Details
| Stereochemistry | ACHIRAL |
| Molecular Formula | C6H15N5.ClH |
| Molecular Weight | 193.678 |
| Optical Activity | NONE |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
Cl.CCCCNC(=N)NC(N)=N
InChI
InChIKey=KKLWSPPIRBIEOV-UHFFFAOYSA-N
InChI=1S/C6H15N5.ClH/c1-2-3-4-10-6(9)11-5(7)8;/h2-4H2,1H3,(H6,7,8,9,10,11);1H
| Molecular Formula | C6H15N5 |
| Molecular Weight | 157.2168 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ACHIRAL |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Optical Activity | NONE |
| Molecular Formula | ClH |
| Molecular Weight | 36.461 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ACHIRAL |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Optical Activity | NONE |
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 Buformin was withdrawn from the market in many countries due to an elevated risk of causing lactic acidosis.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
PubMed
| Title | Date | PubMed |
|---|---|---|
| Treatment of reactive hypoglycemia with buformin. | 1975 Nov |
|
| Effect of a biguanide (buformin) on carnitine palmitoyltransferase activity. | 1977 |
|
| [Lactic acidosis--a possible complication in buformin-treated diabetics (author's transl)]. | 1978 Sep 1 |
|
| Buformin concentrations in a case of fatal lactic acidosis. | 1981 |
|
| The inhibitory action of buformin, a biguanide on gluconeogenesis from alanine and its transport system in rat livers. | 1993 Jan |
|
| Adverse effects of the antimalaria drug, mefloquine: due to primary liver damage with secondary thyroid involvement? | 2002 Mar 25 |
|
| Insulin and longevity: antidiabetic biguanides as geroprotectors. | 2003 |
|
| [Lactic acidosis associated with buformine use]. | 2003 Apr |
|
| Involvement of organic cation transporter 1 in the lactic acidosis caused by metformin. | 2003 Apr |
|
| Plasma BNP levels in the treatment of type 2 diabetes with pioglitazone. | 2003 Aug |
|
| [Lactic acidosis in diabetic patient treated with metformin]. | 2004 Jun |
|
| The combination of metformin and a dipeptidyl peptidase IV inhibitor prevents 5-fluorouracil-induced reduction of small intestine weight. | 2004 Mar 19 |
|
| A validated HPLC method with ultraviolet detection for the determination of buformin in plasma. | 2004 May |
|
| Short-term effect of buformin, a biguanide, on insulin sensitivity, soluble fraction of tumor necrosis factor receptor and serum lipids in overweight patients with type 2 diabetes mellitus. | 2004 Nov |
|
| Buformin-induced lactic acidosis--a symptom of modern healthcare malady. | 2004 Oct |
|
| Diagnostic and therapeutic-restorative procedures for masticatory dysfunctions. | 2005 |
|
| [A new case of lactic acidosis caused by buformin]. | 2005 Feb |
|
| [A case of lactic acidosis caused by buformin in an oldest elderly diabetic patient]. | 2005 Mar |
|
| The medical skills of the Malabar doctors in Tranquebar, India, as recorded by surgeon T L F Folly, 1798. | 2005 Oct |
|
| Buoyancy studies in natural communities of square gas-vacuolate archaea in saltern crystallizer ponds. | 2006 Apr 14 |
|
| Buformin suppresses the expression of glyceraldehyde 3-phosphate dehydrogenase. | 2006 May |
|
| Regulators for blood glucose level affect gene expression of aquaporin 3. | 2006 May |
|
| Determination of antihyperglycemic biguanides in serum and urine using an ion-pair solid-phase extraction technique followed by HPLC-UV on a pentafluorophenylpropyl column and on an octadecyl column. | 2006 Nov |
|
| Methodology for the Randomised Injecting Opioid Treatment Trial (RIOTT): evaluating injectable methadone and injectable heroin treatment versus optimised oral methadone treatment in the UK. | 2006 Sep 27 |
|
| Behavioral genomics of honeybee foraging and nest defense. | 2007 Apr |
|
| Analysis and development of multiprofessional teams in medical rehabilitation. | 2008 Mar 3 |
|
| Processing single-use medical devices for use in surgery - importance, status quo and potential. | 2008 Sep 3 |
|
| Transient Parkinsonism in isolated extrapontine myelinolysis. | 2009 Aug |
|
| General Practitioners' preferences and use of educational media: a German perspective. | 2009 Feb 16 |
|
| Concepts of care for people with dementia. | 2009 Jan 6 |
|
| Regulation of glyceraldehyde 3-phosphate dehydrogenase expression by metformin in HepG2 cells. | 2009 Jul |
|
| Chemical genomics identifies the unfolded protein response as a target for selective cancer cell killing during glucose deprivation. | 2009 May 15 |
|
| Toward 100 Mega-frames per second: design of an ultimate ultra-high-speed image sensor. | 2010 |
|
| Gender differences in metformin effect on aging, life span and spontaneous tumorigenesis in 129/Sv mice. | 2010 Dec |
|
| Metformin for aging and cancer prevention. | 2010 Nov |
|
| Effects of metformin, buformin, and phenformin on the post-initiation stage of chemically induced mammary carcinogenesis in the rat. | 2015 Jun |
|
| Buformin exhibits anti-proliferative and anti-invasive effects in endometrial cancer cells. | 2016 |
Sample Use Guides
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.
| Substance Class |
Chemical
Created
by
admin
on
Edited
Fri Dec 15 15:06:31 GMT 2023
by
admin
on
Fri Dec 15 15:06:31 GMT 2023
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| Record UNII |
D947SXO87P
|
| Record Status |
Validated (UNII)
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| Record Version |
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NCI_THESAURUS |
C98234
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C95329
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1190-53-0
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15537-73-2
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DTXSID50922844
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100000092552
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528218
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113665
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84976
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SUB00892MIG
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m2751
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CHEMBL39736
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239-587-5
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D947SXO87P
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214-723-6
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DBSALT000336
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ACTIVE MOIETY |