D5035
1,1-Dimethylbiguanide hydrochloride
≥97%
Synonym(s):
Metformin
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About This Item
Linear Formula:
NH2C(=NH)NHC(=NH)N(CH3)2 · HCl
CAS Number:
Molecular Weight:
165.62
EC Number:
MDL number:
UNSPSC Code:
12352100
PubChem Substance ID:
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Assay
≥97%
mp
223-226 °C (lit.)
SMILES string
Cl[H].CN(C)C(=N)NC(N)=N
InChI
1S/C4H11N5.ClH/c1-9(2)4(7)8-3(5)6;/h1-2H3,(H5,5,6,7,8);1H
InChI key
OETHQSJEHLVLGH-UHFFFAOYSA-N
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Biochem/physiol Actions
Metformin is an antidiabetic agent that reduces blood glucose levels and improves insulin sensitivity. Its metabolic effects, including the inhibition of hepatic gluconeogenesis, are mediated at least in part by activation of the LKB1-AMPK (AMP-activated protein kinase) pathway. Activation of this pathway also appears to be involved in the antiproliferative and proapoptotic actions of metformin in cancer cell lines.
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Mhairi C Towler et al.
Circulation research, 100(3), 328-341 (2007-02-20)
The AMP-activated protein kinase (AMPK) system acts as a sensor of cellular energy status that is conserved in all eukaryotic cells. It is activated by increases in the cellular AMP:ATP ratio caused by metabolic stresses that either interfere with ATP
Mahvash Zakikhani et al.
Cancer research, 66(21), 10269-10273 (2006-10-26)
Recent population studies provide clues that the use of metformin may be associated with reduced incidence and improved prognosis of certain cancers. This drug is widely used in the treatment of type 2 diabetes, where it is often referred to
A Isakovic et al.
Cellular and molecular life sciences : CMLS, 64(10), 1290-1302 (2007-04-21)
The present study reports for the first time a dual antiglioma effect of the well-known antidiabetic drug metformin. In low-density cultures of the C6 rat glioma cell line, metformin blocked the cell cycle progression in G(0)/G(1) phase without inducing significant
Reuben J Shaw et al.
Science (New York, N.Y.), 310(5754), 1642-1646 (2005-11-26)
The Peutz-Jegher syndrome tumor-suppressor gene encodes a protein-threonine kinase, LKB1, which phosphorylates and activates AMPK [adenosine monophosphate (AMP)-activated protein kinase]. The deletion of LKB1 in the liver of adult mice resulted in a nearly complete loss of AMPK activity. Loss
Nicolas Musi et al.
Diabetes, 51(7), 2074-2081 (2002-06-28)
Metformin is an effective hypoglycemic drug that lowers blood glucose concentrations by decreasing hepatic glucose production and increasing glucose disposal in skeletal muscle; however, the molecular site of metformin action is not well understood. AMP-activated protein kinase (AMPK) activity increases
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