NAV

Ethyl loflazepate

Identification

Generic Name
Ethyl loflazepate
DrugBank Accession Number
DB01545
Background

Not Available

Type
Small Molecule
Groups
Experimental, Illicit
Structure
3D
Similar Structures
Weight
Average: 360.767
Monoisotopic: 360.067698236
Chemical Formula
C18H14ClFN2O3
Synonyms
  • Ethyl fluclozepate
  • Ethyl loflazepate
  • Ethylis loflazepas
  • Loflazepate d'ethyle
  • Loflazepato de etilo
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Pharmacology

Indication

Not Available

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Contraindications & Blackbox Warnings
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Pharmacodynamics

Not Available

Mechanism of action
TargetActionsOrganism
AGABA(A) Receptor
positive allosteric modulator
Humans
AGABA(A) Receptor Benzodiazepine Binding Site
ligand
Humans
Absorption

Not Available

Volume of distribution

Not Available

Protein binding

Not Available

Metabolism
Not Available
Route of elimination

Not Available

Half-life

Not Available

Clearance

Not Available

Adverse Effects
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Toxicity

Not Available

Pathways
Not Available
Pharmacogenomic Effects/ADRs Browse all" title="About SNP Mediated Effects/ADRs" id="snp-actions-info" class="drug-info-popup" href="javascript:void(0);">
Not Available

Interactions

Drug Interactions Learn More" title="About Drug Interactions" id="structured-interactions-info" class="drug-info-popup" href="javascript:void(0);">
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
DrugInteraction
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interactions in your software
1,2-BenzodiazepineThe risk or severity of CNS depression can be increased when Ethyl loflazepate is combined with 1,2-Benzodiazepine.
AcetazolamideThe risk or severity of CNS depression can be increased when Acetazolamide is combined with Ethyl loflazepate.
AcetophenazineThe risk or severity of CNS depression can be increased when Acetophenazine is combined with Ethyl loflazepate.
AgomelatineThe risk or severity of CNS depression can be increased when Ethyl loflazepate is combined with Agomelatine.
AlfentanilThe risk or severity of adverse effects can be increased when Alfentanil is combined with Ethyl loflazepate.
Food Interactions
Not Available

Products

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International/Other Brands
Azutolem (Takata Seiyaku) / Bigson (Hyun Dai) / Medetax (Medisa Shinyaku) / Meilax (Meiji) / Ronlax (Shiono Kemikaru) / Sukarnase (Towa Yakuhin) / Victan (Sanofi-Aventis)

Categories

ATC Codes
N05BA18 — Ethyl loflazepate
Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as alpha amino acid esters. These are ester derivatives of alpha amino acids.
Kingdom
Organic compounds
Super Class
Organic acids and derivatives
Class
Carboxylic acids and derivatives
Sub Class
Amino acids, peptides, and analogues
Direct Parent
Alpha amino acid esters
Alternative Parents
1,4-benzodiazepines / Fluorobenzenes / 1,3-dicarbonyl compounds / Aryl chlorides / Aryl fluorides / Secondary carboxylic acid amides / Carboxylic acid esters / Lactams / Ketimines / Propargyl-type 1,3-dipolar organic compounds
show 7 more
Substituents
1,3-dicarbonyl compound / 1,4-benzodiazepine / Alpha-amino acid ester / Aromatic heteropolycyclic compound / Aryl chloride / Aryl fluoride / Aryl halide / Azacycle / Benzenoid / Benzodiazepine
show 24 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
Not Available
Affected organisms
Not Available

Chemical Identifiers

UNII
VJB5FW9W9J
CAS number
29177-84-2
InChI Key
CUCHJCMWNFEYOM-UHFFFAOYSA-N
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)
IUPAC Name
ethyl 7-chloro-5-(2-fluorophenyl)-2-oxo-2,3-dihydro-1H-1,4-benzodiazepine-3-carboxylate
SMILES
CCOC(=O)C1N=C(C2=CC=CC=C2F)C2=C(NC1=O)C=CC(Cl)=C2

References

Synthesis Reference

British Patent 1,538,165.

General References
Not Available
KEGG Drug
D01293
PubChem Compound
3299
PubChem Substance
46507486
ChemSpider
3183
RxNav
24524
ChEBI
31573
ChEMBL
CHEMBL1213460
Wikipedia
Ethyl_loflazepate

Clinical Trials

Clinical Trials Learn More" title="About Clinical Trials" id="clinical-trials-info" class="drug-info-popup" href="javascript:void(0);">
PhaseStatusPurposeConditionsCount

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage Forms
FormRouteStrength
TabletOral2.000 mg
Tablet, film coated
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)196British Patent 1,538,165.
Predicted Properties
PropertyValueSource
Water Solubility0.00525 mg/mLALOGPS
logP3.36ALOGPS
logP3.85Chemaxon
logS-4.8ALOGPS
pKa (Strongest Acidic)9.49Chemaxon
pKa (Strongest Basic)-1.4Chemaxon
Physiological Charge0Chemaxon
Hydrogen Acceptor Count3Chemaxon
Hydrogen Donor Count1Chemaxon
Polar Surface Area67.76 Å2Chemaxon
Rotatable Bond Count4Chemaxon
Refractivity92.41 m3·mol-1Chemaxon
Polarizability35.03 Å3Chemaxon
Number of Rings3Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterYesChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+1.0
Blood Brain Barrier+0.9536
Caco-2 permeable+0.5691
P-glycoprotein substrateSubstrate0.5
P-glycoprotein inhibitor INon-inhibitor0.6872
P-glycoprotein inhibitor IINon-inhibitor0.9383
Renal organic cation transporterNon-inhibitor0.8524
CYP450 2C9 substrateNon-substrate0.7542
CYP450 2D6 substrateNon-substrate0.8622
CYP450 3A4 substrateSubstrate0.5122
CYP450 1A2 substrateInhibitor0.7947
CYP450 2C9 inhibitorNon-inhibitor0.5444
CYP450 2D6 inhibitorNon-inhibitor0.9018
CYP450 2C19 inhibitorInhibitor0.6447
CYP450 3A4 inhibitorNon-inhibitor0.7437
CYP450 inhibitory promiscuityHigh CYP Inhibitory Promiscuity0.5303
Ames testNon AMES toxic0.6532
CarcinogenicityNon-carcinogens0.6
BiodegradationNot ready biodegradable1.0
Rat acute toxicity1.5886 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9977
hERG inhibition (predictor II)Non-inhibitor0.8853
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Mass Spectrum (Electron Ionization)MSsplash10-0670-1941000000-427495e16cf17300345d
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-03di-0009000000-6f95afaccc44eedd43e1
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-03dj-2059000000-314476e46e14c9992739
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-014i-0019000000-027b294c10175c3f43e6
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-014j-1092000000-623ead6f8334a8e3f519
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-022a-0394000000-2a1a788580f629545f96
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-014l-9130000000-cbe1f8a92020c38247be
Predicted 1H NMR Spectrum1D NMRNot Applicable
Predicted 13C NMR Spectrum1D NMRNot Applicable
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-179.02347
predicted
DeepCCS 1.0 (2019)
[M+H]+181.38147
predicted
DeepCCS 1.0 (2019)
[M+Na]+188.24712
predicted
DeepCCS 1.0 (2019)

Targets

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Details1. GABA(A) Receptor (Protein Group)
Kind
Protein group
Organism
Humans
Pharmacological action
Yes
Actions
Positive allosteric modulator
Curator comments
The GABA(A) receptor is pentameric (i.e. comprising 5 subunit proteins) and therefore has a multitude of potential isoforms. The above target is a collection of all possible GABA(A) subunits that may participate in the formation of the pentameric receptor and is not meant to imply direct a drug-protein interaction for each individual subunit.
General Function
Inhibitory extracellular ligand-gated ion channel activity
Specific Function
Component of the heteropentameric receptor for GABA, the major inhibitory neurotransmitter in the vertebrate brain. Functions also as histamine receptor and mediates cellular responses to histamine...
Components:
NameUniProt ID
Gamma-aminobutyric acid receptor subunit alpha-1P14867
Gamma-aminobutyric acid receptor subunit alpha-2P47869
Gamma-aminobutyric acid receptor subunit alpha-3P34903
Gamma-aminobutyric acid receptor subunit alpha-4P48169
Gamma-aminobutyric acid receptor subunit alpha-5P31644
Gamma-aminobutyric acid receptor subunit alpha-6Q16445
Gamma-aminobutyric acid receptor subunit beta-1P18505
Gamma-aminobutyric acid receptor subunit beta-2P47870
Gamma-aminobutyric acid receptor subunit beta-3P28472
Gamma-aminobutyric acid receptor subunit deltaO14764
Gamma-aminobutyric acid receptor subunit epsilonP78334
Gamma-aminobutyric acid receptor subunit gamma-1Q8N1C3
Gamma-aminobutyric acid receptor subunit gamma-2P18507
Gamma-aminobutyric acid receptor subunit gamma-3Q99928
Gamma-aminobutyric acid receptor subunit piO00591
Gamma-aminobutyric acid receptor subunit thetaQ9UN88
References
  1. Sigel E, Steinmann ME: Structure, function, and modulation of GABA(A) receptors. J Biol Chem. 2012 Nov 23;287(48):40224-31. doi: 10.1074/jbc.R112.386664. Epub 2012 Oct 4. [Article]
  2. Zhu S, Noviello CM, Teng J, Walsh RM Jr, Kim JJ, Hibbs RE: Structure of a human synaptic GABAA receptor. Nature. 2018 Jul;559(7712):67-72. doi: 10.1038/s41586-018-0255-3. Epub 2018 Jun 27. [Article]
Details2. GABA(A) Receptor Benzodiazepine Binding Site (Protein Group)
Kind
Protein group
Organism
Humans
Pharmacological action
Yes
Actions
Ligand
Curator comments
Benzodiazepines modulate GABA(A) function by binding at the interface between alpha (α) and gamma (γ) subunits. Of the 6 α-subunits, only 4 (α-1, -2, -3, and -5) participate in the formation of this binding site. The above target is a collection of all α- and γ-subunits that are known to participate in the formation of the benzodiazepine binding site.
General Function
Inhibitory extracellular ligand-gated ion channel activity
Specific Function
Component of the heteropentameric receptor for GABA, the major inhibitory neurotransmitter in the vertebrate brain. Functions also as histamine receptor and mediates cellular responses to histamine...
Components:
NameUniProt ID
Gamma-aminobutyric acid receptor subunit alpha-1P14867
Gamma-aminobutyric acid receptor subunit alpha-2P47869
Gamma-aminobutyric acid receptor subunit alpha-3P34903
Gamma-aminobutyric acid receptor subunit alpha-5P31644
Gamma-aminobutyric acid receptor subunit gamma-1Q8N1C3
Gamma-aminobutyric acid receptor subunit gamma-2P18507
Gamma-aminobutyric acid receptor subunit gamma-3Q99928
References
  1. Sigel E, Steinmann ME: Structure, function, and modulation of GABA(A) receptors. J Biol Chem. 2012 Nov 23;287(48):40224-31. doi: 10.1074/jbc.R112.386664. Epub 2012 Oct 4. [Article]
  2. Zhu S, Noviello CM, Teng J, Walsh RM Jr, Kim JJ, Hibbs RE: Structure of a human synaptic GABAA receptor. Nature. 2018 Jul;559(7712):67-72. doi: 10.1038/s41586-018-0255-3. Epub 2018 Jun 27. [Article]

Drug created at July 31, 2007 13:10 / Updated at March 04, 2021 09:26