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Metformin

Names

[ CAS No. ]:
657-24-9

[ Name ]:
Metformin

[Synonym ]:
Fluamine
N'-dimethylguanylguanidine
N,N-dimethylimidodicarbonimidic diamide
Diabex
N,N-dimethyl-biguanide
N,N-dimethylbiguanidine
1,1-Dimethylbiguanide
Metiguanide
Metforminum
Glumetza
Dimethylbiguanide
3-(diaminomethylidene)-1,1-dimethylguanidine
EINECS 211-517-8
Diabetosan
Glucophage

Biological Activity

[Description]:

Metformin (1,1-Dimethylbiguanide) inhibits the mitochondrial respiratory chain in the liver, leading to activation of AMPK, enhancing insulin sensitivity for type 2 diabetes research. Metformin can cross the blood-brain barrier and triggers autophagy[1].

[Related Catalog]:

Signaling Pathways >> Epigenetics >> AMPK
Research Areas >> Cardiovascular Disease
Signaling Pathways >> Autophagy >> Autophagy
Signaling Pathways >> PI3K/Akt/mTOR >> AMPK
Signaling Pathways >> Autophagy >> Mitophagy
Research Areas >> Metabolic Disease

[Target]

AMPK


[In Vitro]

Metformin (1,1-Dimethylbiguanide) inhibits proliferation of ESCs in a concentration-dependent manner. The IC50 is 2.45 mM for A-ESCs and 7.87 mM for N-ESCs. Metformin shows pronounced effects on activation of AMPK signaling in A-ESCs from secretory phase than in cells from proliferative phase[3]. Metformin (0-500 μM) decreases glycogen synthesis in a dose-dependent manner with an IC50 value of 196.5 μM in cultured rat hepatocytes[4]. Metformin shows cell viability and cytotoxic effects on PC-3 cells with IC50 of 5 mM[5].

[In Vivo]

Metformin (1,1-Dimethylbiguanide; 100 mg/kg, p.o.) alone, and metformin (25, 50, 100 mg/kg) with isoproterenol groups attenuates myocyte necrosis through histopathological analysis[1]. Metformin (> 900 mg/kg/day, p.o.) results in moribundity/mortality and clinical signs of toxicity in Crl:CD(SD) rats[2].

[References]

[1]. Soraya H, et al. Acute treatment with metformin improves cardiac function following isoproterenol induced myocardial infarction in rats. Pharmacol Rep. 2012;64(6):1476-84.

[2]. Quaile MP, et al. Toxicity and toxicokinetics of metformin in rats. Toxicol Appl Pharmacol. 2010 Mar 15;243(3):340-7.

[3]. Xue J, et al. Metformin inhibits growth of eutopic stromal cells from adenomyotic endometrium via AMPK activation and subsequent inhibition of AKT phosphorylation: a possible role in the treatment of adenomyosis. Reproduction. 2013 Aug 21;146(4):397-406.

[4]. Otto M, et al. Metformin inhibits glycogen synthesis and gluconeogenesis in cultured rat hepatocytes. Diabetes Obes Metab. 2003 May;5(3):189-94.

[5]. Avci CB, et al. Therapeutic potential of an anti-diabetic drug, metformin: alteration of miRNA expression in prostate cancer cells. Asian Pac J Cancer Prev. 2013;14(2):765-8.

Chemical & Physical Properties

[ Density]:
1.0743

[ Boiling Point ]:
229.23°C

[ Melting Point ]:
199-200 °C

[ Molecular Formula ]:
C4H11N5

[ Molecular Weight ]:
129.164

[ Flash Point ]:
58.1±22.6 °C

[ Exact Mass ]:
129.101440

[ PSA ]:
88.99000

[ LogP ]:
-2.31

[ Appearance of Characters ]:
Solid,White to Light Brown

[ Vapour Pressure ]:
1.3±0.3 mmHg at 25°C

[ Index of Refraction ]:
1.576

[ Water Solubility ]:
Acetonitrile (Slightly), Aqueous Acid (Slightly), Dichloromethane (Slightly), DM

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :
DU1790000
CHEMICAL NAME :
Biguanide, 1,1-dimethyl-
CAS REGISTRY NUMBER :
657-24-9
LAST UPDATED :
199601
DATA ITEMS CITED :
8
MOLECULAR FORMULA :
C4-H11-N5
MOLECULAR WEIGHT :
129.20
WISWESSER LINE NOTATION :
MUYZMYUM&N1&1

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Subcutaneous
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
230 mg/kg
TOXIC EFFECTS :
Behavioral - hallucinations, distorted perceptions Behavioral - convulsions or effect on seizure threshold Lungs, Thorax, or Respiration - other changes
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intraperitoneal
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
247 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Subcutaneous
SPECIES OBSERVED :
Rodent - guinea pig
DOSE/DURATION :
146 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Parenteral
SPECIES OBSERVED :
Amphibian - frog
DOSE/DURATION :
5 gm/kg
TOXIC EFFECTS :
Behavioral - hallucinations, distorted perceptions Behavioral - convulsions or effect on seizure threshold Lungs, Thorax, or Respiration - other changes
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
DOSE :
6 gm/kg
SEX/DURATION :
female 1-12 day(s) after conception
TOXIC EFFECTS :
Reproductive - Effects on Embryo or Fetus - fetal death

MUTATION DATA

TYPE OF TEST :
Cytogenetic analysis
TEST SYSTEM :
Rodent - hamster Lung
DOSE/DURATION :
2 gm/L/48H
REFERENCE :
GMCRDC Gann Monograph on Cancer Research. (Plenum Pub. Corp., 233 Spring St., New York, NY 10013) No. 11- 1971- Volume(issue)/page/year: 27,95,1981 *** REVIEWS *** TOXICOLOGY REVIEW CLPTAT Clinical Pharmacology and Therapeutics (St. Louis). (C.V. Mosby Co., 11830 Westline Industrial Dr., St. Louis, MO 63146) V.1- 1960- Volume(issue)/page/year: 5,480,1964 TOXICOLOGY REVIEW ADVPA3 Advances in Pharmacology. (New York, NY) V.1-6, 1962-68. For publisher information, see AVPCAQ. Volume(issue)/page/year: 4,263,1966

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

Related Compounds

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