Identification

Name
Buformin
Accession Number
DB04830
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 It was withdrawn from the market in most countries due to a high risk of causing lactic acidosis.

Type
Small Molecule
Groups
Investigational, Withdrawn
Structure
Thumb
Weight
Average: 157.2168
Monoisotopic: 157.132745505
Chemical Formula
C6H15N5
Synonyms
  • 1-Butylbiguanide
  • Buformina
  • Buformine
  • Buforminum
External IDs
  • W 37
  • W-37

Pharmacology

Indication
Not Available
Contraindications & Blackbox Warnings
Learn about our commercial Contraindications & Blackbox Warnings data.
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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
Adverse Effects
Learn about our commercial Adverse Effects data.
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Toxicity
Not Available
Affected organisms
  • Humans and other mammals
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
DrugInteraction
AcarboseThe risk or severity of hypoglycemia can be increased when Acarbose is combined with Buformin.
AcebutololThe therapeutic efficacy of Buformin can be increased when used in combination with Acebutolol.
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 acidThe risk or severity of hypoglycemia can be increased when Acetylsalicylic acid is combined with Buformin.
AcyclovirThe risk or severity of adverse effects can be increased when Acyclovir is combined with Buformin.
AlbiglutideThe risk or severity of hypoglycemia can be increased when Buformin is combined with Albiglutide.
AlclometasoneThe risk or severity of hyperglycemia can be increased when Alclometasone is combined with Buformin.
AlogliptinThe risk or severity of hypoglycemia can be increased when Buformin is combined with Alogliptin.
Additional Data Available
  • Extended Description
    Extended Description
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    Extended description of the mechanism of action and particular properties of each drug interaction.

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  • Severity
    Severity
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    A severity rating for each drug interaction, from minor to major.

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  • Evidence Level
    Evidence Level
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    A rating for the strength of the evidence supporting each drug interaction.

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  • Action
    Action
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    An effect category for each drug interaction. Know how this interaction affects the subject drug.

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Food Interactions
Not Available

Products

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Product Ingredients
IngredientUNIICASInChI Key
Buformin hydrochlorideD947SXO87P1190-53-0KKLWSPPIRBIEOV-UHFFFAOYSA-N
International/Other Brands
Adebit (Zentiva) / Biforon (Meiji) / Bigunal (Shun Hwa) / Diabrin / Silubin / Ziavetine (Teikoku Kagaku)

Categories

ATC Codes
A10BA03 — Buformin
Drug Categories
Chemical TaxonomyProvided by Classyfire
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
Aliphatic acyclic compound / Biguanide / Carboximidamide / Hydrocarbon derivative / Imine / Organic 1,3-dipolar compound / Organopnictogen compound / Propargyl-type 1,3-dipolar organic compound
Molecular Framework
Aliphatic acyclic compounds
External Descriptors
biguanides (CHEBI:3209)

Chemical Identifiers

UNII
W2115E9C7B
CAS number
692-13-7
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

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]
KEGG Drug
D00595
KEGG Compound
C07674
PubChem Compound
2468
PubChem Substance
46507254
ChemSpider
2374
ChEBI
3209
ChEMBL
CHEMBL39736
ZINC
ZINC000004097425
PDBe Ligand
BFR
Wikipedia
Buformin
PDB Entries
5uii

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
2, 3RecruitingTreatmentDiffuse Large B-Cell Lymphoma (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

Transporters

Kind
Protein
Organism
Humans
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 October 02, 2020 03:12

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