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Etizolam information


Etizolam
Clinical data
Trade namesEtizest, Etilaam, Etizex, Depas, Sedekopan, Pasaden
Dependence
liability
Moderate
Routes of
administration
Oral, sublingual, rectal
ATC code
  • N05BA19 (WHO)
Legal status
Legal status
  • BR: Class B1 (Psychoactive drugs)[1]
  • DE: Anlage III (Special prescription form required)
  • UK: Class C
  • US: Schedule I
  • UN: Psychotropic Schedule IV
Pharmacokinetic data
Bioavailability93%
MetabolismHepatic
Elimination half-life3.4 hours[2][3] (main metabolite is 8.2 hours)[4]
Duration of action5-7 hours
ExcretionKidney
Identifiers
IUPAC name
  • 4-(2-Chlorophenyl)-2-ethyl-9-methyl-6H-thieno[3,2-f][1,2,4]triazolo[4,3-a][1,4]diazepine
CAS Number
  • 40054-69-1 checkY
PubChem CID
  • 3307
ChemSpider
  • 3191 checkY
UNII
  • A76XI0HL37
KEGG
  • D01514 checkY
ChEMBL
  • ChEMBL1289779 ☒N
CompTox Dashboard (EPA)
  • DTXSID0023030 Edit this at Wikidata
ECHA InfoCard100.188.773 Edit this at Wikidata
Chemical and physical data
FormulaC17H15ClN4S
Molar mass342.85 g·mol−1
3D model (JSmol)
  • Interactive image
SMILES
  • ClC1=CC=CC=C1C2=NCC3=NN=C(C)N3C4=C2C=C(CC)S4
InChI
  • 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 checkY
  • Key:VMZUTJCNQWMAGF-UHFFFAOYSA-N checkY
 ☒NcheckY (what is this?)  (verify)
Etizolam powder. Pictured is roughly 150 mg; a standard dose is around 1 mg
Four blister packs of Etizex brand etizolam tablets
Etizex brand etizolam tablets

Etizolam (marketed under many brand names) is a thienodiazepine derivative[5] which is a benzodiazepine analog.[6] The etizolam molecule differs from a benzodiazepine in that the benzene ring has been replaced by a thiophene ring and triazole ring has been fused, making the drug a thienotriazolodiazepine.[7][8]

Although a thienodiazepine, etizolam is clinically regarded as a benzodiazepine because of its mode of action via the benzodiazepine receptor and directly targeting GABAA allosteric modulator receptors.[5]

It possesses anxiolytic, amnesic, anticonvulsant, hypnotic, sedative and skeletal muscle relaxant properties.[9]

It was patented in 1972[10] and approved for medical use[where?] in 1983.[11]

As of April 2021, the export of etizolam has been banned in India.[12]

  1. ^ Anvisa (2023-03-31). "RDC Nº 784 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial" [Collegiate Board Resolution No. 784 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control] (in Brazilian Portuguese). Diário Oficial da União (published 2023-04-04). Archived from the original on 2023-08-03. Retrieved 2023-08-16.
  2. ^ "Etizolam". www.drugbank.ca. Retrieved 2020-09-03.
  3. ^ "Drug & Chemical Evaluation - Etizolam" (PDF). U.S. Drug Enforcement Administration. U.S. Department of Justice. March 2020. Archived (PDF) from the original on 2020-09-03.
  4. ^ Fracasso C, Confalonieri S, Garattini S, Caccia S (1991-02-01). "Single and multiple dose pharmacokinetics of etizolam in healthy subjects". European Journal of Clinical Pharmacology. 40 (2): 181–185. doi:10.1007/BF00280074. PMID 2065698. S2CID 10176681.
  5. ^ a b Sanna E, Pau D, Tuveri F, Massa F, Maciocco E, Acquas C, et al. (February 1999). "Molecular and neurochemical evaluation of the effects of etizolam on GABAA receptors under normal and stress conditions". Arzneimittel-Forschung. 49 (2): 88–95. doi:10.1055/s-0031-1300366. PMID 10083975. S2CID 19732765.
  6. ^ Manchester KR, Maskell PD, Waters L (March 2018). "Experimental versus theoretical log D7.4, pKa and plasma protein binding values for benzodiazepines appearing as new psychoactive substances" (PDF). Drug Testing and Analysis. 10 (8): 1258–1269. doi:10.1002/dta.2387. PMID 29582576. S2CID 31098917.
  7. ^ Niwa T, Shiraga T, Ishii I, Kagayama A, Takagi A (September 2005). "Contribution of human hepatic cytochrome p450 isoforms to the metabolism of psychotropic drugs". Biological & Pharmaceutical Bulletin. 28 (9): 1711–6. doi:10.1248/bpb.28.1711. PMID 16141545.
  8. ^ Catabay A, Taniguchi M, Jinno K, Pesek JJ, Williamsen E (1 March 1998). "Separation of 1,4-Benzodiazepines and Analogues Using Cholesteryl-10-Undecenoate Bonded Phase in Microcolumn Liquid Chromatography". Journal of Chromatographic Science. 36 (3): 111–118. doi:10.1093/chromsci/36.3.111.
  9. ^ Mandrioli R, Mercolini L, Raggi MA (October 2008). "Benzodiazepine metabolism: an analytical perspective". Current Drug Metabolism. 9 (8): 827–844. doi:10.2174/138920008786049258. PMID 18855614.
  10. ^ US 3904641, "Triazolothienodiazepine compounds" 
  11. ^ Fischer J, Ganellin CR (2006). Analogue-based Drug Discovery. John Wiley & Sons. p. 536. ISBN 9783527607495.
  12. ^ "EGazette Home". Archived from the original on 2022-03-14. Retrieved 2021-05-14.

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Etizolam

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Etizolam (marketed under many brand names) is a thienodiazepine derivative which is a benzodiazepine analog. The etizolam molecule differs from a benzodiazepine...

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Deschloroetizolam

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Deschloroetizolam (also known as Etizolam-2) is a thienotriazolodiazepine that is the dechlorinated analog of the closely related etizolam. The compound has been...

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Rilmazolam

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aforementioned prodrug is an approved medication in Japan. Flutazolam Etizolam Phenazepam Mexazolam Rilmazafone Koike M, Norikura R, Sugeno K (March 1986)...

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Clonazolam

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declared all of the following related medications are Schedule I: clonazolam, etizolam, flualprazolam, flubromazolam, and flubromazepam. Minnesota declared clonazolam...

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Flubromazolam

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Adinazolam Bromazolam Desmethyletizolam Desmethylflunitrazepam Diclazepam Etizolam Flualprazolam Flubrotizolam Meclonazepam Nifoxipam Phenazepam Pyrazolam...

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Flubrotizolam

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designer drug. Brotizolam Deschloroclotizolam Flubromazolam Fluclotizolam Etizolam US 4094984, Weber KH, Bauer A, Danneburg P, Kuhn FJ, "6-Phenyl-8-bromo-4H-s-triazolo-[3...

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Metizolam

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thienotriazolodiazepine that is the demethylated analogue of the closely related etizolam. Following its sale as a designer drug, metizolam was classified as controlled...

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Photophobia

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ISBN 978-0-12-709801-2. Wakakura M, Tsubouchi T, Inouye J (March 2004). "Etizolam and benzodiazepine induced blepharospasm". Journal of Neurology, Neurosurgery...

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Sedative

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Rivotril) Clorazepate (Tranxene) Diazepam (Valium) Estazolam (Prosom) Etizolam (Etizex, Etizest) Flunitrazepam (Rohypnol, "roofies") Lorazepam (Ativan)...

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Diclazepam

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"(Proposed Rule) Schedules of Controlled Substances: Temporary Placement of Etizolam, Flualprazolam, Clonazolam, Flubromazolam, and Diclazepam in Schedule I"...

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Flualprazolam

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Fluclotizolam Fludiazepam Flubromazolam Pyrazolam Flurazepam Triazolam Clonazolam Etizolam Phenazepam Nitrazolam Anvisa (31 March 2023). "RDC Nº 784 - Listas de Substâncias...

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Benzene

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Elfazepam Estazolam Ethyl carfluzepate Ethyl dirazepate Ethyl loflazepate Etizolam FG-8205 Fletazepam Flubromazepam Flubromazolam Fludiazepam Flunitrazepam...

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Brazilian Controlled Drugs and Substances Act

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Eszopiclone Ethchlorvynol Ethylamphetamine (N-Ethylamphetamine) Ethinamate Etizolam Phenazepam Phenobarbital Flualprazolam Flubromazolam Fludiazepam Flunitrazepam...

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Venlafaxine

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Clonazepam Clorazepate Clotiazepam Cloxazolam Diazepam# Ethyl loflazepate Etizolam Fludiazepam Halazepam Ketazolam Lorazepam# Medazepam Nordazepam Oxazepam...

Word Count : 6419

Pregabalin

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Clonazepam Clorazepate Clotiazepam Cloxazolam Diazepam# Ethyl loflazepate Etizolam Fludiazepam Halazepam Ketazolam Lorazepam# Medazepam Nordazepam Oxazepam...

Word Count : 8544

Propranolol

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Clonazepam Clorazepate Clotiazepam Cloxazolam Diazepam# Ethyl loflazepate Etizolam Fludiazepam Halazepam Ketazolam Lorazepam# Medazepam Nordazepam Oxazepam...

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Blepharospasm

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blepharospasm, some drugs present the risk of side effects. In Japan, use of etizolam and benzodiazepine was associated with the development of blepharospasm...

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Cetirizine

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Antagonists A-85783 ABT-491 Apafant BN-50739 BN-52063 Cetirizine CV-3988 CV-6209 Etizolam Ginkgolide B (BN-52021) Israpafant Kadsurenone L-652 Lexipafant Loratadine...

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Testosterone

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Elfazepam Estazolam Ethyl carfluzepate Ethyl dirazepate Ethyl loflazepate Etizolam FG-8205 Fletazepam Flubromazepam Flubromazolam Fludiazepam Flunitrazepam...

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Zopiclone

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Elfazepam Estazolam Ethyl carfluzepate Ethyl dirazepate Ethyl loflazepate Etizolam FG-8205 Fletazepam Flubromazepam Flubromazolam Fludiazepam Flunitrazepam...

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Gabapentin

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Clonazepam Clorazepate Clotiazepam Cloxazolam Diazepam# Ethyl loflazepate Etizolam Fludiazepam Halazepam Ketazolam Lorazepam# Medazepam Nordazepam Oxazepam...

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Pentobarbital

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Elfazepam Estazolam Ethyl carfluzepate Ethyl dirazepate Ethyl loflazepate Etizolam FG-8205 Fletazepam Flubromazepam Flubromazolam Fludiazepam Flunitrazepam...

Word Count : 1924

Secobarbital

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Elfazepam Estazolam Ethyl carfluzepate Ethyl dirazepate Ethyl loflazepate Etizolam FG-8205 Fletazepam Flubromazepam Flubromazolam Fludiazepam Flunitrazepam...

Word Count : 1575

Sertraline

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Clonazepam Clorazepate Clotiazepam Cloxazolam Diazepam# Ethyl loflazepate Etizolam Fludiazepam Halazepam Ketazolam Lorazepam# Medazepam Nordazepam Oxazepam...

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Trazodone

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Clonazepam Clorazepate Clotiazepam Cloxazolam Diazepam# Ethyl loflazepate Etizolam Fludiazepam Halazepam Ketazolam Lorazepam# Medazepam Nordazepam Oxazepam...

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Nitric oxide

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Elfazepam Estazolam Ethyl carfluzepate Ethyl dirazepate Ethyl loflazepate Etizolam FG-8205 Fletazepam Flubromazepam Flubromazolam Fludiazepam Flunitrazepam...

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Alprazolam

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Clonazepam Clorazepate Clotiazepam Cloxazolam Diazepam# Ethyl loflazepate Etizolam Fludiazepam Halazepam Ketazolam Lorazepam# Medazepam Nordazepam Oxazepam...

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Cholesterol

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Elfazepam Estazolam Ethyl carfluzepate Ethyl dirazepate Ethyl loflazepate Etizolam FG-8205 Fletazepam Flubromazepam Flubromazolam Fludiazepam Flunitrazepam...

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