Identification

Name
Buformin
Accession Number
DB04830
Type
Small Molecule
Groups
Investigational, Withdrawn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 It was withdrawn from the market in most countries due to a high risk of causing lactic acidosis.

Structure
Thumb
Synonyms
  • 1-Butylbiguanide
  • Buformina
  • Buformine
  • Buforminum
External IDs
W 37 / W-37
Product Ingredients
IngredientUNIICASInChI Key
Buformin HydrochlorideD947SXO87P1190-53-0KKLWSPPIRBIEOV-UHFFFAOYSA-N
International/Other Brands
Adebit (Zentiva) / Biforon (Meiji) / Bigunal (Shun Hwa) / Diabrin / Glybigid / Silubin / Ziavetine (Teikoku Kagaku)
Categories
UNII
W2115E9C7B
CAS number
692-13-7
Weight
Average: 157.2168
Monoisotopic: 157.132745505
Chemical Formula
C6H15N5
InChI Key
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

Pharmacology

Indication
Not Available
Structured Indications
Not Available
Pharmacodynamics
Not Available
Mechanism of action
Not Available
Absorption
Not Available
Volume of distribution
Not Available
Protein binding
Not Available
Metabolism
Not Available
Route of elimination
Not Available
Half life
Not Available
Clearance
Not Available
Toxicity
Not Available
Affected organisms
  • Humans and other mammals
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
DrugInteractionDrug group
AripiprazoleThe therapeutic efficacy of Buformin can be decreased when used in combination with Aripiprazole.Approved, Investigational
Arsenic trioxideThe therapeutic efficacy of Buformin can be decreased when used in combination with Arsenic trioxide.Approved, Investigational
ArticaineThe therapeutic efficacy of Buformin can be decreased when used in combination with Articaine.Approved
AsenapineThe therapeutic efficacy of Buformin can be decreased when used in combination with Asenapine.Approved
AtazanavirThe therapeutic efficacy of Buformin can be decreased when used in combination with Atazanavir.Approved, Investigational
BendroflumethiazideThe therapeutic efficacy of Buformin can be decreased when used in combination with Bendroflumethiazide.Approved
BetamethasoneThe therapeutic efficacy of Buformin can be decreased when used in combination with Betamethasone.Approved, Vet Approved
BrexpiprazoleThe therapeutic efficacy of Buformin can be decreased when used in combination with Brexpiprazole.Approved, Investigational
BumetanideThe therapeutic efficacy of Buformin can be decreased when used in combination with Bumetanide.Approved
BuserelinThe therapeutic efficacy of Buformin can be decreased when used in combination with Buserelin.Approved, Investigational
CeritinibThe therapeutic efficacy of Buformin can be decreased when used in combination with Ceritinib.Approved
ChlorothiazideThe therapeutic efficacy of Buformin can be decreased when used in combination with Chlorothiazide.Approved, Vet Approved
ChlorpropamideBuformin may increase the hypoglycemic activities of Chlorpropamide.Approved, Investigational
ChlorthalidoneThe therapeutic efficacy of Buformin can be decreased when used in combination with Chlorthalidone.Approved
ClozapineThe therapeutic efficacy of Buformin can be decreased when used in combination with Clozapine.Approved
CorticotropinThe therapeutic efficacy of Buformin can be decreased when used in combination with Corticotropin.Approved, Investigational, Vet Approved
Cortisone acetateThe therapeutic efficacy of Buformin can be decreased when used in combination with Cortisone acetate.Approved, Investigational
CyclopenthiazideThe therapeutic efficacy of Buformin can be decreased when used in combination with Cyclopenthiazide.Experimental
Cyproterone acetateThe therapeutic efficacy of Buformin can be decreased when used in combination with Cyproterone acetate.Approved, Investigational
DabrafenibThe therapeutic efficacy of Buformin can be decreased when used in combination with Dabrafenib.Approved, Investigational
DanazolThe therapeutic efficacy of Buformin can be decreased when used in combination with Danazol.Approved
DarunavirThe therapeutic efficacy of Buformin can be decreased when used in combination with Darunavir.Approved
DesogestrelThe therapeutic efficacy of Buformin can be decreased when used in combination with Desogestrel.Approved
DexamethasoneThe therapeutic efficacy of Buformin can be decreased when used in combination with Dexamethasone.Approved, Investigational, Vet Approved
DiazoxideThe therapeutic efficacy of Buformin can be decreased when used in combination with Diazoxide.Approved
DienogestThe therapeutic efficacy of Buformin can be decreased when used in combination with Dienogest.Approved
DisopyramideBuformin may increase the hypoglycemic activities of Disopyramide.Approved
DrospirenoneThe therapeutic efficacy of Buformin can be decreased when used in combination with Drospirenone.Approved
EpinephrineThe therapeutic efficacy of Buformin can be decreased when used in combination with Epinephrine.Approved, Vet Approved
EpitizideThe therapeutic efficacy of Buformin can be decreased when used in combination with Epitizide.Experimental
EstradiolThe therapeutic efficacy of Buformin can be decreased when used in combination with Estradiol.Approved, Investigational, Vet Approved
Estrone sulfateThe therapeutic efficacy of Buformin can be decreased when used in combination with Estrone sulfate.Approved
Etacrynic acidThe therapeutic efficacy of Buformin can be decreased when used in combination with Etacrynic acid.Approved, Investigational
Ethinyl EstradiolThe therapeutic efficacy of Buformin can be decreased when used in combination with Ethinyl Estradiol.Approved
Ethynodiol diacetateThe therapeutic efficacy of Buformin can be decreased when used in combination with Ethynodiol diacetate.Approved
EtonogestrelThe therapeutic efficacy of Buformin can be decreased when used in combination with Etonogestrel.Approved, Investigational
EverolimusThe therapeutic efficacy of Buformin can be decreased when used in combination with Everolimus.Approved
FludrocortisoneThe therapeutic efficacy of Buformin can be decreased when used in combination with Fludrocortisone.Approved, Investigational
FosamprenavirThe therapeutic efficacy of Buformin can be decreased when used in combination with Fosamprenavir.Approved
FurosemideThe therapeutic efficacy of Buformin can be decreased when used in combination with Furosemide.Approved, Vet Approved
GliclazideBuformin may increase the hypoglycemic activities of Gliclazide.Approved
GlimepirideBuformin may increase the hypoglycemic activities of Glimepiride.Approved
GlipizideBuformin may increase the hypoglycemic activities of Glipizide.Approved, Investigational
GlyburideBuformin may increase the hypoglycemic activities of Glyburide.Approved
GoserelinThe therapeutic efficacy of Buformin can be decreased when used in combination with Goserelin.Approved
HistrelinThe therapeutic efficacy of Buformin can be decreased when used in combination with Histrelin.Approved
HydrochlorothiazideThe therapeutic efficacy of Buformin can be decreased when used in combination with Hydrochlorothiazide.Approved, Vet Approved
HydrocortisoneThe therapeutic efficacy of Buformin can be decreased when used in combination with Hydrocortisone.Approved, Vet Approved
HydroflumethiazideThe therapeutic efficacy of Buformin can be decreased when used in combination with Hydroflumethiazide.Approved, Investigational
Hydroxyprogesterone caproateThe therapeutic efficacy of Buformin can be decreased when used in combination with Hydroxyprogesterone caproate.Approved, Investigational
IloperidoneThe therapeutic efficacy of Buformin can be decreased when used in combination with Iloperidone.Approved
IndapamideThe therapeutic efficacy of Buformin can be decreased when used in combination with Indapamide.Approved
IndinavirThe therapeutic efficacy of Buformin can be decreased when used in combination with Indinavir.Approved
Insulin AspartBuformin may increase the hypoglycemic activities of Insulin Aspart.Approved
Insulin DetemirBuformin may increase the hypoglycemic activities of Insulin Detemir.Approved
Insulin GlargineBuformin may increase the hypoglycemic activities of Insulin Glargine.Approved
Insulin GlulisineBuformin may increase the hypoglycemic activities of Insulin Glulisine.Approved
Insulin HumanBuformin may increase the hypoglycemic activities of Insulin Human.Approved, Investigational
Insulin LisproBuformin may increase the hypoglycemic activities of Insulin Lispro.Approved
LanreotideThe therapeutic efficacy of Buformin can be decreased when used in combination with Lanreotide.Approved
LeuprolideThe therapeutic efficacy of Buformin can be decreased when used in combination with Leuprolide.Approved, Investigational
LevonorgestrelThe therapeutic efficacy of Buformin can be decreased when used in combination with Levonorgestrel.Approved, Investigational
Lipoic AcidLipoic Acid may increase the hypoglycemic activities of Buformin.Approved, Investigational, Nutraceutical
LopinavirThe therapeutic efficacy of Buformin can be decreased when used in combination with Lopinavir.Approved
LurasidoneThe therapeutic efficacy of Buformin can be decreased when used in combination with Lurasidone.Approved, Investigational
MecaserminBuformin may increase the hypoglycemic activities of Mecasermin.Approved, Investigational
MedrogestoneThe serum concentration of Buformin can be decreased when it is combined with Medrogestone.Approved
Medroxyprogesterone acetateThe therapeutic efficacy of Buformin can be decreased when used in combination with Medroxyprogesterone acetate.Approved, Investigational
Megestrol acetateThe therapeutic efficacy of Buformin can be decreased when used in combination with Megestrol acetate.Approved, Investigational, Vet Approved
MestranolThe therapeutic efficacy of Buformin can be decreased when used in combination with Mestranol.Approved
MethotrimeprazineThe therapeutic efficacy of Buformin can be decreased when used in combination with Methotrimeprazine.Approved, Investigational
MethyclothiazideThe therapeutic efficacy of Buformin can be decreased when used in combination with Methyclothiazide.Approved
MethylprednisoloneThe therapeutic efficacy of Buformin can be decreased when used in combination with Methylprednisolone.Approved, Vet Approved
MetolazoneThe therapeutic efficacy of Buformin can be decreased when used in combination with Metolazone.Approved
MifepristoneBuformin may increase the hypoglycemic activities of Mifepristone.Approved, Investigational
NateglinideBuformin may increase the hypoglycemic activities of Nateglinide.Approved, Investigational
NelfinavirThe therapeutic efficacy of Buformin can be decreased when used in combination with Nelfinavir.Approved
NiacinThe therapeutic efficacy of Buformin can be decreased when used in combination with Niacin.Approved, Investigational, Nutraceutical
NilotinibThe therapeutic efficacy of Buformin can be decreased when used in combination with Nilotinib.Approved, Investigational
NorethisteroneThe therapeutic efficacy of Buformin can be decreased when used in combination with Norethisterone.Approved
NorgestimateThe therapeutic efficacy of Buformin can be decreased when used in combination with Norgestimate.Approved, Investigational
OctreotideThe therapeutic efficacy of Buformin can be decreased when used in combination with Octreotide.Approved, Investigational
OlanzapineThe therapeutic efficacy of Buformin can be decreased when used in combination with Olanzapine.Approved, Investigational
PaliperidoneThe therapeutic efficacy of Buformin can be decreased when used in combination with Paliperidone.Approved
PasireotideThe therapeutic efficacy of Buformin can be decreased when used in combination with Pasireotide.Approved
PentamidineThe therapeutic efficacy of Buformin can be decreased when used in combination with Pentamidine.Approved, Investigational
PiperazineThe therapeutic efficacy of Buformin can be decreased when used in combination with Piperazine.Approved, Vet Approved
PipotiazineThe therapeutic efficacy of Buformin can be decreased when used in combination with Pipotiazine.Approved, Investigational
PolythiazideThe therapeutic efficacy of Buformin can be decreased when used in combination with Polythiazide.Approved
PrednisoloneThe therapeutic efficacy of Buformin can be decreased when used in combination with Prednisolone.Approved, Vet Approved
PrednisoneThe therapeutic efficacy of Buformin can be decreased when used in combination with Prednisone.Approved, Vet Approved
PregabalinThe risk or severity of heart failure can be increased when Pregabalin is combined with Buformin.Approved, Illicit, Investigational
ProgesteroneThe therapeutic efficacy of Buformin can be decreased when used in combination with Progesterone.Approved, Vet Approved
QuetiapineThe therapeutic efficacy of Buformin can be decreased when used in combination with Quetiapine.Approved
QuinethazoneThe therapeutic efficacy of Buformin can be decreased when used in combination with Quinethazone.Approved
QuinineBuformin may increase the hypoglycemic activities of Quinine.Approved
RepaglinideBuformin may increase the hypoglycemic activities of Repaglinide.Approved, Investigational
RisperidoneThe therapeutic efficacy of Buformin can be decreased when used in combination with Risperidone.Approved, Investigational
RitonavirThe therapeutic efficacy of Buformin can be decreased when used in combination with Ritonavir.Approved, Investigational
SaquinavirThe therapeutic efficacy of Buformin can be decreased when used in combination with Saquinavir.Approved, Investigational
SirolimusThe therapeutic efficacy of Buformin can be decreased when used in combination with Sirolimus.Approved, Investigational
SulfadiazineBuformin may increase the hypoglycemic activities of Sulfadiazine.Approved, Investigational, Vet Approved
SulfamethoxazoleBuformin may increase the hypoglycemic activities of Sulfamethoxazole.Approved
SulfisoxazoleBuformin may increase the hypoglycemic activities of Sulfisoxazole.Approved, Vet Approved
SunitinibBuformin may increase the hypoglycemic activities of Sunitinib.Approved, Investigational
TacrolimusThe therapeutic efficacy of Buformin can be decreased when used in combination with Tacrolimus.Approved, Investigational
TemsirolimusThe therapeutic efficacy of Buformin can be decreased when used in combination with Temsirolimus.Approved
TipranavirThe therapeutic efficacy of Buformin can be decreased when used in combination with Tipranavir.Approved, Investigational
TolazamideBuformin may increase the hypoglycemic activities of Tolazamide.Approved, Investigational
TolbutamideBuformin may increase the hypoglycemic activities of Tolbutamide.Approved, Investigational
TorasemideThe therapeutic efficacy of Buformin can be decreased when used in combination with Torasemide.Approved
TriamcinoloneThe therapeutic efficacy of Buformin can be decreased when used in combination with Triamcinolone.Approved, Vet Approved
TrichlormethiazideThe therapeutic efficacy of Buformin can be decreased when used in combination with Trichlormethiazide.Approved, Vet Approved
TriptorelinThe therapeutic efficacy of Buformin can be decreased when used in combination with Triptorelin.Approved, Vet Approved
UbidecarenoneThe therapeutic efficacy of Buformin can be increased when used in combination with Ubidecarenone.Approved, Investigational, Nutraceutical
VorinostatThe therapeutic efficacy of Buformin can be decreased when used in combination with Vorinostat.Approved, Investigational
ZiprasidoneThe therapeutic efficacy of Buformin can be decreased when used in combination with Ziprasidone.Approved
Food Interactions
Not 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
KEGG Drug
D00595
KEGG Compound
C07674
PubChem Compound
2468
PubChem Substance
46507254
ChemSpider
2374
ChEBI
3209
ChEMBL
CHEMBL39736
HET
BFR
Wikipedia
Buformin
ATC Codes
A10BA03 — Buformin
PDB Entries
5uii

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
2, 3RecruitingTreatmentLymphoma, Large B-Cell, Diffuse (DLBCL)1
Not AvailableCompletedNot AvailableType 2 Diabetes Mellitus3

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Solid
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 FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
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)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-0a4i-0900000000-4c952c2932001fc76bc3
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-08fr-9600000000-75a14777c98b6cd11b79
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-03di-9000000000-6cc376bdd5912ce96059
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-03di-9000000000-4f8114656056dbd77769
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-01ox-9000000000-d70f462a7d168d2bacbd

Taxonomy

Description
This compound belongs to the class of organic compounds known as biguanides. These are organic compounds containing two N-linked guanidines.
Kingdom
Organic compounds
Super Class
Organic nitrogen compounds
Class
Organonitrogen compounds
Sub Class
Guanidines
Direct Parent
Biguanides
Alternative Parents
Propargyl-type 1,3-dipolar organic compounds / Carboximidamides / Organopnictogen compounds / Imines / Hydrocarbon derivatives
Substituents
Biguanide / Organic 1,3-dipolar compound / Propargyl-type 1,3-dipolar organic compound / Carboximidamide / Organopnictogen compound / Hydrocarbon derivative / Imine / Aliphatic acyclic compound
Molecular Framework
Aliphatic acyclic compounds
External Descriptors
biguanides (CHEBI:3209)

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-methylnico...
Gene Name
SLC22A1
Uniprot ID
O15245
Uniprot Name
Solute carrier family 22 member 1
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]

Drug created on September 11, 2007 14:52 / Updated on December 01, 2017 17:13