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Ketazolam

HCID 33746
NotesReactions
Basic informationOverviewNames & identifiersPropertiesSafety & regulationChemistry & industryRelated reactionsCompound notes
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Basic information

CAS
106938-99-2
Standard SMILES
CC1=CC(=O)N2CC(=O)N(C)c3ccc(Cl)cc3C2(c2ccccc2)O1
InChIKey
PWAJCNITSBZRBL-UHFFFAOYSA-N
Molecular formula
C20H17ClN2O3
Average molar mass
368.8 g/mol
Monoisotopic mass
368.0927701

Overview

Ketazolam is a benzodiazepine.

Names & identifiers

Preferred name
Ketazolam
IUPAC
11-chloro-2,8-dimethyl-12b-phenyl-6H-[1,3]oxazino[3,2-d][1,4]benzodiazepine-4,7-dione
English name
ketazolam
Molecular formula
C20H17ClN2O3
Molecular weight
368.81

Names & synonyms

KETAZOLAMUnakalmAnsietenAnxonLoftranAnseren27223-35-4KetazolamumU-28,774NSC-33815892A214MD7YU-28774
Show more names
NSC 338158ketazolam USP/EP/BPKetazolam (1.0mg/ml in Acetonitrile)
DTXSID2086535011-Chloro-8,12b-dihydro-2,8-dimethyl-12b-phenyl-4H-(1,3)oxazino(3,2-d)(1,4)benzodiazepine-4,7(6H)-dione14-chloro-4,10-dimethyl-2-phenyl-3-oxa-7,10-diazatricyclo(9.4.0.0^(2,7))pentadeca-1(11),4,12,14-tetraene-6,9-dione14-chloro-4,10-dimethyl-2-phenyl-3-oxa-7,10-diazatricyclo[9.4.0.0^{2,7}]pentadeca-1(11),4,12,14-tetraene-6,9-dione(+-)-KetazolamRefChem:794268DTXCID50813768N05BA10

Database identifiers

CAS
106938-99-2、106939-00-8、27223-35-4
PubChem CID
33746
DTXSID
DTXSID20865350
ChEMBL
CHEMBL2104356
ChEBI
CHEBI:135556
UNII
424J5HGB8E、92A214MD7Y、9ZBH5G9835
EC Number
248-346-3
Nikkaji
J10.725E

Properties

Computed structural properties

XLogP
3
Topological polar surface area
49.9 Ų
Hydrogen bond donors
0
Hydrogen bond acceptors
3
Rotatable bonds
1
Heavy atoms
26
Formal charge
0
Complexity
631

Experimental & physicochemical properties

Drugs · 2 items

DEA NFLIS-Drug Category -> Benzodiazepines

DEA Schedule IV Controlled Substance -> Depressants

Solubility8.39e-02 g/L
Human DrugsPharmaceuticals
Melting Point174-176
Physical DescriptionSolid

Physicochemical properties

Melting point
182 · 182-183.5° (sinters at 170°)
Boiling point
645 · 645.0±55.0 °C(Predicted)
Density
1.41 · 1.41±0.1 g/cm3(Predicted)
solubility
5 mg/ml; · DMF: 5 mg/ml; DMSO: 5 mg/ml; DMSO:PBS(pH7.2) (1:1): 0.5 mg/ml; Methanol: 1 mg/ml
form
A crystalline solid
pka
-0.84 · -0.84±0.60(Predicted)
Stability
Unstable in Solution

Safety & regulation

Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.

GHS classification

GHS Classification · 3 items

This chemical does not meet GHS hazard criteria for 100% (2 of 2) of all reports.

Not Classified

Aggregated GHS information provided per 2 reports by companies from 2 notifications to the ECHA C&L Inventory.

Hazard information

Regulatory InformationDEA schedule IV controlled substance
Hazard Classes and CategoriesNot Classified

Toxicology

Treatment · 1 item

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.

Chemistry & industry

Pharmacology

ATC Code · 2 items

N - Nervous system

QN - Nervous system

Pharmacodynamics · 1 item

Benzodiazepines enhance the effect of the neurotransmitter gamma-aminobutyric acid (GABA), which results in sedative, hypnotic, anxiolytic, anticonvulsant, muscle relaxant and amnesic action. Benzodiazepines bind nonspecifically to benzodiazepine receptors which mediate sleep, affects muscle relaxation, anticonvulsant activity, motor coordination, and memory. As benzodiazepine receptors are thought to be coupled to gamma-aminobutyric acid-A (GABA<sub>A</sub>) receptors, this enhances the effects of GABA by increasing GABA affinity for the GABA receptor. Binding of GABA to the site opens the chloride channel, resulting in a hyperpolarized cell membrane that prevents further excitation of the cell.

Mechanism of Action · 1 item

Benzodiazepines share a similar chemical structure and their effects in humans are mainly produced by the allosteric modification of a specific kind of neurotransmitter receptor, the GABAA receptor, which increases the conductance of this inhibitory channel; this results in the various therapeutic effects as well as adverse effects of benzodiazepines. Binding of benzodiazepines to this receptor complex promotes binding of GABA, which in turn increases the conduction of chloride ions across the neuronal cell membrane. This increased conductance raises the membrane potential of the neuron resulting in inhibition of neuronal firing. In addition, different GABAA receptor subtypes have varying distributions within different regions of the brain and therefore control distinct neuronal circuits. Hence, activation of different GABAA receptor subtypes by benzodiazepines may result in distinct pharmacological actions.

Biological Half-Life26-200 hours
Metabolism/Metabolites · 2 items

Ketazolam is metabolized to diazepam, followed by demoxepam, and finally desmethyldiazepam.

Ketazolam breaks down in the blood to diazepam which breaks down to demoxepam which breaks down to desmethyldiazepam. Route of Elimination: Diazepam and its metabolites are excreted mainly in the urine, predominantly as their glucuronide conjugates. Half Life: 26-200 hours

Related reactions

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Compound notes

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On this pageBasic informationOverviewNames & identifiersPropertiesSafety & regulationChemistry & industryRelated reactionsCompound notes
FDA UNII
92 A214MD7Y · 92A214MD7Y
ATC code
5 BA10 · N05BA10
RIDADR
3249 · 3249
HazardClass
6.1 · 6.1(b)
PackingGroup
III
Toxicity
50 · cat,LD50,intraperitoneal,3900mg/kg (3900mg/kg),Medicamentos de Actualidad. Vol. 16, Pg. 293, 1980.
Toxicity Summary · 1 item

Benzodiazepines share a similar chemical structure and their effects in humans are mainly produced by the allosteric modification of a specific kind of neurotransmitter receptor, the GABAA receptor, which increases the conductance of this inhibitory channel; this results in the various therapeutic effects as well as adverse effects of benzodiazepines. Binding of benzodiazepines to this receptor complex promotes binding of GABA, which in turn increases the conduction of chloride ions across the neuronal cell membrane. This increased conductance raises the membrane potential of the neuron resulting in inhibition of neuronal firing. In addition, different GABAA receptor subtypes have varying distributions within different regions of the brain and therefore control distinct neuronal circuits. Hence, activation of different GABAA receptor subtypes by benzodiazepines may result in distinct pharmacological actions.

Signs and SymptomsSymptoms of overdose include somnolence, confusion, coma, and diminished reflexes. Respiration, pulse and blood pressure should be monitored.
Carcinogen ClassificationNo indication of carcinogenicity to humans (not listed by IARC).

Safety data

ridadr
3249
Toxicity
cat,LD50,intraperitoneal,3900mg/kg (3900mg/kg),Medicamentos de Actualidad. Vol. 16, Pg. 293, 1980.
hazard_class
6.1(b)
packing_group
III
MeSH Pharmacological Classification · 1 item

Agents that alleviate ANXIETY, tension, and ANXIETY DISORDERS, promote sedation, and have a calming effect without affecting clarity of consciousness or neurologic conditions. ADRENERGIC BETA-ANTAGONISTS are commonly used in the symptomatic treatment of anxiety but are not included here.

Absorption, Distribution and ExcretionDiazepam and its metabolites are excreted mainly in the urine, predominantly as their glucuronide conjugates.
Cellular LocationsCytoplasm

Uses & manufacturing

UsesKetazolam could be used for the treatment of anxiety. In approved countries, it is indicated for the treatment of anxiety, tension, irritability and similar stress related symptoms.
Use ClassificationPharmaceuticals
Applications · 2 items

DescriptionBenzodiazepines are psychoactive compounds that act as sedatives, hypnotics, anxiolytics, anticonvulsants, and muscle relaxants. Ketazolam is a benzodiazepine derivative that was used as an anxiolytic in the 1980s. Tolerance within fifteen days, physical dependence, and benzodiazepine withdrawal syndrome are associated with ketazolam use. This product is intended for forensic purposes.

UsesA psychotropic benzodiazepine derivative with hypnotic and anxiolytic properties. Controlled Substance.

Upstream & downstream products

Upstream raw materials

Acetyl ketene

Additional notes

DefinitionChEBI: Ketazolam is a benzodiazepine.