Mexazolam

Identification

Summary

Mexazolam is a benzodiazepine indicated to treat anxiety with or without psychoneurotic conditions.

Generic Name
Mexazolam
DrugBank Accession Number
DB15489
Background

Mexazolam (CS-386) is a benzodiazepine indicated for the treatment of anxiety with or without psychoneurotic conditions.1 Mexazolam's structure is similar to that of other benzodiazepines such as oxazolam and cloxazolam.1 The use of benzodiazepines in the treatment of anxiety is generally a second line measure.1

Type
Small Molecule
Groups
Experimental
Structure
Thumb
Weight
Average: 363.238
Monoisotopic: 362.05888318
Chemical Formula
C18H16Cl2N2O2
Synonyms
  • Mexazolam
  • Mexazolamum
External IDs
  • CS 386
  • CS-386

Pharmacology

Indication

Mexazolam is indicated for the treatment of anxiety with or without psychoneurotic conditions.1

Pharmacology
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Associated Conditions
Contraindications & Blackbox Warnings
Contraindications
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Pharmacodynamics

Not Available

Mechanism of action

Mexazolam is a benzodiazepine that binds to benzodiazepine-type receptors, inhibiting gamma-aminobutyric acid.1

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

The active metabolite chloronordiazepam has a Tmax of 1-2h.1

Volume of distribution

Not Available

Protein binding

Mexazolam is >90% protein bound in plasma.1

Metabolism

Mexazolam is rapidly metabolized to the active metabolites chloronordiazepam and chloroxazepam.1

Route of elimination

Mexazolam is mainly eliminated in the bile and feces, with <10% eliminated as metabolites in the urine.1 >50% of a dose of mexazolam is eliminated as the metabolite chloroxazepam.1

Half-life

Mexazolam follows a 2 compartment model with a first half life of 1.4h and a second half life of 76h.1

Clearance

Not Available

Adverse Effects
Medicalerrors
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Toxicity

Not Available

Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
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.
Not Available
Food Interactions
Not Available

Products

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International/Other Brands
Melex

Categories

Drug Categories
Classification
Not classified
Affected organisms
Not Available

Chemical Identifiers

UNII
S5969B6237
CAS number
31868-18-5
InChI Key
ANUCDXCTICZJRH-UHFFFAOYSA-N
InChI
InChI=1S/C18H16Cl2N2O2/c1-11-10-24-18(13-4-2-3-5-15(13)20)14-8-12(19)6-7-16(14)21-17(23)9-22(11)18/h2-8,11H,9-10H2,1H3,(H,21,23)
IUPAC Name
13-chloro-2-(2-chlorophenyl)-5-methyl-3-oxa-6,9-diazatricyclo[8.4.0.0^{2,6}]tetradeca-1(10),8,11,13-tetraen-8-ol
SMILES
CC1COC2(N1CC(O)=NC1=C2C=C(Cl)C=C1)C1=CC=CC=C1Cl

References

General References
  1. Fernandes H, Moreira R: Mexazolam: clinical efficacy and tolerability in the treatment of anxiety. Neurol Ther. 2014 Mar 29;3(1):1-14. doi: 10.1007/s40120-014-0016-7. eCollection 2014 Jun. [Article]
  2. INVIMA Product Information: SEDOXIL (mexazolam) oral tablet [Link]
ChemSpider
4033
ChEBI
31842
ChEMBL
CHEMBL1743261
Wikipedia
Mexazolam

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage Forms
FormRouteStrength
TabletOral1 mg
Prices
Not Available
Patents
Not Available

Properties

State
Not Available
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.0126 mg/mLALOGPS
logP3.47ALOGPS
logP5.27ChemAxon
logS-4.5ALOGPS
pKa (Strongest Acidic)3.76ChemAxon
pKa (Strongest Basic)1.68ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area45.06 Å2ChemAxon
Rotatable Bond Count1ChemAxon
Refractivity96.22 m3·mol-1ChemAxon
Polarizability35.53 Å3ChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveNoChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET Features
Not Available

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available

Targets

Drugtargets
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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:
References
  1. Fernandes H, Moreira R: Mexazolam: clinical efficacy and tolerability in the treatment of anxiety. Neurol Ther. 2014 Mar 29;3(1):1-14. doi: 10.1007/s40120-014-0016-7. eCollection 2014 Jun. [Article]
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:
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]

Enzymes

Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Vitamin d3 25-hydroxylase activity
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation react...
Gene Name
CYP3A4
Uniprot ID
P08684
Uniprot Name
Cytochrome P450 3A4
Molecular Weight
57342.67 Da
References
  1. Ishigami M, Honda T, Takasaki W, Ikeda T, Komai T, Ito K, Sugiyama Y: A comparison of the effects of 3-hydroxy-3-methylglutaryl-coenzyme a (HMG-CoA) reductase inhibitors on the CYP3A4-dependent oxidation of mexazolam in vitro. Drug Metab Dispos. 2001 Mar;29(3):282-8. [Article]

Drug created on September 04, 2019 20:33 / Updated on May 14, 2021 01:07