Ethyl loflazepate

Ethyl loflazepate^[2] (marketed under the brand names Meilax, Ronlax and Victan)^[3][4][5] is a drug which is a benzodiazepine derivative. It possesses anxiolytic, anticonvulsant, sedative and skeletal muscle relaxant properties.^[6] In animal studies it was found to have low toxicity, although in rats evidence of pulmonary phospholipidosis occurred with pulmonary foam cells developing with long-term use of very high doses.^[7] Its elimination half-life is 51–103 hours.^[8] Its mechanism of action is similar to other benzodiazepines. Ethyl loflazepate also produces an active metabolite which is stronger than the parent compound.^[9] Ethyl loflazepate was designed to be a prodrug for descarboxyloflazepate, its active metabolite. It is the active metabolite which is responsible for most of the pharmacological effects rather than ethyl loflazepate.^[10] The main metabolites of ethyl loflazepate are descarbethoxyloflazepate, loflazepate and 3-hydroxydescarbethoxyloflazepate.^[11] Accumulation of the active metabolites of ethyl loflazepate are not affected by those with kidney failure or impairment.^[12] The symptoms of an overdose of ethyl loflazepate include sleepiness, agitation and ataxia. Hypotonia may also occur in severe cases. These symptoms occur much more frequently and severely in children.^[13] Death from therapeutic maintenance doses of ethyl loflazepate taken for 2 – 3 weeks has been reported in 3 elderly patients. The cause of death was asphyxia due to benzodiazepine toxicity.^[14] High doses of the antidepressant fluvoxamine may potentiate the adverse effects of ethyl loflazepate.^[15]

Ethyl loflazepate

Clinical data
Trade names	Victan, Meilax, Ronlax
AHFS/Drugs.com	International Drug Names
Pregnancy category	?
Routes of administration	Oral
ATC code	N05BA18 (WHO)
Legal status
Legal status	BR: Class B1 (Psychoactive drugs)[1] CA: Schedule IV DE: Anlage III (Special prescription form required) US: Schedule IV
Pharmacokinetic data
Bioavailability	?
Metabolism	Hepatic
Elimination half-life	51-103 h
Excretion	Renal
Identifiers
IUPAC name ethyl 7-chloro-5-(2-fluorophenyl)-2-oxo-1,3-dihydro-1,4-benzodiazepine-3-carboxylate
CAS Number	29177-84-2 N
PubChem CID	3299
DrugBank	DB01545 Y
ChemSpider	3183 Y
UNII	VJB5FW9W9J
KEGG	D01293 N
ChEMBL	ChEMBL1213460 Y
CompTox Dashboard (EPA)	DTXSID60865475
ECHA InfoCard	100.044.976
Chemical and physical data
Formula	C18H14ClFN2O3
Molar mass	360.77 g·mol−1
3D model (JSmol)	Interactive image
SMILES FC1=CC=CC=C1C2=NC(C(OCC)=O)C(NC3=C2C=C(C=C3)Cl)=O
InChI InChI=1S/C18H14ClFN2O3/c1-2-25-18(24)16-17(23)21-14-8-7-10(19)9-12(14)15(22-16)11-5-3-4-6-13(11)20/h3-9,16H,2H2,1H3,(H,21,23) Y Key:CUCHJCMWNFEYOM-UHFFFAOYSA-N Y
NY (what is this?)  (verify)

Ethyl loflazeplate is commercialized in Mexico, under the trade name Victan. It is officially approved for the following conditions:^[16][17]

• Anxiety
• Post-trauma anxiety
• Anxiety associated with severe neuropathic pain
• Generalized anxiety disorder (GAD)
• Obsessive–compulsive disorder
• Panic attack
• Delirium tremens

See also

• Benzodiazepine