprotection: an open, controlled, randomized study. Scandinavian journal of urology and nephrology. 2008; 42(4):381-8. doi: 10.1080/00365590801905943. [PMID: 19230172]
  • L Tylicki, P Rutkowski, M Renke, B Rutkowski. Addition of aldosterone receptor blocker to dual renin-angiotensin-aldosterone blockade leads to limitation of tubulointerstitial injury of kidney. Kidney international. 2007 Nov; 72(9):1164-5. doi: 10.1038/sj.ki.5002511. [PMID: 17943159]
  • Takashi Nagai, Makoto Imamura, Daishiro Kobayashi, Masatomo Mori. A case report of a diabetic nephropathy patient with cirrhotic ascites treated by peritoneal dialysis. Therapeutic apheresis and dialysis : official peer-reviewed journal of the International Society for Apheresis, the Japanese Society for Apheresis, the Japanese Society for Dialysis Therapy. 2007 Feb; 11(1):74-7. doi: 10.1111/j.1744-9987.2007.00464.x. [PMID: 17309579]
  • Heon-Woo Lee, Wan-Su Park, Sung-Hee Cho, Min-Hwan Kim, Ji-Hyung Seo, Yong-Won Kim, Sung-Su Kim, Yong-Sup Lee, Kyung-Tae Lee. A liquid chromatography/positive ion tandem mass spectrometry method for the determination of cilazapril and cilazaprilat in human plasma. Talanta. 2007 Jan; 71(1):62-7. doi: 10.1016/j.talanta.2006.03.020. [PMID: 19071268]
  • David G Levitt, Rik C Schoemaker. Human physiologically based pharmacokinetic model for ACE inhibitors: ramipril and ramiprilat. BMC clinical pharmacology. 2006 Jan; 6(?):1. doi: 10.1186/1472-6904-6-1. [PMID: 16398929]
  • Zhan Averbukh, Sylvia Berman, Shai Efrati, Elena Manevits, Rosa Rosenberg, Ela Malcev, Elena Galperin, Joshua Weissgarten. Blockade of renin-angiotensin system reduces QT dispersion and improves intracellular Ca/Mg status in hemodialysis patients. Nephron. Clinical practice. 2006; 104(4):c176-84. doi: 10.1159/000095853. [PMID: 17003569]
  • Wei-min Li, Wei Han, Zi-jun Liang, Dong-lai Wu, Yong-lin Huang, Shang-jin Cui, Yue Li. [Effect of Cilazapril on endothelial cell function and fibrinolysis system in the canine atrial fibrillation models]. Zhonghua xin xue guan bing za zhi. 2005 May; 33(5):469-72. doi: NULL. [PMID: 15932713]
  • Masaki Asai, Toshiaki Monkawa, Takeshi Marumo, Seiichi Fukuda, Mihoko Tsuji, Jun Yoshino, Hiroshi Kawachi, Fujio Shimizu, Matsuhiko Hayashi, Takao Saruta. Spironolactone in combination with cilazapril ameliorates proteinuria and renal interstitial fibrosis in rats with anti-Thy-1 irreversible nephritis. Hypertension research : official journal of the Japanese Society of Hypertension. 2004 Dec; 27(12):971-8. doi: 10.1291/hypres.27.971. [PMID: 15894838]
  • Ruan-Jian Ye, Quan-Ying He, Jun Gai, Ying Shang. [A prospective study on the cough mechanism induced by angiotensin-converting enzyme inhibitors in patients with hypertension]. Zhonghua jie he he hu xi za zhi = Zhonghua jiehe he huxi zazhi = Chinese journal of tuberculosis and respiratory diseases. 2004 Sep; 27(9):581-4. doi: NULL. [PMID: 15498266]
  • Chaim Yosefy, Eliahu Magen, Ada Kiselevich, Rita Priluk, Daniel London, Lior Volchek, Reuven J Viskoper. Rosiglitazone improves, while Glibenclamide worsens blood pressure control in treated hypertensive diabetic and dyslipidemic subjects via modulation of insulin resistance and sympathetic activity. Journal of cardiovascular pharmacology. 2004 Aug; 44(2):215-22. doi: 10.1097/00005344-200408000-00011. [PMID: 15243303]
  • R Rachmani, I Slavachevsky, M Amit, Z Levi, Y Kedar, M Berla, M Ravid. The effect of spironolactone, cilazapril and their combination on albuminuria in patients with hypertension and diabetic nephropathy is independent of blood pressure reduction: a randomized controlled study. Diabetic medicine : a journal of the British Diabetic Association. 2004 May; 21(5):471-5. doi: 10.1111/j.1464-5491.2004.01194.x. [PMID: 15089793]
  • Hiroto Matsuda, Koichi Hayashi, Shu Wakino, Eiji Kubota, Masanori Honda, Hirobumi Tokuyama, Ichiro Takamatsu, Satoru Tatematsu, Takao Saruta. Role of endothelium-derived hyperpolarizing factor in ACE inhibitor-induced renal vasodilation in vivo. Hypertension (Dallas, Tex. : 1979). 2004 Mar; 43(3):603-9. doi: 10.1161/01.hyp.0000118053.42262.71. [PMID: 14769805]
  • Koh-Ichi Sugimoto, Shuichi Tsuruoka, Akio Fujimura. Sustained plasma fibrinogen elevation in subtotal nephrectomized rats: effect of cilazapril, an angiotensin-converting enzyme inhibitor. Journal of pharmacological sciences. 2004 Jan; 94(1):67-72. doi: 10.1254/jphs.94.67. [PMID: 14745120]
  • Hui Lin, Songmin Huang, Xuhua Mi, Zhaohui Sha. [Effects of cilazapril on the expression of vascular endothelial growth factor and intercellular adhesion molecule-1 in diabetic rat glomeruli]. Sichuan da xue xue bao. Yi xue ban = Journal of Sichuan University. Medical science edition. 2003 Oct; 34(4):694-7. doi: NULL. [PMID: 14619584]
  • Osamah Hussein, Arman Radan, Viskoper Reuven. Effect of cilazapril with or without low dose thiazide on LDL peroxidation in [correction of peroxidationin] hypertensive patients. American journal of hypertension. 2003 Sep; 16(9 Pt 1):734-8. doi: 10.1016/s0895-7061(03)00977-4. [PMID: 12944031]
  • Su-min Yang, Quan-ying He, Yi-de Miao. [The relationship between polymorphism of angiotensin converting enzyme gene and cough caused by angiotensin converting enzyme inhibitors]. Zhonghua jie he he hu xi za zhi = Zhonghua jiehe he huxi zazhi = Chinese journal of tuberculosis and respiratory diseases. 2003 Apr; 26(4):203-5. doi: NULL. [PMID: 12901825]
  • Noboru Fukuda, Mari Nakayama, Teng Jian, Chikara Satoh, Tomohiro Nakayama, Masayoshi Soma, Yoichi Izumi, Katsuo Kanmatsuse. Leukocyte angiotensin II levels inpatients with essential hypertension:relation to insulin resistance. American journal of hypertension. 2003 Feb; 16(2):129-34. doi: 10.1016/s0895-7061(02)03145-x. [PMID: 12559679]
  • Shuei-Liong Lin, Yung-Ming Chen, Chiang-Ting Chien, Wen-Chih Chiang, Chien-Chen Tsai, Tun-Jun Tsai. Pentoxifylline attenuated the renal disease progression in rats with remnant kidney. Journal of the American Society of Nephrology : JASN. 2002 Dec; 13(12):2916-29. doi: 10.1097/01.asn.0000034909.10994.8a. [PMID: 12444210]
  • Islam Khan, Khaled K Al-Qattan, Majed A Alnaqeeb, Muslim Ali. Altered expression of Na(+)/H(+) exchanger isoforms 1 and 3 in clipped and unclipped kidneys of a 2-kidney-1-clip Goldblatt model of hypertension. Nephron. 2002 Oct; 92(2):346-55. doi: 10.1159/000063308. [PMID: 12218313]
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  • Imran Ahmed Bhutto, Zhong-Yang Lu, Yumiko Takami, Tsugio Amemiya. Retinal and choroidal vasculature in rats with spontaneous diabetes type 2 treated with the angiotensin-converting enzyme inhibitor cilazapril: corrosion cast and electron-microscopic study. Ophthalmic research. 2002 Jul; 34(4):220-31. doi: 10.1159/000063877. [PMID: 12297695]
  • Norio Komai, Mitsuru Ohishi, Ryuichi Morishita, Atsushi Moriguchi, Masaharu Kaibe, Keiko Matsumoto, Hiromi Rakugi, Jitsuo Higaki, Toshio Ogihara. Serum hepatocyte growth factor concentration is correlated with the forearm vasodilator response in hypertensive patients. American journal of hypertension. 2002 Jun; 15(6):499-506. doi: 10.1016/s0895-7061(02)02274-4. [PMID: 12074350]
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