BUFLOMEDIL

Details

Stereochemistry	ACHIRAL
Molecular Formula	C17H25NO4
Molecular Weight	307.3847
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

COC1=CC(OC)=C(C(=O)CCCN2CCCC2)C(OC)=C1

InChI

InChIKey=OWYLAEYXIQKAOL-UHFFFAOYSA-N

InChI=1S/C17H25NO4/c1-20-13-11-15(21-2)17(16(12-13)22-3)14(19)7-6-10-18-8-4-5-9-18/h11-12H,4-10H2,1-3H3

HIDE SMILES / InChI

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/3297620
Curator's Comment: description was created based on several sources, including https://www.drugs.com/international/buflomedil.html | https://www.ncbi.nlm.nih.gov/pubmed/3784966 | https://www.ncbi.nlm.nih.gov/pubmed/26193704 | http://www.medscape.com/viewarticle/753768

Buflomedil (trade name Loftyl) is a vasoactive drug used to treat claudication or the symptoms of peripheral arterial disease. Buﬂomedil has been used for people with diseases of the leg arteries and has shown some beneﬁts for people with a previous stroke. The most common type of stroke is due to narrowing or blockage of an artery in the brain (i.e. ischaemic stroke). Buﬂomedil is a drug that can dilate brain blood vessels, which may have beneﬁt for people with ischaemic stroke. However, it has not been approved to treat stroke in clinical practice. In 2012 the European Medicines Agency has completed a review of the safety and effectiveness of buflomedil-containing medicines, both oral and injectable, due to severe neurological and cardiac side effects seen with buflomedil. The Agency’s Committee for Medicinal Products for Human Use (CHMP) concluded that the benefits of buflomedil do not outweigh its risks, and has recommended that all marketing authorisations for medicines containing buflomedil should be suspended throughout the European Union (EU).

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
3-beta-hydroxysteroid-delta(8),delta(7)-isomerase 7 Target ID: CHEMBL4931 Sources: https://www.ncbi.nlm.nih.gov/pubmed/16033255	Inhibitor 8297		60.0 nM [Ki]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Peripheral arterial disease 22 Sources: https://www.ncbi.nlm.nih.gov/pubmed/3721052	Primary		Approved 8429	Buflomedil Approved Use Unknown
Ischemic stroke 41 Sources: https://www.ncbi.nlm.nih.gov/pubmed/26193704	Primary		Not Provided 504	Buflomedil Approved Use Unknown

PubMed

Title	Date	PubMed
Translocation of drug particles in HPMC matrix gel layer: effect of drug solubility and influence on release rate.	2001 Feb 23	11182208
[Myoclonic coma and severe cardiac insufficiency in a patient with arteritis].	2001 Jun	11433584
[Sudden hearing loss. Clinical case].	2002	12596353
Drug treatment of intermittent claudication.	2004	15257627
Development of pulsatile release tablets with swelling and rupturable layers.	2004 Mar 5	14980764
Protective effect of buflomedil in a rat model of moderate cerebral ischemia.	2005	16149710
Sensitive and rapid LC-ESI-MS method for the determination of trimetazidine in human plasma.	2007 Jun 28	17349764
Simultaneous FTIR spectroscopic imaging and visible photography to monitor tablet dissolution and drug release.	2008 Apr	17612794
Buflomedil in peripheral arterial disease: trials and tribulations.	2008 Feb 12	18268159
Oral buflomedil in the prevention of cardiovascular events in patients with peripheral arterial obstructive disease: a randomized, placebo-controlled, 4-year study.	2008 Feb 12	18212283
Buflomedil for intermittent claudication.	2008 Jan 23	18253982
Bias in benefit-risk appraisal in older products: the case of buflomedil for intermittent claudication.	2009	19388720
Profiling of a prescription drug library for potential renal drug-drug interactions mediated by the organic cation transporter 2.	2011 Jul 14	21599003

Patents

Sample Use Guides

In Vivo Use Guide

600 mg/day

Route of Administration: Oral

In Vitro Use Guide

The effect of buflomedil (Fonzylane; Laboratoire Lafon, Maisons-Alfort, France) on platelet function, a drug used clinically for the treatment of peripheral vascular diseases, was investigated in vitro. The compound significantly inhibits epinephrine-induced aggregation at the micromolar level. At higher doses (approximately 1 mM), a weak inhibition of ADP- and collagen-induced aggregation was observed; at these concentrations, buflomedil inhibits granular secretion and the interaction of fibrinogen with its receptor on platelet. Further investigations indicate that the drug affects calcium uptake at the membrane level and inhibits the binding of [3H]-yohimbine to the same extent as observed with phentolamine. The IC50 determined from competition binding assays was 1 +/- 0.5 microM.

Name

Type

Language

BUFLOMEDIL

Official Name

English

Buflomedil [WHO-DD]

Common Name

English

BUFLOMEDIL [MI]

Common Name

English

buflomedil [INN]

Common Name

English

2',4',6'-TRIMETHOXY-4-(1-PYRROLIDINYL)BUTYROPHENONE

Systematic Name

English

Classification Tree Code System Code

WHO-ATC

C04AX20