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 Buformin was withdrawn from the market in many countries due to an elevated risk of causing lactic acidosis.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
Funbound
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
92.3% EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/5068947/ |
BUFORMIN plasma | Homo sapiens |
Doses
| Dose | Population | Adverse events |
|---|---|---|
100 mg 1 times / day multiple, oral Recommended Dose: 100 mg, 1 times / day Route: oral Route: multiple Dose: 100 mg, 1 times / day Sources: |
unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: F Food Status: UNKNOWN Sources: |
Disc. AE: Lactic acidosis... AEs leading to discontinuation/dose reduction: Lactic acidosis Sources: |
100 mg 2 times / day multiple, oral Recommended Dose: 100 mg, 2 times / day Route: oral Route: multiple Dose: 100 mg, 2 times / day Sources: |
unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: F Food Status: UNKNOWN Sources: |
Disc. AE: Lactic acidosis... AEs leading to discontinuation/dose reduction: Lactic acidosis (grade 5) Sources: |
300 mg 1 times / day multiple, oral Recommended Dose: 300 mg, 1 times / day Route: oral Route: multiple Dose: 300 mg, 1 times / day Sources: |
unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: FED Sources: |
Disc. AE: Lactic acidosis... AEs leading to discontinuation/dose reduction: Lactic acidosis (grade 5) Sources: |
AEs
| AE | Significance | Dose | Population |
|---|---|---|---|
| Lactic acidosis | Disc. AE | 100 mg 1 times / day multiple, oral Recommended Dose: 100 mg, 1 times / day Route: oral Route: multiple Dose: 100 mg, 1 times / day Sources: |
unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: F Food Status: UNKNOWN Sources: |
| Lactic acidosis | grade 5 Disc. AE |
100 mg 2 times / day multiple, oral Recommended Dose: 100 mg, 2 times / day Route: oral Route: multiple Dose: 100 mg, 2 times / day Sources: |
unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: F Food Status: UNKNOWN Sources: |
| Lactic acidosis | grade 5 Disc. AE |
300 mg 1 times / day multiple, oral Recommended Dose: 300 mg, 1 times / day Route: oral Route: multiple Dose: 300 mg, 1 times / day Sources: |
unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: FED Sources: |
PubMed
| Title | Date | PubMed |
|---|---|---|
| Performance of three LED-based fluorescence microscopy systems for detection of tuberculosis in Uganda. | 2010-12-28 |
|
| Insulin tolerance test predicts the effectiveness of insulin sensitizers in japanese type 2 diabetic patients. | 2010-12 |
|
| Gender differences in metformin effect on aging, life span and spontaneous tumorigenesis in 129/Sv mice. | 2010-12 |
|
| A three-phase in-vitro system for studying Pseudomonas aeruginosa adhesion and biofilm formation upon hydrogel contact lenses. | 2010-11-09 |
|
| Metformin for aging and cancer prevention. | 2010-11 |
|
| An economic appraisal of the Australian Medical Sheepskin for the prevention of sacral pressure ulcers from a nursing home perspective. | 2010-08-05 |
|
| Clostridium difficile is not associated with outbreaks of viral gastroenteritis in the elderly in the Netherlands. | 2010-06 |
|
| Toward 100 Mega-frames per second: design of an ultimate ultra-high-speed image sensor. | 2010 |
|
| Culture and healthcare in medical education: migrants' health and beyond. | 2010 |
|
| How should ethnic diversity be represented in medical curricula? A plea for systematic training in cultural competence. | 2010 |
|
| [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 |
|
| Infection control consequences - early Staphylococcal Scalded Skin Syndrome or Kawasaki Syndrome? | 2009-12-16 |
|
| Arthroplasty register for Germany. | 2009-10-02 |
|
| Transient Parkinsonism in isolated extrapontine myelinolysis. | 2009-08 |
|
| A cardiologic approach to non-insulin antidiabetic pharmacotherapy in patients with heart disease. | 2009-07-20 |
|
| Regulation of glyceraldehyde 3-phosphate dehydrogenase expression by metformin in HepG2 cells. | 2009-07 |
|
| Chemical genomics identifies the unfolded protein response as a target for selective cancer cell killing during glucose deprivation. | 2009-05-15 |
|
| General Practitioners' preferences and use of educational media: a German perspective. | 2009-02-16 |
|
| Concepts of care for people with dementia. | 2009-01-06 |
|
| A rare case of diabetic mastopathy in a Japanese man with type 2 diabetes mellitus. | 2009 |
|
| Biguanide-induced mitochondrial dysfunction yields increased lactate production and cytotoxicity of aerobically-poised HepG2 cells and human hepatocytes in vitro. | 2008-12-01 |
|
| Apitherapy: usage and experience in german beekeepers. | 2008-12 |
|
| Framework conditions and requirements to ensure the technical functional safety of reprocessed medical devices. | 2008-09-03 |
|
| Processing single-use medical devices for use in surgery - importance, status quo and potential. | 2008-09-03 |
|
| Analysis and development of multiprofessional teams in medical rehabilitation. | 2008-03-03 |
|
| A high-throughput screening system for barley/powdery mildew interactions based on automated analysis of light micrographs. | 2008-01-23 |
|
| Prediction of the metabolic interaction of nateglinide with other drugs based on in vitro studies. | 2007-12 |
|
| "Maecenates voco!": laudation for Hans-Joachim Molitor. | 2007-09-13 |
|
| Forty years of control of healthcare-associated infections in Scandinavia. | 2007-09-13 |
|
| Reproducibility of goniometric measurement of the knee in the in-hospital phase following total knee arthroplasty. | 2007-08-17 |
|
| Artist versus anatomist, models against dissection: Paul Zeiller of Munich and the revolution of 1848. | 2007-07 |
|
| Behavioral genomics of honeybee foraging and nest defense. | 2007-04 |
|
| Free-living flatworms under the knife: past and present. | 2007-02 |
|
| 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. | 2006-11 |
|
| Methodology for the Randomised Injecting Opioid Treatment Trial (RIOTT): evaluating injectable methadone and injectable heroin treatment versus optimised oral methadone treatment in the UK. | 2006-09-27 |
|
| Buformin suppresses the expression of glyceraldehyde 3-phosphate dehydrogenase. | 2006-05 |
|
| Regulators for blood glucose level affect gene expression of aquaporin 3. | 2006-05 |
|
| Buoyancy studies in natural communities of square gas-vacuolate archaea in saltern crystallizer ponds. | 2006-04-14 |
|
| [Traditional contraindications to the use of metformin -- more harmful than beneficial?]. | 2006-01-20 |
|
| Hypoglycemic effects of the wood of Taxus yunnanensis on streptozotocin-induced diabetic rats and its active components. | 2006-01 |
|
| Screening on urogenital Chlamydia trachomatis. | 2005-12-29 |
|
| Cognitive training for dementia. | 2005-12-21 |
|
| Patterns of prescription of hypoglycaemic drugs in Gran Canaria (Canary islands, Spain) and estimation of the prevalence of diabetes mellitus. | 2005-11 |
|
| The medical skills of the Malabar doctors in Tranquebar, India, as recorded by surgeon T L F Folly, 1798. | 2005-10 |
|
| Antidiabetic drug utilization in hungary. | 2005-06 |
|
| Diagnostic and therapeutic-restorative procedures for masticatory dysfunctions. | 2005 |
|
| [Practice of antidiabetic therapy in Hungary]. | 2005 |
|
| Insufficient depression treatment in outpatient settings. | 2004-02-26 |
|
| Buformin concentrations in a case of fatal lactic acidosis. | 1981 |
|
| [Lactic acidosis--a possible complication in buformin-treated diabetics (author's transl)]. | 1978-09-01 |
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
Mon Mar 31 17:46:43 GMT 2025
by
admin
on
Mon Mar 31 17:46:43 GMT 2025
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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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PARENT -> SALT/SOLVATE |
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ACTIVE MOIETY |