C4522

Sigma-Aldrich

Cimetidine

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
Pricing and availability is not currently available.

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

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 was developed by GlaxoSmithKline. To browse the list of other pharma-developed compounds and Approved Drugs/Drug Candidates, click here.
This compound is also offered as part of Sigma′s Library of Pharmacologically Active Compounds (LOPAC®1280), a biologically annotated collection of high-quality, ready-to-screen compounds. Click here to learn more.
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.

Legal Information

LOPAC is a registered trademark of Sigma-Aldrich Co. LLC

Pictograms

Health hazard

Signal Word

Danger

Hazard Statements

Personal Protective Equipment

dust mask type N95 (US),Eyeshields,Gloves

RIDADR

NONH for all modes of transport

WGK Germany

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

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...
Zane Stromberga et al.
Scientific reports, 9(1), 3899-3899 (2019-03-09)
The mechanisms underlying bladder contractile disorders such as overactive bladder are not fully understood, and there is limited understanding of the receptor systems modulating spontaneous bladder contractions. We investigated the potential for histamine to have a role in mediating contractility...
J A Sprowl et al.
Clinical pharmacology and therapeutics, 94(5), 585-592 (2013-07-19)
The organic cation transporter 2 (OCT2) regulates uptake of cisplatin in proximal tubules, and inhibition of OCT2 protects against severe cisplatin-induced nephrotoxicity. However, it remains uncertain whether potent OCT2 inhibitors, such as cimetidine, can influence the antitumor properties and/or disposition...
A F Shinn
Drug safety, 7(4), 245-267 (1992-07-01)
The excellent efficacy and tolerability profiles of H2-antagonists have established these agents as the leading class of antiulcer drugs. Attention has been focused on drug interactions with H2-antagonists as a means of product differentiation and because many patients are receiving...
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