657-24-9

657-24-9结构式

常用中文名：二甲双胍
常用英文名：Metformin
CAS号：657-24-9
分子式：C₄H₁₁N₅
分子量：129.164
相关类别：原料药激素及调节内分泌功能类药胰腺激素及其它调节血糖药
发布时间：2018-09-23 09:48:56
更新时间：2025-08-20 22:58:03
Metformin (1,1-Dimethylbiguanide) 抑制肝脏中的线粒体呼吸链,导致 AMPK 活化,增强胰岛素敏感性,可用于 2 型糖尿病的研究。Metformin 可以透过血脑屏障,诱导自噬 (autophagy)。
用于轻症糖尿病。主要用于非胰岛素依赖型糖尿病，其中肥胖病人可作为首选药，对于胰岛素依赖型糖尿病亦可与胰岛素联合使用。对某些磺酰脲类无效的病例有效。
本品为双胍类口服降血糖药。具有多种作用机制，包括延缓葡萄糖由胃肠道的摄取，通过提高胰岛素的敏感性而增加外周葡萄糖的利用，以及抑制肝、肾过度的糖原异生。本品不降低非糖尿病患者的血糖水平。患者用药期间体重通常减轻、血浆胆固醇、甘油三酯和前β脂蛋白水平可降低，外周葡萄糖代谢能得到改善。
降糖作用
降糖机制

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中文名	二甲双胍
英文名	metformin
中文别名	1,1-二甲基双胍甲福明
英文别名	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

描述	Metformin (1,1-Dimethylbiguanide) 抑制肝脏中的线粒体呼吸链,导致 AMPK 活化,增强胰岛素敏感性,可用于 2 型糖尿病的研究。Metformin 可以透过血脑屏障,诱导自噬 (autophagy)。
相关类别	信号通路 >> 表观遗传学 >> AMPK 研究领域 >> 心血管疾病信号通路 >> 自噬 >> 自噬信号通路 >> PI3K/Akt/mTOR 信号通路 >> AMPK 信号通路 >> 自噬 >> 自噬研究领域 >> 代谢疾病
靶点	AMPK
体外研究	二甲双胍(1,1-二甲基双胍)以浓度依赖的方式抑制ESCs的增殖。A-ESCs的IC50为2.45 mM,N-ESCs为7.87 mM。二甲双胍对A-ESCs分泌期AMPK信号的激活作用明显强于增殖期细胞[3]。二甲双胍(0-500μM)以剂量依赖性方式减少培养大鼠肝细胞糖原合成,IC50值为196.5μM[4]。二甲双胍对PC-3细胞的IC50为5 mM,显示细胞活力和细胞毒性作用[5]。
体内研究	通过组织病理学分析,二甲双胍(1,1-二甲基双胍；100 mg/kg,p.o.)单独使用,二甲双胍(25,50,100 mg/kg)与异丙肾上腺素组联合使用可减轻心肌细胞坏死[1]。二甲双胍(>900mg/kg/天,p.o.)导致死亡/死亡和Crl:光盘(SD)大鼠[2]。
参考文献	[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.

密度	1.0743
沸点	229.23°C
熔点	199-200 °C
分子式	C₄H₁₁N₅
分子量	129.164
闪点	58.1±22.6 °C
精确质量	129.101440
PSA	88.99000
LogP	-2.31
外观性状	Solid,White to Light Brown
蒸汽压	1.3±0.3 mmHg at 25°C
折射率	1.576
储存条件	室温，避光，保存在惰性气体中
水溶解性	Acetonitrile (Slightly), Aqueous Acid (Slightly), Dichloromethane (Slightly), DM

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