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Identification
NameBuformin
Accession NumberDB04830
Typesmall molecule
Groupswithdrawn
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 It was withdrawn from the market in most countries due to a high risk of causing lactic acidosis.

Structure
Thumb
Synonyms
SynonymLanguageCode
1-ButylbiguanideNot AvailableNot Available
BuforminaSpanishINN
BuformineFrenchINN
BuforminumLatinINN
Salts
Name/CAS Structure Properties
Buformin Hydrochloride
1190-53-0
Thumb
  • InChI Key: KKLWSPPIRBIEOV-UHFFFAOYSA-N
  • Monoisotopic Mass: 193.109423244
  • Average Mass: 193.678
DBSALT000336
Brand names
NameCompany
AdebitZentiva
BiforonMeiji
BigunalShun Hwa
DiabrinNot Available
GlybigidNot Available
SilubinNot Available
ZiavetineTeikoku Kagaku
Brand mixturesNot Available
Categories
CAS number692-13-7
WeightAverage: 157.2168
Monoisotopic: 157.132745505
Chemical FormulaC6H15N5
InChI KeyXSEUMFJMFFMCIU-UHFFFAOYSA-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)
IUPAC Name
(E)-2-butyl-1-(diaminomethylidene)guanidine
SMILES
CCCC\N=C(/N)N=C(N)N
Mass SpecNot Available
Taxonomy
KingdomOrganic Compounds
SuperclassOrganonitrogen Compounds
ClassGuanidines
SubclassBiguanides
Direct parentBiguanides
Alternative parentsPolyamines; Amidines
Substituentsamidine; polyamine; amine
Classification descriptionThis compound belongs to the biguanides. These are organic compounds containing two N-linked guanidines.
Pharmacology
IndicationNot Available
PharmacodynamicsNot Available
Mechanism of actionNot Available
AbsorptionNot Available
Volume of distributionNot Available
Protein bindingNot Available
Metabolism
Route of eliminationNot Available
Half lifeNot Available
ClearanceNot Available
ToxicityNot Available
Affected organisms
  • Humans and other mammals
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
Predicted ADMET features
Property Value Probability
Human Intestinal Absorption + 0.977
Blood Brain Barrier + 0.8194
Caco-2 permeable - 0.5592
P-glycoprotein substrate Substrate 0.5726
P-glycoprotein inhibitor I Non-inhibitor 0.9266
P-glycoprotein inhibitor II Non-inhibitor 0.6179
Renal organic cation transporter Inhibitor 0.5139
CYP450 2C9 substrate Non-substrate 0.7635
CYP450 2D6 substrate Substrate 0.5933
CYP450 3A4 substrate Non-substrate 0.7548
CYP450 1A2 substrate Non-inhibitor 0.7888
CYP450 2C9 substrate Non-inhibitor 0.8986
CYP450 2D6 substrate Inhibitor 0.5887
CYP450 2C19 substrate Non-inhibitor 0.8381
CYP450 3A4 substrate Non-inhibitor 0.9718
CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.9259
Ames test Non AMES toxic 0.7642
Carcinogenicity Non-carcinogens 0.7763
Biodegradation Not ready biodegradable 0.6911
Rat acute toxicity 2.7504 LD50, mol/kg Not applicable
hERG inhibition (predictor I) Weak inhibitor 0.9548
hERG inhibition (predictor II) Non-inhibitor 0.9403
Pharmacoeconomics
ManufacturersNot Available
PackagersNot Available
Dosage formsNot Available
PricesNot Available
PatentsNot Available
Properties
Statesolid
Experimental Properties
PropertyValueSource
logP-1.20HANSCH,C ET AL. (1995)
Predicted Properties
PropertyValueSource
water solubility1.41e+00 g/lALOGPS
logP-0.46ALOGPS
logP-0.35ChemAxon
logS-2ALOGPS
pKa (strongest basic)11.52ChemAxon
physiological charge2ChemAxon
hydrogen acceptor count5ChemAxon
hydrogen donor count3ChemAxon
polar surface area102.78ChemAxon
rotatable bond count3ChemAxon
refractivity44.64ChemAxon
polarizability17.67ChemAxon
number of rings0ChemAxon
bioavailability1ChemAxon
rule of fiveYesChemAxon
Ghose filterNoChemAxon
Veber's ruleNoChemAxon
MDDR-like ruleNoChemAxon
Spectra
SpectraNot Available
References
Synthesis Reference

Shapiro, S.L.; US. Patent 2,961,377; November 22,1960; assigned to U.S.Vitamin & Pharmaceutical Corp.

General Reference
  1. 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
  2. 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
ResourceLink
KEGG DrugD00595
KEGG CompoundC07674
PubChem Compound2468
PubChem Substance46507254
ChemSpider2374
WikipediaBuformin
ATC CodesA10BA03
AHFS CodesNot Available
PDB EntriesNot Available
FDA labelNot Available
MSDSNot Available
Interactions
Drug InteractionsNot Available
Food InteractionsNot Available

Transporters

1. Solute carrier family 22 member 1

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: substrate

Components

Name UniProt ID Details
Solute carrier family 22 member 1 O15245 Details

References:

  1. Wang DS, Jonker JW, Kato Y, Kusuhara H, Schinkel AH, Sugiyama Y: Involvement of organic cation transporter 1 in hepatic and intestinal distribution of metformin. J Pharmacol Exp Ther. 2002 Aug;302(2):510-5. Pubmed

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Drug created on September 11, 2007 14:52 / Updated on April 01, 2014 15:01