Ebrotidine (BioDeep_00000036542)

   

human metabolite


代谢物信息卡片


4-Bromo-N-(((2-(((-((diaminomethylene)amino)-4-thiazolyl)methyl)thio)ethyl)amino)methylene)benzenesulfonamide

化学式: C14H17BrN6O2S3 (475.9758442)
中文名称: 乙溴替丁
谱图信息: 最多检出来源 () 0%

分子结构信息

SMILES: C1=CC(=CC=C1S(=O)(=O)NC=NCCSCC2=CSC(=N2)N=C(N)N)Br
InChI: InChI=1S/C14H17BrN6O2S3/c15-10-1-3-12(4-2-10)26(22,23)19-9-18-5-6-24-7-11-8-25-14(20-11)21-13(16)17/h1-4,8-9H,5-7H2,(H,18,19)(H4,16,17,20,21)

描述信息

Ebrotidine is an H2 receptor antagonist with gastroprotective activity against ethanol-, aspirin- or stress-induced gastric mucosal damage. The antisecretory properties of ebrotidine are similar to those of ranitidine, and approximately 10-fold greater than those of cimetidine. Ebrotidine has anti-Helicobacter pylori activity via inhibition of the urease enzyme and the proteolytic and mucolytic activities of the bacterium. However, its activity is synergistic with a number of antibacterial agents. Ebrotidine counteracts the inhibitory effects of H. pylori lipo-polysaccharides.
C78276 - Agent Affecting Digestive System or Metabolism > C29701 - Anti-ulcer Agent > C29702 - Histamine-2 Receptor Antagonist
D018377 - Neurotransmitter Agents > D018494 - Histamine Agents > D006633 - Histamine Antagonists
D005765 - Gastrointestinal Agents > D000897 - Anti-Ulcer Agents
Ebrotidine(FI 3542) is a competitive H2-receptor antagonist (Ki= 127.5 nM) with a potent antisecretory activity and evidenced gastroprotection. IC50 Value: 127.5 nM (Ki)[1]; 0.21mg/kg (ED50, histamine- stimulated acid secretion) [2] Target: H2 receptor in vitro: Ebrotidine displaced 3H-thiotidine specific binding to histamine H2-receptors (Ki: 127.5 nmol/l), showing a higher affinity (p < 0.05) than ranitidine (Ki: 190.0 nmol/l) and cimetidine (Ki: 246.1 nmol/l) [1]. in vivo: Following intravenous administration to rats, ebrotidine inhibited histamine- and pentagastrin-stimulated acid secretion in a dose-dependent manner, ED50 being 0.21 and 0.44 mg/kg, respectively [2]. The mean number of gastric erosions seen at endoscopy after treatment with ebrotidine plus ASA (2.0 +/- 0.3) was significantly lower than that after placebo plus ASA (3.7 +/- 0.2). This reduction in lesion core by ebrotidine was accompanied by a significant increase in gastric blood flow (by 15\% in corpus and 26\% in antrum), by a rise in transmucosal potential difference (by 12\%), and by a decrease of mucosal microbleeding [3]. Results of macroscopic assessment revealed that ebrotidine at doses of 50mg and higher/kg body weight effectively prevented mucosal injury, and that the maximal protective effect was achieved by 1h. Physicochemical analysis established that ebrotidine evoked 30\% increase in mucus gel dimension, and showed 20\% increase in phospholipids, and the content of sulfo- (18\%) and sialomucins (21\%) [4].

同义名列表

5 个代谢物同义名

4-Bromo-N-(((2-(((-((diaminomethylene)amino)-4-thiazolyl)methyl)thio)ethyl)amino)methylene)benzenesulfonamide; N-(4-Bromobenzenesulphonyl)-n-(2-{[(2-carbamimidamido-1,3-thiazol-4-yl)methyl]sulphanyl}ethyl)methanimidamide; N-(4-bromobenzenesulfonyl)-N-(2-{[(2-carbamimidamido-1,3-thiazol-4-yl)methyl]sulfanyl}ethyl)methanimidamide; Ebrotidine; FI3542



数据库引用编号

8 个数据库交叉引用编号

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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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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

  • S Sentellas, L Puignou, M T Galceran. Determination of ebrotidine and its metabolites by micellar electrokinetic capillary chromatography. Journal of chromatography. A. 2002 Nov; 976(1-2):221-7. doi: 10.1016/s0021-9673(02)01163-9. [PMID: 12462613]
  • S Sentellas, J Saurina, S Hernández-Cassou, M T Galceran, L Puignou. Determination of ebrotidine metabolites in overlapping peaks from capillary zone electrophoresis using chemometric methods. Electrophoresis. 2001 Jan; 22(1):71-6. doi: 10.1002/1522-2683(200101)22:1<71::aid-elps71>3.0.co;2-0. [PMID: 11197182]
  • A Romero, F Gómez, F Villamayor, A Ballesta, A Sacristán, J A Ortiz. Comparative study of plasma gastrin levels in rats after two months of ebrotidine administration. Arzneimittel-Forschung. 1997 Apr; 47(4A):524-7. doi: NULL. [PMID: 9205757]
  • D Palop, J Agut, M Márquez, L Conejo, A Sacristán, J A Ortiz. Histamine H2-receptor antagonist action of ebrotidine. Effects on gastric acid secretion, gastrin levels and NSAID-induced gastrotoxicity in the rat. Arzneimittel-Forschung. 1997 Apr; 47(4A):439-46. doi: NULL. [PMID: 9205740]
  • M Farré, P N Roset, J M Badenas, B Ugena, M Márquez, C Albet, E Herrero, J A Ortiz. Tolerability and pharmacokinetics of ebrotidine in healthy subjects given single and repeated oral doses. Arzneimittel-Forschung. 1997 Apr; 47(4A):528-30. doi: NULL. [PMID: 9205758]
  • C Albet, J A Pérez, E Rozman, M Márquez, E Herrero, J A Ortiz. Pharmacokinetics of ebrotidine in healthy volunteers. A summary. Arzneimittel-Forschung. 1997 Apr; 47(4A):535-9. doi: NULL. [PMID: 9205760]
  • P C Konturek, T Brzozowski, S I Konturek, M Márquez, J Torres, J A Ortiz. Studies on the cytoprotective and antisecretory activity of ebrotidine. A review. Arzneimittel-Forschung. 1997 Apr; 47(4A):578-89. doi: NULL. [PMID: 9205769]
  • A Romero, A Rives, M T Grau, F Villamayor, A Sacristán, J A Ortiz. Carcinogenicity studies on ebrotidine. Arzneimittel-Forschung. 1997 Apr; 47(4A):515-9. doi: NULL. [PMID: 9205755]
  • E Rozman, C Albet, A Sacristán, J A Ortiz. Metabolism of ebrotidine. A review. Arzneimittel-Forschung. 1997 Apr; 47(4A):486-9. doi: NULL. [PMID: 9205749]
  • J Frías, C Esteban, A J Carcas, P Sánchez-García, C Albet, J Torres, M Márquez, J A Ortiz. Pharmacokinetic study of ebrotidine administered in multiple doses to healthy volunteers for 4 days. Arzneimittel-Forschung. 1997 Apr; 47(4A):531-4. doi: NULL. [PMID: 9205759]
  • A Gabryelewicz, A Czajkowski, D Skrodzka, K Marlicz, F Luca de Tena, M Aldeguer, C Chantar, M Márquez, J Torres, J A Ortiz. Comparison of the efficacy and safety of ebrotidine in the treatment of duodenal ulcer. A multicentre, double-blind, placebo-controlled phase II study. Arzneimittel-Forschung. 1997 Apr; 47(4A):545-50. doi: NULL. [PMID: 9205762]
  • E Rozman, M T Galcerán, C Albet. Determination of ebrotidine and its metabolites in human urine by reversed-phase ion-pair high-performance liquid chromatography. Journal of chromatography. B, Biomedical sciences and applications. 1997 Jan; 688(1):107-15. doi: 10.1016/s0378-4347(97)88062-0. [PMID: 9029320]
  • E Rozman, M T Galceran, L Anglada, C Albet. Investigation of the metabolism of ebrotidine in human urine by liquid chromatography-atmospheric pressure chemical ionization mass spectrometry. Drug metabolism and disposition: the biological fate of chemicals. 1995 Sep; 23(9):976-81. doi: NULL. [PMID: 8565788]
  • A Gabryelewicz, S J Konturek, E Butruk, J Dzieniszewski, K Marlicz, A Nowak, J Torres, M Marquez, J A Ortiz. Efficacy and safety of ebrotidine compared with ranitidine in patients with duodenal ulcer. European journal of gastroenterology & hepatology. 1995 Apr; 7(4):361-6. doi: NULL. [PMID: 7600143]
  • E Rozman, M T Galcerán, C Albet. Ebrotidine and its metabolites studied by mass spectrometry with electrospray ionization. Comparison of tandem and in-source fragmentation... Rapid communications in mass spectrometry : RCM. 1995; 9(15):1492-8. doi: 10.1002/rcm.1290091506. [PMID: 8652876]
  • E Rozman, M T Galcerán, L Anglada, C Albet. Metabolites of ebrotidine, a new H2-receptor antagonist, in human urine. Journal of pharmaceutical sciences. 1994 Feb; 83(2):252-4. doi: 10.1002/jps.2600830228. [PMID: 7909553]
  • B L Slomiany, J Piotrowski, H Mojtahed, A Slomiany. Ebrotidine effect on the proteolytic and lipolytic activities of Helicobacter pylori. General pharmacology. 1992 Mar; 23(2):203-6. doi: 10.1016/0306-3623(92)90010-h. [PMID: 1639232]
  • T Brzozowski, J Majka, S J Konturek. Gastroprotective and ulcer-healing activities of a new H2-receptor antagonist: ebrotidine. Digestion. 1992; 51(1):27-36. doi: 10.1159/000200872. [PMID: 1353465]