ContaminantDB: Mexazolam

Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References Targets (18)XML

Record Information

Version

1.0

Creation Date

2014-09-08 02:40:36 UTC

Update Date

2016-11-09 01:09:10 UTC

Accession Number

CHEM003607

Identification

Common Name

Mexazolam

Class

Small Molecule

Description

Mexazolam (marketed under the trade names Melex and Sedoxil) is a drug which is a benzodiazepine derivative. Mexazolam has been trialed for anxiety and was found to be effective in alleviating anxiety at one week follow-up, however, after three weeks of therapy mexazolam had lost its therapeutic anxiolytic properties becoming no more effective than placebo, presumably due to benzodiazepine tolerance. Mexazolam is metabolised via the CYP3A4 pathway. HMG-CoA reductase inhibitors including simvastatin, simvastatin acid, lovastatin, fluvastatin, atorvastatin and cerivastatin inhibit the metabolism of mexazolam, but not the HMG-CoA reductase inhibitor pravastatin.

Contaminant Sources

T3DB toxins
ToxCast & Tox21 Chemicals

Contaminant Type

Amine
Drug
Ether
Organic Compound
Organochloride
Synthetic Compound

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
Melex	Kegg
10-chloro-2,3,7,11b-tetrahydro-3-Methyl-11b-(2-chlorophenyl)oxazolo(3,2-D)(1,4)benzodiazepin-6(5H)-one	MeSH

Chemical Formula

C₁₈H₁₆Cl₂N₂O₂

Average Molecular Mass

363.238 g/mol

Monoisotopic Mass

362.059 g/mol

CAS Registry Number

31868-18-5

IUPAC Name

13-chloro-2-(2-chlorophenyl)-5-methyl-3-oxa-6,9-diazatricyclo[8.4.0.0²,⁶]tetradeca-1(10),8,11,13-tetraen-8-ol

Traditional Name

melex

SMILES

CC1COC2(N1CC(O)=NC1=C2C=C(Cl)C=C1)C1=CC=CC=C1Cl

InChI Identifier

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)

InChI Key

ANUCDXCTICZJRH-UHFFFAOYSA-N

Chemical Taxonomy

Description

belongs to the class of organic compounds known as 1,3-oxazolobenzo-1,4-diazepines. These are aromatic heteropolycyclic compounds containing a 1,3-oxazole ring fused to the 1,-4-diazepine moiety of a 1,4-benzodiazepine ring system.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Benzodiazepines

Sub Class

1,4-benzodiazepines

Direct Parent

1,3-oxazolobenzo-1,4-diazepines

Alternative Parents

Substituents

1,3-oxazolobenzo-1,4-diazepine
Chlorobenzene
Halobenzene
Aryl chloride
Aryl halide
Monocyclic benzene moiety
Benzenoid
Cyclic carboximidic acid
Oxazolidine
Organic 1,3-dipolar compound
Propargyl-type 1,3-dipolar organic compound
Azacycle
Oxacycle
Organooxygen compound
Organonitrogen compound
Organochloride
Organohalogen compound
Organic oxygen compound
Organic nitrogen compound
Hydrocarbon derivative
Organopnictogen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

oxazolobenzodiazepine (CHEBI:31842 )

Biological Properties

Status

Detected and Not Quantified

Origin

Exogenous

Cellular Locations

Membrane

Biofluid Locations

Not Available

Tissue Locations

Not Available

Pathways

Name	SMPDB Link	KEGG Link
Hmg Coa Reductase Inhibitors	Not Available	Not Available

Applications

Not Available

Biological Roles

Not Available

Chemical Roles

Not Available

Physical Properties

State

Solid

Appearance

White powder.

Experimental Properties

Property	Value
Melting Point	Not Available
Boiling Point	Not Available
Solubility	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	0.013 g/L	ALOGPS
logP	3.47	ALOGPS
logP	5.27	ChemAxon
logS	-4.5	ALOGPS
pKa (Strongest Acidic)	3.76	ChemAxon
pKa (Strongest Basic)	1.58	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	35.58 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

Spectra

Spectrum Type	Description	Splash Key	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-03di-0009000000-459d7a1e190778d67508	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-03di-0009000000-dee85c554686525d1a0c	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0udl-1951000000-23872346515083585f82	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-03di-0009000000-a40b66a2ea458a09ebc5	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0ik9-0009000000-13e22b76ea2187bfdcdc	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0f6x-9468000000-314e23769e231d3b63e6	Spectrum

Toxicity Profile

Route of Exposure

Not Available

Mechanism of Toxicity

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.

Metabolism

Not Available

Toxicity Values

Not Available

Lethal Dose

Not Available

Carcinogenicity (IARC Classification)

No indication of carcinogenicity to humans (not listed by IARC).

Uses/Sources

Mexazolam has been trialed for anxiety and was found to be effective in alleviating anxiety at one week follow-up, however, after three weeks of therapy mexazolam had lost its therapeutic anxiolytic properties becoming no more effective than placebo, presumably due to benzodiazepine tolerance.

Minimum Risk Level

Not Available

Health Effects

Not Available

Symptoms

Not Available

Treatment

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.

Concentrations

Not Available

External Links

DrugBank ID

Not Available

HMDB ID

Not Available

FooDB ID

Not Available

Phenol Explorer ID

Not Available

KNApSAcK ID

Not Available

BiGG ID

Not Available

BioCyc ID

Not Available

METLIN ID

Not Available

PDB ID

Not Available

Wikipedia Link

Mexazolam

Chemspider ID

Not Available

ChEBI ID

Not Available

PubChem Compound ID

4177

Kegg Compound ID

Not Available

YMDB ID

Not Available

ECMDB ID

Not Available

References

Synthesis Reference

Not Available

MSDS

Not Available

General References

Not Available

Mexazolam (CHEM003607)

Structure for CHEM003607: Mexazolam