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Ethylloflazepat

Ethyl Loflazepate

HCID 3299
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Grundinformationen

CAS
29177-84-2
Standard-SMILES
CCOC(=O)C1N=C(c2ccccc2F)c2cc(Cl)ccc2NC1=O
InChIKey
CUCHJCMWNFEYOM-UHFFFAOYSA-N
Summenformel
C18H14ClFN2O3
Durchschnittliche Molmasse
360,8 g/mol
Monoisotopische Masse
360,0676982

Überblick

Ethyl loflazepate is an organic molecular entity.

Namen und Bezeichner

Bevorzugter Name
Ethyl Loflazepate
IUPAC
ethyl 7-chloro-5-(2-fluorophenyl)-2-oxo-1,3-dihydro-1,4-benzodiazepine-3-carboxylate
Lokaler Name
Ethylloflazepat
Englischer Name
Ethyl loflazepate
Summenformel
C18H14ClFN2O3
Molmasse
360.77

Namen und Synonyme

ethyl loflazepateVictanMeilaxEthyl fluclozepate29177-84-2Loflazepate d'ethyleLoflazepato de etiloEthylis loflazepasVJB5FW9W9JDTXSID60865475Ethyl 7-chloro-5-(o-fluorophenyl)-2,3-dihydro-2-oxo-1H-1,4-benzodiazepine-3-carboxylate1H-1,4-Benzodiazepine-3-carboxylic acid, 7-chloro-5-(2-fluorophenyl)-2,3-dihydro-2-oxo-, ethyl ester
Weitere Namen anzeigen
cm6912arboxylateEthyl LoazepateethylfluclozepateEthyl lofrazepate
Ethyl 7-chloro-5-(2-fluorophenyl)-2-oxo-2,3-dihydro-1H-1,4-benzodiazepine-3-carboxylateethyl flucozepateRefChem:596253DTXCID40813878N05BA18249-489-4CM 6912Loflazepic acid, ethyl ester

Datenbank-Bezeichner

CAS
29177-84-2
PubChem CID
3299
DTXSID

Eigenschaften

Berechnete Struktureigenschaften

XLogP
2,9
Polarare Oberfläche (TPSA)
67,8 Ų
H-Brücken-Donoren
1
H-Brücken-Akzeptoren
5
Frei drehbare Bindungen
4
Schwere Atome
25
Formalladung
0
Komplexität
556

Experimentelle und physikochemische Eigenschaften

Drugs · 3 Einträge

DEA NFLIS-Drug Category -> Benzodiazepines

DEA Schedule IV Controlled Substance -> Depressants

Pharmaceuticals -> Nervous system -> Anxiolytics

Human DrugsBreast Feeding; Lactation; Milk, Human; Hypnotics and Sedatives; Anti-Anxiety Agents; Benzodiazepines

Physikochemische Eigenschaften

Schmelzpunkt
193 · 193-194°
Siedepunkt
507.7 · 507.7±50.0 °C(Predicted)
Dichte
1.3609 · 1.3609 (estimate)
Löslichkeit
30 mg/ml; · DMF: 30 mg/ml; DMSO: 30 mg/ml; DMSO:PBS (pH 7.2) (1:1): 0.5 mg/ml; Ethanol: 10 mg/ml; Methanol: 1 mg/ml
Aggregatzustand
A crystalline solid
pka
10.56 · 10.56±0.70(Predicted)

Sicherheit und Regulatorisches

Sicherheitsangaben dienen nur zur Orientierung und ersetzen weder das Sicherheitsdatenblatt (SDB) des Lieferanten noch geltende Vorschriften oder eine fachliche Bewertung.

GHS-Klassifizierung

GHS Classification · 4 Einträge

Warning

H336 (100%): May cause drowsiness or dizziness [Warning Specific target organ toxicity, single exposure; Narcotic effects]

P261, P271, P304+P340, P319, P403+P233, P405, and P501 (click each P-code to see the statement)

The GHS information provided by 1 company from 1 notification to the ECHA C&L Inventory.

Gefahrenhinweise

Regulatory InformationDEA schedule IV controlled substance
Hazard Classes and CategoriesSTOT SE 3 (100%)

Toxikologische Informationen

Treatment · 1 Eintrag

General supportive measures should be employed, along with intravenous fluids, and an adequate airway maintained. Hypotension may be combated by the use of norepinephrine or metaraminol. Dialysis is of limited value. Flumazenil (Anexate) is a competitive benzodiazepine receptor antagonist that can be used as an antidote for benzodiazepine overdose. In particular, flumazenil is very effective at reversing the CNS depression associated with benzodiazepines but is less effective at reversing respiratory depression. Its use, however, is controversial as it has numerous contraindications. It is contraindicated in patients who are on long-term benzodiazepines, those who have ingested a substance that lowers the seizure threshold, or in patients who have tachycardia or a history of seizures. As a general rule, medical observation and supportive care are the mainstay of treatment of benzodiazepine overdose. Although benzodiazepines are absorbed by activated charcoal, gastric decontamination with activated charcoal is not beneficial in pure benzodiazepine overdose as the risk of adverse effects often outweigh any potential benefit from the procedure. It is recommended only if benzodiazepines have been taken in combination with other drugs that may benefit from decontamination. Gastric lavage (stomach pumping) or whole bowel irrigation are also not recommended.

Chemie und Industrie

Pharmakologische Informationen

ATC Code · 2 Einträge

N - Nervous system

QN - Nervous system

Metabolism/Metabolites · 1 Eintrag

Ethyl loflazepate also produces an active metabolite which is stronger than the parent compound. 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. 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 renal failure or impairment. (Wikipedia)

MeSH Pharmacological Classification · 1 Eintrag

Agents that alleviate ANXIETY, tension, and ANXIETY DISORDERS, promote sedation, and have a calming effect without affecting clarity of consciousness or neurologic conditions. ADRENERGIC BETA-ANTAGONISTS are commonly used in the symptomatic treatment of anxiety but are not included here.

Verwendung und Herstellung

UsesEthyl loflazepate possesses anxiolytic, anticonvulsant, sedative and skeletal muscle relaxant properties. (Wikipedia)
Anwendungen · 1 Eintrag

VerwendenA new benzodiazepine derivative as a new anti-anxiety drug. Ethyl Loflazepate and its metabolite were compared with those of Diazepam (D416855), Nitrazepam (N490140) and Lorazepam (L469850). The anticonflict effect of Ethyl Loflazepate was slightly more potent than that of Diazepam and much more potent than that of Lorazepam. Controlled substance.

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Auf dieser SeiteGrundinformationenÜberblickNamen und BezeichnerEigenschaftenSicherheit und RegulatorischesChemie und IndustrieZugehörige ReaktionenNotizen zur Verbindung
DTXSID60865475
ChEMBL
CHEMBL1213460
ChEBI
CHEBI:31573
UNII
VJB5FW9W9J
EC Number
249-489-4
Nikkaji
J21.650J
Toxicity Summary · 1 Eintrag

Benzodiazepines bind nonspecifically to benzodiazepine receptors BNZ1, which mediates sleep, and BNZ2, which affects affects muscle relaxation, anticonvulsant activity, motor coordination, and memory. As benzodiazepine receptors are thought to be coupled to gamma-aminobutyric acid-A (GABAA) receptors, this enhances the effects of GABA by increasing GABA affinity for the GABA receptor. Binding of the inhibitory neurotransmitter GABA to the site opens the chloride channel, resulting in a hyperpolarized cell membrane that prevents further excitation of the cell.

Signs and Symptoms · 1 Eintrag

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. (Wikipedia)

Carcinogen ClassificationNo indication of carcinogenicity to humans (not listed by IARC).
Drug Induced Liver Injury · 4 Einträge

Drug-Induced Liver Injury Severity and Toxicity (DILIst)

Ethyl loflazepate

DILI Positive

DOI:10.1016/j.drudis.2019.09.022

Effects During Pregnancy and Lactation◉ Summary of Use during Lactation

Sicherheitsdaten

Alarmwort
Warnung
Gefahrenhinweise
Code Gefahrenhinweise Gefahrenklasse Abteilung Alarmwort Symbol P-Code H336
2-Amino-5-chlor-2'-fluorbenzophenon