T3DB: Etizolam

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

2014-09-05 17:10:55 UTC

Update Date

2014-12-24 20:26:53 UTC

Accession Number

T3D4584

Identification

Common Name

Etizolam

Class

Small Molecule

Description

According to the Italian P.I. sheet etizolam belongs to a new class of diazepines, thienotriazolodiazepines. This new class is easily oxidized, rapidly metabolized, and has a lower risk of accumulation, even after prolonged treatment. Etizolam has an anxiolytic action about 6 times greater than that of diazepam. Etizolam produces, especially at higher dosages, a reduction in time taken to fall asleep, an increase in total sleep time and a reduction in the number of awakenings. During tests there were not substantial changes in deep sleep. There is a reduction of REM sleep. In EEG tests of healthy volunteers Etizolam showed some characteristics of tricyclic antidepressants. Etizolam (marketed under the brand name Etilaam, Etizola, Sedekopan, Pasaden or Depas) is a thienodiazepine drug which is a benzodiazepine analog. The etizolam molecule differs from a benzodiazepine in that the benzene ring has been replaced by a thiophene ring. It possesses amnesic, anxiolytic, anticonvulsant, hypnotic, sedative and skeletal muscle relaxant properties.

Compound Type

Drug
Metabolite
Organic Compound
Organochloride
Synthetic Compound

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Synonym
1-Methyl-6-o-chlorophenyl-8-ethyl-4H-s-triazolo[3,4-c]thieno[2,3-e]1,4-diazepine
4-(2-Chlorophenyl)-2-ethyl-9-methyl-6H-thieno[3,2-f][1,2,4]triazolo[4,3-a][1,4]diazepine
4-(2-Chlorophenyl)-2-ethyl-9-methyl-6H-thieno[3,2-f][1,2,4]triazolo[4,3a][1,4]diazepine
Depas

Chemical Formula

C₁₇H₁₅ClN₄S

Average Molecular Mass

342.846 g/mol

Monoisotopic Mass

342.071 g/mol

CAS Registry Number

40054-69-1

IUPAC Name

7-(2-chlorophenyl)-4-ethyl-13-methyl-3-thia-1,8,11,12-tetraazatricyclo[8.3.0.0²,⁶]trideca-2(6),4,7,10,12-pentaene

Traditional Name

etizolam

SMILES

CCC1=CC2=C(S1)N1C(C)=NN=C1CN=C2C1=CC=CC=C1Cl

InChI Identifier

InChI=1S/C17H15ClN4S/c1-3-11-8-13-16(12-6-4-5-7-14(12)18)19-9-15-21-20-10(2)22(15)17(13)23-11/h4-8H,3,9H2,1-2H3

InChI Key

InChIKey=VMZUTJCNQWMAGF-UHFFFAOYSA-N

Chemical Taxonomy

Description

belongs to the class of organic compounds known as thienodiazepines. These are heteropolycyclic containing a thiophene ring fused to a diazepine ring. Thiophene is 5-membered ring consisting of four carbon and one sulfur atoms. Diazepine is a 7-membered ring consisting of five carbon and two nitrogen atoms.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Thienodiazepines

Sub Class

Not Available

Direct Parent

Thienodiazepines

Alternative Parents

Substituents

Thieno-para-diazepine
2,3,5-trisubstituted thiophene
Para-diazepine
Chlorobenzene
Halobenzene
Aryl chloride
Aryl halide
Monocyclic benzene moiety
Benzenoid
Heteroaromatic compound
Azole
1,2,4-triazole
Thiophene
Ketimine
Azacycle
Organic 1,3-dipolar compound
Propargyl-type 1,3-dipolar organic compound
Organonitrogen compound
Organopnictogen compound
Organic nitrogen compound
Hydrocarbon derivative
Imine
Organochloride
Organohalogen 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	Not Available
Boiling Point	Not Available
Solubility	Not Available
LogP	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	0.042 g/L	ALOGPS
logP	2.98	ALOGPS
logP	2.98	ChemAxon
logS	-3.9	ALOGPS
pKa (Strongest Acidic)	18.28	ChemAxon
pKa (Strongest Basic)	4.64	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	43.07 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	104.72 m³·mol⁻¹	ChemAxon
Polarizability	35.64 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	splash10-06tf-8189000000-7a2ceb12ff7824adfa15	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	splash10-0006-0039000000-6aa13f3ed55cdf58c0b3	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0006-1119000000-93d7efb06b709134261b	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-052p-6941000000-d4507f862b8b2305babe	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-000f-0069000000-275219bc80bff427a3da	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-001i-0192000000-c324182ddc3f89815336	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-03nm-0890000000-c508188c0bd16231d74d	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0006-0009000000-fa3ca2e1cd79c3734194	2021-09-25	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-000x-4039000000-48e95c6351ad62de00cd	2021-09-25	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-001j-8293000000-65ab65f011e0fe3e3532	2021-09-25	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0006-0009000000-7a706823cbf79cb06f31	2021-09-25	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0006-0009000000-860d3e752f1da782d504	2021-09-25	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-03fs-4698000000-1e803a56b7dcb176ceda	2021-09-25	View 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

Etizolam is indicated for short-term treatment of insomnia and for short-term treatment of anxiety or panic attacks, if a benzodiazepine is required. (Wikipedia)

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.

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

External Links

DrugBank ID

Not Available

HMDB ID

PubChem Compound ID

ChEMBL ID

ChemSpider ID

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

etizolam

References

Synthesis Reference

Not Available

MSDS

T3D4584.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 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

3. 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

4. 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

5. 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

6. 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

7. 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

8. 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

9. 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

10. 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

11. 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

12. 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

13. 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

14. 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

15. 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

16. 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

Target Details

17. 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

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

Etizolam (T3D4584)

Structure for T3D4584: Etizolam

Targets

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