112528-12-8

Basic information

• Product Name: Carbamimidothioic acid,N-cyano-N'-[2-[[(5-methyl-1H-imidazol-4-yl)methyl]thio]ethyl]-, methylester, (E)-
• CAS NO: 112528-12-8
• Molecular Formula: C10H15N5S2
• Molecular Weight: 269.395
• Mol File: 112528-12-8.mol
• Article Data: 14

Chemical Properties

• CAS DataBase Reference: Carbamimidothioic acid,N-cyano-N'-[2-[[(5-methyl-1H-imidazol-4-yl)methyl]thio]ethyl]-, methylester, (E)-(CAS DataBase Reference)
• NIST Chemistry Reference: Carbamimidothioic acid,N-cyano-N'-[2-[[(5-methyl-1H-imidazol-4-yl)methyl]thio]ethyl]-, methylester, (E)-(112528-12-8)
• EPA Substance Registry System: Carbamimidothioic acid,N-cyano-N'-[2-[[(5-methyl-1H-imidazol-4-yl)methyl]thio]ethyl]-, methylester, (E)-(112528-12-8)

Safety Data

• Hazardous Substances Data: 112528-12-8(Hazardous Substances Data)

Upstream product

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

Downstream Products

• 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 
• 52378-43-5 N-Cyano-N'-<2-<(5(4)-methyl-4(5)-imidazolyl)-methylthio>-ethyl>-guanidin 

Relevant articles and documents

S-Methylisothioureas, synthons for chain-branched cimetidine derivatives

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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.