T3DB: Ketazolam

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

Targets (18)

Record Information

Version

2.0

Creation Date

2014-08-30 21:06:06 UTC

Update Date

2014-12-24 20:26:52 UTC

Accession Number

T3D4571

Identification

Common Name

Ketazolam

Class

Small Molecule

Description

Ketazolam is a drug which is a benzodiazepine derivative. It possesses anxiolytic, anticonvulsant, sedative and skeletal muscle relaxant properties. Ketazolam is not approved for sale in the United States or Canada.

Compound Type

Amide
Amine
Benzodiazepine
Drug
Ether
Organic Compound
Organochloride
Synthetic Compound

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Synonym
Anseren
Ansieten
Ansietil
Atenual
Marcen
Sedatival F.P.
Sedavital
Sedotime
Solatran
U-28774
Unakalm

Chemical Formula

C₂₀H₁₇ClN₂O₃

Average Molecular Mass

368.814 g/mol

Monoisotopic Mass

368.093 g/mol

CAS Registry Number

27223-35-4

IUPAC Name

14-chloro-4,10-dimethyl-2-phenyl-3-oxa-7,10-diazatricyclo[9.4.0.0²,⁷]pentadeca-1(11),4,12,14-tetraene-6,9-dione

Traditional Name

ketazolam

SMILES

CN1C2=C(C=C(Cl)C=C2)C2(OC(C)=CC(=O)N2CC1=O)C1=CC=CC=C1

InChI Identifier

InChI=1/C20H17ClN2O3/c1-13-10-18(24)23-12-19(25)22(2)17-9-8-15(21)11-16(17)20(23,26-13)14-6-4-3-5-7-14/h3-11H,12H2,1-2H3

InChI Key

InChIKey=PWAJCNITSBZRBL-UHFFFAOYNA-N

Chemical Taxonomy

Description

belongs to the class of organic compounds known as 1,4-benzodiazepines. These are organic compounds containing a benzene ring fused to a 1,4-azepine.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Benzodiazepines

Sub Class

1,4-benzodiazepines

Direct Parent

1,4-benzodiazepines

Alternative Parents

Substituents

1,4-benzodiazepine
Alpha-amino acid or derivatives
Aryl chloride
Aryl halide
Monocyclic benzene moiety
Benzenoid
Tertiary carboxylic acid amide
Vinylogous ester
Carboxamide group
Lactam
Carboxylic acid derivative
Oxacycle
Azacycle
Organochloride
Organohalogen compound
Organic nitrogen compound
Hydrocarbon derivative
Carbonyl group
Organic oxide
Organopnictogen compound
Organonitrogen compound
Organooxygen compound
Organic oxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Biological Properties

Status

Detected and Not Quantified

Origin

Exogenous

Cellular Locations

Membrane

Biofluid Locations

Not Available

Tissue Locations

Not Available

Pathways

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	174-176°C
Boiling Point	Not Available
Solubility	Not Available
LogP	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	0.084 g/L	ALOGPS
logP	2.6	ALOGPS
logP	3.01	ChemAxon
logS	-3.6	ALOGPS
pKa (Strongest Acidic)	14.2	ChemAxon
pKa (Strongest Basic)	-0.89	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	49.85 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	99.78 m³·mol⁻¹	ChemAxon
Polarizability	36.96 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0fri-7794000000-e5f97e7007c42a0e6cae	2017-09-01	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-014i-0009000000-00a0ebc61e31ee5f9fb7	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-014i-1009000000-af371ac384c19582e8cc	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-00kf-7910000000-9de91642147606a3f899	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-014i-0009000000-452e71c58ce51c808f39	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0002-0094000000-854abc1e120fa24f40b8	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-053v-7293000000-24656d4d8f4834731919	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-014i-0009000000-940bacac6459ea82189e	2021-10-11	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-014i-0019000000-15e1445eaba0a4c42fa1	2021-10-11	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0uy4-0295000000-0beb62e6599fbcc102b1	2021-10-11	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-014i-0009000000-de71073cb0d517e7b61e	2021-10-11	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-014i-0009000000-de71073cb0d517e7b61e	2021-10-11	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-014i-5029000000-c65a5a034b12b7c917a6	2021-10-11	View Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-0a59-1290000000-7ef8a75bf466c745a728	2014-09-20	View Spectrum

Toxicity Profile

Route of Exposure

Not Available

Mechanism of Toxicity

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.

Metabolism

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

Toxicity Values

Not Available

Lethal Dose

Not Available

Carcinogenicity (IARC Classification)

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

Uses/Sources

Ketazolam 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.

Minimum Risk Level

Not Available

Health Effects

Not Available

Symptoms

Symptoms of overdose include somnolence, confusion, coma, and diminished reflexes. Respiration, pulse and blood pressure should be monitored.

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.

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

External Links

DrugBank ID

DB01587

HMDB ID

Not Available

PubChem Compound ID

33746

ChEMBL ID

CHEMBL2104356

ChemSpider ID

31110

KEGG ID

Not Available

UniProt ID

Not Available

OMIM ID

ChEBI ID

Not Available

BioCyc ID

Not Available

CTD ID

Not Available

Stitch ID

Not Available

PDB ID

Not Available

ACToR ID

Not Available

Wikipedia Link

Ketazolam

References

Synthesis Reference

U.S. Patent 3,575,965.

MSDS

T3D4571.pdf

General References

Not Available

Gene Regulation

Up-Regulated Genes

Not Available

Down-Regulated Genes

Not Available

Targets

Target Details

1. Gamma-aminobutyric acid receptor subunit alpha-1

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. Functions as receptor for diazepines and various anesthetics, such as pentobarbital; these are bound at a separate allosteric effector binding site. Functions as ligand-gated chloride channel (By similarity).
Gene Name:: GABRA1
Uniprot ID:: P14867
Molecular Weight:: 51801.395 Da

References

Target Details

2. Gamma-aminobutyric acid receptor subunit beta-1

General Function:: 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. Functions as receptor for diazepines and various anesthetics, such as pentobarbital; these are bound at a separate allosteric effector binding site. Functions as ligand-gated chloride channel (By similarity).
Gene Name:: GABRB1
Uniprot ID:: P18505
Molecular Weight:: 54234.085 Da

References

Target Details

3. Translocator protein

General Function:: Cholesterol binding
Specific Function:: Can bind protoporphyrin IX and may play a role in the transport of porphyrins and heme (By similarity). Promotes the transport of cholesterol across mitochondrial membranes and may play a role in lipid metabolism (PubMed:24814875), but its precise physiological role is controversial. It is apparently not required for steroid hormone biosynthesis. Was initially identified as peripheral-type benzodiazepine receptor; can also bind isoquinoline carboxamides (PubMed:1847678).
Gene Name:: TSPO
Uniprot ID:: P30536
Molecular Weight:: 18827.81 Da

References

Target Details

4. Gamma-aminobutyric acid receptor subunit delta

General Function:: Gaba-a receptor activity
Specific Function:: GABA, the major inhibitory neurotransmitter in the vertebrate brain, mediates neuronal inhibition by binding to the GABA/benzodiazepine receptor and opening an integral chloride channel.
Gene Name:: GABRD
Uniprot ID:: O14764
Molecular Weight:: 50707.835 Da

References

Target Details

5. Gamma-aminobutyric acid receptor subunit epsilon

General Function:: Inhibitory extracellular ligand-gated ion channel activity
Specific Function:: GABA, the major inhibitory neurotransmitter in the vertebrate brain, mediates neuronal inhibition by binding to the GABA/benzodiazepine receptor and opening an integral chloride channel.
Gene Name:: GABRE
Uniprot ID:: P78334
Molecular Weight:: 57971.175 Da

References

Target Details

6. Gamma-aminobutyric acid receptor subunit gamma-1

General Function:: Inhibitory extracellular ligand-gated ion channel activity
Specific Function:: GABA, the major inhibitory neurotransmitter in the vertebrate brain, mediates neuronal inhibition by binding to the GABA/benzodiazepine receptor and opening an integral chloride channel.
Gene Name:: GABRG1
Uniprot ID:: Q8N1C3
Molecular Weight:: 53594.49 Da

References

Target Details

7. Gamma-aminobutyric acid receptor subunit alpha-2

General Function:: Inhibitory extracellular ligand-gated ion channel activity
Specific Function:: GABA, the major inhibitory neurotransmitter in the vertebrate brain, mediates neuronal inhibition by binding to the GABA/benzodiazepine receptor and opening an integral chloride channel.
Gene Name:: GABRA2
Uniprot ID:: P47869
Molecular Weight:: 51325.85 Da

References

Target Details

8. Gamma-aminobutyric acid receptor subunit alpha-3

General Function:: Inhibitory extracellular ligand-gated ion channel activity
Specific Function:: GABA, the major inhibitory neurotransmitter in the vertebrate brain, mediates neuronal inhibition by binding to the GABA/benzodiazepine receptor and opening an integral chloride channel.
Gene Name:: GABRA3
Uniprot ID:: P34903
Molecular Weight:: 55164.055 Da

References

Target Details

9. Gamma-aminobutyric acid receptor subunit alpha-5

General Function:: Transporter activity
Specific Function:: GABA, the major inhibitory neurotransmitter in the vertebrate brain, mediates neuronal inhibition by binding to the GABA/benzodiazepine receptor and opening an integral chloride channel.
Gene Name:: GABRA5
Uniprot ID:: P31644
Molecular Weight:: 52145.645 Da

References

Target Details

10. Gamma-aminobutyric acid receptor subunit beta-2

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. Functions as receptor for diazepines and various anesthetics, such as pentobarbital; these are bound at a separate allosteric effector binding site. Functions as ligand-gated chloride channel.
Gene Name:: GABRB2
Uniprot ID:: P47870
Molecular Weight:: 59149.895 Da

References

Target Details

11. Gamma-aminobutyric acid receptor subunit beta-3

General Function:: Gaba-gated chloride 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. Functions as receptor for diazepines and various anesthetics, such as pentobarbital; these are bound at a separate allosteric effector binding site. Functions as ligand-gated chloride channel.
Gene Name:: GABRB3
Uniprot ID:: P28472
Molecular Weight:: 54115.04 Da

References

Target Details

12. Gamma-aminobutyric acid receptor subunit gamma-2

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. Functions as receptor for diazepines and various anesthetics, such as pentobarbital; these are bound at a separate allosteric effector binding site. Functions as ligand-gated chloride channel.
Gene Name:: GABRG2
Uniprot ID:: P18507
Molecular Weight:: 54161.78 Da

References

Target Details

13. Gamma-aminobutyric acid receptor subunit gamma-3

General Function:: Inhibitory extracellular ligand-gated ion channel activity
Specific Function:: GABA, the major inhibitory neurotransmitter in the vertebrate brain, mediates neuronal inhibition by binding to the GABA/benzodiazepine receptor and opening an integral chloride channel.
Gene Name:: GABRG3
Uniprot ID:: Q99928
Molecular Weight:: 54288.16 Da

References

Target Details

14. Gamma-aminobutyric acid receptor subunit pi

General Function:: Gaba-a receptor activity
Specific Function:: GABA, the major inhibitory neurotransmitter in the vertebrate brain, mediates neuronal inhibition by binding to the GABA/benzodiazepine receptor and opening an integral chloride channel. In the uterus, the function of the receptor appears to be related to tissue contractility. The binding of this pI subunit with other GABA(A) receptor subunits alters the sensitivity of recombinant receptors to modulatory agents such as pregnanolone.
Gene Name:: GABRP
Uniprot ID:: O00591
Molecular Weight:: 50639.735 Da

References

Target Details

15. Gamma-aminobutyric acid receptor subunit rho-1

General Function:: Gaba-a receptor activity
Specific Function:: GABA, the major inhibitory neurotransmitter in the vertebrate brain, mediates neuronal inhibition by binding to the GABA/benzodiazepine receptor and opening an integral chloride channel. Rho-1 GABA receptor could play a role in retinal neurotransmission.
Gene Name:: GABRR1
Uniprot ID:: P24046
Molecular Weight:: 55882.91 Da

References

Target Details

16. Gamma-aminobutyric acid receptor subunit rho-2

General Function:: Gaba-a receptor activity
Specific Function:: GABA, the major inhibitory neurotransmitter in the vertebrate brain, mediates neuronal inhibition by binding to the GABA/benzodiazepine receptor and opening an integral chloride channel. Rho-2 GABA receptor could play a role in retinal neurotransmission.
Gene Name:: GABRR2
Uniprot ID:: P28476
Molecular Weight:: 54150.41 Da

References

Target Details

17. Gamma-aminobutyric acid receptor subunit rho-3

General Function:: Gaba-a receptor activity
Specific Function:: GABA, the major inhibitory neurotransmitter in the vertebrate brain, mediates neuronal inhibition by binding to the GABA/benzodiazepine receptor and opening an integral chloride channel.
Gene Name:: GABRR3
Uniprot ID:: A8MPY1
Molecular Weight:: 54271.1 Da

References

18. GABA-A receptor (anion channel) (Protein Group)

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. Functions as receptor for diazepines and various anesthetics, such as pentobarbital; these are bound at a separate allosteric effector binding site. Functions as ligand-gated chloride channel (By similarity).
Included Proteins:: P14867 , P47869 , P34903 , P48169 , P31644 , Q16445 , P18505 , P47870 , P28472 , O14764 , P78334 , Q8N1C3 , P18507 , Q99928 , O00591 , Q9UN88

Ketazolam (T3D4571)

Structure for T3D4571: Ketazolam

Targets

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