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
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)
DescriptionCurator'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
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 Buformin was withdrawn from the market in many countries due to an elevated risk of causing lactic acidosis.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 |
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Target ID: CHEMBL2096907 Sources: https://www.ncbi.nlm.nih.gov/pubmed/27398153 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
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Primary | Silubin Approved UseUnknown |
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Primary | Unknown Approved UseUnknown |
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Primary | Unknown Approved UseUnknown |
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Primary | Unknown Approved UseUnknown |
PubMed
Title | Date | PubMed |
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Treatment of reactive hypoglycemia with buformin. | 1975 Nov |
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Buformin concentrations in a case of fatal lactic acidosis. | 1981 |
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The inhibitory action of buformin, a biguanide on gluconeogenesis from alanine and its transport system in rat livers. | 1993 Jan |
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[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 |
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Involvement of organic cation transporter 1 in the lactic acidosis caused by metformin. | 2003 Apr |
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Plasma BNP levels in the treatment of type 2 diabetes with pioglitazone. | 2003 Aug |
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Insufficient depression treatment in outpatient settings. | 2004 Feb 26 |
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The combination of metformin and a dipeptidyl peptidase IV inhibitor prevents 5-fluorouracil-induced reduction of small intestine weight. | 2004 Mar 19 |
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Cognitive training for dementia. | 2005 Dec 21 |
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[A new case of lactic acidosis caused by buformin]. | 2005 Feb |
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Antidiabetic drug utilization in hungary. | 2005 Jun |
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The medical skills of the Malabar doctors in Tranquebar, India, as recorded by surgeon T L F Folly, 1798. | 2005 Oct |
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Hypoglycemic effects of the wood of Taxus yunnanensis on streptozotocin-induced diabetic rats and its active components. | 2006 Jan |
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Biguanide-induced mitochondrial dysfunction yields increased lactate production and cytotoxicity of aerobically-poised HepG2 cells and human hepatocytes in vitro. | 2008 Dec 1 |
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Framework conditions and requirements to ensure the technical functional safety of reprocessed medical devices. | 2008 Sep 3 |
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Transient Parkinsonism in isolated extrapontine myelinolysis. | 2009 Aug |
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General Practitioners' preferences and use of educational media: a German perspective. | 2009 Feb 16 |
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A cardiologic approach to non-insulin antidiabetic pharmacotherapy in patients with heart disease. | 2009 Jul 20 |
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How should ethnic diversity be represented in medical curricula? A plea for systematic training in cultural competence. | 2010 |
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[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 |
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Gender differences in metformin effect on aging, life span and spontaneous tumorigenesis in 129/Sv mice. | 2010 Dec |
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Effects of metformin, buformin, and phenformin on the post-initiation stage of chemically induced mammary carcinogenesis in the rat. | 2015 Jun |
Sample Use Guides
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/27398153
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.
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WHO-ATC |
A10BA03
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WHO-VATC |
QA10BA03
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NCI_THESAURUS |
C98234
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211-726-4
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C95328
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CHEMBL39736
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100000088440
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SUB05965MIG
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DB04830
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3209
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Buformin
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423
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D002026
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2468
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2004
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DTXSID6046420
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692-13-7
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m2751
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W2115E9C7B
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ACTIVE MOIETY
SALT/SOLVATE (PARENT)