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

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

MedKoo CAT#: 591104

CAS#: 1190-53-0 (HCl)

Description: 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 hydrochloride

CAS# 1190-53-0 (HCl)

Product data Instruction

Theoretical Analysis

MedKoo Cat#: 591104
Name: Buformin hydrochloride
CAS#: 1190-53-0 (HCl)
Chemical Formula: C6H16ClN5
Exact Mass: 193.11
Molecular Weight: 193.680
Elemental Analysis: C, 37.21; H, 8.33; Cl, 18.30; N, 36.16

Price and Availability

Size	Price	Availability	Quantity
100mg	USD 250
250mg	USD 450
500mg	USD 750
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.

Related CAS #: 1190-53-0 (HCl) 692-13-7 (free base)

Synonym: Buformin hydrochloride; 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

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Product Data:

Product Data

Instruction:

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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/

Solubility Data

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

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:	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.
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.

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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.

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