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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 It was withdrawn from the market in most countries due to a high risk of causing lactic acidosis.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
Prescription ProductsNot Available
Generic Prescription ProductsNot Available
Over the Counter ProductsNot Available
International Brands
NameCompany
AdebitZentiva
BiforonMeiji
BigunalShun Hwa
DiabrinNot Available
GlybigidNot Available
SilubinNot Available
ZiavetineTeikoku Kagaku
Brand mixturesNot Available
Salts
Name/CASStructureProperties
Buformin Hydrochloride
1190-53-0
Thumb
  • InChI Key: KKLWSPPIRBIEOV-UHFFFAOYSA-N
  • Monoisotopic Mass: 193.109423244
  • Average Mass: 193.678
DBSALT000336
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
Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as biguanides. These are organic compounds containing two N-linked guanidines.
KingdomOrganic compounds
Super ClassOrganonitrogen compounds
ClassGuanidines
Sub ClassBiguanides
Direct ParentBiguanides
Alternative Parents
Substituents
  • Biguanide
  • Organic 1,3-dipolar compound
  • Propargyl-type 1,3-dipolar organic compound
  • Carboximidamide
  • Hydrocarbon derivative
  • Imine
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External DescriptorsNot Available
Pharmacology
IndicationNot Available
PharmacodynamicsNot Available
Mechanism of actionNot Available
AbsorptionNot Available
Volume of distributionNot Available
Protein bindingNot Available
MetabolismNot Available
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
PropertyValueProbability
Human Intestinal Absorption+0.977
Blood Brain Barrier+0.8194
Caco-2 permeable-0.5592
P-glycoprotein substrateSubstrate0.5726
P-glycoprotein inhibitor INon-inhibitor0.9266
P-glycoprotein inhibitor IINon-inhibitor0.6179
Renal organic cation transporterInhibitor0.5139
CYP450 2C9 substrateNon-substrate0.7635
CYP450 2D6 substrateSubstrate0.5933
CYP450 3A4 substrateNon-substrate0.7548
CYP450 1A2 substrateNon-inhibitor0.7888
CYP450 2C9 substrateNon-inhibitor0.8986
CYP450 2D6 substrateInhibitor0.5887
CYP450 2C19 substrateNon-inhibitor0.8381
CYP450 3A4 substrateNon-inhibitor0.9718
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9259
Ames testNon AMES toxic0.7642
CarcinogenicityNon-carcinogens0.7763
BiodegradationNot ready biodegradable0.6911
Rat acute toxicity2.7504 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9548
hERG inhibition (predictor II)Non-inhibitor0.9403
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 Solubility1.41 mg/mLALOGPS
logP-0.46ALOGPS
logP-0.35ChemAxon
logS-2ALOGPS
pKa (Strongest Basic)11.52ChemAxon
Physiological Charge2ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area102.78 Å2ChemAxon
Rotatable Bond Count3ChemAxon
Refractivity44.64 m3·mol-1ChemAxon
Polarizability17.67 Å3ChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Not Available
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
ATC CodesNot Available
AHFS CodesNot Available
PDB EntriesNot Available
FDA labelNot Available
MSDSNot Available
Interactions
Drug Interactions
Drug
AcarboseAntidiabetic Agents may enhance the hypoglycemic effect of Hypoglycemic Agents.
AlbiglutideAntidiabetic Agents may enhance the hypoglycemic effect of Hypoglycemic Agents.
AlogliptinAntidiabetic Agents may enhance the hypoglycemic effect of Hypoglycemic Agents.
BromocriptineAntidiabetic Agents may enhance the hypoglycemic effect of Hypoglycemic Agents.
CanagliflozinAntidiabetic Agents may enhance the hypoglycemic effect of Hypoglycemic Agents.
ChlorpropamideMay enhance the hypoglycemic effect of other Hypoglycemic Agents.
DapagliflozinAntidiabetic Agents may enhance the hypoglycemic effect of Hypoglycemic Agents.
DisopyramideMay enhance the hypoglycemic effect of other Hypoglycemic Agents.
DulaglutideAntidiabetic Agents may enhance the hypoglycemic effect of Hypoglycemic Agents.
EmpagliflozinAntidiabetic Agents may enhance the hypoglycemic effect of Hypoglycemic Agents.
ExenatideAntidiabetic Agents may enhance the hypoglycemic effect of Hypoglycemic Agents.
GliclazideMay enhance the hypoglycemic effect of other Hypoglycemic Agents.
GlimepirideMay enhance the hypoglycemic effect of other Hypoglycemic Agents.
GlipizideMay enhance the hypoglycemic effect of other Hypoglycemic Agents.
GlyburideMay enhance the hypoglycemic effect of other Hypoglycemic Agents.
inhaled insulinMay enhance the hypoglycemic effect of other Hypoglycemic Agents.
Insulin AspartMay enhance the hypoglycemic effect of other Hypoglycemic Agents.
Insulin DetemirMay enhance the hypoglycemic effect of other Hypoglycemic Agents.
Insulin GlargineMay enhance the hypoglycemic effect of other Hypoglycemic Agents.
Insulin GlulisineMay enhance the hypoglycemic effect of other Hypoglycemic Agents.
Insulin LisproMay enhance the hypoglycemic effect of other Hypoglycemic Agents.
Insulin RegularMay enhance the hypoglycemic effect of other Hypoglycemic Agents.
LanreotideMay enhance the hypoglycemic effect of other Hypoglycemic Agents.
LinagliptinAntidiabetic Agents may enhance the hypoglycemic effect of Hypoglycemic Agents.
LiraglutideAntidiabetic Agents may enhance the hypoglycemic effect of Hypoglycemic Agents.
MecaserminMay enhance the hypoglycemic effect of other Hypoglycemic Agents.
MetforminAntidiabetic Agents may enhance the hypoglycemic effect of Hypoglycemic Agents.
MifepristoneMay enhance the hypoglycemic effect of other Hypoglycemic Agents.
MiglitolAntidiabetic Agents may enhance the hypoglycemic effect of Hypoglycemic Agents.
NateglinideMay enhance the hypoglycemic effect of other Hypoglycemic Agents.
OctreotideMay enhance the hypoglycemic effect of other Hypoglycemic Agents.
PasireotideMay enhance the hypoglycemic effect of other Hypoglycemic Agents.
PentamidineMay enhance the hypoglycemic effect of other Hypoglycemic Agents.
PioglitazoneAntidiabetic Agents may enhance the hypoglycemic effect of Hypoglycemic Agents.
PramlintideAntidiabetic Agents may enhance the hypoglycemic effect of Hypoglycemic Agents.
QuinineMay enhance the hypoglycemic effect of other Hypoglycemic Agents.
RepaglinideMay enhance the hypoglycemic effect of other Hypoglycemic Agents.
RosiglitazoneAntidiabetic Agents may enhance the hypoglycemic effect of Hypoglycemic Agents.
SaxagliptinAntidiabetic Agents may enhance the hypoglycemic effect of Hypoglycemic Agents.
SitagliptinAntidiabetic Agents may enhance the hypoglycemic effect of Hypoglycemic Agents.
SulfadiazineMay enhance the hypoglycemic effect of other Hypoglycemic Agents.
SulfamethoxazoleMay enhance the hypoglycemic effect of other Hypoglycemic Agents.
SulfisoxazoleMay enhance the hypoglycemic effect of other Hypoglycemic Agents.
SunitinibMay enhance the hypoglycemic effect of other Hypoglycemic Agents.
TolazamideMay enhance the hypoglycemic effect of other Hypoglycemic Agents.
TolbutamideMay enhance the hypoglycemic effect of other Hypoglycemic Agents.
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