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)
| 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 |
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 Buformin was withdrawn from the market in many countries due to an elevated risk of causing lactic acidosis.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 |
|---|---|---|
| [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 |
|
| Insufficient depression treatment in outpatient settings. | 2004 Feb 26 |
|
| Diagnostic and therapeutic-restorative procedures for masticatory dysfunctions. | 2005 |
|
| [Practice of antidiabetic therapy in Hungary]. | 2005 |
|
| Cognitive training for dementia. | 2005 Dec 21 |
|
| Screening on urogenital Chlamydia trachomatis. | 2005 Dec 29 |
|
| Antidiabetic drug utilization in hungary. | 2005 Jun |
|
| Patterns of prescription of hypoglycaemic drugs in Gran Canaria (Canary islands, Spain) and estimation of the prevalence of diabetes mellitus. | 2005 Nov |
|
| 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 |
|
| Hypoglycemic effects of the wood of Taxus yunnanensis on streptozotocin-induced diabetic rats and its active components. | 2006 Jan |
|
| [Traditional contraindications to the use of metformin -- more harmful than beneficial?]. | 2006 Jan 20 |
|
| 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 |
|
| Reproducibility of goniometric measurement of the knee in the in-hospital phase following total knee arthroplasty. | 2007 Aug 17 |
|
| Prediction of the metabolic interaction of nateglinide with other drugs based on in vitro studies. | 2007 Dec |
|
| Free-living flatworms under the knife: past and present. | 2007 Feb |
|
| Artist versus anatomist, models against dissection: Paul Zeiller of Munich and the revolution of 1848. | 2007 Jul |
|
| "Maecenates voco!": laudation for Hans-Joachim Molitor. | 2007 Sep 13 |
|
| Forty years of control of healthcare-associated infections in Scandinavia. | 2007 Sep 13 |
|
| Apitherapy: usage and experience in german beekeepers. | 2008 Dec |
|
| Biguanide-induced mitochondrial dysfunction yields increased lactate production and cytotoxicity of aerobically-poised HepG2 cells and human hepatocytes in vitro. | 2008 Dec 1 |
|
| A high-throughput screening system for barley/powdery mildew interactions based on automated analysis of light micrographs. | 2008 Jan 23 |
|
| Analysis and development of multiprofessional teams in medical rehabilitation. | 2008 Mar 3 |
|
| Framework conditions and requirements to ensure the technical functional safety of reprocessed medical devices. | 2008 Sep 3 |
|
| Processing single-use medical devices for use in surgery - importance, status quo and potential. | 2008 Sep 3 |
|
| A rare case of diabetic mastopathy in a Japanese man with type 2 diabetes mellitus. | 2009 |
|
| Transient Parkinsonism in isolated extrapontine myelinolysis. | 2009 Aug |
|
| Infection control consequences - early Staphylococcal Scalded Skin Syndrome or Kawasaki Syndrome? | 2009 Dec 16 |
|
| 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 |
|
| A cardiologic approach to non-insulin antidiabetic pharmacotherapy in patients with heart disease. | 2009 Jul 20 |
|
| Chemical genomics identifies the unfolded protein response as a target for selective cancer cell killing during glucose deprivation. | 2009 May 15 |
|
| Arthroplasty register for Germany. | 2009 Oct 2 |
|
| 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 |
|
| An economic appraisal of the Australian Medical Sheepskin for the prevention of sacral pressure ulcers from a nursing home perspective. | 2010 Aug 5 |
|
| Insulin tolerance test predicts the effectiveness of insulin sensitizers in japanese type 2 diabetic patients. | 2010 Dec |
|
| Gender differences in metformin effect on aging, life span and spontaneous tumorigenesis in 129/Sv mice. | 2010 Dec |
|
| Performance of three LED-based fluorescence microscopy systems for detection of tuberculosis in Uganda. | 2010 Dec 28 |
|
| Clostridium difficile is not associated with outbreaks of viral gastroenteritis in the elderly in the Netherlands. | 2010 Jun |
|
| Metformin for aging and cancer prevention. | 2010 Nov |
|
| A three-phase in-vitro system for studying Pseudomonas aeruginosa adhesion and biofilm formation upon hydrogel contact lenses. | 2010 Nov 9 |
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 15:13:52 GMT 2023
by
admin
on
Fri Dec 15 15:13:52 GMT 2023
|
| Record UNII |
W2115E9C7B
|
| Record Status |
Validated (UNII)
|
| Record Version |
|
-
Download
| Name | Type | Language | ||
|---|---|---|---|---|
|
Official Name | English | ||
|
Systematic Name | English | ||
|
Code | English | ||
|
Code | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Systematic Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Code | English |
| Classification Tree | Code System | Code | ||
|---|---|---|---|---|
|
WHO-ATC |
A10BA03
Created by
admin on Fri Dec 15 15:13:52 GMT 2023 , Edited by admin on Fri Dec 15 15:13:52 GMT 2023
|
||
|
WHO-VATC |
QA10BA03
Created by
admin on Fri Dec 15 15:13:52 GMT 2023 , Edited by admin on Fri Dec 15 15:13:52 GMT 2023
|
||
|
NCI_THESAURUS |
C98234
Created by
admin on Fri Dec 15 15:13:52 GMT 2023 , Edited by admin on Fri Dec 15 15:13:52 GMT 2023
|
| Code System | Code | Type | Description | ||
|---|---|---|---|---|---|
|
211-726-4
Created by
admin on Fri Dec 15 15:13:52 GMT 2023 , Edited by admin on Fri Dec 15 15:13:52 GMT 2023
|
PRIMARY | |||
|
C95328
Created by
admin on Fri Dec 15 15:13:52 GMT 2023 , Edited by admin on Fri Dec 15 15:13:52 GMT 2023
|
PRIMARY | |||
|
CHEMBL39736
Created by
admin on Fri Dec 15 15:13:52 GMT 2023 , Edited by admin on Fri Dec 15 15:13:52 GMT 2023
|
PRIMARY | |||
|
100000088440
Created by
admin on Fri Dec 15 15:13:52 GMT 2023 , Edited by admin on Fri Dec 15 15:13:52 GMT 2023
|
PRIMARY | |||
|
SUB05965MIG
Created by
admin on Fri Dec 15 15:13:52 GMT 2023 , Edited by admin on Fri Dec 15 15:13:52 GMT 2023
|
PRIMARY | |||
|
DB04830
Created by
admin on Fri Dec 15 15:13:52 GMT 2023 , Edited by admin on Fri Dec 15 15:13:52 GMT 2023
|
PRIMARY | |||
|
3209
Created by
admin on Fri Dec 15 15:13:52 GMT 2023 , Edited by admin on Fri Dec 15 15:13:52 GMT 2023
|
PRIMARY | |||
|
Buformin
Created by
admin on Fri Dec 15 15:13:52 GMT 2023 , Edited by admin on Fri Dec 15 15:13:52 GMT 2023
|
PRIMARY | |||
|
423
Created by
admin on Fri Dec 15 15:13:52 GMT 2023 , Edited by admin on Fri Dec 15 15:13:52 GMT 2023
|
PRIMARY | |||
|
D002026
Created by
admin on Fri Dec 15 15:13:52 GMT 2023 , Edited by admin on Fri Dec 15 15:13:52 GMT 2023
|
PRIMARY | |||
|
2468
Created by
admin on Fri Dec 15 15:13:52 GMT 2023 , Edited by admin on Fri Dec 15 15:13:52 GMT 2023
|
PRIMARY | |||
|
2004
Created by
admin on Fri Dec 15 15:13:52 GMT 2023 , Edited by admin on Fri Dec 15 15:13:52 GMT 2023
|
PRIMARY | |||
|
DTXSID6046420
Created by
admin on Fri Dec 15 15:13:52 GMT 2023 , Edited by admin on Fri Dec 15 15:13:52 GMT 2023
|
PRIMARY | |||
|
692-13-7
Created by
admin on Fri Dec 15 15:13:52 GMT 2023 , Edited by admin on Fri Dec 15 15:13:52 GMT 2023
|
PRIMARY | |||
|
m2751
Created by
admin on Fri Dec 15 15:13:52 GMT 2023 , Edited by admin on Fri Dec 15 15:13:52 GMT 2023
|
PRIMARY | Merck Index | ||
|
W2115E9C7B
Created by
admin on Fri Dec 15 15:13:52 GMT 2023 , Edited by admin on Fri Dec 15 15:13:52 GMT 2023
|
PRIMARY |
| Related Record | Type | Details | ||
|---|---|---|---|---|
|
|
SALT/SOLVATE -> PARENT |
| Related Record | Type | Details | ||
|---|---|---|---|---|
|
|
ACTIVE MOIETY |
