1-carbamimidamido-N-(2-phenylethyl)methanimidamide

• ChemBase ID: 790
• Molecular Formular: C10H15N5
• Molecular Mass: 205.2596
• Monoisotopic Mass: 205.13274551
• SMILES: c1(CCNC(=N)NC(=N)N)ccccc1
• Canonical SMILES: N=C(NC(=N)N)NCCc1ccccc1
• InChI: 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)
• InChIKey: ICFJFFQQTFMIBG-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 1-carbamimidamido-N-(2-phenylethyl)methanimidamide
• IUPAC Traditional name: phenethylbiguanide
• Brand Name: Azucaps; Cronoformin; D Bretard; DBI; DB Comb; DB-Retard; DBI Monohydrochloride; Debeone; Debinyl; Diabis; Dibein; Dibiraf; Dibotin; Dipar; Feguanide; Fenfoduron; Fenormin; Glukopostin; Glyphen; Insoral; Lentobetic; Meltrol; Meltrol-50; Normoglucina; Phenformix; Retardo
• Synonyms: Fenformina [INN-Spanish]; Fenformin; N-Phenethylbiguanide Hydrochloride; Phenethylbiguanide Hydrochloride; PEDG; Phenethyldiguanide; Phenformin HCl; Phenformin Hydrochloride; Phenformine; Phenformine HCl; Phenformine [INN-French]; Phenforminum [INN-Latin]; Phenoformine Hydrochloride; Phenylethylbiguanide; Beta-Phenethylbiguanide; Beta-Phenethybiguanide; Beta-Pebg; Phenformin

Database IDs

• CAS Number: 114-86-3
• PubChem SID: 160964253; 46505230
• PubChem CID: 8249

CALCULATED PROPERTIES

JChem

• H Acceptors: 5
• H Donor: 5
• LogD (pH = 5.5): -3.9934607
• LogD (pH = 7.4): -3.7257519
• Log P: 0.832729
• Molar Refractivity: 80.7156 cm^3
• Polarizability: 22.477764 Å^3
• Polar Surface Area: 97.78 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: -0.72
• LOG S: -2.95
• Solubility (Water): 2.32e-01 g/l

PROPERTIES

Physical Property

• Solubility: 210 mg/mL
• Hydrophobicity(logP): 0.1

DETAILS

DrugBank - DB00914

• Drug Groups: approved; withdrawn
• Description: 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. (From Martindale, The Extra Pharmacopoeia, 30th ed, p290)
• Indication: For the reatment of type II diabetes mellitus.
• Pharmacology: Used to treat diabetes, phenformin is a biguanide (contains 2 guanidino groups) hypoglycemic agent with actions and uses similar to those of metformin (Glucophage). Both drugs work by (1) decreasing the absorption of glucose by the intestines, (2) decreasing the production of glucose in the liver, and by (3) increasing the body's ability to use insulin more effectively. More specifically, phenformin improves glycemic control by improving insulin sensitivity. Phenformin is generally considered to be associated with an unacceptably high incidence of actic acidosis. In general biguanides should be used only in stable type II diabetics who are free of liver, kidney and cardiovascular problems and who cannot be controlled with diet.
• Affected Organisms: Humans and other mammals
• References: Enia G, Garozzo M, Zoccali C: Lactic acidosis induced by phenformin is still a public health problem in Italy. BMJ. 1997 Nov 29;315(7120):1466-7. [Pubmed] ; Rosand J, Friedberg JW, Yang JM: Fatal phenformin-associated lactic acidosis. Ann Intern Med. 1997 Jul 15;127(2):170. [Pubmed]
• External Links: Wikipedia

REFERENCES

• Enia G, Garozzo M, Zoccali C: Lactic acidosis induced by phenformin is still a public health problem in Italy. BMJ. 1997 Nov 29;315(7120):1466-7. Pubmed
• Rosand J, Friedberg JW, Yang JM: Fatal phenformin-associated lactic acidosis. Ann Intern Med. 1997 Jul 15;127(2):170. Pubmed