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MedKoo Cat#: 341530 | Name: Buformin

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
Buformin
CAS#692-13-7 (free base)

Theoretical Analysis

MedKoo Cat#: 341530

Name: Buformin

CAS#: 692-13-7 (free base)

Chemical Formula: C6H15N5

Exact Mass: 157.1327

Molecular Weight: 157.22

Elemental Analysis: C, 45.84; H, 9.62; N, 44.55

Price and Availability

This product is currently not in stock but may be available through custom synthesis. To ensure cost efficiency, the minimum order quantity is 1 gram. The estimated lead time is 2 to 4 months, with pricing dependent on the complexity of the synthesis (typically high for intricate chemistries). Quotes for quantities below 1 gram will not be provided. To request a quote, please click the button below. Note: If this product becomes available in stock in the future, pricing will be listed accordingly.
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Related CAS #
1190-53-0 (HCl) 692-13-7 (free base)
Synonym
Buformin; H 224; W 37; W-37; W37.
IUPAC/Chemical Name
1-Butylbiguanide
InChi Key
XSEUMFJMFFMCIU-UHFFFAOYSA-N
InChi Code
InChI=1S/C6H15N5/c1-2-3-4-10-6(9)11-5(7)8/h2-4H2,1H3,(H6,7,8,9,10,11)
SMILES Code
N=C(NC(N)=N)NCCCC
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

Preparing Stock Solutions

The following data is based on the product molecular weight 157.22 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.

Recalculate based on batch purity %
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
1: 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. PubMed PMID: 29400636; PubMed Central PMCID: PMC5927663. 2: Alshishani A, Salhimi SM, Saad B. Salting-out assisted liquid-liquid extraction coupled with hydrophilic interaction chromatography for the determination of biguanides in biological and environmental samples. J Chromatogr B Analyt Technol Biomed Life Sci. 2018 Jan 15;1073:51-59. doi: 10.1016/j.jchromb.2017.12.013. Epub 2017 Dec 9. PubMed PMID: 29241085. 3: Bailey CJ. Metformin: historical overview. Diabetologia. 2017 Sep;60(9):1566-1576. doi: 10.1007/s00125-017-4318-z. Epub 2017 Aug 3. PubMed PMID: 28776081. 4: Gabel SA, Duff MR, Pedersen LC, DeRose EF, Krahn JM, Howell EE, London RE. A Structural Basis for Biguanide Activity. Biochemistry. 2017 Sep 12;56(36):4786-4798. doi: 10.1021/acs.biochem.7b00619. Epub 2017 Aug 29. PubMed PMID: 28766937; PubMed Central PMCID: PMC5740485. 5: 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. PubMed PMID: 28193239; PubMed Central PMCID: PMC5307817. 6: Alshishani A, Makahleh A, Yap HF, Gubartallah EA, Salhimi SM, Saad B. Ion-pair vortex assisted liquid-liquid microextraction with back extraction coupled with high performance liquid chromatography-UV for the determination of metformin in plasma. Talanta. 2016 Dec 1;161:398-404. doi: 10.1016/j.talanta.2016.08.067. Epub 2016 Aug 26. PubMed PMID: 27769423. 7: Rhee CM, Kovesdy CP, Kalantar-Zadeh K. Risks of Metformin in Type 2 Diabetes and Chronic Kidney Disease: Lessons Learned from Taiwanese Data. Nephron. 2017;135(2):147-153. doi: 10.1159/000450862. Epub 2016 Oct 20. PubMed PMID: 27760420; PubMed Central PMCID: PMC5316472. 8: 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. eCollection 2016. PubMed PMID: 27398153; PubMed Central PMCID: PMC4931164. 9: Futatsugi A, Masuo Y, Kawabata S, Nakamichi N, Kato Y. L503F variant of carnitine/organic cation transporter 1 efficiently transports metformin and other biguanides. J Pharm Pharmacol. 2016 Sep;68(9):1160-9. doi: 10.1111/jphp.12574. Epub 2016 Jun 28. PubMed PMID: 27350110. 10: 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. PubMed PMID: 27328723. 11: Isono T, Chano T, Yonese J, Yuasa T. Therapeutic inhibition of mitochondrial function induces cell death in starvation-resistant renal cell carcinomas. Sci Rep. 2016 May 9;6:25669. doi: 10.1038/srep25669. PubMed PMID: 27157976; PubMed Central PMCID: PMC4860706. 12: Anisimov VN. Metformin for cancer and aging prevention: is it a time to make the long story short? Oncotarget. 2015 Nov 24;6(37):39398-407. doi: 10.18632/oncotarget.6347. PubMed PMID: 26583576; PubMed Central PMCID: PMC4741834. 13: 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. PubMed PMID: 25804611; PubMed Central PMCID: PMC4452421. 14: Anisimov VN. Metformin for Prevention and Treatment of Colon Cancer: A Reappraisal of Experimental and Clinical Data. Curr Drug Targets. 2016;17(4):439-46. Review. PubMed PMID: 25738299. 15: Anisimov VN. Do metformin a real anticarcinogen? A critical reappraisal of experimental data. Ann Transl Med. 2014 Jun;2(6):60. doi: 10.3978/j.issn.2305-5839.2014.06.02. Review. PubMed PMID: 25333035; PubMed Central PMCID: PMC4200660. 16: Bridges HR, Jones AJ, Pollak MN, Hirst J. Effects of metformin and other biguanides on oxidative phosphorylation in mitochondria. Biochem J. 2014 Sep 15;462(3):475-87. doi: 10.1042/BJ20140620. PubMed PMID: 25017630; PubMed Central PMCID: PMC4148174. 17: Isono T, Chano T, Kitamura A, Yuasa T. Glucose deprivation induces G2/M transition-arrest and cell death in N-GlcNAc2-modified protein-producing renal carcinoma cells. PLoS One. 2014 May 5;9(5):e96168. doi: 10.1371/journal.pone.0096168. eCollection 2014. PubMed PMID: 24796485; PubMed Central PMCID: PMC4010426. 18: Jin GY, Li H, Xu WB. Sensitive determination of buformin using poly-aminobenzoic acid modified glassy carbon electrode. J Pharm Anal. 2012 Dec;2(6):458-461. doi: 10.1016/j.jpha.2012.05.005. Epub 2012 Jun 2. PubMed PMID: 29403783; PubMed Central PMCID: PMC5760928. 19: Matsuo J, Tsukumo Y, Saito S, Tsukahara S, Sakurai J, Sato S, Kondo H, Ushijima M, Matsuura M, Watanabe T, Tomida A. Hyperactivation of 4E-binding protein 1 as a mediator of biguanide-induced cytotoxicity during glucose deprivation. Mol Cancer Ther. 2012 May;11(5):1082-91. doi: 10.1158/1535-7163.MCT-11-0871. Epub 2012 Mar 8. PubMed PMID: 22402126. 20: Kołodziejczyk MK, Kołodziejska J, Zgoda MM. [The use of natural and synthetic hydrophilic polymers in the formulation of metformin hydrochloride tablets with different profile release]. Polim Med. 2012;42(3-4):167-84. Polish. PubMed PMID: 23457958.

View History

VU0080241

VU0080241

Safironil

Safironil

NA 0359

NA 0359

GT-2016

GT-2016

TAK-137

TAK-137

TAK-802

TAK-802