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Identification
NameBuformin
Accession NumberDB04830
TypeSmall Molecule
GroupsWithdrawn
DescriptionBuformin 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 It was withdrawn from the market in most countries due to a high risk of causing lactic acidosis.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
1-Butylbiguanide
Buformina
Buformine
Buforminum
External Identifiers Not Available
Approved Prescription ProductsNot Available
Approved Generic Prescription ProductsNot Available
Approved Over the Counter ProductsNot Available
Unapproved/Other Products Not 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
UNIIW2115E9C7B
CAS number692-13-7
WeightAverage: 157.2168
Monoisotopic: 157.132745505
Chemical FormulaC6H15N5
InChI KeyInChIKey=XSEUMFJMFFMCIU-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
Related Articles
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 inhibitorNon-inhibitor0.8986
CYP450 2D6 inhibitorInhibitor0.5887
CYP450 2C19 inhibitorNon-inhibitor0.8381
CYP450 3A4 inhibitorNon-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
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397 )
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
Spectra
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot Available
References
Synthesis Reference

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

General References
  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:7202882 ]
  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:713413 ]
External Links
ATC CodesA10BA03
AHFS CodesNot Available
PDB EntriesNot Available
FDA labelNot Available
MSDSNot Available
Interactions
Drug Interactions
Drug
AripiprazoleThe therapeutic efficacy of Buformin can be decreased when used in combination with Aripiprazole.
Arsenic trioxideThe therapeutic efficacy of Buformin can be decreased when used in combination with Arsenic trioxide.
ArticaineThe therapeutic efficacy of Buformin can be decreased when used in combination with Articaine.
AsenapineThe therapeutic efficacy of Buformin can be decreased when used in combination with Asenapine.
AtazanavirThe therapeutic efficacy of Buformin can be decreased when used in combination with Atazanavir.
BendroflumethiazideThe therapeutic efficacy of Buformin can be decreased when used in combination with Bendroflumethiazide.
BetamethasoneThe therapeutic efficacy of Buformin can be decreased when used in combination with Betamethasone.
BrexpiprazoleThe therapeutic efficacy of Buformin can be decreased when used in combination with Brexpiprazole.
BumetanideThe therapeutic efficacy of Buformin can be decreased when used in combination with Bumetanide.
BuserelinThe therapeutic efficacy of Buformin can be decreased when used in combination with Buserelin.
CeritinibThe therapeutic efficacy of Buformin can be decreased when used in combination with Ceritinib.
ChlorothiazideThe therapeutic efficacy of Buformin can be decreased when used in combination with Chlorothiazide.
ChlorpropamideBuformin may increase the hypoglycemic activities of Chlorpropamide.
ChlorthalidoneThe therapeutic efficacy of Buformin can be decreased when used in combination with Chlorthalidone.
ClozapineThe therapeutic efficacy of Buformin can be decreased when used in combination with Clozapine.
CorticotropinThe therapeutic efficacy of Buformin can be decreased when used in combination with Corticotropin.
Cortisone acetateThe therapeutic efficacy of Buformin can be decreased when used in combination with Cortisone acetate.
Cyproterone acetateThe therapeutic efficacy of Buformin can be decreased when used in combination with Cyproterone acetate.
DabrafenibThe therapeutic efficacy of Buformin can be decreased when used in combination with Dabrafenib.
DanazolThe therapeutic efficacy of Buformin can be decreased when used in combination with Danazol.
DarunavirThe therapeutic efficacy of Buformin can be decreased when used in combination with Darunavir.
DesogestrelThe therapeutic efficacy of Buformin can be decreased when used in combination with Desogestrel.
DexamethasoneThe therapeutic efficacy of Buformin can be decreased when used in combination with Dexamethasone.
DiazoxideThe therapeutic efficacy of Buformin can be decreased when used in combination with Diazoxide.
DienogestThe therapeutic efficacy of Buformin can be decreased when used in combination with Dienogest.
DisopyramideBuformin may increase the hypoglycemic activities of Disopyramide.
DrospirenoneThe therapeutic efficacy of Buformin can be decreased when used in combination with Drospirenone.
EpinephrineThe therapeutic efficacy of Buformin can be decreased when used in combination with Epinephrine.
EstradiolThe therapeutic efficacy of Buformin can be decreased when used in combination with Estradiol.
Estrone sulfateThe therapeutic efficacy of Buformin can be decreased when used in combination with Estrone sulfate.
Etacrynic acidThe therapeutic efficacy of Buformin can be decreased when used in combination with Etacrynic acid.
Ethinyl EstradiolThe therapeutic efficacy of Buformin can be decreased when used in combination with Ethinyl Estradiol.
Ethynodiol diacetateThe therapeutic efficacy of Buformin can be decreased when used in combination with Ethynodiol diacetate.
EtonogestrelThe therapeutic efficacy of Buformin can be decreased when used in combination with Etonogestrel.
EverolimusThe therapeutic efficacy of Buformin can be decreased when used in combination with Everolimus.
FludrocortisoneThe therapeutic efficacy of Buformin can be decreased when used in combination with Fludrocortisone.
FosamprenavirThe therapeutic efficacy of Buformin can be decreased when used in combination with Fosamprenavir.
FurosemideThe therapeutic efficacy of Buformin can be decreased when used in combination with Furosemide.
GliclazideBuformin may increase the hypoglycemic activities of Gliclazide.
GlimepirideBuformin may increase the hypoglycemic activities of Glimepiride.
GlipizideBuformin may increase the hypoglycemic activities of Glipizide.
GlyburideBuformin may increase the hypoglycemic activities of Glyburide.
GoserelinThe therapeutic efficacy of Buformin can be decreased when used in combination with Goserelin.
HistrelinThe therapeutic efficacy of Buformin can be decreased when used in combination with Histrelin.
HydrochlorothiazideThe therapeutic efficacy of Buformin can be decreased when used in combination with Hydrochlorothiazide.
HydrocortisoneThe therapeutic efficacy of Buformin can be decreased when used in combination with Hydrocortisone.
HydroflumethiazideThe therapeutic efficacy of Buformin can be decreased when used in combination with Hydroflumethiazide.
Hydroxyprogesterone caproateThe therapeutic efficacy of Buformin can be decreased when used in combination with Hydroxyprogesterone caproate.
IloperidoneThe therapeutic efficacy of Buformin can be decreased when used in combination with Iloperidone.
IndapamideThe therapeutic efficacy of Buformin can be decreased when used in combination with Indapamide.
IndinavirThe therapeutic efficacy of Buformin can be decreased when used in combination with Indinavir.
Insulin AspartBuformin may increase the hypoglycemic activities of Insulin Aspart.
Insulin DetemirBuformin may increase the hypoglycemic activities of Insulin Detemir.
Insulin GlargineBuformin may increase the hypoglycemic activities of Insulin Glargine.
Insulin GlulisineBuformin may increase the hypoglycemic activities of Insulin Glulisine.
Insulin HumanBuformin may increase the hypoglycemic activities of Insulin Human.
Insulin LisproBuformin may increase the hypoglycemic activities of Insulin Lispro.
LanreotideThe therapeutic efficacy of Buformin can be decreased when used in combination with Lanreotide.
LanreotideBuformin may increase the hypoglycemic activities of Lanreotide.
LeuprolideThe therapeutic efficacy of Buformin can be decreased when used in combination with Leuprolide.
LevonorgestrelThe therapeutic efficacy of Buformin can be decreased when used in combination with Levonorgestrel.
Lipoic AcidLipoic Acid may increase the hypoglycemic activities of Buformin.
LopinavirThe therapeutic efficacy of Buformin can be decreased when used in combination with Lopinavir.
LurasidoneThe therapeutic efficacy of Buformin can be decreased when used in combination with Lurasidone.
MecaserminBuformin may increase the hypoglycemic activities of Mecasermin.
Medroxyprogesterone acetateThe therapeutic efficacy of Buformin can be decreased when used in combination with Medroxyprogesterone acetate.
Megestrol acetateThe therapeutic efficacy of Buformin can be decreased when used in combination with Megestrol acetate.
MestranolThe therapeutic efficacy of Buformin can be decreased when used in combination with Mestranol.
MethotrimeprazineThe therapeutic efficacy of Buformin can be decreased when used in combination with Methotrimeprazine.
MethyclothiazideThe therapeutic efficacy of Buformin can be decreased when used in combination with Methyclothiazide.
MethylprednisoloneThe therapeutic efficacy of Buformin can be decreased when used in combination with Methylprednisolone.
MetolazoneThe therapeutic efficacy of Buformin can be decreased when used in combination with Metolazone.
MifepristoneBuformin may increase the hypoglycemic activities of Mifepristone.
NateglinideBuformin may increase the hypoglycemic activities of Nateglinide.
NelfinavirThe therapeutic efficacy of Buformin can be decreased when used in combination with Nelfinavir.
NiacinThe therapeutic efficacy of Buformin can be decreased when used in combination with Niacin.
NilotinibThe therapeutic efficacy of Buformin can be decreased when used in combination with Nilotinib.
NorethisteroneThe therapeutic efficacy of Buformin can be decreased when used in combination with Norethisterone.
NorgestimateThe therapeutic efficacy of Buformin can be decreased when used in combination with Norgestimate.
OctreotideThe therapeutic efficacy of Buformin can be decreased when used in combination with Octreotide.
OctreotideBuformin may increase the hypoglycemic activities of Octreotide.
OlanzapineThe therapeutic efficacy of Buformin can be decreased when used in combination with Olanzapine.
PaliperidoneThe therapeutic efficacy of Buformin can be decreased when used in combination with Paliperidone.
PasireotideThe therapeutic efficacy of Buformin can be decreased when used in combination with Pasireotide.
PasireotideBuformin may increase the hypoglycemic activities of Pasireotide.
PentamidineThe therapeutic efficacy of Buformin can be decreased when used in combination with Pentamidine.
PentamidineBuformin may increase the hypoglycemic activities of Pentamidine.
PiperazineThe therapeutic efficacy of Buformin can be decreased when used in combination with Piperazine.
PipotiazineThe therapeutic efficacy of Buformin can be decreased when used in combination with Pipotiazine.
PolythiazideThe therapeutic efficacy of Buformin can be decreased when used in combination with Polythiazide.
PrednisoloneThe therapeutic efficacy of Buformin can be decreased when used in combination with Prednisolone.
PrednisoneThe therapeutic efficacy of Buformin can be decreased when used in combination with Prednisone.
ProgesteroneThe therapeutic efficacy of Buformin can be decreased when used in combination with Progesterone.
QuetiapineThe therapeutic efficacy of Buformin can be decreased when used in combination with Quetiapine.
QuinethazoneThe therapeutic efficacy of Buformin can be decreased when used in combination with Quinethazone.
QuinineBuformin may increase the hypoglycemic activities of Quinine.
RepaglinideBuformin may increase the hypoglycemic activities of Repaglinide.
RisperidoneThe therapeutic efficacy of Buformin can be decreased when used in combination with Risperidone.
RitonavirThe therapeutic efficacy of Buformin can be decreased when used in combination with Ritonavir.
SaquinavirThe therapeutic efficacy of Buformin can be decreased when used in combination with Saquinavir.
SirolimusThe therapeutic efficacy of Buformin can be decreased when used in combination with Sirolimus.
SulfadiazineBuformin may increase the hypoglycemic activities of Sulfadiazine.
SulfamethoxazoleBuformin may increase the hypoglycemic activities of Sulfamethoxazole.
SulfisoxazoleBuformin may increase the hypoglycemic activities of Sulfisoxazole.
SunitinibBuformin may increase the hypoglycemic activities of Sunitinib.
TacrolimusThe therapeutic efficacy of Buformin can be decreased when used in combination with Tacrolimus.
TemsirolimusThe therapeutic efficacy of Buformin can be decreased when used in combination with Temsirolimus.
TipranavirThe therapeutic efficacy of Buformin can be decreased when used in combination with Tipranavir.
TolazamideBuformin may increase the hypoglycemic activities of Tolazamide.
TolbutamideBuformin may increase the hypoglycemic activities of Tolbutamide.
TorasemideThe therapeutic efficacy of Buformin can be decreased when used in combination with Torasemide.
TriamcinoloneThe therapeutic efficacy of Buformin can be decreased when used in combination with Triamcinolone.
TrichlormethiazideThe therapeutic efficacy of Buformin can be decreased when used in combination with Trichlormethiazide.
TriptorelinThe therapeutic efficacy of Buformin can be decreased when used in combination with Triptorelin.
VorinostatThe therapeutic efficacy of Buformin can be decreased when used in combination with Vorinostat.
ZiprasidoneThe therapeutic efficacy of Buformin can be decreased when used in combination with Ziprasidone.
Food InteractionsNot Available

Transporters

Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
substrate
General Function:
Secondary active organic cation transmembrane transporter activity
Specific Function:
Translocates a broad array of organic cations with various structures and molecular weights including the model compounds 1-methyl-4-phenylpyridinium (MPP), tetraethylammonium (TEA), N-1-methylnicotinamide (NMN), 4-(4-(dimethylamino)styryl)-N-methylpyridinium (ASP), the endogenous compounds choline, guanidine, histamine, epinephrine, adrenaline, noradrenaline and dopamine, and the drugs quinine...
Gene Name:
SLC22A1
Uniprot ID:
O15245
Molecular Weight:
61153.345 Da
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:12130709 ]
Comments
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Drug created on September 11, 2007 14:52 / Updated on August 17, 2016 12:24