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

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 Buformin was withdrawn from the market in many countries due to an elevated risk of causing lactic acidosis.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Type 2 diabetes mellitus 259 Sources: https://clinicaltrials.gov/ct2/show/NCT01584232	Primary	Withdrawn	Silubin Approved Use Unknown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
Buformin concentrations in a case of fatal lactic acidosis.	1981	7202882
Acrylic microspheres for oral controlled release of the biguanide buformin.	2001 May 7	11337146
A new method for determination of buformin in plasma and urine by ion-paired reversed-phase HPLC with ultraviolet detection.	2002 Oct	12378556
[Lactic acidosis associated with buformine use].	2003 Apr	12681211
Plasma BNP levels in the treatment of type 2 diabetes with pioglitazone.	2003 Aug	12915698
Buformin-induced lactic acidosis--a symptom of modern healthcare malady.	2004 Oct	15450070
The medical skills of the Malabar doctors in Tranquebar, India, as recorded by surgeon T L F Folly, 1798.	2005 Oct	16562332
Reproducibility of goniometric measurement of the knee in the in-hospital phase following total knee arthroplasty.	2007 Aug 17	17705860
Prediction of the metabolic interaction of nateglinide with other drugs based on in vitro studies.	2007 Dec	18159128
Artist versus anatomist, models against dissection: Paul Zeiller of Munich and the revolution of 1848.	2007 Jul	17603655
Forty years of control of healthcare-associated infections in Scandinavia.	2007 Sep 13	20200670
Apitherapy: usage and experience in german beekeepers.	2008 Dec	18955222
A high-throughput screening system for barley/powdery mildew interactions based on automated analysis of light micrographs.	2008 Jan 23	18215267
Framework conditions and requirements to ensure the technical functional safety of reprocessed medical devices.	2008 Sep 3	20204095
A rare case of diabetic mastopathy in a Japanese man with type 2 diabetes mellitus.	2009	19483361
Concepts of care for people with dementia.	2009 Jan 6	21289888
Gender differences in metformin effect on aging, life span and spontaneous tumorigenesis in 129/Sv mice.	2010 Dec	21164223
Effects of metformin, buformin, and phenformin on the post-initiation stage of chemically induced mammary carcinogenesis in the rat.	2015 Jun	25804611
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.

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