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transporters (1)
for drugs
Identification
Name Buformin
Accession Number DB04830
Type small molecule
Groups withdrawn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 It was withdrawn from the market in most countries due to a high risk of causing lactic acidosis.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
Download: MOL | SDF | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms
1-Butylbiguanide
1-Butyldiguanide
Buformin hydrochloride
Buformina [inn-spanish]
Buformine
Buformine [inn-french]
Buformine HCL
Buforminum [inn-latin]
Butformin
Butyl guanylguanidine
Butylbiguanide
Butylbiguanide hydrochloride
Butylbiguanidum
Butyldiguanide
DBV hydrochloride
N-butylbiguanide
First Prev Next Last
Salts Not Available
Brand names
Name Company
Adebit
Andere
Biforon
Diabrin
Glybigid
Glybigidum
Panformin
Silubin
Sindiatil
Brand mixtures Not Available
Categories
  • Hypoglycemic Agents
CAS number 692-13-7
Weight Average: 157.2168
Monoisotopic: 157.132745505
Chemical Formula C6H15N5
InChI Key InChIKey=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)
Plain Text
IUPAC Name
(E)-2-butyl-1-(diaminomethylidene)guanidine
SMILES
CCCC\N=C(/N)N=C(N)N
Plain Text
Mass Spec Not Available
Taxonomy
Kingdom Organic
Classes
  • Biguanides
Substructures
  • Biguanides
  • Guanidines
  • Carboxamidines
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
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 1.41e+00 g/l 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 ChemAxon
rotatable bond count 3 ChemAxon
refractivity 44.64 ChemAxon
polarizability 17.67 ChemAxon
References
Synthesis Reference Not Available
General Reference
  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
  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
External Links
Resource Link
KEGG Drug D00595 Link_out
KEGG Compound C07674 Link_out
PubChem Compound 2468 Link_out
PubChem Substance 46507254 Link_out
ChemSpider 2374 Link_out
Wikipedia http://en.wikipedia.org/wiki/Buformin Link_out
ATC Codes
  • A10BA03
AHFS Codes Not Available
PDB Entries Not Available
FDA label Not Available
MSDS Not Available
Interactions
Drug Interactions Not Available
Food Interactions Not Available
Transporters

1. Solute carrier family 22 member 1

Actions: substrate

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, and metformin. The transport of organic cations is inhibited by a broad array of compounds like tetramethylammonium (TMA), cocaine, lidocaine, NMDA receptor antagonists, atropine, prazosin, cimetidine, TEA and NMN, guanidine, cimetidine, choline, procainamide, quinine, tetrabutylammonium, and tetrapentylammonium. Translocates organic cations in an electrogenic and pH-independent manner. Translocates organic cations across the plasma membrane in both directions. Transports the polyamines spermine and spermidine. Transports pramipexole across the basolateral membrane of the proximal tubular epithelial cells. The choline transport is activated by MMTS. Regulated by various intracellular signaling pathways including inhibition by protein kinase A activation, and endogenously activation by the calmodulin complex, the calmodulin- dependent kinase II and LCK tyrosine kinase

UniProt ID: O15245 Link_out
Gene: SLC22A1 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

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

Comments
Drug created on September 11, 2007 14:52 / Updated on February 08, 2013 16:23