2-butyl-1-(diaminomethylidene)guanidine

• ChemBase ID: 4374
• Molecular Formular: C6H15N5
• Molecular Mass: 157.2168
• Monoisotopic Mass: 157.13274551
• SMILES: N(=C(\N=C(N)N)/N)/CCCC
• Canonical SMILES: CCCC/N=C(/N=C(N)N)\N
• InChI: InChI=1S/C6H15N5/c1-2-3-4-10-6(9)11-5(7)8/h2-4H2,1H3,(H6,7,8,9,10,11)
• InChIKey: XSEUMFJMFFMCIU-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-butyl-1-(diaminomethylidene)guanidine; (E)-2-butyl-1-(diaminomethylidene)guanidine
• IUPAC Traditional name: 2-butyl-1-(diaminomethylidene)guanidine; buformin
• Brand Name: Adebit; Andere; Biforon; Diabrin; Glybigid; Glybigidum; Panformin; Silubin; Sindiatil
• Synonyms: N-BUTYL BIGUANIDE HCl; 1-Butylbiguanide; 1-Butyldiguanide; Buformin hydrochloride; Buformina [inn-spanish]; Buformine; Buformine HCL; Buformine [inn-french]; Buforminum [inn-latin]; Butformin; Butyl guanylguanidine; Butylbiguanide; Butylbiguanide hydrochloride; Butylbiguanidum; Butyldiguanide; DBV; DBV hydrochloride; N-butylbiguanide; Buformin

Database IDs

• CAS Number: 1190-53-0; 692-13-7
• PubChem SID: 160967806; 46507254
• PubChem CID: 2468

CALCULATED PROPERTIES

JChem

• H Acceptors: 5
• H Donor: 3
• LogD (pH = 5.5): -4.783011
• LogD (pH = 7.4): -4.279902
• Log P: -0.3501763
• Molar Refractivity: 44.636 cm^3
• Polarizability: 16.660162 Å^3
• Polar Surface Area: 102.78 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: -0.46
• LOG S: -2.05
• Solubility (Water): 1.41e+00 g/l

PROPERTIES

Physical Property

• Hydrophobicity(logP): -1.20 [HANSCH,C ET AL. (1995)]

DETAILS

MP Biomedicals - 05220318

MP Biomedicals Rare Chemical collection

DrugBank - DB04830

• Drug Groups: withdrawn
• Description: Buformin is an anti-diabetic drug of the biguanide class, chemically related to metformin and phenformin. It was withdrawn from the market in most countries due to a high risk of causing lactic acidosis.
• Affected Organisms: Humans and other mammals
• References: Verdonck LF, Sangster B, van Heijst AN, de Groot G, Maes RA: Buformin concentrations in a case of fatal lactic acidosis. Diabetologia. 1981;20(1):45-6. [Pubmed] ; Deppermann D, Heidland A, Ritz E, Horl W: [Lactic acidosis--a possible complication in buformin-treated diabetics (author's transl)] Klin Wochenschr. 1978 Sep 1;56(17):843-53. [Pubmed]
• External Links: Wikipedia

REFERENCES

• Verdonck LF, Sangster B, van Heijst AN, de Groot G, Maes RA: Buformin concentrations in a case of fatal lactic acidosis. Diabetologia. 1981;20(1):45-6. Pubmed
• Deppermann D, Heidland A, Ritz E, Horl W: [Lactic acidosis--a possible complication in buformin-treated diabetics (author's transl)] Klin Wochenschr. 1978 Sep 1;56(17):843-53. Pubmed