Synonym
Phenformin Hydrochloride; Phenformin HCl; Meltrol; Dipar; Phenethylbiguanide hydrochloride; W-104144; ST50409947; D08352;
IUPAC/Chemical Name
1-(diaminomethylidene)-2-(2-phenylethyl)guanidine;hydrochloride
InChi Key
YSUCWSWKRIOILX-UHFFFAOYSA-N
InChi Code
InChI=1S/C10H15N5.ClH/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);1H
SMILES Code
C1=CC=C(C=C1)CCN=C(N)N=C(N)N.Cl
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, not in water
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
Biological target:
Phenformin hydrochloride is an anti-diabetic agent from the biguanide class, can activate AMPK activity.
In vitro activity:
This study found that exosomes (Phen-Exo) derived from phenformin-treated oral squamous cell carcinoma (OSCC) cells significantly suppress the proliferation, migration and tube formation of human umbilical vein endothelial cells (HUVECs) in vitro. This study discovered that the expression of microRNA-1246 (miR-1246) and microRNA-205 (miR-205) was significantly increased in exosomes secreted by OSCC cells treated with phenformin, while high expression levels of miR-1246 or miR-205 in vascular endothelial cells inhibited their angiogenic effects and decreased expression of the angiogenic factor VEGFA. In conclusion, these results reveal that phenformin can inhibit angiogenesis by regulating the levels of miR-1246 and miR-205 in exosomes secreted by OSCC cells, suggesting that phenformin has the potential to alter the tumor microenvironment to antagonize the growth of OSCCs, which provides a theoretical basis for developing new strategies to treat OSCCs in the future.
Reference: Front Oncol. 2022 Sep 8;12:943477. https://pubmed.ncbi.nlm.nih.gov/36158698/
In vivo activity:
As expected, mice subjected to 3dUUO had an increased kidney weight (KW) as compared to sham mice. Metformin treatment (500 mg/kg/day) further increased KW, while phenformin treatment (100 mg/kg/day) did not significantly affect KW as compared to untreated UUO mice (Table 3). In addition, treatment with phenformin (100 mg/kg/day) significantly decreased blood pH and glucose, and increased blood lactate levels as compared to UUO mice, which might be associated with lactic acidosis. Nonetheless, all mice displayed normal intake of water and food and were considered to be in good condition by our animal caretakers.
Reference: Pharmaceutics. 2020 Mar 26;12(4):301. https://pubmed.ncbi.nlm.nih.gov/32224876/
|
Solvent |
mg/mL |
mM |
comments |
| Solubility |
| DMF |
17.0 |
70.33 |
|
| DMSO |
17.0 |
70.33 |
|
| Ethanol |
6.0 |
24.82 |
|
| PBS (pH 7.2) |
5.0 |
20.69 |
|
| Water |
30.3 |
125.14 |
|
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
241.72
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. Zhuang D, Wang S, Liu G, Liu P, Deng H, Sun J, Liu C, Leng X, Zhang Q, Bai F, Mi J, Wu X. Phenformin suppresses angiogenesis through the regulation of exosomal microRNA-1246 and microRNA-205 levels derived from oral squamous cell carcinoma cells. Front Oncol. 2022 Sep 8;12:943477. doi: 10.3389/fonc.2022.943477. PMID: 36158698; PMCID: PMC9492847.
2. Alves-Silva AB, Fenerich BA, Fonseca NP, Fernandes JC, Coelho-Silva JL, Pereira-Martins DA, Bianco TM, Scheucher PS, Rego EM, Chahud F, Machado-Neto JA, Figueiredo-Pontes LL, Traina F. Phenformin increases early hematopoietic progenitors in the Jak2V617F murine model. Invest New Drugs. 2022 Jun;40(3):576-585. doi: 10.1007/s10637-022-01212-y. Epub 2022 Jan 11. PMID: 35015172.
3. Zhou Q, Kim SH, Pérez-Lorenzo R, Liu C, Huang M, Dotto GP, Zheng B, Wu X. Phenformin Promotes Keratinocyte Differentiation via the Calcineurin/NFAT Pathway. J Invest Dermatol. 2021 Jan;141(1):152-163. doi: 10.1016/j.jid.2020.05.114. Epub 2020 Jun 30. PMID: 32619504; PMCID: PMC8179313.
4. Nørgård MØ, Christensen M, Mutsaers HAM, Nørregaard R. Phenformin Attenuates Renal Injury in Unilateral Ureteral Obstructed Mice without Affecting Immune Cell Infiltration. Pharmaceutics. 2020 Mar 26;12(4):301. doi: 10.3390/pharmaceutics12040301. PMID: 32224876; PMCID: PMC7238166.
In vitro protocol:
1. Zhuang D, Wang S, Liu G, Liu P, Deng H, Sun J, Liu C, Leng X, Zhang Q, Bai F, Mi J, Wu X. Phenformin suppresses angiogenesis through the regulation of exosomal microRNA-1246 and microRNA-205 levels derived from oral squamous cell carcinoma cells. Front Oncol. 2022 Sep 8;12:943477. doi: 10.3389/fonc.2022.943477. PMID: 36158698; PMCID: PMC9492847.
2. Alves-Silva AB, Fenerich BA, Fonseca NP, Fernandes JC, Coelho-Silva JL, Pereira-Martins DA, Bianco TM, Scheucher PS, Rego EM, Chahud F, Machado-Neto JA, Figueiredo-Pontes LL, Traina F. Phenformin increases early hematopoietic progenitors in the Jak2V617F murine model. Invest New Drugs. 2022 Jun;40(3):576-585. doi: 10.1007/s10637-022-01212-y. Epub 2022 Jan 11. PMID: 35015172.
In vivo protocol:
1. Zhou Q, Kim SH, Pérez-Lorenzo R, Liu C, Huang M, Dotto GP, Zheng B, Wu X. Phenformin Promotes Keratinocyte Differentiation via the Calcineurin/NFAT Pathway. J Invest Dermatol. 2021 Jan;141(1):152-163. doi: 10.1016/j.jid.2020.05.114. Epub 2020 Jun 30. PMID: 32619504; PMCID: PMC8179313.
2. Nørgård MØ, Christensen M, Mutsaers HAM, Nørregaard R. Phenformin Attenuates Renal Injury in Unilateral Ureteral Obstructed Mice without Affecting Immune Cell Infiltration. Pharmaceutics. 2020 Mar 26;12(4):301. doi: 10.3390/pharmaceutics12040301. PMID: 32224876; PMCID: PMC7238166.
1: 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 Mar 9;162:98-104. doi: 10.1016/j.saa.2016.03.006. [Epub
ahead of print] PubMed PMID: 26994318.
2: 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.
3: Liu Z, Jia F, Wang W, Wang C, Liu Y. Determination of phenformin hydrochloride
using molecular imprinting technology coupled with flow-injection
chemiluminescence. Luminescence. 2012 Jul-Aug;27(4):297-301. doi:
10.1002/bio.1350. Epub 2011 Oct 12. PubMed PMID: 21990141.
4: Pandey VP, Kannappan N, Manavalan R, Subburaj T. Sustaining pattern of
phenformin hydrochloride using various polymers and waxes. Boll Chim Farm. 2002
Sep-Oct;141(5):361-6. PubMed PMID: 12481378.
5: Danowski TS. Diabetes mellitus and obesity: phenformin hydrochloride as a
research tool. Concluding remarks. Ann N Y Acad Sci. 1968 Mar 26;148(3):958-62.
PubMed PMID: 5241487.
6: Danowski TS. Diabetes mellitus and obesity: phenformin hydrochloride as a
research tool. Can Fam Physician. 1968 Feb;14(2):45-7. PubMed PMID: 20468186;
PubMed Central PMCID: PMC2280979.
7: Schwartz MJ, Mirsky S, Schaefer LE. The effect of phenformin hydrochloride on
serum cholesterol and triglyceride levels of the stable adult diabetic.
Metabolism. 1966 Sep;15(9):808-22. PubMed PMID: 5929037.
8: Mitra PP, Sanyal DC. Phenformin hydrochloride (D.B.I.) in diabetes mellitus.
Bull Calcutta Sch Trop Med. 1965 Oct;13(4):145-6. PubMed PMID: 5882336.
9: WALKER RS, LINTON AL, THOMSON WS. Mode of action and side-effects of
phenformin hydrochloride. Br Med J. 1960 Nov 26;2(5212):1567-9. PubMed PMID:
13782756; PubMed Central PMCID: PMC2098383.
10: Babad F. Psoriasis and phenformin hydrochloride: a report on 2 cases. J Med
Soc N J. 1974 May;71(5):412. PubMed PMID: 4524262.
11: Wickramasinghe JA, Shaw SR. Gas chromatographic behavior of buformin
hydrochloride, phenformin hydrochloride and phenylbiguanide. The pyrolytic
formation of substituted 2,4,6-triamino-1,3,5-triazines from biguanides. J
Chromatogr. 1972 Sep 6;71(2):265-73. PubMed PMID: 5057114.
12: Stone DB, Brown JD. In vitro effects of phenformin hydrochloride:
observations using isolated fat cells. Ann N Y Acad Sci. 1968 Mar
26;148(3):623-30. PubMed PMID: 4297861.
13: Burstein J, Jakobson T, Lindell KA, Nikiforow RE. The effect of phenformin
hydrochloride on serum cholesterol, triglycerides and body weight of nondiabetic
hypercholesterolemic subjects. Ann Med Intern Fenn. 1968;57(1):15-21. PubMed
PMID: 5726760.
14: Danowski TS. Diabetes mellitus and obesity: phenformin hydrochloride as a
research tool. Metabolism. 1967 Sep;16(9):865-9. PubMed PMID: 4860366.
15: BERNIER GM, MILLER M, SPRINGATE CS. Lactic acidosis and phenformin
hydrochloride. JAMA. 1963 Apr 6;184:43-6. PubMed PMID: 13967650.
16: SADOW HS, BAXTER N, TELLER FF. Phenformin hydrochloride. A biased but
informed review. Md State Med J. 1962 Feb;11:76-90. PubMed PMID: 14495933.
