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

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

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 Buformin was withdrawn from the market in many countries due to an elevated risk of causing lactic acidosis.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 1447

Conditions

Condition	Modality	Highest Phase	Product
Type 2 diabetes mellitus 262 Sources: https://clinicaltrials.gov/ct2/show/NCT01584232	Primary	Withdrawn	Silubin Approved Use Unknown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 1147	Unknown Approved Use Unknown
Endometrial cancer 44 Sources: https://www.ncbi.nlm.nih.gov/pubmed/27398153	Primary	Basic research	Unknown Approved Use Unknown

F_unbound

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: https://pubmed.ncbi.nlm.nih.gov/15450070/	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/15450070/	Disc. AE: Lactic acidosis... AEs leading to discontinuation/dose reduction: Lactic acidosis Sources: https://pubmed.ncbi.nlm.nih.gov/15450070/
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: https://pubmed.ncbi.nlm.nih.gov/7202882/	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/7202882/	Disc. AE: Lactic acidosis... AEs leading to discontinuation/dose reduction: Lactic acidosis (grade 5) Sources: https://pubmed.ncbi.nlm.nih.gov/7202882/
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: https://www.mims.com/malaysia/drug/info/buformin?mtype=generic	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: FED Sources: https://www.mims.com/malaysia/drug/info/buformin?mtype=generic	Disc. AE: Lactic acidosis... AEs leading to discontinuation/dose reduction: Lactic acidosis (grade 5) Sources: https://www.mims.com/malaysia/drug/info/buformin?mtype=generic

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: https://pubmed.ncbi.nlm.nih.gov/15450070/	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/15450070/
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: https://pubmed.ncbi.nlm.nih.gov/7202882/	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/7202882/
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: https://www.mims.com/malaysia/drug/info/buformin?mtype=generic	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: FED Sources: https://www.mims.com/malaysia/drug/info/buformin?mtype=generic

PubMed

Title	Date	PubMed
Performance of three LED-based fluorescence microscopy systems for detection of tuberculosis in Uganda.	2010-12-28	21203398
Insulin tolerance test predicts the effectiveness of insulin sensitizers in japanese type 2 diabetic patients.	2010-12	22127749
Gender differences in metformin effect on aging, life span and spontaneous tumorigenesis in 129/Sv mice.	2010-12	21164223
A three-phase in-vitro system for studying Pseudomonas aeruginosa adhesion and biofilm formation upon hydrogel contact lenses.	2010-11-09	21062489
Metformin for aging and cancer prevention.	2010-11	21084729
An economic appraisal of the Australian Medical Sheepskin for the prevention of sacral pressure ulcers from a nursing home perspective.	2010-08-05	20687915
Clostridium difficile is not associated with outbreaks of viral gastroenteritis in the elderly in the Netherlands.	2010-06	20339889
Toward 100 Mega-frames per second: design of an ultimate ultra-high-speed image sensor.	2010	22315524
Culture and healthcare in medical education: migrants' health and beyond.	2010	21818207
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
Infection control consequences - early Staphylococcal Scalded Skin Syndrome or Kawasaki Syndrome?	2009-12-16	20204087
Arthroplasty register for Germany.	2009-10-02	21289900
Transient Parkinsonism in isolated extrapontine myelinolysis.	2009-08	19444382
A cardiologic approach to non-insulin antidiabetic pharmacotherapy in patients with heart disease.	2009-07-20	19619327
Regulation of glyceraldehyde 3-phosphate dehydrogenase expression by metformin in HepG2 cells.	2009-07	19571378
Chemical genomics identifies the unfolded protein response as a target for selective cancer cell killing during glucose deprivation.	2009-05-15	19435925
General Practitioners' preferences and use of educational media: a German perspective.	2009-02-16	19220905
Concepts of care for people with dementia.	2009-01-06	21289888
A rare case of diabetic mastopathy in a Japanese man with type 2 diabetes mellitus.	2009	19483361
Biguanide-induced mitochondrial dysfunction yields increased lactate production and cytotoxicity of aerobically-poised HepG2 cells and human hepatocytes in vitro.	2008-12-01	18817800
Apitherapy: usage and experience in german beekeepers.	2008-12	18955222
Framework conditions and requirements to ensure the technical functional safety of reprocessed medical devices.	2008-09-03	20204095
Processing single-use medical devices for use in surgery - importance, status quo and potential.	2008-09-03	20204093
Analysis and development of multiprofessional teams in medical rehabilitation.	2008-03-03	19742278
A high-throughput screening system for barley/powdery mildew interactions based on automated analysis of light micrographs.	2008-01-23	18215267
Prediction of the metabolic interaction of nateglinide with other drugs based on in vitro studies.	2007-12	18159128
"Maecenates voco!": laudation for Hans-Joachim Molitor.	2007-09-13	20200688
Forty years of control of healthcare-associated infections in Scandinavia.	2007-09-13	20200670
Reproducibility of goniometric measurement of the knee in the in-hospital phase following total knee arthroplasty.	2007-08-17	17705860
Artist versus anatomist, models against dissection: Paul Zeiller of Munich and the revolution of 1848.	2007-07	17603655
Behavioral genomics of honeybee foraging and nest defense.	2007-04	17171388
Free-living flatworms under the knife: past and present.	2007-02	17146688
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	16799926
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	17002810
Buformin suppresses the expression of glyceraldehyde 3-phosphate dehydrogenase.	2006-05	16651735
Regulators for blood glucose level affect gene expression of aquaporin 3.	2006-05	16651733
Buoyancy studies in natural communities of square gas-vacuolate archaea in saltern crystallizer ponds.	2006-04-14	16613609
[Traditional contraindications to the use of metformin -- more harmful than beneficial?].	2006-01-20	16418951
Hypoglycemic effects of the wood of Taxus yunnanensis on streptozotocin-induced diabetic rats and its active components.	2006-01	16360940
Screening on urogenital Chlamydia trachomatis.	2005-12-29	21289934
Cognitive training for dementia.	2005-12-21	21289931
Patterns of prescription of hypoglycaemic drugs in Gran Canaria (Canary islands, Spain) and estimation of the prevalence of diabetes mellitus.	2005-11	16357789
The medical skills of the Malabar doctors in Tranquebar, India, as recorded by surgeon T L F Folly, 1798.	2005-10	16562332
Antidiabetic drug utilization in hungary.	2005-06	16096899
Diagnostic and therapeutic-restorative procedures for masticatory dysfunctions.	2005	22073067
[Practice of antidiabetic therapy in Hungary].	2005	16318232
Insufficient depression treatment in outpatient settings.	2004-02-26	19675684
Buformin concentrations in a case of fatal lactic acidosis.	1981	7202882
[Lactic acidosis--a possible complication in buformin-treated diabetics (author's transl)].	1978-09-01	713413

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.

Substance Class	Chemical Created by `admin` on `Mon Mar 31 17:51:01 GMT 2025` Edited by `admin` on `Mon Mar 31 17:51:01 GMT 2025`
Record UNII	W2115E9C7B
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

DBV

Preferred Name

English

BUFORMIN

Official Name

English

1-Butylbiguanide

Systematic Name

English

W-37

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