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1115-70-4

1115-70-4 structure
1115-70-4 structure
Name Metformin Hydrochloride
Synonyms Metformin HCl
1,1-Dimethylbiguanide hydrochloride,Metformin
3-(diaminomethylidene)-1,1-dimethylguanidine,hydrochloride
Imidodicarbonimidic diamide, N,N-dimethyl-, hydrochloride (1:1)
1,1-Dimethylbiguanide hydrochloride
MFCD00012582
N,N-Dimethylimidodicarbonimidic diamide hydrochloride (1:1)
N1,N1-Dimethylbiguanide hydrochloride
Metformin hydrochloride
EINECS 214-230-6
Metformin (hydrochloride)
Description Metformin (hydrochloride) is an FDA approved first-line drug for the treatment of type 2 diabetes. Metformin decreases hepatic glucose production, mostly through a mild and transient inhibition of the mitochondrial respiratory-chain complex 1.
Related Catalog
Target

AMPK

Autophagy

Mitophagy

In Vitro Metformin 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 (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].
Cell Assay ESCs are plated in 96-well plates at a concentration of 1×103cells/well. After attachment, cells are treated with different doses of metformin/compound C for 0 min, 15 min, 1 h, and 24 h. MTT assays are performed as described previously. In brief, MTT (5 mg/mL) is added to the 96-well plates at a volume of 10 μL/well, and the plates are incubated for 4 h. The MTT reaction is terminated by removal of the culture medium containing MTT, and 100 μL DMSO per well are added and incubated at RT on a shaker for 10 min to ensure that the crystals had dissolved sufficiently. Absorbance values are measured at 595 nm. Cell proliferation (percentage of control) is calculated as follows: absorbance (experimental group)/absorbance (control group). Cell proliferation inhibition (percentage of control) is calculated as follows: 100%−cell proliferation (percentage of control). Each experiment is performed in duplicate and repeated six times to assess result consistency.
Animal Admin The animals are randomized into six groups consisting of six rats each. Rats in group 1 (control) receives a subcutaneous injection of physiological saline (0.5 mL) and are left untreated for the entire experimental period. Rats in group 2 receives an oral administration of metformin (100 mg/kg; twice daily) for 2 days and are subcutaneously injected with saline at an interval of 24 h for 2 consecutive days. Rats in group 3 (MI control) receives an oral administration of saline (twice daily) for 2 days and are sc injected with isoproterenol (100 mg/kg) daily for 2 consecutive days at an interval of 24 h. Rats in groups 4 to 6 are treated with metformin at 25, 50, and 100 mg/kg. Metformin is dissolved in saline and is gavaged at a volume of 0.25-0.5 mL twice a day at an interval of 12 h, started immediately before isoproterenol injection.
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.

[6]. Nie L, et al. The Landscape of Histone Modifications in a High-Fat Diet-Induced Obese (DIO) Mouse Model. Mol Cell Proteomics. 2017 Jul;16(7):1324-1334.

[7]. Zhang D, et al. Metformin ameliorates BSCB disruption by inhibiting neutrophil infiltration and MMP-9 expression but not direct TJ proteins expression regulation. J Cell Mol Med. 2017 Jul 12.
Boiling Point 224.1ºC at 760 mmHg
Melting Point 223-226 °C(lit.)
Molecular Formula C4H12ClN5
Molecular Weight 165.625
Flash Point 89.3ºC
Exact Mass 165.078125
PSA 88.99000
LogP 1.05850
Vapour Pressure 0.0929mmHg at 25°C
Storage condition Store at RT

CHEMICAL IDENTIFICATION

RTECS NUMBER :
DU1800000
CHEMICAL NAME :
Biguanide, 1,1-dimethyl-, hydrochloride
CAS REGISTRY NUMBER :
1115-70-4
LAST UPDATED :
199801
DATA ITEMS CITED :
16
MOLECULAR FORMULA :
C4-H11-N5.Cl-H
MOLECULAR WEIGHT :
165.66
WISWESSER LINE NOTATION :
MUYZMYUM&N1&1 &GH

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :
Standard Draize test
ROUTE OF EXPOSURE :
Administration onto the skin
SPECIES OBSERVED :
Rodent - rabbit
REFERENCE :
FCTOD7 Food and Chemical Toxicology. (Pergamon Press Inc., Maxwell House, Fairview Park, Elmsford, NY 10523) V.20- 1982- Volume(issue)/page/year: 20,563,1982
TYPE OF TEST :
Standard Draize test
ROUTE OF EXPOSURE :
Administration into the eye
SPECIES OBSERVED :
Rodent - rabbit
REFERENCE :
FCTOD7 Food and Chemical Toxicology. (Pergamon Press Inc., Maxwell House, Fairview Park, Elmsford, NY 10523) V.20- 1982- Volume(issue)/page/year: 20,573,1982
TYPE OF TEST :
Rinsed with water
ROUTE OF EXPOSURE :
Administration into the eye
SPECIES OBSERVED :
Rodent - rabbit
REFERENCE :
FCTOD7 Food and Chemical Toxicology. (Pergamon Press Inc., Maxwell House, Fairview Park, Elmsford, NY 10523) V.20- 1982- Volume(issue)/page/year: 20,573,1982 ** ACUTE TOXICITY DATA **
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
1 gm/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
85KYAH "Merck Index; an Encyclopedia of Chemicals, Drugs, and Biologicals", 11th ed., Rahway, NJ 07065, Merck & Co., Inc. 1989 Volume(issue)/page/year: 11,934,1989
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Subcutaneous
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
300 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
85KYAH "Merck Index; an Encyclopedia of Chemicals, Drugs, and Biologicals", 11th ed., Rahway, NJ 07065, Merck & Co., Inc. 1989 Volume(issue)/page/year: 11,934,1989
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
1450 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
NIIRDN Drugs in Japan (Ethical Drugs). (Yakugyo Jiho Co., Ltd., Tokyo, Japan) Volume(issue)/page/year: 6,841,1982
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intraperitoneal
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
420 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
NIIRDN Drugs in Japan (Ethical Drugs). (Yakugyo Jiho Co., Ltd., Tokyo, Japan) Volume(issue)/page/year: 6,841,1982
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Subcutaneous
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
225 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
NIIRDN Drugs in Japan (Ethical Drugs). (Yakugyo Jiho Co., Ltd., Tokyo, Japan) Volume(issue)/page/year: -,1193,1990
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intravenous
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
180 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
CSLNX* U.S. Army Armament Research & Development Command, Chemical Systems Laboratory, NIOSH Exchange Chemicals. (Aberdeen Proving Ground, MD 21010) Volume(issue)/page/year: NX#04012
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - rabbit
DOSE/DURATION :
350 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
NIIRDN Drugs in Japan (Ethical Drugs). (Yakugyo Jiho Co., Ltd., Tokyo, Japan) Volume(issue)/page/year: -,1193,1990
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Subcutaneous
SPECIES OBSERVED :
Rodent - rabbit
DOSE/DURATION :
150 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
NIIRDN Drugs in Japan (Ethical Drugs). (Yakugyo Jiho Co., Ltd., Tokyo, Japan) Volume(issue)/page/year: -,1193,1990
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - guinea pig
DOSE/DURATION :
500 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
NIIRDN Drugs in Japan (Ethical Drugs). (Yakugyo Jiho Co., Ltd., Tokyo, Japan) Volume(issue)/page/year: -,1193,1990
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intraperitoneal
SPECIES OBSERVED :
Rodent - guinea pig
DOSE/DURATION :
200 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
TXAPA9 Toxicology and Applied Pharmacology. (Academic Press, Inc., 1 E. First St., Duluth, MN 55802) V.1- 1959- Volume(issue)/page/year: 2,474,1960
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Subcutaneous
SPECIES OBSERVED :
Rodent - guinea pig
DOSE/DURATION :
150 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
NIIRDN Drugs in Japan (Ethical Drugs). (Yakugyo Jiho Co., Ltd., Tokyo, Japan) Volume(issue)/page/year: -,1193,1990
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intramuscular
SPECIES OBSERVED :
Rodent - guinea pig
DOSE/DURATION :
200 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
TXAPA9 Toxicology and Applied Pharmacology. (Academic Press, Inc., 1 E. First St., Duluth, MN 55802) V.1- 1959- Volume(issue)/page/year: 2,474,1960 ** OTHER MULTIPLE DOSE TOXICITY DATA **
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Intracerebral
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
40 mg/kg/10D-C
TOXIC EFFECTS :
Behavioral - changes in motor activity (specific assay) Vascular - BP lowering not characterized in autonomic section Related to Chronic Data - death
REFERENCE :
PHTOEH Pharmacology and Toxicology (Copenhagen). (Munksgaard International Pub., POB 2148, DK-1016 Copenhagen K, Denmark) V.60- 1987- Volume(issue)/page/year: 81,7,1997
Symbol GHS07
GHS07
Signal Word Warning
Hazard Statements H302-H315-H319
Precautionary Statements P305 + P351 + P338
Personal Protective Equipment dust mask type N95 (US);Eyeshields;Gloves
Hazard Codes Xn
Risk Phrases R22;R36/38
Safety Phrases S26-S36
RIDADR NONH for all modes of transport
WGK Germany 3
RTECS DU1800000
HS Code 2925290090
657-24-9 structure

657-24-9

~77%

1115-70-4 structure

1115-70-4

Literature: HANALL PHARMACEUTICAL COMPANY. LTD Patent: WO2008/93984 A1, 2008 ; Location in patent: Page/Page column 29 ;
506-59-2 structure

506-59-2

127099-85-8 structure

127099-85-8

~94%

1115-70-4 structure

1115-70-4

Literature: Kelarev, V. I.; Bellul', M.; Zav'yalov, V. I.; Ammar Dibi; Golovin, A. N.; et al. Journal of Organic Chemistry USSR (English Translation), 1988 , vol. 24, # 5 p. 994 - 998 Zhurnal Organicheskoi Khimii, 1988 , vol. 24, # 5 p. 1100 - 1105
124-40-3 structure

124-40-3

127099-85-8 structure

127099-85-8

~%

1115-70-4 structure

1115-70-4

Literature: Pharmaceutical Chemistry Journal, , vol. 21, # 12 p. 892 - 894 Khimiko-Farmatsevticheskii Zhurnal, , vol. 21, # 12 p. 1517 - 1518
HS Code 2925290090
Summary 2925290090 other imines and their derivatives; salts thereof。Supervision conditions:None。VAT:17.0%。Tax rebate rate:9.0%。MFN tariff:6.5%。General tariff:30.0%
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