All Photos(2)

Documents

C4522

Cimetidine

Name: Cimetidine
Brand: SIGMA

Sign Into View Organizational & Contract Pricing

All Photos(2)

Synonym(s):

SKF-92334

Empirical Formula (Hill Notation):

C₁₀H₁₆N₆S

CAS Number:

51481-61-9

Molecular Weight:

252.34

EC Number:

257-232-2

MDL number:

MFCD00133296

PubChem Substance ID:

24277766

NACRES:

NA.77

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)

Looking for similar products? Visit Product Comparison Guide

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

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

Already Own This Product?

Documents related to the products that you have purchased in the past have been gathered in the Document Library for your convenience.

Visit the Document Library

Difficulty Finding Your Product Or Lot/Batch Number?

How to Find the Product Number

Product numbers are combined with Pack Sizes/Quantity when displayed on the website (example: T1503-25G). Please make sure you enter ONLY the product number in the Product Number field (example: T1503).

Example:

T1503

Product Number

25G

Pack Size/Quantity

Additional examples:

705578-5MG-PW

PL860-CGA/SHF-1EA

MMYOMAG-74K-13

1000309185

enter as 1.000309185)

Having trouble? Feel free to contact Technical Service for assistance.

How to Find a Lot/Batch Number for COA

Lot and Batch Numbers can be found on a product's label following the words 'Lot' or 'Batch'.

Aldrich Products

For a lot number such as TO09019TO, enter it as 09019TO (without the first two letters 'TO').
For a lot number with a filling-code such as 05427ES-021, enter it as 05427ES (without the filling-code '-021').
For a lot number with a filling-code such as STBB0728K9, enter it as STBB0728 without the filling-code 'K9'.

Not Finding What You Are Looking For?

In some cases, a COA may not be available online. If your search was unable to find the COA you can request one.

Request COA

Cimetidine inhibits cancer cell adhesion to endothelial cells and prevents metastasis by blocking E-selectin expression.

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

Selective ligands as tools to study histamine receptors.

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

Nuclear localization of histamine receptor 2 in primary human lymphatic endothelial cells.

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.

Famotidine activates the vagus nerve inflammatory reflex to attenuate cytokine storm.

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

Systematic Exploration of Passive Permeability in Tetrapeptides with Hydrogen-Bond-Accepting Amino Acid Side Chains.

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

View All Related Papers