Cimetidine sulfoxide

Names

[ Name ]:
Cimetidine sulfoxide

[Synonym ]:
Guanidine, N-cyano-N'-methyl-N''-[2-[[(5-methyl-1H-imidazol-4-yl)methyl]sulfinyl]ethyl]-, hydrochloride (1:2)
1-cyano-2-methyl-3-[2-[(5-methyl-1H-imidazol-4-yl)methylsulfinyl]ethyl]guanidine
Cimetidine sulfoxide
1-Cyano-3-methyl-2-(2-{[(5-methyl-1H-imidazol-4-yl)methyl]sulfinyl}ethyl)guanidine dihydrochloride

Biological Activity

[Description]:

Cimetidine sulfoxide (Cimetidine sulphoxide) is a sulfoxide metabolite of Cimetidine. Cimetidine is a histamine H2-receptor antagonist. Cimetidine has the potential for peptic ulcer disease and upper gastrointestinal haemorrhage treatment[1].

[Related Catalog]:

Signaling Pathways >> Immunology/Inflammation >> Histamine Receptor

Research Areas >> Inflammation/Immunology

Signaling Pathways >> GPCR/G Protein >> Histamine Receptor

[Target]

Histamine H2-receptor[1]

[In Vitro]

Active transport of Cimetidine across the rat small intestine is observable at lower substrate concentrations (40 and 200 μM), but is masked by passive transfer at higher concentrations (400 μM). Cimetidine sulfoxide is detected after some incubations[2].

[In Vivo]

The enantiomeric composition of Cimetidine sulfoxide is also determined in rat urine (24 h) following the administration of Cimetidine (30 mg/kg; po) to male Wistar rats. The enantiomeric ratio in this case is found to be (+/−) 57:43[3].

[References]

[1]. Larsson R, et al. The pharmacokinetics of cimetidine and its sulphoxide metabolite in patients with normal and impaired renal function. Br J Clin Pharmacol. 1982;13(2):163-170.

[2]. HE Barber, et al. The Transport of Cimetidine Across the Rat Small Intestine in Vitro. B r J Pharmacol. 1979 Jul;66(3):496P-497P.

[3]. Ryta A. Kuzel, et al. Investigations into the chirality of the metabolic sulfoxidation of cimetidine. Chirality (1994), 6(8), 607-14.

Chemical & Physical Properties

[ Density]:
1.39g/cm3

[ Boiling Point ]:
608.6ºC at 760mmHg

[ Molecular Formula ]:
C₁₀H₁₆N₆OS

[ Molecular Weight ]:
341.260

[ Flash Point ]:
321.8ºC

[ Exact Mass ]:
340.063995

[ PSA ]:
125.17000

[ LogP ]:
2.86438

[ Index of Refraction ]:
1.665

Safety Information

[ Hazard Codes ]:
Xi

Related Compounds

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