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a frequently prescribed sleeping pill (trade name ProSom) (同)ProSom

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出典(authority):フリー百科事典『ウィキペディア（Wikipedia）』「2017/01/20 00:19:58」(JST)

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Estazolam^[1] (desmethylalprazolam, marketed under the brand names ProSom, Eurodin) is a benzodiazepine derivative drug developed by Upjohn in the 1970s.^[2] It possesses anxiolytic, anticonvulsant, sedative and skeletal muscle relaxant properties. Estazolam is an intermediate-acting oral benzodiazepine.

It is commonly prescribed for short-term treatment of insomnia.

Indications

Estazolam 1mg pills, sold as Eurodin, from Japan.

From United States, sold as ProSom (2MG)

Estazolam is prescribed for the short-term treatment of certain sleep disorders. It is an effective hypnotic drug showing efficacy in increasing the time spent asleep as well as reducing awakenings during the night. Combination with non-pharmacological options for sleep management results in long-term improvements in sleep quality after discontinuation of short-term estazolam therapy.^[3]^[4] Estazolam is also sometimes used as a preoperative sleep aid. It was found to be superior to triazolam in side effect profile in preoperative patients in a trial.^[5] Estazolam also has anxiolytic properties and due to its long half life can be an effective short-term treatment for insomnia associated with anxiety.^[6]

Side effects

A hang-over effect commonly occurs with next day impairments of mental and physical performance.^[7] Other side effects of estazolam include somnolence, dizziness, hypokinesia, and abnormal coordination.^[8]

Tolerance and dependence

The main safety concern of benzodiazepines such as estazolam is a benzodiazepine dependence and the subsequent benzodiazepine withdrawal syndrome which can occur upon discontinuation of the estazolam. A review of the literature found that long-term use of benzodiazepines such as estazolam is associated with drug tolerance, drug dependence, rebound insomnia and CNS related adverse effects. Estazolam should only be used short term and at the lowest effective dose to avoid complications related to long-term use. Non-pharmacological treatment options however, were found to have sustained improvements in sleep quality.^[9]^[10] The short-term benefits of benzodiazepines on sleep begin to reduce after a few days due to tolerance to the hypnotic effects of benzodiazepines in the elderly.^[11]

Contraindications and special caution

Benzodiazepines require special precaution if used in the elderly, during pregnancy, in children, alcohol or drug-dependent individuals and individuals with comorbid psychiatric disorders.^[12]

Elderly

An extensive review of the medical literature regarding the management of insomnia and the elderly found that there is considerable evidence of the effectiveness and durability of non-drug treatments for insomnia in adults of all ages and that these interventions are underutilized. Compared with the benzodiazepines including estazolam, the nonbenzodiazepine sedative-hypnotics appeared to offer few, if any, significant clinical advantages in efficacy or tolerability in elderly persons. It was found that newer agents with novel mechanisms of action and improved safety profiles, such as the melatonin agonists, hold promise for the management of chronic insomnia in elderly people. Long-term use of sedative-hypnotics for insomnia lacks an evidence base and has traditionally been discouraged for reasons that include concerns about such potential adverse drug effects as cognitive impairment (anterograde amnesia), daytime sedation, motor incoordination, and increased risk of motor vehicle accidents and falls. In addition, the effectiveness and safety of long-term use of these agents remain to be determined. It was concluded that more research is needed to evaluate the long-term effects of treatment and the most appropriate management strategy for elderly persons with chronic insomnia.^[13]

Pharmacology

Estazolam is classed as a "triazolo" benzodiazepine drug.^[14] Estazolam exerts its therapeutic effects via its benzodiazepines receptor agonist properties.^[15] Estazolam at high doses decreases histamine turnover via its action at the benzodiazepine-GABA receptor complex in mouse brains.^[16]

Pharmacokinetics

Peak plasma levels are achieved within 1 – 6 hours. Estazolam is an intermediate acting benzodiazepine. The elimination half life of estazolam is an average of 19 hours, with a range of 8 – 31 hours.^[17]^[18] The major metabolite of estazolam is 4-hydroxyestazolam.^[19]

Interactions

Alcohol enhances the sedative hypnotic properties of estazolam.^[20] Manufacturers warn in package inserts about an interaction with Ritonavir, but clinical interactions of Ritonavir with estazolam have not yet been described.^[21]

EEG effects in rabbits

An animal study in rabbits demonstrated that estazolam induces a drowsy pattern of spontaneous EEG including high voltage slow waves and spindle bursts increase in the cortex and amygdala, while the hippocampal theta rhythm is desynchronized. Also low voltage fast waves occur particularly in the cortical EEG. The EEG arousal response to auditory stimulation and to electric stimulation of the mesencephalic reticular formation, posterior hypothalamus and centromedian thalamus is significantly suppressed. The photic driving response elicited by a flash light in the visual cortex is significantly suppressed by estazolam.^[22]

Abuse

A primate study found that estazolam has abuse potential.^[23] Estazolam is a drug with the potential for misuse. Two types of drug misuse can occur either recreational misuse is where the drug is taken to achieve a high or when the drug is continued long term against medical advice.^[24] Estazolam became notorious in 1998 when a large amount of an 'herbal sleeping mix' called Sleeping Buddha was recalled from the shelves after the FDA discovered that it contained estazolam.^[25]

References

^ US Patent 4116956
^ US Patent 3701782 - 1-CARBOLOWER ALKOXY-6-PHENYL-4H-S-TRIAZOLO(1,4)BENZODIAZEPINE COMPOUNDS
^ Roehrs T, Zorick F, Lord N, Koshorek GL, Roth T (June 1983). "Dose-related effects of estazolam on sleep of patients with insomnia". J Clin Psychopharmacol. 3 (3): 152–6. doi:10.1097/00004714-198306000-00002. PMID 6135720.
^ Rosen RC, Lewin DS, Goldberg L, Woolfolk RL (October 2000). "Psychophysiological insomnia: combined effects of pharmacotherapy and relaxation-based treatments". Sleep Med. 1 (4): 279–288. doi:10.1016/S1389-9457(00)00042-3. PMID 11040460.
^ Mauro C, Sperlongano P (September 1987). "[Controlled clinical evaluation of 2 hypnotic triazole benzodiazepines, estazolam and triazolam, used the night before surgical interventions]". Minerva Med. (in Italian). 78 (18): 1381–4. PMID 2889169.
^ Post GL; Patrick RO; Crowder JE; et al. (August 1991). "Estazolam treatment of insomnia in generalized anxiety disorder: a placebo-controlled study". J Clin Psychopharmacol. 11 (4): 249–53. doi:10.1097/00004714-199108000-00005. PMID 1918423.
^ Müller KW, Müller-Limmroth W, Strasser H (1982). "[Alterations of sleep stage pattern in human beings and hang-over effects under the influence of estazolam/2nd Comm.: Studies on the hang-over effect in psycho-physiological performance (author's transl)]". Arzneimittelforschung (in German). 32 (4): 456–60. PMID 6125155.
^ Pierce MW, Shu VS, Groves LJ (March 1990). "Safety of estazolam. The United States clinical experience". Am. J. Med. 88 (3A): 12S–17S. doi:10.1016/0002-9343(90)90280-Q. PMID 1968713.
^ Kirkwood CK (1999). "Management of insomnia". J Am Pharm Assoc (Wash). 39 (5): 688–96; quiz 713–4. PMID 10533351.
^ Lee YJ (2004). "Overview of the therapeutic management of insomnia with zolpidem". CNS Drugs. 18 Suppl 1: 17–23; discussion 41, 43–5. doi:10.2165/00023210-200418001-00005. PMID 15291010.
^ Grad RM (November 1995). "Benzodiazepines for insomnia in community-dwelling elderly: a review of benefit and risk". J Fam Pract. 41 (5): 473–81. PMID 7595266.
^ Authier, N.; Balayssac, D.; Sautereau, M.; Zangarelli, A.; Courty, P.; Somogyi, AA.; Vennat, B.; Llorca, PM.; Eschalier, A. (November 2009). "Benzodiazepine dependence: focus on withdrawal syndrome". Ann Pharm Fr. 67 (6): 408–13. doi:10.1016/j.pharma.2009.07.001. PMID 19900604.
^ Bain KT (June 2006). "Management of chronic insomnia in elderly persons". Am J Geriatr Pharmacother. 4 (2): 168–92. doi:10.1016/j.amjopharm.2006.06.006. PMID 16860264.
^ Braestrup C; Squires RF. (1 April 1978). "Pharmacological characterization of benzodiazepine receptors in the brain". Eur J Pharmacol. 48 (3): 263–70. doi:10.1016/0014-2999(78)90085-7. PMID 639854.
^ Akbarzadeh T, Tabatabai SA, Khoshnoud MJ, Shafaghi B, Shafiee A (March 2003). "Design and synthesis of 4H-3-(2-phenoxy)phenyl-1,2,4-triazole derivatives as benzodiazepine receptor agonists". Bioorg. Med. Chem. 11 (5): 769–73. doi:10.1016/S0968-0896(02)00469-8. PMID 12538007.
^ Oishi R; Nishibori M; Itoh Y; Saeki K. (May 27, 1986). "Diazepam-induced decrease in histamine turnover in mouse brain". Eur J Pharmacol. 124 (3): 337–42. doi:10.1016/0014-2999(86)90236-0. PMID 3089825.
^ Allen MD, Greenblatt DJ, Arnold JD (1979). "Single- and multiple-dose kinetics of estazolam, a triazolo benzodiazepine". Psychopharmacology (Berl.). 66 (3): 267–74. doi:10.1007/BF00428318. PMID 43552.
^ Mancinelli A, Guiso G, Garattini S, Urso R, Caccia S (March 1985). "Kinetic and pharmacological studies on estazolam in mice and man". Xenobiotica. 15 (3): 257–65. doi:10.3109/00498258509045357. PMID 2862746.
^ Miura M, Otani K, Ohkubo T (May 2005). "Identification of human cytochrome P450 enzymes involved in the formation of 4-hydroxyestazolam from estazolam". Xenobiotica. 35 (5): 455–65. doi:10.1080/00498250500111612. PMID 16012077.
^ Wang JS, DeVane CL (2003). "Pharmacokinetics and drug interactions of the sedative hypnotics" (PDF). Psychopharmacol Bull. 37 (1): 10–29. doi:10.1007/BF01990373. PMID 14561946.
^ Miura M, Ohkubo T, Sugawara K, Okuyama N, Otani K (May 2002). "Determination of estazolam in plasma by high-performance liquid chromatography with solid-phase extraction" (PDF). Anal Sci. 18 (5): 525–8. doi:10.2116/analsci.18.525. PMID 12036118.
^ Watanabe S; Ohta H; Sakurai Y; Takao K; Ueki S. (July 1986). "[Electroencephalographic effects of 450191-S and its metabolites in rabbits with chronic electrode implants]". Nippon Yakurigaku Zasshi. 88 (1): 19–32. doi:10.1254/fpj.88.19. PMID 3758874.
^ Johanson CE (March 1987). "Benzodiazepine self-administration in rhesus monkeys: estazolam, flurazepam and lorazepam". Pharmacol. Biochem. Behav. 26 (3): 521–6. doi:10.1016/0091-3057(87)90159-6. PMID 2883668.
^ Griffiths RR, Johnson MW (2005). "Relative abuse liability of hypnotic drugs: a conceptual framework and algorithm for differentiating among compounds". J Clin Psychiatry. 66 Suppl 9: 31–41. PMID 16336040.
^ Food and Drug Administration; U.S. Department of Health and Human Services (10 March 1998). "FDA WARNS CONSUMERS AGAINST TAKING DIETARY SUPPLEMENT "SLEEPING BUDDHA"". FDA. Archived from the original on October 6, 2008. Retrieved 21 December 2008.

External links

Rx-List - Estazolam
Inchem - Estazolam

UpToDate Contents

全文を閲覧するには購読必要です。 To read the full text you will need to subscribe.

1. 不眠症の治療 treatment of insomnia
2. 患者情報：不眠症の治療（詳細） insomnia treatments beyond the basics
3. 患者情報：不眠症（詳細） insomnia beyond the basics

English Journal

Dependence, misuse, and beliefs regarding use of hypnotics by elderly psychiatric patients taking zolpidem, estazolam, or flunitrazepam.

Yen CF1, Ko CH, Chang YP, Yu CY, Huang MF, Yeh YC, Lin JJ, Chen CS.
Asia-Pacific psychiatry : official journal of the Pacific Rim College of Psychiatrists.Asia Pac Psychiatry.2014 Oct 8. doi: 10.1111/appy.12147. [Epub ahead of print]
INTRODUCTION: To examine the prevalence rates and correlates of dependence on, misuse of, and beliefs regarding use of hypnotics in elderly psychiatric patients with long-term use of zolpidem, estazolam, or flunitrazepam.METHODS: A total of 139 psychiatric outpatients 65 or more years of age who use
PMID 25296384

Simple and sensitive LC-MS/MS-based assay for the quantification of dimemorfan in human plasma for use in a pharmacokinetic study.

Tan H1, Peng J, Pei Q, Yang L, Chen J, Guo C, Hua Y, Yuan H, Yang G.
Biomedical chromatography : BMC.Biomed Chromatogr.2014 Sep 29. doi: 10.1002/bmc.3325. [Epub ahead of print]
Dimemorfan phosphate has been widely used for 40 years throughout the world for the treatment of coughs. This is the first report on the use of an LC-MS/MS-based assay for the determination of dimemorfan in human plasma using estazolam as an internal standard after one-step protein precipitation w
PMID 25262813

Detection of abused drugs in human blood by using the on-site drug-screening device Oratect® III.

Toubou H1, Namera A2, Arima Y1, Uchida Y3, Torikoshi A1, Moriya F4, Nagao M1.
Legal medicine (Tokyo, Japan).Leg Med (Tokyo).2014 Sep;16(5):308-13. doi: 10.1016/j.legalmed.2014.04.004. Epub 2014 May 9.
A simple and precise drug screening method was developed for the detection of abused drugs in whole blood by using the Oratect® III device that is usually employed for the detection of drugs in saliva. Whole blood was acidified with phosphoric acid, following which the hemolyzed solution was filter
PMID 24877596

Japanese Journal

Determination of 13 Organic Toxicants in Human Blood by Liquid–Liquid Extraction Coupling High-Performance Liquid Chromatography Tandem Mass Spectrometry

Analytical Sciences 32(6), 645-652, 2016
NAID 130005156490

福山型先天性筋ジストロフィーにおける不眠の検討

東京女子医科大学雑誌 83(E1), E42-E46, 2013-01-31
NAID 110009559371

Effects of the CYP2C19 genotype and cigarette smoking on the single oral dose pharmacokinetics and pharmacodynamics of estazolam

Prog Neuro-Psychopharmacol Biol Psychiatry 27, 535-538, 2003
NAID 30008401846

Related Pictures

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リンク元

「エスタゾラム」

Estazolam
Clinical data
Trade names	ProSom
AHFS/Drugs.com	Monograph
MedlinePlus	a691003
Pregnancy; category	US: X (Contraindicated); ;
Routes of; administration	Oral
ATC code	N05CD04 (WHO)
Legal status
Legal status	CA: Schedule IV; DE: Anlage III (Prescription only); UK: Class C; US: Schedule IV;
Pharmacokinetic data
Bioavailability	93%
Metabolism	Hepatic
Biological half-life	10–24 hours
Excretion	Renal
Identifiers
	IUPAC name 8-chloro-6-phenyl-4H-[1,2,4]triazolo[4,3-a][1,4]benzodiazepine;
CAS Number	29975-16-4
PubChem (CID)	3261
IUPHAR/BPS	7550
DrugBank	DB01215
ChemSpider	3146
UNII	36S3EQV54C
KEGG	D00311
ChEBI	CHEBI:4858
ChEMBL	CHEMBL285674
ECHA InfoCard	100.045.424
Chemical and physical data
Formula	C16H11ClN4
Molar mass	294.7
3D model (Jmol)	Interactive image
	SMILES ClC1=CC2=C(C=C1)N3C=NN=C3CN=C2C4=CC=CC=C4 ;
	InChI InChI=1S/C16H11ClN4/c17-12-6-7-14-13(8-12)16(11-4-2-1-3-5-11)18-9-15-20-19-10-21(14)15/h1-8,10H,9H2 ; Key:CDCHDCWJMGXXRH-UHFFFAOYSA-N ;
(verify)

　　[★]

英: estazolam
商: ユーロジン

-estazolam

[1] US Patent 4116956

[2] US Patent 3701782 - 1-CARBOLOWER ALKOXY-6-PHENYL-4H-S-TRIAZOLO(1,4)BENZODIAZEPINE COMPOUNDS

[3] Roehrs T, Zorick F, Lord N, Koshorek GL, Roth T (June 1983). "Dose-related effects of estazolam on sleep of patients with insomnia". J Clin Psychopharmacol. 3 (3): 152–6. doi:10.1097/00004714-198306000-00002. PMID 6135720.

[4] Rosen RC, Lewin DS, Goldberg L, Woolfolk RL (October 2000). "Psychophysiological insomnia: combined effects of pharmacotherapy and relaxation-based treatments". Sleep Med. 1 (4): 279–288. doi:10.1016/S1389-9457(00)00042-3. PMID 11040460.

[5] Mauro C, Sperlongano P (September 1987). "[Controlled clinical evaluation of 2 hypnotic triazole benzodiazepines, estazolam and triazolam, used the night before surgical interventions]". Minerva Med. (in Italian). 78 (18): 1381–4. PMID 2889169.

[6] Post GL; Patrick RO; Crowder JE; et al. (August 1991). "Estazolam treatment of insomnia in generalized anxiety disorder: a placebo-controlled study". J Clin Psychopharmacol. 11 (4): 249–53. doi:10.1097/00004714-199108000-00005. PMID 1918423.

[7] Müller KW, Müller-Limmroth W, Strasser H (1982). "[Alterations of sleep stage pattern in human beings and hang-over effects under the influence of estazolam/2nd Comm.: Studies on the hang-over effect in psycho-physiological performance (author's transl)]". Arzneimittelforschung (in German). 32 (4): 456–60. PMID 6125155.

[8] Pierce MW, Shu VS, Groves LJ (March 1990). "Safety of estazolam. The United States clinical experience". Am. J. Med. 88 (3A): 12S–17S. doi:10.1016/0002-9343(90)90280-Q. PMID 1968713.

[9] Kirkwood CK (1999). "Management of insomnia". J Am Pharm Assoc (Wash). 39 (5): 688–96; quiz 713–4. PMID 10533351.

[10] Lee YJ (2004). "Overview of the therapeutic management of insomnia with zolpidem". CNS Drugs. 18 Suppl 1: 17–23; discussion 41, 43–5. doi:10.2165/00023210-200418001-00005. PMID 15291010.

[11] Grad RM (November 1995). "Benzodiazepines for insomnia in community-dwelling elderly: a review of benefit and risk". J Fam Pract. 41 (5): 473–81. PMID 7595266.

[12] Authier, N.; Balayssac, D.; Sautereau, M.; Zangarelli, A.; Courty, P.; Somogyi, AA.; Vennat, B.; Llorca, PM.; Eschalier, A. (November 2009). "Benzodiazepine dependence: focus on withdrawal syndrome". Ann Pharm Fr. 67 (6): 408–13. doi:10.1016/j.pharma.2009.07.001. PMID 19900604.

[13] Bain KT (June 2006). "Management of chronic insomnia in elderly persons". Am J Geriatr Pharmacother. 4 (2): 168–92. doi:10.1016/j.amjopharm.2006.06.006. PMID 16860264.

[14] Braestrup C; Squires RF. (1 April 1978). "Pharmacological characterization of benzodiazepine receptors in the brain". Eur J Pharmacol. 48 (3): 263–70. doi:10.1016/0014-2999(78)90085-7. PMID 639854.

[15] Akbarzadeh T, Tabatabai SA, Khoshnoud MJ, Shafaghi B, Shafiee A (March 2003). "Design and synthesis of 4H-3-(2-phenoxy)phenyl-1,2,4-triazole derivatives as benzodiazepine receptor agonists". Bioorg. Med. Chem. 11 (5): 769–73. doi:10.1016/S0968-0896(02)00469-8. PMID 12538007.

[16] Oishi R; Nishibori M; Itoh Y; Saeki K. (May 27, 1986). "Diazepam-induced decrease in histamine turnover in mouse brain". Eur J Pharmacol. 124 (3): 337–42. doi:10.1016/0014-2999(86)90236-0. PMID 3089825.

[17] Allen MD, Greenblatt DJ, Arnold JD (1979). "Single- and multiple-dose kinetics of estazolam, a triazolo benzodiazepine". Psychopharmacology (Berl.). 66 (3): 267–74. doi:10.1007/BF00428318. PMID 43552.

[18] Mancinelli A, Guiso G, Garattini S, Urso R, Caccia S (March 1985). "Kinetic and pharmacological studies on estazolam in mice and man". Xenobiotica. 15 (3): 257–65. doi:10.3109/00498258509045357. PMID 2862746.

[19] Miura M, Otani K, Ohkubo T (May 2005). "Identification of human cytochrome P450 enzymes involved in the formation of 4-hydroxyestazolam from estazolam". Xenobiotica. 35 (5): 455–65. doi:10.1080/00498250500111612. PMID 16012077.

[20] Wang JS, DeVane CL (2003). "Pharmacokinetics and drug interactions of the sedative hypnotics" (PDF). Psychopharmacol Bull. 37 (1): 10–29. doi:10.1007/BF01990373. PMID 14561946.

[21] Miura M, Ohkubo T, Sugawara K, Okuyama N, Otani K (May 2002). "Determination of estazolam in plasma by high-performance liquid chromatography with solid-phase extraction" (PDF). Anal Sci. 18 (5): 525–8. doi:10.2116/analsci.18.525. PMID 12036118.

[22] Watanabe S; Ohta H; Sakurai Y; Takao K; Ueki S. (July 1986). "[Electroencephalographic effects of 450191-S and its metabolites in rabbits with chronic electrode implants]". Nippon Yakurigaku Zasshi. 88 (1): 19–32. doi:10.1254/fpj.88.19. PMID 3758874.

[23] Johanson CE (March 1987). "Benzodiazepine self-administration in rhesus monkeys: estazolam, flurazepam and lorazepam". Pharmacol. Biochem. Behav. 26 (3): 521–6. doi:10.1016/0091-3057(87)90159-6. PMID 2883668.

[24] Griffiths RR, Johnson MW (2005). "Relative abuse liability of hypnotic drugs: a conceptual framework and algorithm for differentiating among compounds". J Clin Psychiatry. 66 Suppl 9: 31–41. PMID 16336040.

[25] Food and Drug Administration; U.S. Department of Health and Human Services (10 March 1998). "FDA WARNS CONSUMERS AGAINST TAKING DIETARY SUPPLEMENT "SLEEPING BUDDHA"". FDA. Archived from the original on October 6, 2008. Retrieved 21 December 2008.

v t e Benzodiazepines

1,4-Benzodiazepines	2-Oxoquazepam 3-Hydroxyphenazepam Bromazepam Camazepam Carburazepam Chlordiazepoxide Cinazepam Cinolazepam Clonazepam Clorazepate Cyprazepam Delorazepam Demoxepam Desmethylflunitrazepam Devazepide* Diazepam Diclazepam Doxefazepam Elfazepam Ethyl carfluzepate Ethyl dirazepate Ethyl loflazepate Flubromazepam Fletazepam Fludiazepam Flunitrazepam Flurazepam Flutemazepam Flutoprazepam Fosazepam Gidazepam Halazepam Iclazepam Irazepine Kenazepine Ketazolam Lorazepam Lormetazepam Lufuradom* Meclonazepam Medazepam Menitrazepam Metaclazepam Motrazepam N-Desalkylflurazepam Nifoxipam Nimetazepam Nitrazepam Nitrazepate Nordazepam Nortetrazepam Oxazepam Phenazepam Pinazepam Pivoxazepam Prazepam Proflazepam Quazepam QH-II-66 Reclazepam RO4491533* Ro5-4864* Sulazepam Temazepam Tetrazepam Tifluadom* Tolufazepam Triflunordazepam Tuclazepam Uldazepam

1,5-Benzodiazepines	Arfendazam Clobazam CP-1414S Lofendazam Triflubazam

2,3-Benzodiazepines*	Girisopam GYKI-52466 GYKI-52895 Nerisopam Talampanel Tofisopam

Triazolobenzodiazepines	Adinazolam Alprazolam Clonazolam Estazolam Flubromazolam Nitrazolam Pyrazolam Triazolam

Imidazobenzodiazepines	Bretazenil Climazolam EVT-201 FG-8205 Flumazenil Imidazenil ¹²³I-Iomazenil L-655,708 Loprazolam Midazolam PWZ-029 Remimazolam Ro15-4513 Ro48-6791 Ro48-8684 Ro4938581 Sarmazenil SH-053-R-CH3-2′F

Oxazolobenzodiazepines	Cloxazolam Flutazolam Haloxazolam Mexazolam Oxazolam

Thienodiazepines	Bentazepam Clotiazepam

Thienotriazolodiazepines	Brotizolam Ciclotizolam Deschloroetizolam Etizolam Israpafant* JQ1* Metizolam

Thienobenzodiazepines*	Olanzapine Telenzepine

Pyridodiazepines	Lopirazepam

Pyridotriazolodiazepines	Zapizolam

Pyrazolodiazepines	Razobazam* Ripazepam Zolazepam Zomebazam Zometapine*

Pyrrolodiazepines	Premazepam

Tetrahydroisoquinobenzodiazepines	Clazolam

Pyrrolobenzodiazepines*	Anthramycin

Benzodiazepine prodrugs	Avizafone Rilmazafone

* atypical activity profile (not GABA_A receptor ligands)

v t e GABA_A receptor positive allosteric modulators

Alcohols	Brometone Butanol Chloralodol Chlorobutanol (cloretone) Ethanol (drinking alcohol) Ethchlorvynol Isobutanol Isopropanol Menthol Methanol Methylpentynol Pentanol Petrichloral Propanol tert-Butanol (2M2P) tert-Pentanol (2M2B) Tribromoethanol Trichloroethanol Triclofos Trifluoroethanol

Barbiturates	(-)-DMBB Allobarbital Alphenal Amobarbital Aprobarbital Barbexaclone Barbital Benzobarbital Benzylbutylbarbiturate Brallobarbital Brophebarbital Butabarbital/Secbutabarbital Butalbital Buthalital Butobarbital Butallylonal Carbubarb CP-1414S Crotylbarbital Cyclobarbital Cyclopentobarbital Difebarbamate Enallylpropymal Ethallobarbital Eterobarb Febarbamate Heptabarb Heptobarbital Hexethal Hexobarbital Metharbital Methitural Methohexital Methylphenobarbital Narcobarbital Nealbarbital Pentobarbital Phenallymal Phenobarbital Phetharbital Primidone Probarbital Propallylonal Propylbarbital Proxibarbital Reposal Secobarbital Sigmodal Spirobarbital Talbutal Tetrabamate Tetrabarbital Thialbarbital Thiamylal Thiobarbital Thiobutabarbital Thiopental Thiotetrabarbital Valofane Vinbarbital Vinylbital

Benzodiazepines	2-Oxoquazepam 3-Hydroxyphenazepam Adinazolam Alprazolam Arfendazam Avizafone Bentazepam Bretazenil Bromazepam Brotizolam Camazepam Carburazepam Chlordiazepoxide Ciclotizolam Cinazepam Cinolazepam Clazolam Climazolam Clobazam Clonazepam Clonazolam Clorazepate Clotiazepam Cloxazolam Cyprazepam Delorazepam Demoxepam Diazepam Diclazepam Doxefazepam Elfazepam Estazolam Ethyl carfluzepate Ethyl dirazepate Ethyl loflazepate Etizolam EVT-201 FG-8205 Fletazepam Flubromazepam Flubromazolam Fludiazepam Flunitrazepam Flurazepam Flutazolam Flutemazepam Flutoprazepam Fosazepam Gidazepam Halazepam Haloxazolam Iclazepam Imidazenil Irazepine Ketazolam Lofendazam Lopirazepam Loprazolam Lorazepam Lormetazepam Meclonazepam Medazepam Menitrazepam Metaclazepam Mexazolam Midazolam Motrazepam N-Desalkylflurazepam Nifoxipam Nimetazepam Nitrazepam Nitrazepate Nitrazolam Nordazepam Nortetrazepam Oxazepam Oxazolam Phenazepam Pinazepam Pivoxazepam Prazepam Premazepam Proflazepam Pyrazolam QH-II-66 Quazepam Reclazepam Remimazolam Rilmazafone Ripazepam Ro48-6791 Ro48-8684 SH-053-R-CH3-2′F Sulazepam Temazepam Tetrazepam Tolufazepam Triazolam Triflubazam Triflunordazepam (Ro5-2904) Tuclazepam Uldazepam Zapizolam Zolazepam Zomebazam

Carbamates	Carisbamate Carisoprodol Clocental Cyclarbamate Difebarbamate Emylcamate Ethinamate Febarbamate Felbamate Hexapropymate Lorbamate Mebutamate Meprobamate Nisobamate Pentabamate Phenprobamate Procymate Styramate Tetrabamate Tybamate

Flavonoids	6-Methylapigenin Ampelopsin (dihydromyricetin) Apigenin Baicalein Baicalin Catechin EGC EGCG Hispidulin Linarin Luteolin Rc-OMe Skullcap constituents (e.g., baicalin) Wogonin

Imidazoles	Etomidate Metomidate Propoxate

Kava constituents	10-Methoxyyangonin 11-Methoxyyangonin 11-Hydroxyyangonin Desmethoxyyangonin 11-Methoxy-12-hydroxydehydrokavain 7,8-Dihydroyangonin Kavain 5-Hydroxykavain 5,6-Dihydroyangonin 7,8-Dihydrokavain 5,6,7,8-Tetrahydroyangonin 5,6-Dehydromethysticin Methysticin 7,8-Dihydromethysticin Yangonin

Monoureides	Acecarbromal Apronal (apronalide) Bromisoval Carbromal Capuride Ectylurea

Neuroactive steroids	Acebrochol Allopregnanolone (SAGE-547) Alfadolone Alfaxalone Anabolic steroids 3α-Androstanediol Androstenol Androsterone Cholesterol DHDOC 3α-DHP 5α-DHP 5β-DHP DHT Etiocholanolone Ganaxolone Hydroxydione Minaxolone Org 20599 Org 21465 P1-185 Pregnanolone (eltanolone) Progesterone Renanolone SAGE-105 SAGE-217 SAGE-324 SAGE-516 SAGE-689 SAGE-872 Testosterone THDOC

Nonbenzodiazepines	β-Carbolines: Abecarnil Gedocarnil Harmane SL-651,498 ZK-93423; Cyclopyrrolones: Eszopiclone Pagoclone Pazinaclone Suproclone Suriclone Zopiclone; Imidazopyridines: Alpidem DS-1 Necopidem Saripidem Zolpidem; Pyrazolopyrimidines: Divaplon Fasiplon Indiplon Lorediplon Ocinaplon Panadiplon Taniplon Zaleplon; Others: Adipiplon CGS-8216 CGS-9896 CGS-13767 CGS-20625 CL-218,872 CP-615,003 CTP-354 ELB-139 GBLD-345 JM-1232 L-838,417 Lirequinil (Ro41-3696) NS-2664 NS-2710 NS-11394 Pipequaline ROD-188 RWJ-51204 SB-205,384 SX-3228 TGSC01AA TP-003 TPA-023 TP-13 U-89843A U-90042 Viqualine Y-23684

Phenols	Fospropofol Propofol Thymol

Piperidinediones	Glutethimide Methyprylon Piperidione Pyrithyldione

Pyrazolopyridines	Cartazolate Etazolate ICI-190,622 Tracazolate

Quinazolinones	Afloqualone Cloroqualone Diproqualone Etaqualone Mebroqualone Mecloqualone Methaqualone Methylmethaqualone Nitromethaqualone SL-164

Volatiles/gases	Acetone Acetophenone Acetylglycinamide chloral hydrate Aliflurane Benzene Butane Butylene Centalun Chloral Chloral betaine Chloral hydrate Chloroform Cryofluorane Desflurane Dichloralphenazone Dichloromethane Diethyl ether Enflurane Ethyl chloride Ethylene Fluroxene Gasoline Halopropane Halothane Isoflurane Kerosine Methoxyflurane Methoxypropane Nitric oxide Nitrogen Nitrous oxide Norflurane Paraldehyde Propane Propylene Roflurane Sevoflurane Synthane Teflurane Toluene Trichloroethane (methyl chloroform) Trichloroethylene Vinyl ether

Others/unsorted	3-Hydroxybutanal α-EMTBL AA-29504 Avermectins (e.g., ivermectin) Bromide compounds (e.g., lithium bromide, potassium bromide, sodium bromide) Carbamazepine Chloralose Chlormezanone Clomethiazole DEABL Dihydroergolines (e.g., dihydroergocryptine, dihydroergosine, dihydroergotamine, ergoloid (dihydroergotoxine)) DS2 Efavirenz Etazepine Etifoxine Fenamates (e.g., flufenamic acid, mefenamic acid, niflumic acid, tolfenamic acid) Fluoxetine Flupirtine Hopantenic acid Lanthanum Lavender oil Lignans (e.g., 4-O-methylhonokiol, honokiol, magnolol, obovatol) Loreclezole Menthyl isovalerate (validolum) Monastrol Niacin Nicotinamide (niacinamide) Org 25,435 Phenytoin Propanidid Retigabine (ezogabine) Safranal Seproxetine Stiripentol Sulfonylalkanes (e.g., sulfonmethane (sulfonal), tetronal, trional) Terpenoids (e.g., borneol) Topiramate Valerian constituents (e.g., isovaleric acid, isovaleramide, valerenic acid, valerenol) Unsorted benzodiazepine site PAMs: MRK-409 (MK-0343) TCS-1105 TCS-1205

See also: GABAergics

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estazolam