| Record Information |
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| Version | 1.0 |
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| Creation Date | 2014-08-30 21:05:15 UTC |
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| Update Date | 2016-11-09 01:09:09 UTC |
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| Accession Number | CHEM003525 |
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| Identification |
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| Common Name | Haloxazolam |
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| Class | Small Molecule |
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| Description | Haloxazolam is a benzodiazepine drug marketed primarily in Japan. It has similar hypnotic properties as the benzodiazepine drugs triazolam, temazepam, and flunitrazepam. It is indicated for the treatment insomnia. |
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| Contaminant Sources | |
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| Contaminant Type | - Amide
- Amine
- Bromide Compound
- Drug
- Ether
- Organic Compound
- Organobromide
- Organofluoride
- Synthetic Compound
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| Chemical Structure | |
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| Synonyms | |
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| Chemical Formula | C17H14BrFN2O2 |
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| Average Molecular Mass | 377.208 g/mol |
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| Monoisotopic Mass | 376.022 g/mol |
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| CAS Registry Number | 59128-97-1 |
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| IUPAC Name | 13-bromo-2-(2-fluorophenyl)-3-oxa-6,9-diazatricyclo[8.4.0.0²,⁶]tetradeca-1(10),11,13-trien-8-one |
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| Traditional Name | haloxazolam |
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| SMILES | FC1=CC=CC=C1C12OCCN1CC(=O)NC1=C2C=C(Br)C=C1 |
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| InChI Identifier | InChI=1S/C17H14BrFN2O2/c18-11-5-6-15-13(9-11)17(12-3-1-2-4-14(12)19)21(7-8-23-17)10-16(22)20-15/h1-6,9H,7-8,10H2,(H,20,22) |
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| InChI Key | XDKCGKQHVBOOHC-UHFFFAOYSA-N |
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| Chemical Taxonomy |
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| 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. |
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| Kingdom | Organic compounds |
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| Super Class | Organoheterocyclic compounds |
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| Class | Benzodiazepines |
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| Sub Class | 1,4-benzodiazepines |
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| Direct Parent | 1,3-oxazolobenzo-1,4-diazepines |
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| Alternative Parents | |
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| Substituents | - 1,3-oxazolobenzo-1,4-diazepine
- Alpha-amino acid or derivatives
- Fluorobenzene
- Halobenzene
- Aryl bromide
- Aryl fluoride
- Aryl halide
- Monocyclic benzene moiety
- Benzenoid
- Oxazolidine
- Carboxamide group
- Secondary carboxylic acid amide
- Lactam
- Oxacycle
- Carboxylic acid derivative
- Azacycle
- Organonitrogen compound
- Organooxygen compound
- Organic oxygen compound
- Organic nitrogen compound
- Carbonyl group
- Hydrocarbon derivative
- Organic oxide
- Organopnictogen compound
- Organohalogen compound
- Organobromide
- Organofluoride
- Aromatic heteropolycyclic compound
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| Molecular Framework | Aromatic heteropolycyclic compounds |
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| External Descriptors | Not Available |
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| Biological Properties |
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| Status | Detected and Not Quantified |
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| Origin | Exogenous |
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| Cellular Locations | |
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| Biofluid Locations | Not Available |
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| Tissue Locations | Not Available |
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| Pathways | Not Available |
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| Applications | Not Available |
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| Biological Roles | Not Available |
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| Chemical Roles | Not Available |
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| Physical Properties |
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| State | Solid |
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| Appearance | White powder. |
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| Experimental Properties | | Property | Value |
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| Melting Point | Not Available | | Boiling Point | Not Available | | Solubility | Not Available |
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| Predicted Properties | |
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| Spectra |
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| Spectra | | Spectrum Type | Description | Splash Key | View |
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| Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-004i-0009000000-41a28a0c321981e657b7 | Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-004i-0019000000-239e4e7e704da45a9b81 | Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-000b-1492000000-7533bca99f093ea2c64a | Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-004i-0009000000-51bf8b47a42bf2137d67 | Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-004i-0009000000-9224988bb784dc986675 | Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-002f-7359000000-fda1239bd8a8e4f9d04b | Spectrum | | MS | Mass Spectrum (Electron Ionization) | splash10-001i-5491000000-0eba028e442c3174bead | Spectrum |
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| Toxicity Profile |
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| Route of Exposure | Not Available |
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| 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. |
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| Metabolism | Not Available |
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| Toxicity Values | Not Available |
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| Lethal Dose | Not Available |
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| Carcinogenicity (IARC Classification) | No indication of carcinogenicity to humans (not listed by IARC). |
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| Uses/Sources | Haloxazolam is indicated for the treatment insomnia. |
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| Minimum Risk Level | Not Available |
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| Health Effects | Not Available |
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| Symptoms | Not Available |
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| 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. |
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| Concentrations |
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| Not Available |
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| External Links |
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| DrugBank ID | DB01476 |
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| HMDB ID | Not Available |
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| FooDB ID | Not Available |
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| Phenol Explorer ID | Not Available |
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| KNApSAcK ID | Not Available |
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| BiGG ID | Not Available |
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| BioCyc ID | Not Available |
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| METLIN ID | Not Available |
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| PDB ID | Not Available |
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| Wikipedia Link | Haloxazolam |
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| Chemspider ID | Not Available |
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| ChEBI ID | Not Available |
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| PubChem Compound ID | 3563 |
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| Kegg Compound ID | Not Available |
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| YMDB ID | Not Available |
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| ECMDB ID | Not Available |
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| References |
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| Synthesis Reference | Not Available |
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| MSDS | Not Available |
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| General References | Not Available |
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