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KI1085Cimetidine50 mg$154

Chemical Characteristic

Product NameCimetidine
SynonymsTagamet
CAS No.51481-61-9
Molecular Weight 252.34
FormulaC10H16N6S
Chemical Name1-cyano-2-methyl-3-[2-[(5-methyl-1H-imidazol-4-yl)methylsulfanyl]ethyl]guanidine
SmilesN(/C(=N\C#N)/NCCSCc1nc[nH]c1C)C
Chemical Structure

Biological activities

Cimetidine is a histamine H2-receptor antagonist. Cimetidine is widely used to treat peptic ulcer disease. Cimetidine in vitro inhibits the hydroxylation of benzopyrene and coumarin, as well as the O-deethylation of 7-ethoxycoumarin, by homogenised liver biopsies.[1] Histamine having a trophic effect on at least two colorectal cell lines is antagonised by cimetidine. Cimetidine inhibits the growth of carcinogen induced colorectal cancer. [2] The [3H] cimetidine binding site in the rat brain has a dissociation constant Kd of 0.22 µM. [3] In vivo, cimetidine inhibits hepatic microsomal enzyme activities mediated by cytochrome P450 (CYP) 2C11 in adult male rats. Cimetidine inhibits MROD and EROD activities in microsomes from uninduced rats by 50% and 65%, respectively. Cimetidine inhibits progesterone 21-hydroxylase activity by 62% and progesterone 2α-hydroxylase activity by 39% but has no effect on progesterone 6β-hydroxylase activity (mediated by CYP3A). [4]

Protocols

Cimetidine is dissolved in distilled water. [4]

References

[1] Puurunen J, et al. Effect of cimetidine on microsomal drug metabolism in man. Eur J Clin Pharmacol. 1980, 18(2): 185-187.
[2] Adams WJ, et al. Cimetidine inhibits in vivo growth of human colon cancer and reverses histamine stimulated in vitro and in vivo growth. Gut. 1994, 35(11): 1632-1636.
[3] Smith IR, et al. Binding of [3H]cimetidine to rat brain tissue. Agents Actions. 1980, 10(5): 422-426.
[4] Levine M, et al. In vivo cimetidine inhibits hepatic CYP2C6 and CYP2C11 but not CYP1A1 in adult male rats. J Pharmacol Exp Ther. 1998, 284(2): 493-499.

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