Benazeprilat (BioDeep_00000014099)

 

Secondary id: BioDeep_00000448345

human metabolite Endogenous blood metabolite


代谢物信息卡片


(2S)-2-{[(3S)-1-(carboxymethyl)-2-oxo-2,3,4,5-tetrahydro-1H-1-benzazepin-3-yl]amino}-4-phenylbutanoic acid

化学式: C22H24N2O5 (396.1685134)
中文名称: 苯那普利拉
谱图信息: 最多检出来源 Homo sapiens(blood) 37.76%

分子结构信息

SMILES: C1CC2=CC=CC=C2N(C(=O)C1NC(CCC3=CC=CC=C3)C(=O)O)CC(=O)O
InChI: InChI=1S/C22H24N2O5/c25-20(26)14-24-19-9-5-4-8-16(19)11-13-17(21(24)27)23-18(22(28)29)12-10-15-6-2-1-3-7-15/h1-9,17-18,23H,10-14H2,(H,25,26)(H,28,29)/t17-,18-/m0/s1

描述信息

Benazeprilat is a metabolite of benazepril. Benazepril, brand name Lotensin, is a medication used to treat high blood pressure, congestive heart failure, and chronic renal failure. Upon cleavage of its ester group by the liver, benazepril is converted into its active form benazeprilat, a non-sulfhydryl angiotensin-converting enzyme (ACE) inhibitor. (Wikipedia)
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

11 个代谢物同义名

(2S)-2-{[(3S)-1-(carboxymethyl)-2-oxo-2,3,4,5-tetrahydro-1H-1-benzazepin-3-yl]amino}-4-phenylbutanoic acid; (3S)-3-(((1S)-1-Carboxy-3-phenylpropyl)amino)-2,3,4,5-tetrahydro-2-oxo-1H-1-benzazepine-1-acetic acid; (3S)-3-(((1S)-1-Carboxy-3-phenylpropyl)amino)-2,3,4,5-tetrahydro-2-oxo-1H-1-benzazepine-1-acetate; Benazepril diacid; Benazeprilic acid; Benazeprilatum; Benazeprilate; Benezaprilat; benazeprilat; CHEMBL80906; CGS 14831



数据库引用编号

14 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

2 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(2)

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

  • Juan Manuel Serrano-Rodríguez, Manuel Gómez-Díez, María Esgueva, Cristina Castejón-Riber, Antonio Mena-Bravo, Feliciano Priego-Capote, Nahúm Ayala, Juan Manuel Serrano Caballero, Ana Muñoz. Pharmacokinetic/pharmacodynamic modeling of benazepril and benazeprilat after administration of intravenous and oral doses of benazepril in healthy horses. Research in veterinary science. 2017 Oct; 114(?):117-122. doi: 10.1016/j.rvsc.2017.03.016. [PMID: 28371693]
  • Mamdouh R Rezk, Kamal A Badr. Development, optimization and validation of a highly sensitive UPLC-ESI-MS/MS method for simultaneous quantification of amlodipine, benazeprile and benazeprilat in human plasma: application to a bioequivalence study. Journal of pharmaceutical and biomedical analysis. 2014 Sep; 98(?):1-8. doi: 10.1016/j.jpba.2014.05.005. [PMID: 24863555]
  • Hua-Ling Pan, Li-Shan Lin, Jue-Fang Ding, Xiao-Yan Chen, Da-Fang Zhong. [Simultaneous determination of amlodipine, benazepril and benazeprilat in human plasma by LC-HESI/MS/MS method]. Yao xue xue bao = Acta pharmaceutica Sinica. 2014 Jan; 49(1):95-100. doi: NULL. [PMID: 24783513]
  • K Kelers, J L Devi, G A Anderson, P Zahra, J H Vine, T Whittem. Bioequivalence of a new liquid formulation of benazepril compared with the reference tablet product. Australian veterinary journal. 2013 Aug; 91(8):312-9. doi: 10.1111/avj.12080. [PMID: 23889096]
  • Keguang Chen, Jing Zhang, Sha Liu, Dujuan Zhang, Yanni Teng, Chunmin Wei, Benjie Wang, Xiaoyan Liu, Guiyan Yuan, Rui Zhang, Wenjing Zhao, Ruichen Guo. Simultaneous determination of lercanidipine, benazepril and benazeprilat in plasma by LC-MS/MS and its application to a toxicokinetics study. Journal of chromatography. B, Analytical technologies in the biomedical and life sciences. 2012 Jun; 899(?):1-7. doi: 10.1016/j.jchromb.2012.04.014. [PMID: 22622066]
  • Vivencio Barrios, Carlos Escobar. Antihypertensive and organ-protective effects of benazepril. Expert review of cardiovascular therapy. 2010 Dec; 8(12):1653-71. doi: 10.1586/erc.10.159. [PMID: 21108548]
  • Xue-Ding Wang, Eli Chan, Xiao Chen, Xiao-Xing Liao, Cheng Tang, Zhi-Wei Zhou, Min Huang, Shu-Feng Zhou. Simultaneous and rapid quantitation of benazepril and benazeprilat in human plasma by high performance liquid chromatography with ultraviolet detection. Journal of pharmaceutical and biomedical analysis. 2007 May; 44(1):224-30. doi: 10.1016/j.jpba.2007.01.009. [PMID: 17289327]
  • Ariadni Vonaparti, Michael Kazanis, Irene Panderi. Development and validation of a liquid chromatographic/electrospray ionization mass spectrometric method for the determination of benazepril, benazeprilat and hydrochlorothiazide in human plasma. Journal of mass spectrometry : JMS. 2006 May; 41(5):593-605. doi: 10.1002/jms.1014. [PMID: 16541390]
  • Weitao Xiao, Bo Chen, Shouzhuo Yao, Zeneng Cheng. Simultaneous determination of benazepril hydrochloride and benazeprilat in plasma by high-performance liquid chromatography/electrospray-mass spectrometry. Journal of chromatography. B, Analytical technologies in the biomedical and life sciences. 2005 Jan; 814(2):303-8. doi: 10.1016/j.jchromb.2004.10.047. [PMID: 15639452]
  • J N King, M Maurer, P L Toutain. Pharmacokinetic/pharmacodynamic modelling of the disposition and effect of benazepril and benazeprilat in cats. Journal of veterinary pharmacology and therapeutics. 2003 Jun; 26(3):213-24. doi: 10.1046/j.1365-2885.2003.00468.x. [PMID: 12755906]
  • Hitoshi Kitagawa, Yasunori Ohba, Yasuhito Kuwahara, Rieko Ohne, Masahiro Kondo, Masakazu Nakano, Yoshihide Sasaki, Katsuya Kitoh. An angiotensin converting enzyme inhibitor, benazepril can be transformed to an active metabolite, benazeprilat, by the liver of dogs with ascitic pulmonary heartworm disease. The Journal of veterinary medical science. 2003 Jun; 65(6):701-6. doi: 10.1292/jvms.65.701. [PMID: 12867730]
  • F Pommier, F Boschet, G Gosset. Quantitative determination of benazepril and benazeprilat in human plasma by gas chromatography-mass spectrometry using automated 96-well disk plate solid-phase extraction for sample preparation. Journal of chromatography. B, Analytical technologies in the biomedical and life sciences. 2003 Jan; 783(1):199-205. doi: 10.1016/s1570-0232(02)00660-8. [PMID: 12450539]
  • J N King, G Strehlau, J Wernsing, S A Brown. Effect of renal insufficiency on the pharmacokinetics and pharmacodynamics of benazepril in cats. Journal of veterinary pharmacology and therapeutics. 2002 Oct; 25(5):371-8. doi: 10.1046/j.1365-2885.2002.00427.x. [PMID: 12423228]
  • P L Toutain, H P Lefebvre, J N King. Benazeprilat disposition and effect in dogs revisited with a pharmacokinetic/pharmacodynamic modeling approach. The Journal of pharmacology and experimental therapeutics. 2000 Mar; 292(3):1087-93. doi: NULL. [PMID: 10688627]
  • H Kitagawa, T Eguchi, K Kitoh, Y Ohba, M Kondo, M Nakano, Y Sasaki. Plasma concentrations of an angiotensin-converting enzyme inhibitor, benazepril, and its active metabolite, benazeprilat, after repeated administrations of benazepril in dogs with experimental kidney impairment. The Journal of veterinary medical science. 2000 Feb; 62(2):179-85. doi: 10.1292/jvms.62.179. [PMID: 10720188]
  • J N King, E Humbert-Droz, M Maurer. Plasma angiotensin converting enzyme activity and pharmacokinetics of benazepril and benazeprilat in cats after single and repeated oral administration of benazepril.HCl. Journal of veterinary pharmacology and therapeutics. 1999 Dec; 22(6):360-7. doi: 10.1046/j.1365-2885.1999.00230.x. [PMID: 10651464]
  • A Virdis, L Ghiadoni, M Marzilli, E Orsini, S Favilla, P Duranti, S Taddei, P Marraccini, A Salvetti. Adenosine causes the release of active renin and angiotensin II in the coronary circulation of patients with essential hypertension. Journal of the American College of Cardiology. 1999 May; 33(6):1677-84. doi: 10.1016/s0735-1097(99)00078-9. [PMID: 10334442]
  • R L Webb, B W Barclay, A E Navarrete, N J Wosu, P Sahota. Protective effects of valsartan and benazeprilat in salt-loaded stroke-prone spontaneously hypertensive rats. Clinical and experimental hypertension (New York, N.Y. : 1993). 1998 Oct; 20(7):775-93. doi: 10.3109/10641969809052119. [PMID: 9764721]
  • R S Krombach, M J Clair, J W Hendrick, W V Houck, J L Zellner, S B Kribbs, S Whitebread, R Mukherjee, M de Gasparo, F G Spinale. Angiotensin converting enzyme inhibition, AT1 receptor inhibition, and combination therapy with pacing induced heart failure: effects on left ventricular performance and regional blood flow patterns. Cardiovascular research. 1998 Jun; 38(3):631-45. doi: 10.1016/s0008-6363(98)00050-9. [PMID: 9747431]
  • F G Spinale, M de Gasparo, S Whitebread, L Hebbar, M J Clair, D M Melton, R S Krombach, R Mukherjee, J P Iannini, S J O. Modulation of the renin-angiotensin pathway through enzyme inhibition and specific receptor blockade in pacing-induced heart failure: I. Effects on left ventricular performance and neurohormonal systems. Circulation. 1997 Oct; 96(7):2385-96. doi: 10.1161/01.cir.96.7.2385. [PMID: 9337215]
  • J N King, M Maurer, C A Morrison, C Mauron, G Kaiser. Pharmacokinetics of the angiotensin-converting-enzyme inhibitor, benazepril, and its active metabolite, benazeprilat, in dog. Xenobiotica; the fate of foreign compounds in biological systems. 1997 Aug; 27(8):819-29. doi: 10.1080/004982597240181. [PMID: 9293618]
  • C A Fink, Y Qiao, C J Berry, Y Sakane, R D Ghai, A J Trapani. New alpha-thiol dipeptide dual inhibitors of angiotensin-I converting enzyme and neutral endopeptidase EC 3.4.24.11. Journal of medicinal chemistry. 1995 Dec; 38(26):5023-30. doi: 10.1021/jm00026a009. [PMID: 8544178]
  • J N King, C Mauron, G Kaiser. Pharmacokinetics of the active metabolite of benazepril, benazeprilat, and inhibition of plasma angiotensin-converting enzyme activity after single and repeated administrations to dogs. American journal of veterinary research. 1995 Dec; 56(12):1620-8. doi: NULL. [PMID: 8599524]
  • N J Samani, F Cumin, M Kelly, J M Wood. Expression of components of the RAS during prolonged blockade at different levels in primates. The American journal of physiology. 1994 Oct; 267(4 Pt 1):E612-9. doi: 10.1152/ajpendo.1994.267.4.e612. [PMID: 7943312]
  • A Sioufi, F Pommier, N Gauducheau, J Godbillon, L Choi, V John. The absence of a pharmacokinetic interaction between aspirin and the angiotensin-converting enzyme inhibitor benazepril in healthy volunteers. Biopharmaceutics & drug disposition. 1994 Aug; 15(6):451-61. doi: 10.1002/bdd.2510150603. [PMID: 7993983]
  • J L Stanton, D M Sperbeck, A J Trapani, D Cote, Y Sakane, C J Berry, R D Ghai. Heterocyclic lactam derivatives as dual angiotensin converting enzyme and neutral endopeptidase 24.11 inhibitors. Journal of medicinal chemistry. 1993 Nov; 36(24):3829-33. doi: 10.1021/jm00076a010. [PMID: 8254612]
  • J R Wade, D M Hughes, A W Kelman, C A Howie, P A Meredith. A novel statistical approach for the comparison of analytical methods to measure angiotensin converting enzyme activity, enalaprilat, and benazeprilat. Journal of pharmaceutical sciences. 1993 May; 82(5):471-4. doi: 10.1002/jps.2600820508. [PMID: 8395597]
  • J H Schwieler, T Kahan, J Nussberger, P Hjemdahl. Converting enzyme inhibition modulates sympathetic neurotransmission in vivo via multiple mechanisms. The American journal of physiology. 1993 Apr; 264(4 Pt 1):E631-7. doi: 10.1152/ajpendo.1993.264.4.e631. [PMID: 8386457]
  • C Schweizer, G Kaiser, W Dieterle, J Mann. Pharmacokinetics and pharmacodynamics of benazepril hydrochloride in patients with major proteinuria. European journal of clinical pharmacology. 1993; 44(5):463-6. doi: 10.1007/bf00315544. [PMID: 8359184]
  • J H Schwieler, T Kahan, J Nussberger, M C Johansson, P Hjemdahl. Influence of angiotensin II, alpha- and beta-adrenoceptors on peripheral noradrenergic neurotransmission in canine gracilis muscle in vivo. Acta physiologica Scandinavica. 1992 Aug; 145(4):333-43. doi: 10.1111/j.1748-1716.1992.tb09373.x. [PMID: 1326853]
  • B Bunkenburg, C Schnell, H P Baum, F Cumin, J M Wood. Prolonged angiotensin II antagonism in spontaneously hypertensive rats. Hemodynamic and biochemical consequences. Hypertension (Dallas, Tex. : 1979). 1991 Sep; 18(3):278-88. doi: 10.1161/01.hyp.18.3.278. [PMID: 1889842]
  • S LeRoy, B Berner. Steady-state pharmacokinetics and pharmacodynamics of benazeprilat in spontaneously hypertensive rats (SHR) and Wistar-Kyoto (WKY) rats. Pharmaceutical research. 1991 Jul; 8(7):883-7. doi: 10.1023/a:1015803529013. [PMID: 1924139]
  • F Waldmeier, G Kaiser, R Ackermann, J W Faigle, J Wagner, A Barner, K C Lasseter. The disposition of [14C]-labelled benazepril HCl in normal adult volunteers after single and repeated oral dose. Xenobiotica; the fate of foreign compounds in biological systems. 1991 Feb; 21(2):251-61. doi: 10.3109/00498259109039467. [PMID: 2058180]
  • G Kaiser, R Ackermann, H P Gschwind, I M James, D Sprengers, N McIntyre, A Defalco, I B Holmes. The influence of hepatic cirrhosis on the pharmacokinetics of benazepril hydrochloride. Biopharmaceutics & drug disposition. 1990 Dec; 11(9):753-64. doi: 10.1002/bdd.2510110903. [PMID: 2271751]
  • R A Santos, J M Brum, K B Brosnihan, C M Ferrario. The renin-angiotensin system during acute myocardial ischemia in dogs. Hypertension (Dallas, Tex. : 1979). 1990 Feb; 15(2 Suppl):I121-7. doi: 10.1161/01.hyp.15.2_suppl.i121. [PMID: 2404854]
  • M F Rousseau, O Gurné, C van Eyll, C R Benedict, H Pouleur. Effects of benazeprilat on left ventricular systolic and diastolic function and neurohumoral status in patients with ischemic heart disease. Circulation. 1990 Feb; 81(2 Suppl):III123-9. doi: NULL. [PMID: 2297877]
  • G Kaiser, R Ackermann, S Brechbühler, W Dieterle. Pharmacokinetics of the angiotensin converting enzyme inhibitor benazepril.HCl (CGS 14 824 A) in healthy volunteers after single and repeated administration. Biopharmaceutics & drug disposition. 1989 Jul; 10(4):365-76. doi: 10.1002/bdd.2510100404. [PMID: 2758102]
  • G Kaiser, R Ackermann, A Sioufi. Pharmacokinetics of a new angiotensin-converting enzyme inhibitor, benazepril hydrochloride, in special populations. American heart journal. 1989 Mar; 117(3):746-51. doi: 10.1016/0002-8703(89)90765-5. [PMID: 2919553]
  • F Waldmeier, K Schmid. Disposition of [14C]-benazepril hydrochloride in rat, dog and baboon. Absorption, distribution, kinetics, biotransformation and excretion. Arzneimittel-Forschung. 1989 Jan; 39(1):62-7. doi: NULL. [PMID: 2719745]
  • A Sioufi, F Pommier, G Kaiser, J P Dubois. Determination of benazepril, a new angiotensin-converting enzyme inhibitor, and its active metabolite, benazeprilat, in plasma and urine by capillary gas chromatography-mass-selective detection. Journal of chromatography. 1988 Dec; 434(1):239-46. doi: 10.1016/0378-4347(88)80082-3. [PMID: 3243821]
  • P Graf, F Frueh, K Schmid. Determination of the angiotensin converting enzyme inhibitor benazeprilat in plasma and urine by an enzymic method. Journal of chromatography. 1988 Mar; 425(2):353-61. doi: 10.1016/0378-4347(88)80039-2. [PMID: 2836452]
  • P Reydel-Bax, E Redalieu, A Rakhit. Direct determination of angiotensin-converting enzyme inhibitors in plasma by radioenzymatic assay. Clinical chemistry. 1987 Apr; 33(4):549-53. doi: 10.1093/clinchem/33.4.549. [PMID: 3030582]
  • J M Wood, R A Jobber, H P Baum, K G Hofbauer. Comparison of chronic inhibition of renin and converting enzyme in the marmoset. Clinical and experimental hypertension. Part A, Theory and practice. 1987; 9(2-3):337-43. doi: 10.3109/10641968709164193. [PMID: 3038392]