Ebrotidine (BioDeep_00000624669)

代谢物信息卡片

N-[(4-bromobenzene)sulfonyl]-N-(2-{[(2-carbamimidamido-1,3-thiazol-4-yl)methyl]sulfanyl}ethyl)methanimidamide

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

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

3 个代谢物同义名

Ebrotidine; N-[(4-bromobenzene)sulfonyl]-N-(2-{[(2-carbamimidamido-1,3-thiazol-4-yl)methyl]sulfanyl}ethyl)methanimidamide; FI3542

数据库引用编号

6 个数据库交叉引用编号

ChEBI: CHEBI:135774
PubChem: 65869
Metlin: METLIN96163
ChEMBL: CHEMBL1742471
CAS: 100981-43-9
medchemexpress: HY-15538

分类词条

代谢反应

0 个相关的代谢反应过程信息。

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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]