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Merck

C4522

Sigma-Aldrich

Cimetidine

histamine H2 receptor antagonist, powder

Synonym(s):

SKF-92334

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About This Item

Empirical Formula (Hill Notation):
C10H16N6S
CAS Number:
51481-61-9
Molecular Weight:
252.34
EC Number:
257-232-2
MDL number:
MFCD00133296
UNSPSC Code:
12352200
PubChem Substance ID:
24277766
NACRES:
NA.77

Key Documents

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Product Name

Cimetidine,

form

powder

Quality Level

200

originator

GlaxoSmithKline

storage temp.

2-8°C

SMILES string

CN\C(NC#N)=N\CCSCc1nc[nH]c1C

InChI

1S/C10H16N6S/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)

InChI key

AQIXAKUUQRKLND-UHFFFAOYSA-N

Gene Information

human ... ABCB1(5243), CYP1A2(1544), CYP3A4(1576), HRH2(3274), SLC9A2(6549), SLC9A5(6553)
mouse ... Abcb1a(18671), Abcb1b(18669)
rat ... Slc9a1(24782), Slc9a3(24784), Slc9a5(192215)

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Biochem/physiol Actions

H2 histamine receptor antagonist; I1 imidazoline receptor agonist; anti-ulcer agent. Blocks cancer metastasis by inhibiting the expression of E-selectin on the surface of endothelial cells, thus blocking tumor cell adhesion.

Features and Benefits

This compound is a featured product for ADME Tox research. Click here to discover more featured ADME Tox products. Learn more about bioactive small molecules for other areas of research at sigma.com/discover-bsm.
This compound was developed by GlaxoSmithKline. To browse the list of other pharma-developed compounds and Approved Drugs/Drug Candidates, click here.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
BCCG8282
BCCC3082
BCBT1578
BCBP2916V
BCBP2916

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K Kobayashi et al.
Cancer research, 60(14), 3978-3984 (2000-08-05)
Although the beneficial effect of cimetidine on survival in cancer has been clinically demonstrated in colorectal cancer patients, the mode of action of cimetidine has not been elucidated. In this report, we have demonstrated for the first time that cimetidine
Huan Yang et al.
Molecular medicine (Cambridge, Mass.), 28(1), 57-57 (2022-05-17)
Severe COVID-19 is characterized by pro-inflammatory cytokine release syndrome (cytokine storm) which causes high morbidity and mortality. Recent observational and clinical studies suggest famotidine, a histamine 2 receptor (H2R) antagonist widely used to treat gastroesophageal reflux disease, attenuates the clinical
H van der Goot et al.
European journal of medicinal chemistry, 35(1), 5-20 (2000-03-25)
In this review the histaminergic ligands for the histamine H(1), H(2) and H(3) receptors, which are currently used as tools in pharmacological studies, are described. To study interactions with the histamine H(1) receptor, the H(1) agonist 2-aminoethylthiazole has long since
Hiroki Shimizu et al.
ChemMedChem, 17(16), e202200204-e202200204 (2022-06-14)
We synthesized and experimentally tested the passive permeability of more than thirty tetrapeptides mimicking the N-terminus of the pro-apoptotic protein Smac (Second mitochondria-derived activator of caspases). Each peptide bore one or two unnatural Hydrogen Bond Acceptor-bearing Amino Acid (HBA-AA) residues
Y Edrei et al.
British journal of cancer, 107(4), 658-666 (2012-07-19)
The poor prognosis of patients with colorectal-cancer liver metastases (CRLM) and the insufficiency of available treatments have raised the need for alternative curative strategies. We aimed to assess the therapeutic potential of TL-118, a new anti-angiogenic drug combination, for CRLM
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