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C4522

Sigma-Aldrich

Cimetidine

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Synonym(s):
SKF-92334
Empirical Formula (Hill Notation):
C10H16N6S
CAS Number:
Molecular Weight:
252.34
EC Number:
MDL number:
PubChem Substance ID:
NACRES:
NA.77

form

powder

Quality Level

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

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This Item
1134062Y0001130BP475
vibrant-m

C4522

Cimetidine

vibrant-m

1134062

Cimetidine

vibrant-m

BP475

Cimetidine

Quality Level

200

Quality Level

-

Quality Level

-

Quality Level

-

storage temp.

2-8°C

storage temp.

2-8°C

storage temp.

2-8°C

storage temp.

2-8°C

originator

GlaxoSmithKline

originator

-

originator

-

originator

-

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)

Gene Information

human ... HRH2(3274)

Gene Information

human ... HRH2(3274)

Gene Information

human ... HRH2(3274)

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

11 - Combustible Solids

wgk_germany

WGK 3

ppe

Eyeshields, Gloves, type P3 (EN 143) respirator cartridges


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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
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
Sarit Pal et al.
Biology open, 11(7) (2022-07-02)
Histamine exerts its physiological functions through its four receptor subtypes. In this work, we report the subcellular localization of histamine receptor 2 (H2R), a G protein-coupled receptor (GPCR), which is expressed in a wide variety of cell and tissue types.
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
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

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