Identification
- Generic Name
- Buformin
- DrugBank Accession Number
- DB04830
- Background
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 It was withdrawn from the market in most countries due to a high risk of causing lactic acidosis.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- Investigational, Withdrawn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
Structure for Buformin (DB04830)
- Weight
- Average: 157.2168
Monoisotopic: 157.132745505 - Chemical Formula
- C6H15N5
- Synonyms
- 1-Butylbiguanide
- Buformin
- Buformina
- Buformine
- Buforminum
- External IDs
- W 37
- W-37
Pharmacology
- Indication
Not Available
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Avoid life-threatening adverse drug eventsImprove clinical decision support with information on contraindications & blackbox warnings, population restrictions, harmful risks, & more.Avoid life-threatening adverse drug events & improve clinical decision support.- 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
Improve decision support & research outcomesWith structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates.Improve decision support & research outcomes with our structured adverse effects data.- Toxicity
Not Available
- 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.
Drug Interaction Integrate drug-drug
interactions in your softwareAcarbose The risk or severity of hypoglycemia can be increased when Acarbose is combined with Buformin. Acebutolol The therapeutic efficacy of Buformin can be increased when used in combination with Acebutolol. Acetazolamide The therapeutic efficacy of Buformin can be increased when used in combination with Acetazolamide. Acetohexamide The risk or severity of hypoglycemia can be increased when Acetohexamide is combined with Buformin. Acetyl sulfisoxazole The therapeutic efficacy of Buformin can be increased when used in combination with Acetyl sulfisoxazole. Acetylsalicylic acid The risk or severity of hypoglycemia can be increased when Acetylsalicylic acid is combined with Buformin. Acyclovir The risk or severity of adverse effects can be increased when Acyclovir is combined with Buformin. Albiglutide The risk or severity of hypoglycemia can be increased when Buformin is combined with Albiglutide. Alclometasone The risk or severity of hyperglycemia can be increased when Alclometasone is combined with Buformin. Alogliptin The risk or severity of hypoglycemia can be increased when Buformin is combined with Alogliptin. 
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- Not Available
Products
Drug product information from 10+ global regionsOur datasets provide approved product information including:dosage, form, labeller, route of administration, and marketing period.Access drug product information from over 10 global regions.- Product Ingredients
Ingredient UNII CAS InChI Key Buformin hydrochloride D947SXO87P 1190-53-0 KKLWSPPIRBIEOV-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)
- Affected organisms
- Humans and other mammals
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
- 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. [Article]
- 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. [Article]
- External Links
- 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
Phase Status Purpose Conditions Count 2, 3 Recruiting Treatment Diffuse Large B-Cell Lymphoma (DLBCL) 1 Not Available Completed Not Available Type 2 Diabetes Mellitus 3
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage Forms
- Not Available
- Prices
- Not Available
- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
Property Value Source logP -1.20 HANSCH,C ET AL. (1995) - Predicted Properties
Property Value Source Water Solubility 1.41 mg/mL ALOGPS logP -0.46 ALOGPS logP -0.35 ChemAxon logS -2 ALOGPS pKa (Strongest Basic) 11.52 ChemAxon Physiological Charge 2 ChemAxon Hydrogen Acceptor Count 5 ChemAxon Hydrogen Donor Count 3 ChemAxon Polar Surface Area 102.78 Å2 ChemAxon Rotatable Bond Count 3 ChemAxon Refractivity 44.64 m3·mol-1 ChemAxon Polarizability 17.67 Å3 ChemAxon Number of Rings 0 ChemAxon Bioavailability 1 ChemAxon Rule of Five Yes ChemAxon Ghose Filter No ChemAxon Veber's Rule No ChemAxon MDDR-like Rule No ChemAxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption + 0.977 Blood Brain Barrier + 0.8194 Caco-2 permeable - 0.5592 P-glycoprotein substrate Substrate 0.5726 P-glycoprotein inhibitor I Non-inhibitor 0.9266 P-glycoprotein inhibitor II Non-inhibitor 0.6179 Renal organic cation transporter Inhibitor 0.5139 CYP450 2C9 substrate Non-substrate 0.7635 CYP450 2D6 substrate Substrate 0.5933 CYP450 3A4 substrate Non-substrate 0.7548 CYP450 1A2 substrate Non-inhibitor 0.7888 CYP450 2C9 inhibitor Non-inhibitor 0.8986 CYP450 2D6 inhibitor Inhibitor 0.5887 CYP450 2C19 inhibitor Non-inhibitor 0.8381 CYP450 3A4 inhibitor Non-inhibitor 0.9718 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.9259 Ames test Non AMES toxic 0.7642 Carcinogenicity Non-carcinogens 0.7763 Biodegradation Not ready biodegradable 0.6911 Rat acute toxicity 2.7504 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.9548 hERG inhibition (predictor II) Non-inhibitor 0.9403
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS Not Available LC-MS/MS Spectrum - LC-ESI-QQ , positive LC-MS/MS splash10-0a4i-0900000000-4c952c2932001fc76bc3 LC-MS/MS Spectrum - LC-ESI-QQ , positive LC-MS/MS splash10-08fr-9600000000-75a14777c98b6cd11b79 LC-MS/MS Spectrum - LC-ESI-QQ , positive LC-MS/MS splash10-03di-9000000000-6cc376bdd5912ce96059 LC-MS/MS Spectrum - LC-ESI-QQ , positive LC-MS/MS splash10-03di-9000000000-4f8114656056dbd77769 LC-MS/MS Spectrum - LC-ESI-QQ , positive LC-MS/MS splash10-01ox-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
- 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. [Article]
- 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. [Article]
Drug created at September 11, 2007 20:52 / Updated at October 03, 2021 00:53