phenformin

Names

[ CAS No. ]:
114-86-3

[ Name ]:
phenformin

[Synonym ]:
[3H]-Phenformin
Fenformin
Normoglucina
1-(diaminomethylidene)-2-(2-phenylethyl)guanidine
[14C]-Phenformin
1-phenethylbiguanide
MFCD00035039
Imidodicarbonimidic diamide, N-(2-phenylethyl)-
Feguanide
Phenforminum
phenylethyl biguanide
phenethylbiguanide
Phenformine
EINECS 204-057-4
phenformin
Cronoformin
Fenfoduron
Fenformina
N-(2-Phenylethyl)imidodicarbonimidic diamide

Biological Activity

[Description]:

Phenformin (1-phenethylbiguanide) is an orally active antidiabetic and anticancer agent. Phenformin has an incidence of associated lactic acidosis. Phenformin acts through acting AMPK activation and blocking mTOR pathway. Phenformin is also a substrate of P-glycoprotein (P-gp), and an OXPHOS inhibitor. Phenformin induces cancer cell apoptosis[1][2].

[Related Catalog]:

Signaling Pathways >> Epigenetics >> AMPK

Signaling Pathways >> Apoptosis >> Apoptosis

Research Areas >> Cancer

Signaling Pathways >> PI3K/Akt/mTOR >> AMPK

Research Areas >> Metabolic Disease

[References]

[1]. García Rubiño ME, et al. Phenformin as an Anticancer Agent: Challenges and Prospects. Int J Mol Sci. 2019 Jul 5;20(13):3316.

[2]. Yendapally R, et al. A review of phenformin, metformin, and imeglimin. Drug Dev Res. 2020 Jun;81(4):390-401.

Chemical & Physical Properties

[ Density]:
1.2±0.1 g/cm3

[ Boiling Point ]:
332.2±35.0 °C at 760 mmHg

[ Melting Point ]:
280-282°C

[ Molecular Formula ]:
C₁₀H₁₅N₅

[ Molecular Weight ]:
205.260

[ Flash Point ]:
154.7±25.9 °C

[ Exact Mass ]:
205.132751

[ PSA ]:
97.78000

[ LogP ]:
-0.60

[ Vapour Pressure ]:
0.0±0.7 mmHg at 25°C

[ Index of Refraction ]:
1.620

[ Storage condition ]:
2-8°C

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: DU2100000

CHEMICAL NAME :: Biguanide, 1-phenethyl-

CAS REGISTRY NUMBER :: 114-86-3

BEILSTEIN REFERENCE NO. :: 1977317

LAST UPDATED :: 199612

DATA ITEMS CITED :: 6

MOLECULAR FORMULA :: C10-H15-N5

MOLECULAR WEIGHT :: 205.30

WISWESSER LINE NOTATION :: MUYZMYUM&M2R

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 650 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: APPHAX Acta Poloniae Pharmaceutica. For English translation, see APPFAR. (Ars Polona, POB 1001, 00-680 Warsaw 1, Poland) V.1- 1937- Volume(issue)/page/year: 42,236,1985

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 450 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: APPHAX Acta Poloniae Pharmaceutica. For English translation, see APPFAR. (Ars Polona, POB 1001, 00-680 Warsaw 1, Poland) V.1- 1937- Volume(issue)/page/year: 42,236,1985

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 140 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: BCFAAI Bollettino Chimico Farmaceutico. (Societa Editoriale Farmaceutica, Via Ausonio 12, 20123 Milan, Italy) V.33- 1894- Volume(issue)/page/year: 97,396,1958

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Subcutaneous

SPECIES OBSERVED :: Rodent - guinea pig

DOSE/DURATION :: 16 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: MEXPAG Medicina Experimentalis. (Basel, Switzerland) V.1-11, 1959-64; V.18-19, 1968-69. For publisher information, see JNMDBO. Volume(issue)/page/year: 8,237,1963

TYPE OF TEST :: LDLo - Lowest published lethal dose

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Rodent - guinea pig

DOSE/DURATION :: 30 mg/kg

TOXIC EFFECTS :: Nutritional and Gross Metabolic - metabolic acidosis

REFERENCE :: 43ZRAD "Hemoperfusion: Kidney and Liver Support and Detoxification, Proceedings of the International Symposium, Haifa, 1979," Sideman, S., and T.M.S. Chang, eds., Multiple parts, New York, Hemisphere Pub. Corp., 1980- Volume(issue)/page/year: 1,337,1980

Safety Information

[ Hazard Codes ]:
Xn: Harmful;

[ Risk Phrases ]:
R22

[ Safety Phrases ]:
S36

[ WGK Germany ]:
3

[ RTECS ]:
DU2200000

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

Related Compounds

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