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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 of BUFLOMEDIL

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

Molecular Formula C17H25NO4
Molecular Weight 307.3847
Charge 0
Count
MOL RATIO 1 MOL RATIO (average)
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description

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 TargetPharmacologyConditionPotency
60.0 nM [Ki]

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Buflomedil
Primary
Buflomedil

AUC

ValueDoseCo-administeredAnalytePopulation
2.32 mg × h/L
50 mg single, intravenous
BUFLOMEDIL serum
Homo sapiens
4.52 mg × h/L
100 mg single, intravenous
BUFLOMEDIL serum
Homo sapiens
9.26 mg × h/L
200 mg single, intravenous
BUFLOMEDIL serum
Homo sapiens

T1/2

ValueDoseCo-administeredAnalytePopulation
3.29 h
50 mg single, intravenous
BUFLOMEDIL serum
Homo sapiens
3.07 h
100 mg single, intravenous
BUFLOMEDIL serum
Homo sapiens
3.39 h
200 mg single, intravenous
BUFLOMEDIL serum
Homo sapiens

Doses

PubMed

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.
Substance Class Chemical
Record UNII
V7I71DQ432
Record Status Validated (UNII)
Record Version