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MedKoo Cat#: 581250 | Name: Phenformin

Description:

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

Phenformin is an antidiabetic drug from the biguanide class. It was marketed as DBI by Ciba-Geigy, but was withdrawn from most markets in the late 1970s due to a high risk of lactic acidosis, which was fatal in 50% of cases.Phenformin was discovered in 1957 by Ungar, Freedman and Seymour Shapiro, working for the US Vitamin Corporation. Clinical trials begun in 1958 showed it to be effective, but with gastrointestinal side effects. A biguanide hypoglycemic agent with actions and uses similar to those of METFORMIN. Although it is generally considered to be associated with an unacceptably high incidence of lactic acidosis, often fatal, it is still available in some countries.

Chemical Structure

Phenformin
Phenformin
CAS#114-86-3 (free base)

Theoretical Analysis

MedKoo Cat#: 581250

Name: Phenformin

CAS#: 114-86-3 (free base)

Chemical Formula: C10H15N5

Exact Mass: 205.1327

Molecular Weight: 205.27

Elemental Analysis: C, 58.51; H, 7.37; N, 34.12

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 #
834-28-6 (HCl) 114-86-3 (free base)
Synonym
Phenformin; BRN 1977317; Debeone; Insoral; Azucaps;
IUPAC/Chemical Name
Imidodicarbonimidic diamide, N-(2-phenylethyl)-
InChi Key
ICFJFFQQTFMIBG-UHFFFAOYSA-N
InChi Code
InChI=1S/C10H15N5/c11-9(12)15-10(13)14-7-6-8-4-2-1-3-5-8/h1-5H,6-7H2,(H6,11,12,13,14,15)
SMILES Code
NC(NC(NCCC1=CC=CC=C1)=N)=N
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 205.27 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: Liu Z, Ren L, Liu C, Xia T, Zha X, Wang S. Phenformin Induces Cell Cycle Change, Apoptosis, and Mesenchymal-Epithelial Transition and Regulates the AMPK/mTOR/p70s6k and MAPK/ERK Pathways in Breast Cancer Cells. PLoS One. 2015 Jun 26;10(6):e0131207. doi: 10.1371/journal.pone.0131207. eCollection 2015. PubMed PMID: 26114294; PubMed Central PMCID: PMC4482683. 2: Yuan P, Ito K, Perez-Lorenzo R, Del Guzzo C, Lee JH, Shen CH, Bosenberg MW, McMahon M, Cantley LC, Zheng B. Phenformin enhances the therapeutic benefit of BRAF(V600E) inhibition in melanoma. Proc Natl Acad Sci U S A. 2013 Nov 5;110(45):18226-31. doi: 10.1073/pnas.1317577110. Epub 2013 Oct 21. PubMed PMID: 24145418; PubMed Central PMCID: PMC3831456. 3: Krishnamurthy S, Ng VW, Gao S, Tan MH, Yang YY. Phenformin-loaded polymeric micelles for targeting both cancer cells and cancer stem cells in vitro and in vivo. Biomaterials. 2014 Nov;35(33):9177-86. doi: 10.1016/j.biomaterials.2014.07.018. Epub 2014 Aug 5. PubMed PMID: 25106770. 4: Wang J, Xia S, Zhu Z. Synergistic effect of phenformin in non-small cell lung cancer (NSCLC) ionizing radiation treatment. Cell Biochem Biophys. 2015 Mar;71(2):513-8. doi: 10.1007/s12013-014-0283-z. PubMed PMID: 25312480. 5: Barkhuizen M, Petzer A, Petzer JP. The inhibition of monoamine oxidase by phenformin and pentamidine. Drug Res (Stuttg). 2014 Sep;64(9):454-61. doi: 10.1055/s-0033-1361129. Epub 2013 Dec 4. PubMed PMID: 24307270. 6: Shitara Y, Nakamichi N, Norioka M, Shima H, Kato Y, Horie T. Role of organic cation/carnitine transporter 1 in uptake of phenformin and inhibitory effect on complex I respiration in mitochondria. Toxicol Sci. 2013 Mar;132(1):32-42. doi: 10.1093/toxsci/kfs330. Epub 2012 Dec 5. PubMed PMID: 23221006. 7: Appleyard MV, Murray KE, Coates PJ, Wullschleger S, Bray SE, Kernohan NM, Fleming S, Alessi DR, Thompson AM. Phenformin as prophylaxis and therapy in breast cancer xenografts. Br J Cancer. 2012 Mar 13;106(6):1117-22. doi: 10.1038/bjc.2012.56. Epub 2012 Feb 23. PubMed PMID: 22361631; PubMed Central PMCID: PMC3304424. 8: Oh-Hashi K, Irie N, Sakai T, Okuda K, Nagasawa H, Hirata Y, Kiuchi K. Elucidation of a novel phenformin derivative on glucose-deprived stress responses in HT-29 cells. Mol Cell Biochem. 2016 Aug;419(1-2):29-40. doi: 10.1007/s11010-016-2747-5. Epub 2016 Jul 8. PubMed PMID: 27392906. 9: Deng Y, Li N, Cui M, Xiong ZL, Li FM. [Effect of phenformin hydrochloride on pharmacokinetics of puerarin in rats]. Zhongguo Zhong Yao Za Zhi. 2012 Oct;37(19):2960-3. Chinese. PubMed PMID: 23270242. 10: Shi L, Xie JH, Du LM, Chang YX, Wu H. Determination of phenformin hydrochloride employing a sensitive fluorescent probe. Spectrochim Acta A Mol Biomol Spectrosc. 2016 Jun 5;162:98-104. doi: 10.1016/j.saa.2016.03.006. Epub 2016 Mar 9. PubMed PMID: 26994318. 11: 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. 12: Nicholls TJ, Leese HJ. The effects of phenformin on the transport and metabolism of sugars by the rat small intestine. Biochem Pharmacol. 1984 Mar 1;33(5):771-7. PubMed PMID: 6712708. 13: Conlay LA, Karam JH, Matin SB, Loewenstein JE. Serum phenformin concentrations in patients with phenformin-associated lactic acidosis. Diabetes. 1977 Jul;26(7):628-31. PubMed PMID: 406157. 14: Cavallo-Perin P, Aluffi E, Estivi P, Bruno A, Carta Q, Pagano G, Lenti G. The hyperlactatemic effect of biguanides: a comparison between phenformin and metformin during a 6-month treatment. Riv Eur Sci Med Farmacol. 1989 Feb;11(1):45-9. PubMed PMID: 2798990. 15: Gardner ML, Langlow DR. The absorption of phenformin and its effects on glucose and water absorption in isolated perfused rat small intestine. Q J Exp Physiol Cogn Med Sci. 1977 Jul;62(3):247-55. PubMed PMID: 588021. 16: Bosisio E, Kienle MG, Galli G, Ciconali M, Negri A, Sessa A, Morosati S, Sirtori CR. Defective hydroxylation of phenformin as a determinant of drug toxicity. Diabetes. 1981 Aug;30(8):644-9. PubMed PMID: 7250534. 17: Oates NS, Shah RR, Idle JR, Smith RL. Influence of oxidation polymorphism on phenformin kinetics and dynamics. Clin Pharmacol Ther. 1983 Dec;34(6):827-34. PubMed PMID: 6641100. 18: Blayac JP, Ribes G, Valette G, Loubatières-Mariani MM. [Toxic effect of the combination of propranolol and phenformin combination in anesthetized dogs]. C R Seances Soc Biol Fil. 1981;175(6):821-7. French. PubMed PMID: 6459826. 19: Lea MA, Chacko J, Bolikal S, Hong JY, Chung R, Ortega A, desbordes C. Addition of 2-deoxyglucose enhances growth inhibition but reverses acidification in colon cancer cells treated with phenformin. Anticancer Res. 2011 Feb;31(2):421-6. PubMed PMID: 21378320. 20: Oates NS, Shah RR, Idle JR, Smith RL. Genetic polymorphism of phenformin 4-hydroxylation. Clin Pharmacol Ther. 1982 Jul;32(1):81-9. PubMed PMID: 7083735.