54237-72-8

54237-72-8 structure

Name: Cimetidine sulfoxide
Chemical Name: cimetidine S-oxide
CAS Number: 54237-72-8
Molecular Formula: C₁₀H₁₆N₆OS
Molecular Weight: 341.260
Catalog: Signaling Pathways GPCR/G Protein Histamine Receptor
Create Date: 2016-12-25 17:32:58
Modify Date: 2026-07-16 09:47:12
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].

Name	cimetidine S-oxide
Synonyms	CIMETIDINE IMPURITY E (CIMETIDINE SULPHOXIDE) 2-Cyano-1-methyl-3-[2-[[(5-methyl-1 Cimetidine impurity E 1-Cyano-3-methyl-2-(2-(((4-methyl-1H-imidazol-5-yl)methyl)sulfinyl)ethyl)guanidine Cimetidine Hydrochloride Impurity E (+/-)-Cimetidine S-oxide CIMETIDINE SULPHOXIDE DIHYDROCHLORIDE Cimetidine Sulphoxide Impurity E) SKF-92452 2-Cyano-1-methyl-3-[2-[[(5-methyl-1H-imidazol-4-yl)methyl]sulphinyl]ethyl]guanidine (Cimetidine Sulphoxide) 1-Cyano-3-methyl-2-(2-{[(5-methyl-1H-imidazol-4-yl)methyl]sulfinyl}ethyl)guanidine dihydrochloride 2-Cyano-1-methyl-3-[2-[[(5-methyl-1H-imidazol-4-yl)methyl]sulphinyl]ethyl]guanidine (Cimetidine Sulp Cimetidine impurity 5/Cimetidine Impurity E/Cimetidine Sulfoxide /2-Cyano-1-methyl-3-[2-[[(5-methyl-1H-imidazol-4-yl)methyl]sulfinyl]-ethyl]guanidine 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 1-Cyano-3-methyl-2-[2-[[(5-methyl-1H-imidazole-4-yl)methyl]sulfinyl]ethyl]guanidine N-Cyano-N'-methyl-N''-[2-[(5-methyl-1H-imidazol-4-yl)methylsulphinyl]ethyl]guanidine 1-[2-[(5-Methyl-1H-imidazole-4-yl)methylsulfinyl]ethyl]-3-methyl-2-cyanoguanidine cimetidine sulfoxide Cimetidine sulphoxide Guanidine, N-cyano-N'-methyl-N''-[2-[[(4-methyl-1H-imidazol-5-yl)methyl]sulfinyl]ethyl] 2-Cyano-1-methyl-3-[2-[[(5-methyl-1H-imidazol-4-yl)methyl]sulfinyl]ethyl]guanidine Cimetidine Impurity 5（Cimetidine Impurity E） Cimetidine S-oxide Cimetidine sulfoxide, H2 rector antagonist

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.

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

Hazard Codes	Xi

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