Buformin HCl | CAS#1190-53-0 | hypoglycemic agent

MedKoo Cat#: 591104 | Name: Buformin HCl

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Description:

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

Buformin (1-butylbiguanide) is an oral antidiabetic drug of the biguanide class, chemically related to metformin and phenformin. Buformin was marketed by German pharmaceutical company Grünenthal as Silubin. Buformin delays absorption of glucose from the gastrointestinal tract, increases insulin sensitivity and glucose uptake into cells, and inhibits synthesis of glucose by the liver. Buformin and the other biguanides are not hypoglycemic, but rather antihyperglycemic agents. They do not produce hypoglycemia; instead, they reduce basal and postprandial hyperglycemia in diabetics.[5] Biguanides may antagonize the action of glucagon, thus reducing fasting glucose levels.

Chemical Structure

Buformin HCl

CAS#1190-53-0 (HCl)

Theoretical Analysis

MedKoo Cat#: 591104

Name: Buformin HCl

CAS#: 1190-53-0 (HCl)

Chemical Formula: C6H16ClN5

Exact Mass: 0.0000

Molecular Weight: 193.68

Elemental Analysis: C, 37.21; H, 8.33; Cl, 18.30; N, 36.16

Price and Availability

Size	Price	Availability	Quantity
50mg	USD 250.00	2 Weeks
250mg	USD 550.00	2 Weeks

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Related CAS #

1190-53-0 (HCl) 692-13-7 (free base)

Synonym

Buformin hydrochloride; Buformin HCl; NSC 528218; NSC-528218; NSC528218

IUPAC/Chemical Name

1-Butylbiguanide monohydrochloride

InChi Key

KKLWSPPIRBIEOV-UHFFFAOYSA-N

InChi Code

InChI=1S/C6H15N5.ClH/c1-2-3-4-10-6(9)11-5(7)8;/h2-4H2,1H3,(H6,7,8,9,10,11);1H

SMILES Code

N=C(NC(N)=N)NCCCC.[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

Product Data

Product Data

Instruction

View handling instruction

Biological target:

Buformin hydrochloride (1-Butylbiguanide hydrochloride), a potent AMPK activator, acts as an orally active biguanide antidiabetic agent.

In vitro activity:

According to the results of the CCK-8 assay, buformin exerted a significant dose-dependent suppressive effect on the growth of U-2 OS cells (Figure 1a, IC50 = 69.1 µM, P = 0.017, treated with buformin for 72 h). Moreover, this study then repeated this assay using 100 µM buformin and found that buformin exerted suppressive effects in a time-dependent manner (Figure 1b). Reference: Open Life Sci. 2020 Jun 30;15(1):409-417. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7874575/

In vivo activity:

To further test the buformin-associated inhibitory effects in vivo, this study used a syngeneic tumor model in MMTV-erbB-2 mice that were fed a buformin diet (1.2 g buformin/kg chow) for 12 days after inoculation with 78617 breast cancer cells. Mice fed the buformin diet exhibited significantly reduced tumor volumes and weights as compared to the control mice (Fig. 2). Reference: J Exp Clin Cancer Res. 2017; 36: 28. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5307817/

	Solvent	mg/mL	mM
Solubility
	PBS (pH 7.2)	1.0	5.16

Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 193.68 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. Ding Y, Lv S, Li G, Cui J, Chen Y. Buformin suppresses osteosarcoma via targeting AMPK signaling pathway. Open Life Sci. 2020 Jun 30;15(1):409-417. doi: 10.1515/biol-2020-0041. PMID: 33817229; PMCID: PMC7874575. 2. Chen L, Zhang T, Liu Q, Tang M, Yang Y, Wang Y, Qiu H, Yu J. Buformin increases radiosensitivity in cervical cancer cells via cell-cycle arrest and delayed DNA-damage repair. Exp Biol Med (Maywood). 2018 Oct;243(14):1133-1140. doi: 10.1177/1535370218813320. PMID: 32459508; PMCID: PMC6327368. 3. Parris AB, Zhao Q, Howard EW, Zhao M, Ma Z, Yang X. Buformin inhibits the stemness of erbB-2-overexpressing breast cancer cells and premalignant mammary tissues of MMTV-erbB-2 transgenic mice. J Exp Clin Cancer Res. 2017 Feb 13;36(1):28. doi: 10.1186/s13046-017-0498-0. PMID: 28193239; PMCID: PMC5307817.

In vitro protocol:

In vivo protocol:

1. Parris AB, Zhao Q, Howard EW, Zhao M, Ma Z, Yang X. Buformin inhibits the stemness of erbB-2-overexpressing breast cancer cells and premalignant mammary tissues of MMTV-erbB-2 transgenic mice. J Exp Clin Cancer Res. 2017 Feb 13;36(1):28. doi: 10.1186/s13046-017-0498-0. PMID: 28193239; PMCID: PMC5307817.

1: Liu B, Wang Z, He R, Xiong R, Li G, Zhang L, Fu T, Li C, Li N, Geng Q. Buformin alleviates sepsis-induced acute lung injury via inhibiting NLRP3-mediated pyroptosis through an AMPK-dependent pathway. Clin Sci (Lond). 2022 Feb 25;136(4):273-289. doi: 10.1042/CS20211156. PMID: 35132999. 2: Ding Y, Lv S, Li G, Cui J, Chen Y. Buformin suppresses osteosarcoma via targeting AMPK signaling pathway. Open Life Sci. 2020 Jun 30;15(1):409-417. doi: 10.1515/biol-2020-0041. PMID: 33817229; PMCID: PMC7874575. 3: Bailey CJ. Metformin: historical overview. Diabetologia. 2017 Sep;60(9):1566-1576. doi: 10.1007/s00125-017-4318-z. Epub 2017 Aug 3. PMID: 28776081. 4: Lu M, Xing H, Cheng L, Liu H, Lang L, Yang T, Zhao X, Xu H, Ding P. A dual- functional buformin-mimicking poly(amido amine) for efficient and safe gene delivery. J Drug Target. 2020 Nov;28(9):923-932. doi: 10.1080/1061186X.2020.1729770. Epub 2020 Apr 21. PMID: 32312081. 5: Kilgore J, Jackson AL, Clark LH, Guo H, Zhang L, Jones HM, Gilliam TP, Gehrig PA, Zhou C, Bae-Jump VL. Buformin exhibits anti-proliferative and anti-invasive effects in endometrial cancer cells. Am J Transl Res. 2016 Jun 15;8(6):2705-15. PMID: 27398153; PMCID: PMC4931164. 6: Li J, Chen L, Liu Q, Tang M, Wang Y, Yu J. Buformin suppresses proliferation and invasion via AMPK/S6 pathway in cervical cancer and synergizes with paclitaxel. Cancer Biol Ther. 2018 Jun 3;19(6):507-517. doi: 10.1080/15384047.2018.1433504. Epub 2018 Feb 27. PMID: 29400636; PMCID: PMC5927663. 7: Parris AB, Zhao Q, Howard EW, Zhao M, Ma Z, Yang X. Buformin inhibits the stemness of erbB-2-overexpressing breast cancer cells and premalignant mammary tissues of MMTV-erbB-2 transgenic mice. J Exp Clin Cancer Res. 2017 Feb 13;36(1):28. doi: 10.1186/s13046-017-0498-0. PMID: 28193239; PMCID: PMC5307817. 8: Banella C, Catalano G, Travaglini S, Pelosi E, Ottone T, Zaza A, Guerrera G, Angelini DF, Niscola P, Divona M, Battistini L, Screnci M, Ammatuna E, Testa U, Nervi C, Voso MT, Noguera NI. Ascorbate Plus Buformin in AML: A Metabolic Targeted Treatment. Cancers (Basel). 2022 May 23;14(10):2565. doi: 10.3390/cancers14102565. PMID: 35626170; PMCID: PMC9139619. 9: Wurita A, Hasegawa K, Nozawa H, Yamagishi I, Minakata K, Watanabe K, Suzuki O. Postmortem distribution/redistribution of buformin in body fluids and solid tissues in an autopsy case using liquid chromatography-tandem mass spectrometry with QuEChERS extraction method. Forensic Sci Int. 2020 Sep;314:110376. doi: 10.1016/j.forsciint.2020.110376. Epub 2020 Jun 20. PMID: 32615395. 10: Yano A, Kubota M, Iguchi K, Usui S, Hirano K. Buformin suppresses the expression of glyceraldehyde 3-phosphate dehydrogenase. Biol Pharm Bull. 2006 May;29(5):1006-9. doi: 10.1248/bpb.29.1006. PMID: 16651735. 11: Bratusch-Marrain PR, Korn A, Waldhäusl WK, Gasić S, Nowotny P. Effect of buformin on splanchnic carbohydrate and substrate metabolism in healthy man. Metabolism. 1981 Oct;30(10):946-52. doi: 10.1016/0026-0495(81)90091-3. PMID: 7024721. 12: Chen L, Zhang T, Liu Q, Tang M, Yang Y, Wang Y, Qiu H, Yu J. Buformin increases radiosensitivity in cervical cancer cells via cell-cycle arrest and delayed DNA-damage repair. Exp Biol Med (Maywood). 2018 Oct;243(14):1133-1140. doi: 10.1177/1535370218813320. PMID: 32459508; PMCID: PMC6327368. 13: Ohara S, Komatsu R, Matsuyama T. Short-term effect of buformin, a biguanide, on insulin sensitivity, soluble fraction of tumor necrosis factor receptor and serum lipids in overweight patients with type 2 diabetes mellitus. Diabetes Res Clin Pract. 2004 Nov;66(2):133-8. doi: 10.1016/j.diabres.2004.03.007. PMID: 15533580. 14: Sekso M, Solter M, Zjacić V, Cabrijan T. Treatment of reactive hypoglycemia with buformin. Am J Clin Nutr. 1975 Nov;28(11):1271-6. doi: 10.1093/ajcn/28.11.1271. PMID: 1190104. 15: Zhu Z, Jiang W, Thompson MD, Echeverria D, McGinley JN, Thompson HJ. Effects of metformin, buformin, and phenformin on the post-initiation stage of chemically induced mammary carcinogenesis in the rat. Cancer Prev Res (Phila). 2015 Jun;8(6):518-27. doi: 10.1158/1940-6207.CAPR-14-0121. Epub 2015 Mar 24. PMID: 25804611; PMCID: PMC4452421. 16: Nattrass M, Alberti KG. Biguanides. Diabetologia. 1978 Feb;14(2):71-4. doi: 10.1007/BF01263443. PMID: 631459. 17: Wang G, Lin F, Wan Q, Wu J, Luo M. Mechanisms of action of metformin and its regulatory effect on microRNAs related to angiogenesis. Pharmacol Res. 2021 Feb;164:105390. doi: 10.1016/j.phrs.2020.105390. Epub 2020 Dec 19. PMID: 33352227. 18: Krishnamurthy M, Sahouria JJ, Desai R, Caguiat J. Buformin-induced lactic acidosis--a symptom of modern healthcare malady. J Am Geriatr Soc. 2004 Oct;52(10):1785. doi: 10.1111/j.1532-5415.2004.52479_7.x. PMID: 15450070. 19: Matsuura T, Miyao M, Mizuno Y. [A case of lactic acidosis caused by buformin in an oldest elderly diabetic patient]. Nihon Ronen Igakkai Zasshi. 2005 Mar;42(2):235-40. Japanese. doi: 10.3143/geriatrics.42.235. PMID: 15852659. 20: Ohnishi S, Mizutani H, Kawanishi S. The enhancement of oxidative DNA damage by anti-diabetic metformin, buformin, and phenformin, via nitrogen-centered radicals. Free Radic Res. 2016 Aug;50(8):929-37. doi: 10.1080/10715762.2016.1204651. PMID: 27328723.