Metformin HCl | CAS#1115-70-4 | AMPK Activator

Metformin HCl
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WARNING: This product is for research use only, not for human or veterinary use.

MedKoo CAT#: 328609

CAS#: 1115-70-4 (HCl)

Description: Metformin is an AMP-activated protein kinase (AMPK) activator that improves glycemic control by improving insulin sensitivity and decreasing intestinal absorption of glucose. Metformin exerts an anorexiant effect, decreasing caloric intake. Metformin decreases gluconeogenesis (glucose production) in the liver. Metformin inhibits basal secretion from the pituitary gland of growth hormone, adrenocorticotropic hormone, follicle stimulating hormone, and expression of proopiomelanocortin, which in part accounts for its insulin-sensitizing effect with multiple actions on tissues including the liver, skeletal muscle, endothelium, adipose tissue, and the ovaries.

Chemical Structure

Metformin HCl

CAS# 1115-70-4 (HCl)

Product data Instruction

Theoretical Analysis

MedKoo Cat#: 328609
Name: Metformin HCl
CAS#: 1115-70-4 (HCl)
Chemical Formula: C4H12ClN5
Exact Mass: 0.00
Molecular Weight: 165.625
Elemental Analysis: C, 29.01; H, 7.30; Cl, 21.40; N, 42.29

Price and Availability

Size	Price	Availability
5g	USD 90	Ready to ship
10g	USD 150	Ready to ship
25g	USD 250	Ready to ship
50g	USD 350	Ready to ship
Bulk inquiry Welcome, Customer: Please do not inquire quote if your intended use is for a patient since our products are for research use and for chemical synthesis use, not for human use . For in-stock products, we listed price in the web page. You may inquire prices for which sizes were not listed. If no price is listed, this means the product is not in stock at the moment, which may be available via custom synthesis. For cost-effective reason, minimum order of 1g is requested (typically very expensive). The lead time is usually 2-4 months. Quote of less than 1g will not be provided. MedKoo may not offer quote for below reasons: (1) current available synthetic method appears to be extremely expensive which is obviously not affordable to most customers; (2) Key raw material to make the product is temporally not available; (3) DEA controlled substances; (4) the product is under patent protection in customer’s country.

Synonym: Metformin Hydrochloride; ADX-155; EFB-0027; EX-404; La-6023; SMP-862; ADX 155; EFB 0027; EX 404; La 6023; SMP 862; ADX155; EFB0027; EX404; La6023; SMP862; Fortamet

IUPAC/Chemical Name: 1,1-Dimethylbiguanide hydrochloride

InChi Key: OETHQSJEHLVLGH-UHFFFAOYSA-N

InChi Code: InChI=1S/C4H11N5.ClH/c1-9(2)4(7)8-3(5)6;/h1-2H3,(H5,5,6,7,8);1H

SMILES Code: N=C(NC(N)=N)N(C)C.[H]Cl

Appearance: Solid powder

Purity: >98% (or refer to the Certificate of Analysis)

Shipping Condition: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility: Soluble in DMSO

Shelf Life: >2 years if stored properly

Drug Formulation: This drug may be formulated in DMSO

Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code: 2934.99.9001

More Info: AMPK probably also plays a role in increased peripheral insulin sensitivity, as metformin administration increases AMPK activity in skeletal muscle. AMPK is known to cause GLUT4 deployment to the plasma membrane, resulting in insulin-independent glucose uptake. Some metabolic actions of metformin do appear to occur by AMPK-independent mechanisms, however AMPK likely has a modest overall effect and its activity is not likely to directly decrease gluconeogenesis in the liver. Metformin has indirect antiandrogenic effects in women with insulin resistance, such as those with PCOS, due to its beneficial effects on insulin sensitivity. It may reduce testosterone levels in such women by as much as 50%. A Cochrane review, though, found that metformin was only slightly effective for decreasing androgen levels in women with PCOS. Metformin also has significant effects on the gut microbiome, such as its effect on increasing agmatine production by gut bacteria, but the relative importance of this mechanism compared to other mechanisms is uncertain. Due to its effect on GLUT4 and AMPK, metformin has been described as an exercise mimetic.

Product Data:

Product Data

Certificate of Analysis:

View CoA: current batch, Lot#B7B07C03

QC Data:

View QC data: current batch, Lot#B7B07C03

Safety Data Sheet (SDS):

View Safety Data Sheet (SDS)

Instruction:

View handling instruction

Biological target:	Metformin hydrochloride (1,1-Dimethylbiguanide hydrochloride) inhibits the mitochondrial respiratory chain in the liver, leading to activation of AMPK, enhancing insulin sensitivity.
In vitro activity:	To explore the mechanism of metformin’s inhibition of the proliferation of colorectal cancer cells, HCT116 and SW480 cells were treated with increasing concentrations of metformin (0, 10, 20, and 40 mM) for 24 h. The colony-formation results show that metformin decreased the proliferation of HCT116 and SW480 cells (Figure 5b–c) in a concentration-dependent manner. The levels of AMPK, p-AMPK, and proteins in the urea cycle and putrescine generation pathways were assessed by Western blotting to explore the mechanism of metformin’s activity. The expression of p-AMPK/AMPK was significantly increased, and the protein levels of ARG1, OTC, and ODC were decreased in both HCT116 and SW480 cells (Figure 5d–e), in a dose-dependent manner. Reference: Molecules. 2021 Apr; 26(7): 1990. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8038129/
In vivo activity:	A complete loss of DCX+Ki67+ neuroblasts in the SEZ (subependymal zone) at 2 days post-IR and a near-complete loss in metformin preTx (pretreatment) mice (Figures 3B and 3C) was observed. DCX+Ki67+ cells were observed in both treated and untreated mice by 30 days post-IR; however, although a significant ∼33% reduction persisted in untreated mice, metformin preTx completely rescued this deficit (Figure 3D). A similar rescue of DCX+Ki67+ cells was observed along the RMS (rostral migratory stream) at 30 days post-IR in metformin preTx mice (Figures 3E and 3F). Interestingly, metformin preTx did not significantly alter the total number of neuroblasts (DCX+) or proliferating (Ki67+) cells in the SEZ (Figure S3), suggesting that metformin preTx specifically supported the recovery of proliferating neuroblasts following cranial IR. Reference: Cell Rep Med. 2021 Apr 20; 2(4): 100231. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8080112/

Solubility Data

	Solvent	Max Conc. mg/mL	Max Conc. mM
Solubility
	DMSO	2.5	15.15
	PBS (pH 7.2)	1.0	6.04
	Water	32.5	196.23

Preparing Stock Solutions

The following data is based on the product molecular weight 165.63 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Concentration / Solvent Volume / Mass	1 mg	5 mg	10 mg
1 mM	1.15 mL	5.76 mL	11.51 mL
5 mM	0.23 mL	1.15 mL	2.3 mL
10 mM	0.12 mL	0.58 mL	1.15 mL
50 mM	0.02 mL	0.12 mL	0.23 mL

Formulation protocol:	1. Zhang T, Hu L, Tang JF, Xu H, Tian K, Wu MN, Huang SY, Du YM, Zhou P, Lu RJ, He S, Xu JM, Si JJ, Li J, Chen DL, Ran JH. Metformin Inhibits the Urea Cycle and Reduces Putrescine Generation in Colorectal Cancer Cell Lines. Molecules. 2021 Apr 1;26(7):1990. doi: 10.3390/molecules26071990. PMID: 33915902; PMCID: PMC8038129. 2. Farfan-Morales CN, Cordero-Rivera CD, Osuna-Ramos JF, Monroy-Muñoz IE, De Jesús-González LA, Muñoz-Medina JE, Hurtado-Monzón AM, Reyes-Ruiz JM, Del Ángel RM. The antiviral effect of metformin on zika and dengue virus infection. Sci Rep. 2021 Apr 22;11(1):8743. doi: 10.1038/s41598-021-87707-9. PMID: 33888740; PMCID: PMC8062493. 3. Derkach D, Kehtari T, Renaud M, Heidari M, Lakshman N, Morshead CM. Metformin pretreatment rescues olfactory memory associated with subependymal zone neurogenesis in a juvenile model of cranial irradiation. Cell Rep Med. 2021 Apr 6;2(4):100231. doi: 10.1016/j.xcrm.2021.100231. PMID: 33948569; PMCID: PMC8080112. 4. Moon J, Lee SY, Choi JW, Lee AR, Yoo JH, Moon SJ, Park SH, Cho ML. Metformin ameliorates scleroderma via inhibiting Th17 cells and reducing mTOR-STAT3 signaling in skin fibroblasts. J Transl Med. 2021 May 4;19(1):192. doi: 10.1186/s12967-021-02860-z. PMID: 33947424; PMCID: PMC8097822.
In vitro protocol:	1. Zhang T, Hu L, Tang JF, Xu H, Tian K, Wu MN, Huang SY, Du YM, Zhou P, Lu RJ, He S, Xu JM, Si JJ, Li J, Chen DL, Ran JH. Metformin Inhibits the Urea Cycle and Reduces Putrescine Generation in Colorectal Cancer Cell Lines. Molecules. 2021 Apr 1;26(7):1990. doi: 10.3390/molecules26071990. PMID: 33915902; PMCID: PMC8038129. 2. Farfan-Morales CN, Cordero-Rivera CD, Osuna-Ramos JF, Monroy-Muñoz IE, De Jesús-González LA, Muñoz-Medina JE, Hurtado-Monzón AM, Reyes-Ruiz JM, Del Ángel RM. The antiviral effect of metformin on zika and dengue virus infection. Sci Rep. 2021 Apr 22;11(1):8743. doi: 10.1038/s41598-021-87707-9. PMID: 33888740; PMCID: PMC8062493.
In vivo protocol:	1. Derkach D, Kehtari T, Renaud M, Heidari M, Lakshman N, Morshead CM. Metformin pretreatment rescues olfactory memory associated with subependymal zone neurogenesis in a juvenile model of cranial irradiation. Cell Rep Med. 2021 Apr 6;2(4):100231. doi: 10.1016/j.xcrm.2021.100231. PMID: 33948569; PMCID: PMC8080112. 2. Moon J, Lee SY, Choi JW, Lee AR, Yoo JH, Moon SJ, Park SH, Cho ML. Metformin ameliorates scleroderma via inhibiting Th17 cells and reducing mTOR-STAT3 signaling in skin fibroblasts. J Transl Med. 2021 May 4;19(1):192. doi: 10.1186/s12967-021-02860-z. PMID: 33947424; PMCID: PMC8097822.

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1: Sutter A, Landis D, Nugent K. Metformin has immunomodulatory effects which support its potential use as adjunctive therapy in tuberculosis. Indian J Tuberc. 2024 Jan;71(1):89-95. doi: 10.1016/j.ijtb.2023.05.011. Epub 2023 May 16. PMID: 38296396.

2: Kelleni MT. Repurposing metformin to manage idiopathic or long COVID Tinnitus: self-report adopting a pathophysiological and pharmacological approach. Inflammopharmacology. 2024 Jan 31. doi: 10.1007/s10787-023-01421-8. Epub ahead of print. PMID: 38294616.

3: Wang Q, Wei X. Research Progress on the Use of Metformin in Leukemia Treatment. Curr Treat Options Oncol. 2024 Jan 30. doi: 10.1007/s11864-024-01179-3. Epub ahead of print. PMID: 38286894.

4: Pedreañez A, Carrero Y, Vargas R, Hernandez-Fonseca JP, Mosquera-Sulbaran J. Paolo Brambilla, PhD, MD Possible role of metformin as an antidepressant in diabetes. Review. J Affect Disord. 2024 Jan 27:S0165-0327(24)00247-7. doi: 10.1016/j.jad.2024.01.228. Epub ahead of print. PMID: 38286229.

5: Xie H, Li M, Zheng Y. Associations of metformin therapy treatment with endometrial cancer risk and prognosis: A systematic review and meta-analysis. Gynecol Oncol. 2024 Jan 20;182:15-23. doi: 10.1016/j.ygyno.2024.01.007. Epub ahead of print. PMID: 38246042.

6: Dewangga R, Winston K, Ilhami LG, Indriani S, Siddiq T, Adiarto S. Association of metformin use with abdominal aortic aneurysm: A systematic review and meta-analysis. Asian Cardiovasc Thorac Ann. 2024 Jan 18:2184923231225794. doi: 10.1177/02184923231225794. Epub ahead of print. PMID: 38239055.

7: Pujalte-Martin M, Belaïd A, Bost S, Kahi M, Peraldi P, Rouleau M, Mazure NM, Bost F. Targeting cancer and immune cell metabolism with the complex I inhibitors metformin and IACS-010759. Mol Oncol. 2024 Jan 12. doi: 10.1002/1878-0261.13583. Epub ahead of print. PMID: 38214418.

8: Almeida-Nunes DL, Silvestre R, Dinis-Oliveira RJ, Ricardo S. Enhancing Immunotherapy in Ovarian Cancer: The Emerging Role of Metformin and Statins. Int J Mol Sci. 2023 Dec 25;25(1):323. doi: 10.3390/ijms25010323. PMID: 38203494; PMCID: PMC10779012.

9: Alatawi AM. Metformin versus sodium glucose co-transporters inhibitors as first-line for atherosclerotic cardiovascular disease: A meta-analysis. Pak J Med Sci. 2024 Jan-Feb;40(1Part-I):209-213. doi: 10.12669/pjms.40.1.6982. PMID: 38196460; PMCID: PMC10772430.

10: Ruan G, Wu F, Shi D, Sun H, Wang F, Xu C. Metformin: update on mechanisms of action on liver diseases. Front Nutr. 2023 Dec 14;10:1327814. doi: 10.3389/fnut.2023.1327814. PMID: 38192642; PMCID: PMC10773879.

11: Zhao D, Sohouli MH, Rohani P, Fotros D, Velu P, Ziamanesh F, Fatahi S, Shojaie S, Li Y. The effect of metformin on adipokines levels: A systematic review and meta-analysis of randomized-controlled trials. Diabetes Res Clin Pract. 2023 Dec 26;207:111076. doi: 10.1016/j.diabres.2023.111076. Epub ahead of print. PMID: 38154535.

12: Sacco M, Ribaldone DG, Saracco GM. Metformin and Hepatocellular Carcinoma Risk Reduction in Diabetic Patients with Chronic Hepatitis C: Fact or Fiction? Viruses. 2023 Dec 17;15(12):2451. doi: 10.3390/v15122451. PMID: 38140692; PMCID: PMC10748230.

13: Isop LM, Neculau AE, Necula RD, Kakucs C, Moga MA, Dima L. Metformin: The Winding Path from Understanding Its Molecular Mechanisms to Proving Therapeutic Benefits in Neurodegenerative Disorders. Pharmaceuticals (Basel). 2023 Dec 11;16(12):1714. doi: 10.3390/ph16121714. PMID: 38139841; PMCID: PMC10748332.

14: Rittenhouse BE, Alolayan S, Eguale T, Segal AR, Doucette J. The cost- effectiveness of metformin in the US diabetes prevention program trial: Simple interpretations need not apply. Prev Med. 2024 Jan;178:107819. doi: 10.1016/j.ypmed.2023.107819. Epub 2023 Dec 11. PMID: 38092328.

15: Cho M, Woo YR, Cho SH, Lee JD, Kim HS. Metformin: A Potential Treatment for Acne, Hidradenitis Suppurativa and Rosacea. Acta Derm Venereol. 2023 Dec 11;103:adv18392. doi: 10.2340/actadv.v103.18392. PMID: 38078688; PMCID: PMC10726377.

16: Chang W, Li W, Li P. The anti-diabetic effects of metformin are mediated by regulating long non-coding RNA. Front Pharmacol. 2023 Nov 20;14:1256705. doi: 10.3389/fphar.2023.1256705. PMID: 38053839; PMCID: PMC10694297.

17: Li R, Li H, Yang Z, Zhang X. Combination of metformin with liraglutide in treating HAIR-AN syndrome in children: A case report and literature review. Zhong Nan Da Xue Xue Bao Yi Xue Ban. 2023 Sept 28;48(9):1425-1431. English, Chinese. doi: 10.11817/j.issn.1672-7347.2023.230100. PMID: 38044655.

18: Tiwari A, Kumar Singh R, Satone PD, Meshram RJ. Metformin-Induced Vitamin B12 Deficiency in Patients With Type-2 Diabetes Mellitus. Cureus. 2023 Oct 26;15(10):e47771. doi: 10.7759/cureus.47771. PMID: 38034222; PMCID: PMC10688235.

19: Huang Z, Li J, Chen H, Yu D, Sun S. The efficacy of metformin for the treatment of psoriasis: a meta-analysis study. Postepy Dermatol Alergol. 2023 Oct;40(5):606-610. doi: 10.5114/ada.2023.130524. Epub 2023 Aug 22. PMID: 38028405; PMCID: PMC10646712.

20: Lin H, Ao H, Guo G, Liu M. The Role and Mechanism of Metformin in Inflammatory Diseases. J Inflamm Res. 2023 Nov 23;16:5545-5564. doi: 10.2147/JIR.S436147. PMID: 38026260; PMCID: PMC10680465.

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