Doxefazepam
Basic information
- CAS
40762-15-0- Standard SMILES
O=C1C(O)N=C(c2ccccc2F)c2cc(Cl)ccc2N1CCO- InChIKey
VOJLELRQLPENHL-UHFFFAOYSA-N- Molecular formula
- C17H14ClFN2O3
- Average molar mass
- 348.8 g/mol
- Monoisotopic mass
- 348.0676982
Overview
Doxefazepam is a benzodiazepine.
Names & identifiers
- Preferred name
- Doxefazepam
- IUPAC
- 7-chloro-5-(2-fluorophenyl)-3-hydroxy-1-(2-hydroxyethyl)-3H-1,4-benzodiazepin-2-one
- English name
- Doxefazepam
- Molecular formula
- C17H14ClFN2O3
- Molecular weight
- 348.76
Names & synonyms
Doxefazepam40762-15-0DoxefazepamumSAS-643N-1-Hydroxyethyl-3-hydroxyflurazepam231RV72C8LDTXSID20205511-(2-hydroxyethyl)-3-hydroxy-7-chloro-1,3-dihydro-5-(o-fluorophenyl)-2H-1,4-benzodiazepin-2-oneRefChem:135726DTXCID80551N05CD127-chloro-5-(2-fluorophenyl)-3-hydroxy-1-(2-hydroxyethyl)-2,3-dihydro-1H-1,4-benzodiazepin-2-one
Show more names
doxefaxepamDUFLURAZEPAMDoxefazepam USP/EP/BP7-Chloro-5-(2-fluorophenyl)-1,3-dihydro-3-hydroxy-1-(2-hydroxyethyl)-2H-1,4-benzodiazepin-2-one1,3-Dihydro-7-chloro-5-(o-fluorophenyl)-3-hydroxy-1-(2-hydroxyethyl)-2H-1,4-benzodiazepin-2-one2H-1,4-Benzodiazepin-2-one, 7-chloro-5-(2-fluorophenyl)-1,3-dihydro-3-hydroxy-1-(2-hydroxyethyl)-
DoxansDoxefazepam [INN]7-chloro-5-(2-fluorophenyl)-3-hydroxy-1-(2-hydroxyethyl)-3H-1,4-benzodiazepin-2-oneDoxefazepam (INN)7-chloro-5-(2-fluorophenyl)-3-hydroxy-1-(2-hydroxyethyl)-1,3-dihydro-2H-1,4-benzodiazepin-2-one7-Chloro-5-(o-fluorophenyl)-1,3-dihydro-3-hydroxy-1-(2-hydroxyethyl)-2H-1,4-benzodiazepin-2-oneDoxefazepamum [INN-Latin]Sas 643
Database identifiers
- CAS
40762-15-0- PubChem CID
- 38668
- DTXSID
DTXSID2020551- ChEMBL
CHEMBL64677- ChEBI
CHEBI:82460- UNII
- 231RV72C8L
- Nikkaji
- J16.569G
Properties
Computed structural properties
- XLogP
- 1.6
- Topological polar surface area
- 73.1 Ų
- Hydrogen bond donors
- 2
- Hydrogen bond acceptors
- 5
- Rotatable bonds
- 3
- Heavy atoms
- 24
- Formal charge
- 0
- Complexity
- 504
Experimental & physicochemical properties
Drugs
Pharmaceuticals -> Nervous system -> Anxiolytics
Pharmaceuticals -> Benzodiazepines
LogP1.52
Physicochemical properties
- Melting point
- 138 · 138-140°
- Boiling point
- 204.52 °C · 204.52°C (rough estimate)
- Density
- 1.3534 · 1.3534 (estimate)
- storage temp.
- -20 °C · Store at -20°C
- pka
- 11.55 · 11.55±0.40(Predicted)
- form
- Solid
- color
- White to off-white
- InChI
- InChI=1S/C17H14ClFN2O3/c18-10-5-6-14-12(9-10)15(11-3-1-2-4-13(11)19)20-16(23)17(24)21(14)7-8-22/h1-6,9,16,22-23H,7-8H2
- InChIKey
- VOJLELRQLPENHL-UHFFFAOYSA-N
- SMILES
- N1(CCO)C2=CC=C(Cl)C=C2C(C2=CC=CC=C2F)=NC(O)C1=O
- FDA UNII
- 231 RV72C8L · 231RV72C8L
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
Toxicology
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.
Toxicity Summary
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.
Carcinogen Classification
Doxefazepam
Group 3: Not classifiable as to its carcinogenicity to humans
Volume 66: (1996) Some Pharmaceutical Drugs
1996
1996
3, not classifiable as to its carcinogenicity to humans. (L135)
Chemistry & industry
Pharmacology
ATC Code
N - Nervous system
QN - Nervous system
Uses & manufacturing
UsesDoxefazepam is used therapeutically as a hypnotic.
Applications
DescriptionDoxefazepam is a benzodiazepine hypnotic somewhat more potent than flurazepam.
Additional notes
DefinitionChEBI: Doxefazepam is a benzodiazepine.
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Related reactions
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Compound notes
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