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Cimetidine (hydrochloride)

CAT: 0804-HY-14289ASize: 1 EachDry Ice: NoHazardous: No
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Description
Cimetidine (SKF-92334) hydrochloride is an orally active and inverse histamine H2 receptor antagonist with a Ki of 0.6 μM. Cimetidine hydrochloride is a gastric acid reducer, and can be used for duodenal and gastric ulcers research. Cimetidine hydrochloride has anti-cancer and anti-inflammatory activity[1][2][5].
CAS Number
70059-30-2
Product Name Alternative
SKF-92334 (hydrochloride)
UNSPSC
12352005
Hazard Statement
H315-H319-H320
Target
Bacterial; Histamine Receptor
Type
Reference compound
Related Pathways
Anti-infection; GPCR/G Protein; Immunology/Inflammation; Neuronal Signaling
Applications
Metabolism-protein/nucleotide metabolism
Field of Research
Cancer; Endocrinology
Assay Protocol
https://www.medchemexpress.com/cimetidine-hydrochloride.html
Solubility
10 mM in DMSO
Smiles
CC1=C(CSCC/N=C(NC)/NC#N)NC=N1.[H]Cl
Molecular Formula
C10H17ClN6S
Molecular Weight
288.80
Precautions
P264-P280-P302+P352-P305+P351+P338-P362
References & Citations
[1]M J Smit, et al. Inverse agonism of histamine H2 antagonist accounts for upregulation of spontaneously active histamine H2 receptors. Proc Natl Acad Sci U S A. 1996 Jun 25;93 (13) :6802-7.|[2]Takahashi, H.K., et al., Cimetidine induces interleukin-18 production through H2-agonist activity in monocytes. Mol Pharmacol, 2006. 70 (2) : p. 450-3.|[3]Sprowl, J.A., et al., Conjunctive therapy of cisplatin with the OCT2 inhibitor cimetidine: influence on antitumor efficacy and systemic clearance. Clin Pharmacol Ther, 2013. 94 (5) : p. 585-92.|[4]Zheng, Y., et al., Cimetidine suppresses lung tumor growth in mice through proapoptosis of myeloid-derived suppressor cells. Mol Immunol, 2013. 54 (1) : p. 74-83.|[5]Fukuda, M., K. Kusama, and H. Sakashita, Cimetidine inhibits salivary gland tumor cell adhesion to neural cells and induces apoptosis by blocking NCAM expression. BMC Cancer, 2008. 8: p. 376.|[6]Longhini, R., et al., Cimetidine Reduces the Alveolar Bone Loss in Induced Periodontitis in Rat Molars. J Periodontol, 2013.
Shipping Conditions
Room temperature
Scientific Category
Reference compound1
Clinical Information
Launched
Isoform
H2 Receptor

Chemical Information

Cimetidine Hydrochloride

A histamine congener, it competitively inhibits histamine binding to histamine H2 receptors. Cimetidine has a range of pharmacological actions. It inhibits gastric acid secretion, as well as pepsin and gastrins output. It also blocks the activity of cytochrome P-450 which might explain proposals for use in neoadjuvant therapy.

CAS Number70059-30-2
PubChem CID50963
IUPAC Name1-cyano-2-methyl-3-[2-[(5-methyl-1H-imidazol-4-yl)methylsulfanyl]ethyl]guanidine;hydrochloride
Molecular FormulaC10H17ClN6S
Molecular Weight288.80
Topological Polar Surface Area114
Hydrogen Bond Donor Count4
Hydrogen Bond Acceptor Count4
Rotatable Bond Count7
Heavy Atom Count18
Formal Charge0
Complexity296
SMILES
CC1=C(N=CN1)CSCCNC(=NC)NC#N.Cl
InChI
InChI=1S/C10H16N6S.ClH/c1-8-9(16-7-15-8)5-17-4-3-13-10(12-2)14-6-11;/h7H,3-5H2,1-2H3,(H,15,16)(H2,12,13,14);1H
InChIKey
QJHCNBWLPSXHBL-UHFFFAOYSA-N
Chemical Structure
2D Structure
2D structure of Cimetidine Hydrochloride
CAS: 70059-30-2
CID: 50963
Formula: C10H17ClN6S
MW: 288.80
Interactive 3D Structure
Loading 3D structure...
View on PubChemRaw 3D data
Computed Properties
PropertyValue
Molecular Weight288.80
Hydrogen Bond Donor Count4
Hydrogen Bond Acceptor Count4
Rotatable Bond Count7
Exact Mass288.0923934
Monoisotopic Mass288.0923934
Topological Polar Surface Area114 Ų
Heavy Atom Count18
Formal Charge0
Complexity296
Isotope Atom Count0
Defined Atom Stereocenter Count0
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently-Bonded Unit Count2
Compound Is CanonicalizedYes

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