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
Structure for Mexazolam (DB15489)
- 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
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- Contraindications & Blackbox Warnings
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Not Available
- Mechanism of action
Mexazolam is a benzodiazepine that binds to benzodiazepine-type receptors, inhibiting gamma-aminobutyric acid.1
Target Actions Organism AGABA(A) Receptor Benzodiazepine Binding Site ligandHumans AGABA(A) Receptor positive allosteric modulatorHumans - 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
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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.
Drug Interaction Integrate drug-drug
interactions in your softwareNaphazoline The risk or severity of CNS depression can be increased when Naphazoline is combined with Mexazolam. Yohimbine The therapeutic efficacy of Mexazolam can be increased when used in combination with Yohimbine. 
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- Not Available
Products
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- Melex
Categories
- ATC Codes
- N05BA25 — Mexazolam
- 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
- External Links
- ChemSpider
- 4033
- ChEBI
- 31842
- ChEMBL
- CHEMBL1743261
- Wikipedia
- Mexazolam
Clinical Trials
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage Forms
Form Route Strength Tablet Oral 1 mg - Prices
- Not Available
- Patents
- Not Available
Properties
- State
- Not Available
- Experimental Properties
- Not Available
- Predicted Properties
Property Value Source Water Solubility 0.0126 mg/mL ALOGPS logP 3.47 ALOGPS logP 5.27 Chemaxon logS -4.5 ALOGPS pKa (Strongest Acidic) 3.76 Chemaxon pKa (Strongest Basic) 1.68 Chemaxon Physiological Charge 0 Chemaxon Hydrogen Acceptor Count 4 Chemaxon Hydrogen Donor Count 1 Chemaxon Polar Surface Area 45.06 Å2 Chemaxon Rotatable Bond Count 1 Chemaxon Refractivity 96.22 m3·mol-1 Chemaxon Polarizability 35.53 Å3 Chemaxon Number of Rings 4 Chemaxon Bioavailability 1 Chemaxon Rule of Five No Chemaxon Ghose Filter Yes Chemaxon Veber's Rule No Chemaxon MDDR-like Rule No Chemaxon - Predicted ADMET Features
- Not Available
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS Not Available
Targets
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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
- 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
- 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]
- 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
- 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 at September 04, 2019 20:33 / Updated at May 14, 2021 01:07