52378-40-2

Usage

Uses

Used in Pharmaceutical Industry:
N-Cyano-N-[2-(5-methylimidazole-4-methylthio)ethyl]-S-methyl isothiourea is used as a reference compound for the identification and quantification of impurities in the manufacturing process of Cimetidine (C441650). As a related impurity, it helps ensure the quality, safety, and efficacy of the final drug product by providing a benchmark for purity and consistency.
Used in Research and Development:
In the field of pharmaceutical research and development, N-Cyano-N-[2-(5-methylimidazole-4-methylthio)ethyl]-S-methyl isothiourea serves as a valuable tool for studying the structure-activity relationship of histamine H2-receptor antagonists. This understanding can lead to the design and development of new, more effective medications with improved pharmacological properties.
Used in Quality Control:
N-Cyano-N-[2-(5-methylimidazole-4-methylthio)ethyl]-S-methyl isothiourea is used as a reference material in the quality control of Cimetidine (C441650) and its formulations. It aids in the development and validation of analytical methods, such as high-performance liquid chromatography (HPLC) and mass spectrometry, to accurately measure and control the levels of impurities in the final drug product.
Used in the Preparation of Histamine H2 Receptor Antagonists:
Although N-Cyano-N-[2-(5-methylimidazole-4-methylthio)ethyl]-S-methyl isothiourea is an impurity, it may also be used in the synthesis and preparation of novel histamine H2 receptor antagonists. By studying its chemical properties and interactions, researchers can gain insights into the design of new compounds with potential therapeutic applications in the treatment of conditions such as peptic ulcers, gastroesophageal reflux disease (GERD), and other acid-related disorders.

InChI:InChI=1/C10H15N5S2/c1-8-9(15-7-14-8)5-17-4-3-12-10(16-2)13-6-11/h7H,3-5H2,1-2H3,(H,12,13)(H,14,15)

Upstream product

• 38603-72-4 2-[((5-methyl-1H-imidazol-4-yl)methyl)thio]ethanamine dihydrochloride 
• 10191-60-3 dimethyl N-cyanodithioiminocarbonate 
• 38585-67-0 4-{[(2-aminoethyl)thio]methyl}-5-methylimidazole 
• 38585-67-0 4-methyl-5-<(2-aminoethyl)-thiomethyl>-imidazole 

Downstream Products

• 52378-43-5 N-Cyano-N'-<2-<(5(4)-methyl-4(5)-imidazolyl)-methylthio>-ethyl>-guanidin 
• 51481-61-9 Cimetidine 
• 270574-63-5 cimetidine 
• 52378-43-5 N-Cyano-N'-[2-((4-methyl-5-imidazolyl)methylthio)ethyl]-guanidine 
• 51481-61-9 Cimetidine 

Relevant academic research and scientific papers

Importance of the azole moiety of cimetidine derivatives for the inhibition of human multidrug and toxin extrusion transporter 1 (hmate1)

Herein, we describe the design and synthesis of cimetidine analogs, as well as their inhibitory activity toward the human multidrug and toxin extrusion transporter 1 (hMATE1), which is related to nephrotoxicity of drugs. Cimetidine is the histamine H2-receptor antagonist, but also inhibits hMATE1, which is known to cause renal impairment. We designed and synthesized cimetidine analogs to evaluate hMATE1 inhibitory activity to reveal whether the analogs could reduce the inhibition of hMATE1. The results showed that all analogs with an unsubstituted guanidino group exhibited hMATE1 inhibitory activity. On the other hand, there was a clear difference in the hMATE1 inhibitory activity for the other compounds. That is, compounds with a methylimidazole ring exhibited hMATE1 inhibition, while compounds with a phenyl ring did not. The results suggest that the ability to form hydrogen bonds at the azole moiety is strongly involved in the hMATE1 inhibition.

Isohistamines and homologues as components of H2-antagonists. 22nd Comm.: H2-antihistaminics

Starting with isohistamines and their homologues or from appropriately hydrogenated imidazo[1,2-c]pyrimidines, imidazo[1,2-c][1,3]diazepines and -diazocines, H2-antihistaminics with cyanoguanidine and 2-nitro-1,1-ethenediamine structure were prepared and tested for their H2-antagonistic activity on the isolated guinea-pig atrium and on the histamine-stimulated acid secretion of the anaesthetized rat. While four of the cyanoguanidines were weaker in comparison to cimetidine, or inactive, thirteen others possessed markedly stronger activity, whereby the activity reaches a maximal effect at the rat stomach when cyanoguanidine and imidazole ring are connected with a three-membered chain. The activity of the 2-nitro-1,1-ethenediamines exceeds that of the comparable cyanoguanidines in both test models.

Synthesis and h2-antihistaminic activity of n,n'-bisimidazole-substituted thioureas, cyanoguanidines and 2-nitro-1,1-ethenediamines 10. C: H2-antihistaminics

In studies on structure-activity relationships of histamine H2-receptor antagonists, N,N'-bis(2-[(4-imidazolyl)-methylthio]-ethyl)-substituted thioureas, cyanoguinidines, and 2-nitro-1,1-ethenediamines with different C-5 methylation of the imidazole rings were prepared and tested for their H2-antihistaminic activity on the isolated guinea-pig atrium and the stimulated gastric acid secretion of the anaesthetized rat. When tested on isolated guinea-pig atrium, substances with both C-5 positions methylated (5b, 7b, 9b) proved to be up to seven times more active than metiamide, whereas inhibition of gastric acid secretion turned out to be less marked. While equally methylated thioureas and cyanoguanidines showed same potency, the 2-nitro-1,1-ethenediamines clearly possessed lower activity.

Process for preparing 5-methyl-4-imidazolecarboxylic acid esters

A process for the preparation of 5-methyl-4-imidazolecarboxylic acid esters from acetoacetic acid esters. The products of this process are useful as intermediates for preparing cimetidine.

Imidazolemethylphosphonium salts

New imidazolemethylphosphonium salts having a degradable group at the 2-position which are useful intermediates for preparing histamine H2 antagonists.

Process for preparing 4-substituted imidazole compounds

A process for preparing 4-(oxy, thio or amino)methylimidazole compounds via displacement of the trisubstituted phosphonium group from 4-(trisubstituted phosphonium)methylimidazole compounds is disclosed.

CERTAIN THIAZOLES AND OXAZOLES

The compounds are N,N'-substituted thioureas, ureas and guanidines which are H-2 histamine receptor inhibitors. Two compounds of this invention are N,N'-bis 2-((4-methyl-5-imidazolyl)methylthio) ethyl!thiourea and N,N'-bis 2-((4-methyl-5-imidazolyl)methylthio)ethyl!-N"-cyanoguanidine. "