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Investigational, Withdrawn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 It was withdrawn from the market in most countries due to a high risk of causing lactic acidosis.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
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
DrugInteraction
2,4-thiazolidinedioneThe risk or severity of hypoglycemia can be increased when Buformin is combined with 2,4-thiazolidinedione.
5-(2-methylpiperazine-1-sulfonyl)isoquinolineThe therapeutic efficacy of Buformin can be increased when used in combination with 5-(2-methylpiperazine-1-sulfonyl)isoquinoline.
AcarboseThe risk or severity of hypoglycemia can be increased when Acarbose is combined with Buformin.
AcetazolamideThe therapeutic efficacy of Buformin can be increased when used in combination with Acetazolamide.
AcetohexamideThe risk or severity of hypoglycemia can be increased when Acetohexamide is combined with Buformin.
Acetyl sulfisoxazoleThe therapeutic efficacy of Buformin can be increased when used in combination with Acetyl sulfisoxazole.
Acetylsalicylic acidAcetylsalicylic acid may increase the hypoglycemic activities of Buformin.
AcyclovirThe risk or severity of adverse effects can be increased when Acyclovir is combined with Buformin.
AgmatineThe risk or severity of hypoglycemia can be increased when Agmatine is combined with Buformin.
AICA ribonucleotideThe risk or severity of hypoglycemia can be increased when AICA ribonucleotide is combined with Buformin.
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]
  2. Shitara Y, Nakamichi N, Norioka M, Shima H, Kato Y, Horie T: Role of organic cation/carnitine transporter 1 in uptake of phenformin and inhibitory effect on complex I respiration in mitochondria. Toxicol Sci. 2013 Mar;132(1):32-42. doi: 10.1093/toxsci/kfs330. Epub 2012 Dec 5. [PubMed:23221006]

Drug created on September 11, 2007 14:52 / Updated on November 22, 2018 14:43