BUFORMIN

Details

Stereochemistry	ACHIRAL
Molecular Formula	C6H15N5
Molecular Weight	157.2168
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CCCCNC(=N)NC(N)=N

InChI

InChIKey=XSEUMFJMFFMCIU-UHFFFAOYSA-N

InChI=1S/C6H15N5/c1-2-3-4-10-6(9)11-5(7)8/h2-4H2,1H3,(H6,7,8,9,10,11)

HIDE SMILES / InChI

Description
Sources: https://books.google.ru/books?id=Z67nCAAAQBAJ&pg=PA249&lpg=PA249&dq=The+daily+dose+of+buformin+is+150–300+mg+by+mouth&source=bl&ots=EM59SDVL8z&sig=-fbXFH-S52UJfKLPHv65RAhJ9Ts&hl=ru&sa=X&ved=0ahUKEwiDx8zAwLXPAhVBOywKHbcwAfAQ6AEIJTAB#v=onepage&q=The%20daily%20dose%20of%20buformin%20is%20150%E2%80%93300%20mg%20by%20mouth&f=false
Curator's Comment: description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/7310831 http://www.sigmaaldrich.com/catalog/product/sigma/sml1496?lang=en®ion=RU http://www.ndrugs.com/?s=buformin http://library.nuft.edu.ua/ebook/file/Sittig1988.pdf https://www.ncbi.nlm.nih.gov/pubmed/19273282 https://www.ncbi.nlm.nih.gov/pubmed/21428801 http://curriculum.toxicology.wikispaces.net/2.1.7.1.3.1+Biguanides

Buformin (1-butylbiguanide) is an oral antidiabetic drug of the biguanide class. AMPK activator. AMPK is a potential therapeutic target in the prevention and the treatment of type 2 diabetes and insulin resistance. Major classes of antidiabetic drugs have been reported to activate AMPK. Buformin exerts its anti-tumorigenic activity via activation of AMPK and inhibition of the mTOR signaling pathways in endometrial cancer cells. Toxicity: guinea pig LD50 subcutaneous 18 mg/kg; mouse LD50 intraperitoneal 140 mg/kg and 300 mg/kg oral. Buformin was withdrawn from the market in many countries due to an elevated risk of causing lactic acidosis.

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
AMP-activated protein kinase, AMPK 17 Target ID: CHEMBL2096907 Sources: https://www.ncbi.nlm.nih.gov/pubmed/27398153	Activator 1430

Conditions

Condition	Modality	Highest Phase	Product
Type 2 diabetes mellitus 259 Sources: https://clinicaltrials.gov/ct2/show/NCT01584232	Primary	Withdrawn	Silubin Approved Use Unknown
Mammary cancer 2 Sources: https://www.ncbi.nlm.nih.gov/pubmed/25804611	Primary	Preclinical	Unknown Approved Use Unknown
Reactive hypoglycemia 2 Sources: https://www.ncbi.nlm.nih.gov/pubmed/1190104	Primary	Phase II 1132	Unknown Approved Use Unknown
Endometrial cancer 43 Sources: https://www.ncbi.nlm.nih.gov/pubmed/27398153	Primary	Basic research	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
Treatment of reactive hypoglycemia with buformin.	1975 Nov	1190104
Buformin concentrations in a case of fatal lactic acidosis.	1981	7202882
The inhibitory action of buformin, a biguanide on gluconeogenesis from alanine and its transport system in rat livers.	1993 Jan	8472619
[A 50-year history of new drugs in Japan-the development and progress of anti-diabetic drugs and the epidemiological aspects of diabetes mellitus].	2003	14570054
Involvement of organic cation transporter 1 in the lactic acidosis caused by metformin.	2003 Apr	12644585
Plasma BNP levels in the treatment of type 2 diabetes with pioglitazone.	2003 Aug	12915698
Insufficient depression treatment in outpatient settings.	2004 Feb 26	19675684
The combination of metformin and a dipeptidyl peptidase IV inhibitor prevents 5-fluorouracil-induced reduction of small intestine weight.	2004 Mar 19	15044053
Cognitive training for dementia.	2005 Dec 21	21289931
[A new case of lactic acidosis caused by buformin].	2005 Feb	15898889
Antidiabetic drug utilization in hungary.	2005 Jun	16096899
The medical skills of the Malabar doctors in Tranquebar, India, as recorded by surgeon T L F Folly, 1798.	2005 Oct	16562332
Hypoglycemic effects of the wood of Taxus yunnanensis on streptozotocin-induced diabetic rats and its active components.	2006 Jan	16360940
Biguanide-induced mitochondrial dysfunction yields increased lactate production and cytotoxicity of aerobically-poised HepG2 cells and human hepatocytes in vitro.	2008 Dec 1	18817800
Framework conditions and requirements to ensure the technical functional safety of reprocessed medical devices.	2008 Sep 3	20204095
Transient Parkinsonism in isolated extrapontine myelinolysis.	2009 Aug	19444382
General Practitioners' preferences and use of educational media: a German perspective.	2009 Feb 16	19220905
A cardiologic approach to non-insulin antidiabetic pharmacotherapy in patients with heart disease.	2009 Jul 20	19619327
How should ethnic diversity be represented in medical curricula? A plea for systematic training in cultural competence.	2010	21818195
[The alphabet of nature and the alphabet of culture in the eighteenth century. botany, diplomatics, and ethno-linguistics according to Carl von Linné, Johann Christoph Gatterer, and Christian Wilhelm Büttner : Botany, Diplomatics, and ethno-linguistics according to Carl von Linné, Johann Christoph Gatterer, and Christian Wilhelm Büttner].	2010	20665241
Gender differences in metformin effect on aging, life span and spontaneous tumorigenesis in 129/Sv mice.	2010 Dec	21164223
Effects of metformin, buformin, and phenformin on the post-initiation stage of chemically induced mammary carcinogenesis in the rat.	2015 Jun	25804611

Patents

Sample Use Guides

In Vivo Use Guide

Tablets 50-300 mg in divided doses

Route of Administration: Oral

In Vitro Use Guide

The effects of buformin on cell proliferation were examined in the endometrial cancer cell lines, ECC-1 and Ishikawa. Both cell lines were exposed to varying doses of buformin for 72 hours. Buformin inhibited cell growth in a dosedependent manner in both endometrial cancer cell lines. The mean IC50 value was approximately 150 μM and 8 μM for the ECC-1 and Ishikawa cells at 72 hours, respectively.

Name

Type

Language

BUFORMIN

Official Name

English

1-Butylbiguanide

Systematic Name

English

W-37

Code

English

DBV

Code

English

BUFORMIN [USAN]

Common Name

English

BUFORMIN [MI]

Common Name

English

IMIDODICARBONIMIDIC DIAMIDE, N-BUTYL-

Systematic Name

English

Buformin [WHO-DD]

Common Name

English

buformin [INN]

Common Name

English

BUFORMIN [MART.]

Common Name

English

W 37

Code

English

Classification Tree Code System Code

WHO-ATC

A10BA03