BUFORMIN HYDROCHLORIDE

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

Structure Search

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

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

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

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 Buformin was withdrawn from the market in many countries due to an elevated risk of causing lactic acidosis.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 1430

Conditions

Condition	Modality	Highest Phase	Product
Type 2 diabetes mellitus 259 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 1132	Unknown Approved Use Unknown
Endometrial cancer 43 Sources: https://www.ncbi.nlm.nih.gov/pubmed/27398153	Primary	Basic research	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
Treatment of reactive hypoglycemia with buformin.	1975 Nov	1190104
Effect of a biguanide (buformin) on carnitine palmitoyltransferase activity.	1977	602670
[Lactic acidosis--a possible complication in buformin-treated diabetics (author's transl)].	1978 Sep 1	713413
The inhibitory action of buformin, a biguanide on gluconeogenesis from alanine and its transport system in rat livers.	1993 Jan	8472619
Adverse effects of the antimalaria drug, mefloquine: due to primary liver damage with secondary thyroid involvement?	2002 Mar 25	11914150
[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	14570054
[Lactic acidosis associated with buformine use].	2003 Apr	12681211
Involvement of organic cation transporter 1 in the lactic acidosis caused by metformin.	2003 Apr	12644585
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	15533580
Buformin-induced lactic acidosis--a symptom of modern healthcare malady.	2004 Oct	15450070
Metformin transport by renal basolateral organic cation transporter hOCT2.	2005 Feb	15783073
Antidiabetic drug utilization in hungary.	2005 Jun	16096899
Buoyancy studies in natural communities of square gas-vacuolate archaea in saltern crystallizer ponds.	2006 Apr 14	16613609
[Traditional contraindications to the use of metformin -- more harmful than beneficial?].	2006 Jan 20	16418951
Regulators for blood glucose level affect gene expression of aquaporin 3.	2006 May	16651733
Forty years of control of healthcare-associated infections in Scandinavia.	2007 Sep 13	20200670
Biguanide-induced mitochondrial dysfunction yields increased lactate production and cytotoxicity of aerobically-poised HepG2 cells and human hepatocytes in vitro.	2008 Dec 1	18817800
Analysis and development of multiprofessional teams in medical rehabilitation.	2008 Mar 3	19742278
A rare case of diabetic mastopathy in a Japanese man with type 2 diabetes mellitus.	2009	19483361
Transient Parkinsonism in isolated extrapontine myelinolysis.	2009 Aug	19444382
Regulation of glyceraldehyde 3-phosphate dehydrogenase expression by metformin in HepG2 cells.	2009 Jul	19571378
Arthroplasty register for Germany.	2009 Oct 2	21289900
[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
An economic appraisal of the Australian Medical Sheepskin for the prevention of sacral pressure ulcers from a nursing home perspective.	2010 Aug 5	20687915
Gender differences in metformin effect on aging, life span and spontaneous tumorigenesis in 129/Sv mice.	2010 Dec	21164223
Performance of three LED-based fluorescence microscopy systems for detection of tuberculosis in Uganda.	2010 Dec 28	21203398
Metformin for aging and cancer prevention.	2010 Nov	21084729
Buformin exhibits anti-proliferative and anti-invasive effects in endometrial cancer cells.	2016	27398153

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 `Fri Dec 15 15:06:31 GMT 2023` Edited by `admin` on `Fri Dec 15 15:06:31 GMT 2023`
Record UNII	D947SXO87P
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

BUFORMIN HYDROCHLORIDE

Common Name

English

IMIDODICARBONIMIDIC DIAMIDE, N-BUTYL-, HYDROCHLORIDE

Systematic Name

English

NSC-528218

Code

English

1-BUTYLBIGUANIDE HYDROCHLORIDE

Systematic Name

English

BUFORMIN HYDROCHLORIDE [MI]

Common Name

English

Buformin hydrochloride [WHO-DD]

Common Name

English

BUFORMIN HCL

Common Name

English

BUFORMIN HYDROCHLORIDE [JAN]

Common Name

English

NSC-113665

Code

English

Classification Tree Code System Code

NCI_THESAURUS

C98234