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Ethyl loflazepate

February 25, 2023

Ethyl loflazepate[1] (marketed under the brand names Meilax, Ronlax and Victan)[2][3][4] is a drug which is a benzodiazepine derivative. It possesses anxiolytic, anticonvulsant, sedative and skeletal muscle relaxant properties.[5] 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.[6] Its elimination half-life is 51–103 hours.[7] Its mechanism of action is similar to other benzodiazepines. Ethyl loflazepate also produces an active metabolite which is stronger than the parent compound.[8] 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.[9] The main metabolites of ethyl loflazepate are descarbethoxyloflazepate, loflazepate and 3-hydroxydescarbethoxyloflazepate.[10] Accumulation of the active metabolites of ethyl loflazepate are not affected by those with kidney failure or impairment.[11] 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.[12] 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.[13] High doses of the antidepressant fluvoxamine may potentiate the adverse effects of ethyl loflazepate.[14]

Ethyl loflazepate
Clinical data
Trade namesVictan, Meilax, Ronlax
AHFS/Drugs.comInternational Drug Names
Pregnancy
category
  • ?
Routes of
administration		Oral
ATC code
Legal status
Legal status
Pharmacokinetic data
Bioavailability?
MetabolismHepatic
Elimination half-life51-103 h
ExcretionRenal
Identifiers
  • 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
ECHA InfoCard100.044.976
Chemical and physical data
FormulaC18H14ClFN2O3
Molar mass360.7 g·mol−1
3D model (JSmol)
  • Interactive image
  • FC1=CC=CC=C1C2=NC(C(OCC)=O)C(NC3=C2C=C(C=C3)Cl)=O
  • 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:[15][16]

See also

References

  1. ^ DE Patent 2012190
  2. ^ Ba, BB; Iliadis, A; Durand, A; Berger, Y; Cano, JP (Oct 1988). "New approach in bioavailability study of two formulations of ethyl loflazepate". Arzneimittel-Forschung. 38 (10): 1486–9. ISSN 0004-4172. PMID 2904268.
  3. ^ Ba, BB; Iliadis, A; Cano, JP (1989). "Pharmacokinetic modeling of ethyl loflazepate (Victan) and its main active metabolites". Annals of Biomedical Engineering. 17 (6): 633–46. doi:10.1007/BF02367467. ISSN 0090-6964. PMID 2574017. S2CID 31310535.
  4. ^ . non-benzodiazepines.org.uk. Archived from the original on 2008-12-08. Retrieved 2009-04-05.
  5. ^ Ueki, S; Watanabe, S; Yamamoto, T; Shibata, S; Shibata, K; Ohta, H; Ikeda, K; Kiyota, Y; Sato, Y (Nov 1983). "Behavioral effects of ethyl loflazepate and its metabolites". Nippon Yakurigaku Zasshi. Folia Pharmacologica Japonica. 82 (5): 395–409. doi:10.1254/fpj.82.395. ISSN 0015-5691. PMID 6142848.
  6. ^ Mazue, G; Berthe, J; Newmann, AJ; Brunaud, M (Oct 1981). "A toxicologic evaluation of ethyl fluclozepate (CM 6912)". International Journal of Clinical Pharmacology, Therapy, and Toxicology. 19 (10): 453–72. ISSN 0174-4879. PMID 6116677.
  7. ^ Cautreels, W; Jeanniot, JP (Nov 1980). "Quantitative analysis of CM 6912 (ethyl loflazepate) and its metabolites in plasma and urine by chemical ionization gas chromatography mass spectrometry. Application to pharmacokinetic studies in man". Biomedical Mass Spectrometry. 7 (11–12): 565–71. doi:10.1002/bms.1200071124. ISSN 0306-042X. PMID 6112027.
  8. ^ Sakai, Y; Namima, M (Apr 1985). "Inhibitory effect on 3H-diazepam binding and potentiating action on GABA of ethyl loflazepate, a new minor tranquilizer". Japanese Journal of Pharmacology. 37 (4): 373–9. doi:10.1254/jjp.37.373. ISSN 0021-5198. PMID 2861304.
  9. ^ Chambon, JP; Perio, A; Demarne, H; Hallot, A; Dantzer, R; Roncucci, R; Bizière, K (1985). "Ethyl loflazepate: a prodrug from the benzodiazepine series designed to dissociate anxiolytic and sedative activities". Arzneimittel-Forschung. 35 (10): 1573–7. ISSN 0004-4172. PMID 2866771.
  10. ^ Davi, H; Guyonnet, J; Sales, Y; Cautreels, W (1985). "Metabolism of ethyl loflazepate in the rat, the dog, the baboon and in man". Arzneimittel-Forschung. 35 (7): 1061–5. ISSN 0004-4172. PMID 2864933.
  11. ^ Ba, BB; Iliadis, A; Durand, A; Berger, Y; Necciari, J; Cano, JP (1989). "Effect of renal failure on the pharmacokinetics of ethyl loflazepate (Victan) in man". Fundamental & Clinical Pharmacology. 3 (1): 11–7. doi:10.1111/j.1472-8206.1989.tb00025.x. ISSN 0767-3981. PMID 2714728. S2CID 2850707.
  12. ^ Pulce C, Mollon P, Pham E, Frantz P, Descotes J (April 1992). "Acute poisonings with ethyle loflazepate, flunitrazepam, prazepam and triazolam in children". Vet Hum Toxicol. 34 (2): 141–3. ISSN 0145-6296. PMID 1354907.
  13. ^ Kamijo, Y; Hayashi, I; Nishikawa, T; Yoshimura, K; Soma, K (Mar 2005). "Pharmacokinetics of the active metabolites of ethyl loflazepate in elderly patients who died of asphyxia associated with benzodiazepine-related toxicity". Journal of Analytical Toxicology. 29 (2): 140–4. doi:10.1093/jat/29.2.140. ISSN 0146-4760. PMID 15902983.
  14. ^ Imanishi, T; Onozawa, K; Hayashi, A; Baba, J (Dec 2001). "Effects of fluvoxamine on both the desired anxiolytic effect and the adverse motor incoordination and amnesia induced by benzodiazepines". Nippon Yakurigaku Zasshi. Folia Pharmacologica Japonica. 118 (6): 403–10. doi:10.1254/fpj.118.403. ISSN 0015-5691. PMID 11778459.
  15. ^ . saludzac.gob.mx/. Archived from the original on 2009-05-26. Retrieved 2009-12-25.
  16. ^ "VICTAN". Farmacia Guerra. Retrieved 2009-12-25.

External links

  • (in Japanese) Meilax Fine Granules

February 25, 2023
ethyl, loflazepate, marketed, under, brand, names, meilax, ronlax, victan, drug, which, benzodiazepine, derivative, possesses, anxiolytic, anticonvulsant, sedative, skeletal, muscle, relaxant, properties, animal, studies, found, have, toxicity, although, rats,. Ethyl loflazepate 1 marketed under the brand names Meilax Ronlax and Victan 2 3 4 is a drug which is a benzodiazepine derivative It possesses anxiolytic anticonvulsant sedative and skeletal muscle relaxant properties 5 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 6 Its elimination half life is 51 103 hours 7 Its mechanism of action is similar to other benzodiazepines Ethyl loflazepate also produces an active metabolite which is stronger than the parent compound 8 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 9 The main metabolites of ethyl loflazepate are descarbethoxyloflazepate loflazepate and 3 hydroxydescarbethoxyloflazepate 10 Accumulation of the active metabolites of ethyl loflazepate are not affected by those with kidney failure or impairment 11 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 12 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 13 High doses of the antidepressant fluvoxamine may potentiate the adverse effects of ethyl loflazepate 14 Ethyl loflazepateClinical dataTrade namesVictan Meilax RonlaxAHFS Drugs comInternational Drug NamesPregnancycategory Routes ofadministrationOralATC codeN05BA18 WHO Legal statusLegal statusCA Schedule IV DE Anlage III Special prescription form required US Schedule IVPharmacokinetic dataBioavailability MetabolismHepaticElimination half life51 103 hExcretionRenalIdentifiersIUPAC name ethyl 7 chloro 5 2 fluorophenyl 2 oxo 1 3 dihydro 1 4 benzodiazepine 3 carboxylateCAS Number29177 84 2 NPubChem CID3299DrugBankDB01545 YChemSpider3183 YUNIIVJB5FW9W9JKEGGD01293 NChEMBLChEMBL1213460 YECHA InfoCard100 044 976Chemical and physical dataFormulaC 18H 14Cl F N 2O 3Molar mass360 7 g mol 13D model JSmol Interactive imageSMILES FC1 CC CC C1C2 NC C OCC O C NC3 C2C C C C3 Cl OInChI 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 YKey CUCHJCMWNFEYOM UHFFFAOYSA N Y N Y what is this verify Ethyl loflazeplate is commercialized in Mexico under the trade name Victan It is officially approved for the following conditions 15 16 Anxiety Post trauma anxiety Anxiety associated with severe neuropathic pain Generalized anxiety disorder GAD Obsessive compulsive disorder Panic attack Delirium tremensSee also EditBenzodiazepineReferences Edit DE Patent 2012190 Ba BB Iliadis A Durand A Berger Y Cano JP Oct 1988 New approach in bioavailability study of two formulations of ethyl loflazepate Arzneimittel Forschung 38 10 1486 9 ISSN 0004 4172 PMID 2904268 Ba BB Iliadis A Cano JP 1989 Pharmacokinetic modeling of ethyl loflazepate Victan and its main active metabolites Annals of Biomedical Engineering 17 6 633 46 doi 10 1007 BF02367467 ISSN 0090 6964 PMID 2574017 S2CID 31310535 Benzodiazepine Names non benzodiazepines org uk Archived from the original on 2008 12 08 Retrieved 2009 04 05 Ueki S Watanabe S Yamamoto T Shibata S Shibata K Ohta H Ikeda K Kiyota Y Sato Y Nov 1983 Behavioral effects of ethyl loflazepate and its metabolites Nippon Yakurigaku Zasshi Folia Pharmacologica Japonica 82 5 395 409 doi 10 1254 fpj 82 395 ISSN 0015 5691 PMID 6142848 Mazue G Berthe J Newmann AJ Brunaud M Oct 1981 A toxicologic evaluation of ethyl fluclozepate CM 6912 International Journal of Clinical Pharmacology Therapy and Toxicology 19 10 453 72 ISSN 0174 4879 PMID 6116677 Cautreels W Jeanniot JP Nov 1980 Quantitative analysis of CM 6912 ethyl loflazepate and its metabolites in plasma and urine by chemical ionization gas chromatography mass spectrometry Application to pharmacokinetic studies in man Biomedical Mass Spectrometry 7 11 12 565 71 doi 10 1002 bms 1200071124 ISSN 0306 042X PMID 6112027 Sakai Y Namima M Apr 1985 Inhibitory effect on 3H diazepam binding and potentiating action on GABA of ethyl loflazepate a new minor tranquilizer Japanese Journal of Pharmacology 37 4 373 9 doi 10 1254 jjp 37 373 ISSN 0021 5198 PMID 2861304 Chambon JP Perio A Demarne H Hallot A Dantzer R Roncucci R Biziere K 1985 Ethyl loflazepate a prodrug from the benzodiazepine series designed to dissociate anxiolytic and sedative activities Arzneimittel Forschung 35 10 1573 7 ISSN 0004 4172 PMID 2866771 Davi H Guyonnet J Sales Y Cautreels W 1985 Metabolism of ethyl loflazepate in the rat the dog the baboon and in man Arzneimittel Forschung 35 7 1061 5 ISSN 0004 4172 PMID 2864933 Ba BB Iliadis A Durand A Berger Y Necciari J Cano JP 1989 Effect of renal failure on the pharmacokinetics of ethyl loflazepate Victan in man Fundamental amp Clinical Pharmacology 3 1 11 7 doi 10 1111 j 1472 8206 1989 tb00025 x ISSN 0767 3981 PMID 2714728 S2CID 2850707 Pulce C Mollon P Pham E Frantz P Descotes J April 1992 Acute poisonings with ethyle loflazepate flunitrazepam prazepam and triazolam in children Vet Hum Toxicol 34 2 141 3 ISSN 0145 6296 PMID 1354907 Kamijo Y Hayashi I Nishikawa T Yoshimura K Soma K Mar 2005 Pharmacokinetics of the active metabolites of ethyl loflazepate in elderly patients who died of asphyxia associated with benzodiazepine related toxicity Journal of Analytical Toxicology 29 2 140 4 doi 10 1093 jat 29 2 140 ISSN 0146 4760 PMID 15902983 Imanishi T Onozawa K Hayashi A Baba J Dec 2001 Effects of fluvoxamine on both the desired anxiolytic effect and the adverse motor incoordination and amnesia induced by benzodiazepines Nippon Yakurigaku Zasshi Folia Pharmacologica Japonica 118 6 403 10 doi 10 1254 fpj 118 403 ISSN 0015 5691 PMID 11778459 Victan saludzac gob mx Archived from the original on 2009 05 26 Retrieved 2009 12 25 VICTAN Farmacia Guerra Retrieved 2009 12 25 External links Edit in Japanese Meilax Fine Granules Retrieved from https en wikipedia org w index php title Ethyl loflazepate amp oldid 1084239061, wikipedia, wiki, book, books, library,

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