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Ethyl Loflazepate

HCID 3299
NotesReactions
Basic informationOverviewNames & identifiersPropertiesSafety & regulationChemistry & industryRelated reactionsCompound notes
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Basic information

CAS
29177-84-2
Standard SMILES
CCOC(=O)C1N=C(c2ccccc2F)c2cc(Cl)ccc2NC1=O
InChIKey
CUCHJCMWNFEYOM-UHFFFAOYSA-N
Molecular formula
C18H14ClFN2O3
Average molar mass
360.8 g/mol
Monoisotopic mass
360.0676982

Overview

Ethyl loflazepate is an organic molecular entity.

Names & identifiers

Preferred name
Ethyl Loflazepate
IUPAC
ethyl 7-chloro-5-(2-fluorophenyl)-2-oxo-1,3-dihydro-1,4-benzodiazepine-3-carboxylate
English name
Ethyl loflazepate
Molecular formula
C18H14ClFN2O3
Molecular weight
360.77

Names & synonyms

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
Show more names
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

Database identifiers

CAS
29177-84-2
PubChem CID
3299
DTXSID
DTXSID60865475

Properties

Computed structural properties

XLogP
2.9
Topological polar surface area
67.8 Ų
Hydrogen bond donors
1
Hydrogen bond acceptors
5
Rotatable bonds
4
Heavy atoms
25
Formal charge
0
Complexity
556

Experimental & physicochemical properties

Drugs · 3 items

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

Physicochemical properties

Melting point
193 · 193-194°
Boiling point
507.7 · 507.7±50.0 °C(Predicted)
Density
1.3609 · 1.3609 (estimate)
solubility
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
form
A crystalline solid
pka
10.56 · 10.56±0.70(Predicted)
FDA UNII
5 FW9W9J · VJB5FW9W9J
ATC code
5 BA18 · N05BA18
Symbol(GHS)
7 · GHS07

Safety & regulation

Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.

GHS classification

GHS Classification · 4 items

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.

Hazard information

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

Toxicology

Treatment · 1 item

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.

Chemistry & industry

Pharmacology

ATC Code · 2 items

N - Nervous system

QN - Nervous system

Metabolism/Metabolites · 1 item

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 item

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.

Uses & manufacturing

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

UsesA 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.

Upstream & downstream products

Upstream raw materials

Related reactions

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Compound notes

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On this pageBasic informationOverviewNames & identifiersPropertiesSafety & regulationChemistry & industryRelated reactionsCompound notes
ChEMBL
CHEMBL1213460
ChEBI
CHEBI:31573
UNII
VJB5FW9W9J
EC Number
249-489-4
Nikkaji
J21.650J
Signal word
Warning
Hazard statements
336 · H336
Precautionary statements
261 · P261-P271-P304+P340-P312-P403+P233-P405-P501
Toxicity Summary · 1 item

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 item

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 items

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

Safety data

Signal word
Warning
Symbol(GHS)
GHS07
Hazard statements
H336
Precautionary statements
P261-P271-P304+P340-P312-P403+P233-P405-P501
2-Amino-5-chloro-2'-fluorobenzophenone

Additional notes

DefinitionChEBI: Ethyl loflazepate is an organic molecular entity.