CAS 657-24-9|Metformin

Introduction：Basic information about CAS 657-24-9|Metformin, including its chemical name, molecular formula, synonyms, physicochemical properties, and safety information, etc.

Table of Contents

1. Names
2. Metformin BiologicalActivity
3. Chemical & Physical Properties
4. Toxicological Information
CHEMICAL IDENTIFICATION
HEALTH HAZARD DATA
ACUTE TOXICITY DATA
MUTATION DATA
5. Synonyms

Common Name	Metformin
CAS Number	657-24-9	Molecular Weight	129.164
Density	1.0743	Boiling Point	229.23°C
Molecular Formula	C₄H₁₁N₅	Melting Point	199-200 °C
MSDS	/	Flash Point	58.1±22.6 °C

Names

Name	metformin
Synonym	More Synonyms

Metformin BiologicalActivity

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 >>AMPKResearch Areas >>Cardiovascular DiseaseSignaling Pathways >>Autophagy >>AutophagySignaling Pathways >>PI3K/Akt/mTOR >>AMPKSignaling Pathways >>Autophagy >>MitophagyResearch 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
InChIKey	XZWYZXLIPXDOLR-UHFFFAOYSA-N
SMILES	CN(C)C(=N)N=C(N)N
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

Synonyms

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

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