List of benzodiazepines

The below tables contain a sample list of benzodiazepines and benzodiazepine analogs that are commonly prescribed, with their basic pharmacological characteristics such as half-life and equivalent doses to other benzodiazepines also listed, along with their trade names and primary uses. The elimination half-life is how long it takes for half of the drug to be eliminated by the body. "Time to peak" refers to when maximum levels of the drug in the blood occur after a given dose. Benzodiazepines generally share the same pharmacological properties, such as anxiolytic, sedative, hypnotic, skeletal muscle relaxant, amnesic and anticonvulsant (hypertension in combination with other antihypertensive medications). Variation in potency of certain effects may exist amongst individual benzodiazepines. Some benzodiazepines produce active metabolites. Active metabolites are produced when a person's body metabolizes the drug into compounds that share a similar pharmacological profile to the parent compound and thus are relevant when calculating how long the pharmacological effects of a drug will last. Long-acting benzodiazepines with long-acting active metabolites such as diazepam and chlordiazepoxide are often prescribed for benzodiazepine or alcohol withdrawal as well as for anxiety if constant dose levels are required throughout the day. Shorter-acting benzodiazepines are often preferred for insomnia due to their lesser hangover effect.^{[1][2][3][4][5]}

It is fairly important to note that elimination half-life of diazepam and chlordiazepoxide as well as other long half-life benzodiazepines is twice as long in the elderly compared to younger individuals. Individuals with an impaired liver also metabolize benzodiazepines more slowly. Many doctors make the mistake of not adjusting benzodiazepine dosage according to age in elderly patients. Thus, the approximate equivalent of doses below may need to be adjusted accordingly in individuals on short acting benzodiazepines who metabolize long-acting benzodiazepines more slowly and vice versa. The changes are most notable with long acting benzodiazepines as these are prone to significant accumulation in such individuals. For example, the equivalent dose of diazepam in an elderly individual on lorazepam may be half of what would be expected in a younger individual.^[6][7] Equivalencies between individual benzodiazepines can differ by 400 fold on a mg per mg basis; awareness of this fact is necessary for the safe and effective use of benzodiazepines.^[8]

A variety of Benzodiazepines along with their molecular structure.

Pharmacological properties of common benzodiazepines

Data in the table below is taken from the Ashton "Benzodiazepine Equivalency Table".^[9]

Drug Name	Common Brand Names*	Initial Approval Year	Time to Peak (Onset of action in hours)	Elimination Half-Life (h)^† [active metabolite] (Average hours and days)	Therapeutic use
Adinazolam	Deracyn		1-2	3h (=0.12d)	anxiolytic, antidepressant
Alprazolam	Helex, Xanax, Xanor, Onax, Alprox, Restyl, Solanax, Tafil, Neurol	1981	1-2	10–20 hours (15h=0.62d)	anxiolytic, antidepressant
Bentazepam	Thiadipona		1-3	2–4 hours (3h=0.12d)	anxiolytic
Bretazenil[10]	N/A		?	2.5 hours (=0.10d)	anxiolytic, anticonvulsant
Bromazepam	Lectopam, Lexaurin, Lexotanil, Lexotan, Bromam		1-3	20–40 hours (30h=1.25d)	anxiolytic, hypnotic
Brotizolam	Lendormin, Dormex, Sintonal, Noctilan		0.5-2	4–5 hours (4.5h=0.19d)	hypnotic
Camazepam	Albego, Limpidon, Paxor		0.5-2	6–29 hours (17.5h=0.73d)	anxiolytic
Chlordiazepoxide	Librium, Risolid, Elenium	1960	1.5-4	5–30 hours [36–200 hours] (17,5h=0,73d [118h=4.92d])	anxiolytic
Cinazepam			2-4	60h (=2.5d)	hypnotic, anxiolytic
Cinolazepam	Gerodorm		0.5-2	9 hours (=0.37d)	hypnotic
Clobazam	Onfi, Frisium, Urbanol	2011	1–3 hours	8–60 hours (34h=1.41d)	anxiolytic, anticonvulsant
Clonazepam	Rivatril, Rivotril, Klonopin, Iktorivil, Paxam	1975	1-4	19.5–50 hours (34.75h=1.45d)	anticonvulsant, anxiolytic, muscle relaxant
Clonazolam	N/A	Research chemical	0.5-1.5	10–18 hours	anxiolytic, anticonvulsant, hypnotic, muscle relaxant
Clorazepate	Tranxene, Tranxilium	1972	Variable	32–152 hours (92h=3.83d)	anxiolytic, anticonvulsant
Clotiazepam	Veratran, Clozan, Rize		1-3	4 hours (=0.17d)	anxiolytic
Cloxazolam	Sepazon, Olcadil		2-5 (?)	80–105 hours (92.5h= 3.85d)	anxiolytic, anticonvulsant
Delorazepam	Dadumir		1-2	80–105 hours (92,5hh=3.85d)	anxiolytic, amnesic
Diazepam	Antenex, Apaurin, Apzepam, Apozepam, Hexalid, Pax, Stesolid, Stedon, Valium, Vival, Valaxona	1963	1-1.5	32–47 hours [32–205] (39.5h=1.64d [118.5h=4.94d]	anxiolytic, anticonvulsant, muscle relaxant
Diclazepam[11]		Research chemical	1.5-3	220 hours (=7days+)	anxiolytic, amnesic, anticonvulsant, hypnotic, muscle relaxant
Estazolam	ProSom, Nuctalon	1990	1-5	10–31 hours (20.5h=0.85d)	hypnotic, anxiolytic
Ethyl carfluzepate		N/A	1-5	11–24 hours (17.5h=0.73d)	hypnotic
Etizolam	Etilaam, Etizest, Pasaden, Depas		1-2	6 hours (=0.25d)	anxiolytic, hypnotic, amnesic, muscle relaxant, anticonvulsant
Ethyl loflazepate	Victan, Meilax, Ronlax		2.5-3	73–119 hours (96h=4d)	anxiolytic
Flubromazepam[12]		Research chemical	1.5-4 (4-8)	100–220 hours (160h=6.67d)	anxiolytic, hypnotic, amnesic, muscle relaxant, anticonvulsant
Flubromazolam		Research chemical	?	?	hypnotic
Flunitrazepam	Rohypnol, Hipnosedon, Vulbegal, Fluscand, Flunipam, Ronal, Rohydorm,	1983	0.5-3	18–26 hours [36–200 hours] (22h=0.92d [118h=4.92d])	hypnotic
Flurazepam	Dalmadorm, Dalmane	1970	1-1.5	40–250 hours (145h=6.04d)	hypnotic
Flutazolam	Coreminal		?	3.5 hours	hypnotic
Flutoprazepam	Restas		0.5-9	60–90 hours (75h=3.12d)	hypnotic, anticonvulsant
Halazepam	Paxipam	1981	1-3	30–100 hours (65h=2.71d)	anxiolytic
Ketazolam	Anxon	N/A	2.5-3	30–100 hours [36–200] (65h=2.71d [118h=4.92d])	anxiolytic
Loprazolam	Dormonoct		0.5-4	3.3–14.8 hours (9.05h=0.38d)	hypnotic
Lorazepam	Ativan, Lorenin, Lorsilan, Temesta, Tavor, Lorabenz	1977	2-4	9.5–20 hours (14.75h=0.61d)	anxiolytic, amnesic, anticonvulsant, hypnotic, muscle relaxant[13][14][15]
Lormetazepam	Loramet, Noctamid, Pronoctan		0.5-2	10 hours (=0.42d)	hypnotic
Medazepam	Nobrium, Ansilan, Mezapam, Rudotel, Raporan		1-1.5	36–200 hours (118h=4.92d)	anxiolytic
Mexazolam	Melex		1-2	[16]	anxiolytic
Midazolam	Dormicum, Versed, Hypnovel, Dormonid	1985	0.5-1	1.5–2.5 hours (2h=0.08d)	hypnotic, anticonvulsant, amnesic, anxiolytic
Nifoxipam		Research chemical	?	?	hypnotic
Nimetazepam	Erimin		0.5-3	14–30 hours (27h=1.12d)	hypnotic
Nitrazepam	Mogadon, Alodorm, Pacisyn, Dumolid, Nitrazadon	1965	0.5-3	17–48 hours (32.5h=1.35d)	hypnotic, anticonvulsant
Nordiazepam	Madar, Stilny		?	30–150 hours (90h=3.75d)	anxiolytic
Oxazepam	Seresta, Serax, Serenid, Serepax, Sobril, Oxabenz, Oxapax, Opamox	1965	3-4	4–11 hours (7.5h=0.31d)	anxiolytic
Phenazepam	Phenazepam		1.5-4	60 hours (=2.5d)	anxiolytic, anticonvulsant
Pinazepam	Domar		?	40–100 hours (70h=2.92d)	anxiolytic
Prazepam	Lysanxia, Centrax	N/A	2-6	36–200 hours (118h=4.92d)	anxiolytic
Premazepam		N/A	2-6	10–13 hours (11.5h=0.48d)	anxiolytic
Pyrazolam	Pyrazolam, Bromazolam	Research chemical	1-1.5	16-18[17] hours (17h=0.71d)	anxiolytic, amnesic
Quazepam	Doral	1985	1-5	39–120 hours (79.5h=3.31d)	hypnotic
Rilmazafone	Rhythmy		?	[10.5 hours]	hypnotic
Temazepam	Restoril, Normison, Euhypnos, Temaze, Tenox	1981	0.5-3	4–10.5 hours (7.25h=0.30d)	hypnotic, anxiolytic, muscle relaxant
Thienalprazolam	Thienalprazolam, Deschloroetizolam, Thialprazolam	Research chemical	1-2	10–40 hours (25h=1.04d)	anxiolytic
Tetrazepam	Myolastan		1-3	3–26 hours (14.5h=0.60d)	Muscle relaxant
Triazolam	Halcion, Rilamir	1982	0.5-2	2 hours (=0.08d)	hypnotic

Atypical benzodiazepine receptor ligands

Drug Name	Common Brand Names*	Approval Date (FDA)	Elimination Half-Life (h)^† [active metabolite]	Primary Effects
DMCM	?		?	anxiogenic, convulsant
Flumazenil**	Anexate, Lanexat, Mazicon, Romazicon		1 hour	antidote
Eszopiclone^§	Lunesta	2004	6 hours	hypnotic
Zaleplon^§	Sonata, Starnoc	1999	1 hour	hypnotic
Zolpidem^§	Ambien, Nytamel, Sanval, Stilnoct, Stilnox, Sublinox (Canada), Xolnox, Zoldem, Zolnod	1992	2.6 hours	hypnotic
Zopiclone^§	Imovane, Rhovane, Ximovan; Zileze; Zimoclone; Zimovane; Zopitan; Zorclone,		4–6 hours	hypnotic

* Not all trade names are listed. Click on drug name to see a more comprehensive list.

** Flumazenil is an imidazobenzodiazepine derivative,^[18] and in layman's terms, it is a benzodiazepine overdose antidote that is given intravenously in Intensive Care Units (ICUs) to reverse the effects of benzodiazepine overdoses, as well for overdoses of the non-benzodiazepine "Z-drugs" such as Ambien and Lunesta.^[19] Flumazenil is contraindicated for benzodiazepine-tolerant patients in overdose cases.^[20] In such cases, the benefits are far outweighed by the risks, which include potential and severe seizures.^[18][21] The method by which Flumazenil acts to prevent non-benzodiazepine tolerant overdose from causing potential harm is via preventing the benzodiazepines and Z-drugs from binding to the GABA_A receptors via competitive inhibition which the Flumazenil creates. Clinical observation notating the patient's oxygen levels, respiratory, heart and blood pressure rates are used, as they are much safer than the potential seizure effects from Flumazenil. Supportive care to mediate any problems resulting from abnormal rates of the pulmonary, respiratory, and cardiovascular systems is typically the only treatment that is required in benzodiazepine-only overdoses.^[22] In most cases, activated charcoal/carbon is often used to prevent benzodiazepines from being absorbed by the gastrointestinal tract, and the use of stomach-pumping/gastric lavage is no longer commonly used nor suggested by some toxicologists.^[23] Even in cases where other central nervous system (CSN) depressants (such as in combined benzodiazepine and tricyclic antidepressant/TCA overdoses) are detected and/or suspected, endotrachial intubation for the airway path and supportive oxygen are typically implemented and are much safer than Flumazenil.^[22]

Controversy

The UK's House of Commons has attempted to get a two to four week limit mandate for prescribing benzodiazepines to replace the two to four week benzodiazepine prescribing guidelines, which are merely recommended.^[24][25]

Binding data and structure-activity relationship

A large number of benzodiazepine derivatives have been synthesised and their structure-activity relationships explored in detail.^[26][27] This chart contains binding data for benzodiazepines and related drugs investigated by Roche up to the late 1990s (though in some cases the compounds were originally synthesised by other companies such as Takeda or Upjohn).^{[28][29][30][31][32][33]} Other benzodiazepines are also listed for comparison purposes, but it does not however include binding data for;

• Benzodiazepines developed in the former Soviet Union (e.g. phenazepam, gidazepam etc.)
• Benzodiazepines predominantly used only in Japan (e.g. nimetazepam, flutoprazepam etc.)
• 4,5-cyclised benzodiazepines (e.g. ketazolam, cloxazolam etc.), and other compounds not researched by Roche
• Benzodiazepines developed more recently (e.g. remimazolam, QH-ii-066, Ro48-6791 etc.)
• "Designer" benzodiazepines for which in vitro binding data is unavailable (e.g. flubromazolam, pyrazolam etc.)^[34]

While binding or activity data is available for most of these compounds also, the assay conditions vary between sources, meaning that in many cases the values are not suitable for a direct comparison. Many older sources used animal measures of activity (i.e. sedation or anticonvulsant activity) but did not measure in vitro binding to benzodiazepine receptors.^[35][36] See for instance Table 2 vs Table 11 in the Chem Rev paper, Table 2 lists in vitro pIC₅₀ values matching those below, while Table 11 has pEC₅₀ values derived from in vivo assays in mice, which show the same activity trends but cannot be compared directly, and includes data for compounds such as diclazepam and flubromazepam which are not available in the main data set.

Also note;

• IC₅₀ / pIC₅₀ values represent binding affinity only and do not reflect efficacy or pharmacokinetics, and some compounds listed are GABA_A antagonists rather than agonists (e.g. flumazenil).
• Low IC₅₀ or high pIC₅₀ values indicate tighter binding (pIC₅₀ of 8.0 = IC₅₀ of 10nM, pIC₅₀ of 9.0 = IC₅₀ of 1nM, etc.)
• These are non subtype selective IC₅₀ values averaged across all GABA_A receptor subtypes, so subtype selective compounds with strong binding at one subtype but weak at others will appear unusually weak due to averaging of binding values (see e.g. CL-218,872)
• Finally, note that the benzodiazepine core is a privileged scaffold, which has been used to derive drugs with diverse activity that is not limited to the GABA_A modulatory action of the classical benzodiazepines,^[37] such as devazepide and tifluadom, however these have not been included in the list below. 2,3-benzodiazepines such as tofisopam are also not listed, as these act primarily as AMPA receptor modulators, and are inactive at GABA_A receptors.

Table of benzodiazepines: click to

Code pIC50 / IC50 Chemical name PubChem CAS number Ro05-3061 7.3979 / 40nM 7-fluoro-5-phenyl-1H-benzo[e] [1,4]diazepin-2(3H)-one 75849 2648-00-2 Ro05-4865 7.7696 / 17nM 7-fluoro-5-phenyl-1-methyl-1H-benzo[e] [1,4]diazepin-2(3H)-one 44366179 Ro05-6820 8.1308 / 7.4nM 7-fluoro-5-(2-fluorophenyl)-1H-benzo[e] [1,4]diazepin-2(3H)-one 44366116 Ro05-6822 8.2924 / 5.1nM 7-fluoro-5-(2-fluorophenyl)-1-methyl-1H-benzo[e] [1,4]diazepin-2(3H)-one 23275675 2024-34-2 Nordazepam 8.0269 / 9.4nM 7-chloro-5-phenyl-1H-benzo[e] [1,4]diazepin-2(3H)-one 2997 1088-11-5 Diazepam 8.0915 / 8.1nM 7-chloro-5-phenyl-1-methyl-1H-benzo[e] [1,4]diazepin-2(3H)-one 3016 439-14-5 Ro05-3367 8.699 7-chloro-5-(2-fluorophenyl)-1H-benzo[e] [1,4]diazepin-2(3H)-one 4540 2886-65-9 Fludiazepam 7-chloro-5-(2-fluorophenyl)-1-methyl-1H-benzo[e] [1,4]diazepin-2(3H)-one 3369 3900-31-0 Ro07-3953 8.7959 / 1.6nM 7-chloro-5-(2,6-difluorophenyl)-1H-benzo[e] [1,4]diazepin-2(3H)-one 23275763 Difludiazepam (Ro07-4065) 8.3872 / 4.1nM 7-chloro-5-(2,6-difluorophenyl)-1-methyl-1H-benzo[e] [1,4]diazepin-2(3H)-one 44366236 39080-67-6 Delorazepam 8.7447 / 1.8nM 7-chloro-5-(2-chlorophenyl)-1H-benzo[e] [1,4]diazepin-2(3H)-one 17925 2894-67-9 Diclazepam (Ro05-3448) 7-chloro-5-(2-chlorophenyl)-1-methyl-1H-benzo[e] [1,4]diazepin-2(3H)-one 76168 2894-68-0 Ro05-4864 TSPO ligand 7-chloro-5-(4-chlorophenyl)-1-methyl-1H-benzo[e] [1,4]diazepin-2(3H)-one 1688 14439-61-3 Ro07-5193 8.5229 7-chloro-5-(2-chloro-6-fluorophenyl)-1H-benzo[e] [1,4]diazepin-2(3H)-one 44366219 Ro22-3294 8.1549 7-chloro-5-(2,6-dichlorophenyl)-1H-benzo[e] [1,4]diazepin-2(3H)-one 12790028 Ro07-5220 8.2596 7-chloro-5-(2,6-dichlorophenyl)-1-methyl-1H-benzo[e] [1,4]diazepin-2(3H)-one 9975396 7-BPDBD 7-bromo-5-phenyl-1H-benzo[e] [1,4]diazepin-2(3H)-one 76167 2894-61-3 Phenazepam 7-bromo-5-(2-chlorophenyl)-1H-benzo[e] [1,4]diazepin-2(3H)-one 40113 51753-57-2 Flubromazepam 7-bromo-5-(2-fluorophenyl)-1H-benzo[e] [1,4]diazepin-2(3H)-one 12947024 2647-50-9 Flubrometazepam 7-bromo-5-(2-fluorophenyl)-1-methyl-1H-benzo[e] [1,4]diazepin-2(3H)-one 135809 86890-79-1 Gidazepam 2-(7-bromo-2-oxo-5-phenyl-2,3-dihydro-1H-benzo[e] [1,4]diazepin-1-yl)acetohydrazide 121919 129186-29-4 Ro13-3780 8.6198 7-bromo-5-(2,6-difluorophenyl)-1-methyl-1H-benzo[e] [1,4]diazepin-2(3H)-one 9975396 103380-73-0 Ro07-9749 7-iodo-5-(2-fluorophenyl)-1H-benzo[e] [1,4]diazepin-2(3H)-one 3082318 30843-56-2 Ro07-9957 8.5376 7-iodo-5-(2-fluorophenyl)-1-methyl-1H-benzo[e] [1,4]diazepin-2(3H)-one 118749 Ro05-2904 7.8861 / 13nM 7-trifluoromethyl-5-phenyl-1H-benzo[e] [1,4]diazepin-2(3H)-one 16795 2285-16-7 Ro14-3074 8.2757 / 5.3nM 7-azido-5-(2-fluorophenyl)-1H-benzo[e] [1,4]diazepin-2(3H)-one Nitrazepam 8.0 / 10nM 7-nitro-5-phenyl-1H-benzo[e] [1,4]diazepin-2(3H)-one 4506 146-22-5 Nimetazepam 7-nitro-5-phenyl-1-methyl-1H-benzo[e] [1,4]diazepin-2(3H)-one 4496 2011-67-8 Ro05-4435 8.829 / 1.5nM 7-nitro-5-(2-fluorophenyl)-1H-benzo[e] [1,4]diazepin-2(3H)-one 520217 2558-30-7 Flunitrazepam 8.4202 / 3.8nM 7-nitro-5-(2-fluorophenyl)-1-methyl-1H-benzo[e] [1,4]diazepin-2(3H)-one 3380 1622-62-4 Clonazepam 8.7447 / 1.8nM 7-nitro-5-(2-chlorophenyl)-1H-benzo[e] [1,4]diazepin-2(3H)-one 2802 1622-61-3 Ro05-4082 8.6576 7-nitro-5-(2-chlorophenyl)-1-methyl-1H-benzo[e] [1,4]diazepin-2(3H)-one 528222 5527-71-9 Ro05-3590 8.4559 / 3.5nM 7-nitro-5-[2-(trifluoromethyl)phenyl]-1H-benzo[e] [1,4]diazepin-2(3H)-one 15024 1427-45-8 Ro20-7736 7.0177 / 96nM 7-hydroxyamino-5-(2-fluorophenyl)-1-methyl-1H-benzo[e] [1,4]diazepin-2(3H)-one Ro05-3072 6.4134 / 386nM 7-amino-5-phenyl-1H-benzo[e] [1,4]diazepin-2(3H)-one 78641 4928-02-3 Ro05-4318 6.3372 / 460nM 7-amino-5-phenyl-1-methyl-1H-benzo[e] [1,4]diazepin-2(3H)-one 23275339 4959-16-4 Ro20-1815 7.1871 / 65nM 7-amino-5-(2-fluorophenyl)-1-methyl-1H-benzo[e] [1,4]diazepin-2(3H)-one 92294 34084-50-9 Ro05-4619 7.1249 / 75nM 7-amino-5-(2-chlorophenyl)-1H-benzo[e] [1,4]diazepin-2(3H)-one 188298 4959-17-5 Ro05-3308 IC50 >1000nM N-(2-oxo-5-phenyl-2,3-dihydro-1H-benzo[e] [1,4]diazepin-7-yl)acetamide Ro12-6377 7.1249 / 455nM 1-(5-(2-fluorophenyl)-1-methyl-2-oxo-2,5-dihydro-1H-benzo[e] [1,4]diazepin-7-yl)-3-methylurea Ro05-9090 IC50 >1000nM 7-(aminomethyl)-1-methyl-5-phenyl-1H-benzo[e] [1,4]diazepin-2(3H)-one Ro05-3343 IC50 >1000nM N,N-dimethyl-2-oxo-5-phenyl-2,3-dihydro-1H-benzo[e] [1,4]diazepine-7-sulfonamide 214460 12037-79-5 Ro05-4528 6.4202 / 380nM 7-cyano-5-phenyl-1-methyl-1H-benzo[e] [1,4]diazepin-2(3H)-one Ro20-2541 7.5229 / 30nM 7-cyano-5-(2-fluorophenyl)-1-methyl-1H-benzo[e] [1,4]diazepin-2(3H)-one Ro20-2533 7.4437 / 36nM 7-ethyl-5-phenyl-1H-benzo[e] [1,4]diazepin-2(3H)-one 10264786 Ro20-5747 7.6198 / 24nM 7-vinyl-5-phenyl-1H-benzo[e] [1,4]diazepin-2(3H)-one 44366036 QH-ii-066 7-ethynyl-5-phenyl-1-methyl-1H-benzo[e] [1,4]diazepin-2(3H)-one 9838431 183239-39-6 Ro20-5397 7.3665 / 43nM 7-formyl-5-phenyl-1H-benzo[e] [1,4]diazepin-2(3H)-one Ro20-3053 7.7447 / 18nM 7-acetyl-5-phenyl-1H-benzo[e] [1,4]diazepin-2(3H)-one 21828109 Ro05-2921 6.4559 / 350nM 5-phenyl-1H-benzo[e] [1,4]diazepin-2(3H)-one 76175 2898-08-0 Ro05-3663 IC50 >1000nM 5-methyl-1H-benzo[e] [1,4]diazepin-2(3H)-one 5080 70656-87-0 Ro05-4336 7.6778 / 21nM 5-(2-fluorophenyl)-1H-benzo[e] [1,4]diazepin-2(3H)-one 13292074 Ro07-4419 7.7212 / 19nM 5-(2,6-difluorophenyl)-1H-benzo[e] [1,4]diazepin-2(3H)-one 44366255 Ro05-4520 7.8539 / 14nM 5-(2-fluorophenyl)-1-methyl-1H-benzo[e] [1,4]diazepin-2(3H)-one 193319 844-11-1 Ro05-4608 8.4202 5-(2-chlorophenyl)-1-methyl-1H-benzo[e] [1,4]diazepin-2(3H)-one 10469149 Ro05-3546 6.4949 / 320nM 6-chloro-5-phenyl-1H-benzo[e] [1,4]diazepin-2(3H)-one 14590445 Ro13-0699 6.8239 / 150nM 6-chloro-5-(2-fluorophenyl)-1-methyl-1H-benzo[e] [1,4]diazepin-2(3H)-one 44377764 Ro07-6198 7.5528 / 28nM 8-chloro-5-(2,6-difluorophenyl)-1H-benzo[e] [1,4]diazepin-2(3H)-one 23275762 Ro20-8895 7.7212 / 19nM 8-methyl-5-(2-fluorophenyl)-1H-benzo[e] [1,4]diazepin-2(3H)-one 44366169 Ro13-0593 7.1427 / 72nM 9-chloro-5-(2-fluorophenyl)-1-methyl-1H-benzo[e] [1,4]diazepin-2(3H)-one Ro13-0882 IC50 300nM 6,8-dichloro-5-(2-fluorophenyl)-1-methyl-1H-benzo[e] [1,4]diazepin-2(3H)-one Ro22-6762 7.3979 / 40nM 7,8-dichloro-5-phenyl-1-methyl-1H-benzo[e] [1,4]diazepin-2(3H)-one 44366089 Ro20-8065 8.4437 / 3.6nM 7,8-dichloro-5-(2-fluorophenyl)-1H-benzo[e] [1,4]diazepin-2(3H)-one 10358803 88695-06-1 Ro20-8552 7.8539 / 14nM 7-methyl-8-chloro-5-(2-fluorophenyl)-1H-benzo[e] [1,4]diazepin-2(3H)-one 44366138 Ro05-2750 7.4318 / 37nM 6,8-dichloro-5-phenyl-1H-benzo[e] [1,4]diazepin-2(3H)-one Ro14-2312 IC50 >1000nM 6-amino-8-chloro-5-(2-fluorophenyl)-1-methyl-1H-benzo[e] [1,4]diazepin-2(3H)-one Ro07-3609 7.284 Ro11-8125 7.4318 / 37nM 5-(2-chlorophenyl)-1H-thieno[2,3-e] [1,4]diazepin-2(3H)-one Ro09-9212 8.4089 / 3.9nM 7-chloro-5-(2-chlorophenyl)-1H-thieno[2,3-e] [1,4]diazepin-2(3H)-one Ro10-2643 IC50 9.4nM 7-chloro-5-(2-chlorophenyl)-1H-thieno[3,2-e] [1,4]diazepin-2(3H)-one Premazepam 6.7696 / 170nM 6,7-dimethyl-5-phenyl-3,7-dihydropyrrolo[3,4-e] [1,4]diazepin-2(1H)-one 72104 57435-86-6 Ripazepam 1-ethyl-3-methyl-8-phenyl-4,6-dihydropyrazolo[4,3-e] [1,4]diazepin-5(1H)-one 33474 26308-28-1 Zolazepam 1,3,8-trimethyl-4-(2-fluorophenyl)-6,8-dihydropyrazolo[3,4-e] [1,4]diazepin-7(1H)-one 35775 31352-82-6 Zomebazam 1,3,8-trimethyl-4-phenyl-6,8-dihydropyrazolo[4,3-b] [1,4]diazepine-5,7(1H,4H)-dione 132677 78466-70-3 Ro17-2221 6.585 / 260nM 1-(2-aminoethyl)-5-phenyl-1H-benzo[e] [1,4]diazepin-2(3H)-one Ro07-5096 IC50 >1000nM 2-(7-chloro-5-(2-fluorophenyl)-2-oxo-2,3-dihydro-1H-benzo[e] [1,4]diazepin-1-yl)acetic acid Ro08-3026 7.2007 Halazepam 7.0362 / 92nM 7-chloro-5-phenyl-1-(2,2,2-trifluoroethyl)-1H-benzo[e] [1,4]diazepin-2(3H)-one 31640 23092-17-3 Quazepam 7-chloro-5-(2-fluorophenyl)-1-(2,2,2-trifluoroethyl)-1H-benzo[e] [1,4]diazepin-2(3H)-thione 4999 36735-22-5 Fletazepam 7-chloro-5-(2-fluorophenyl)-1-(2,2,2-trifluoroethyl)-1H-benzo[e] [1,4]diazepine 36834 34482-99-0 Pinazepam 7.0339 / 92.5nM 7-chloro-5-phenyl-1-(prop-2-yn-1-yl)-1H-benzo[e] [1,4]diazepin-2(3H)-one 40391 52463-83-9 Prazepam IC50 110nM 7-chloro-5-phenyl-1-cyclopropylmethyl-1H-benzo[e] [1,4]diazepin-2(3H)-one 4890 2955-38-6 Flutoprazepam 7-chloro-5-(2-fluorophenyl)-1-cyclopropylmethyl-1H-benzo[e] [1,4]diazepin-2(3H)-one 3400 25967-29-7 Cloniprazepam 7-nitro-5-(2-chlorophenyl)-1-cyclopropylmethyl-1H-benzo[e] [1,4]diazepin-2(3H)-one Ro20-1310 6.2076 / 620nM 7-chloro-5-phenyl-1-(t-butyl)-1H-benzo[e] [1,4]diazepin-2(3H)-one Fosazepam 7-chloro-5-phenyl-1-(dimethylphosphorylmethyl)-1H-benzo[e] [1,4]diazepin-2(3H)-one 37114 35322-07-7 Iclazepam 7-chloro-5-phenyl-1-[2-(cyclopropylmethoxy)ethyl]-1H-benzo[e] [1,4]diazepin-2(3H)-one 68777 57916-70-8 Tolufazepam 7-chloro-5-(2-chlorophenyl)-1-[2-(4-methylphenyl)sulfonylethyl]-1H-benzo[e] [1,4]diazepin-2(3H)-one 65647 86273-92-9 Elfazepam 7-chloro-5-(2-fluorophenyl)-1-(2-ethylsulfonylethyl)-1H-benzo[e] [1,4]diazepin-2(3H)-one 65445 52042-01-0 Reclazepam 2-[7-chloro-5-(2-chlorophenyl)-2,3-dihydro-1H-1,4-benzodiazepin-1-yl]-1,3-oxazol-4(5H)-one 3052777 76053-16-2 Ro07-1986 8.0809 / 8.3nM 1-(2-aminoethyl)-7-chloro-5-(2-fluorophenyl)-1H-benzo[e] [1,4]diazepin-2(3H)-one Flurazepam 7.8297 7-chloro-1-[2-(diethylamino)ethyl]-5-(2-fluorophenyl)-1,3-dihydro-2H-1,4-benzodiazepin-2-one 3393 17617-23-1 Ro07-2750 7.6108 / 24.5nM 7-chloro-5-(2-fluorophenyl)-1-(2-hydroxyethyl)-1H-benzo[e] [1,4]diazepin-2(3H)-one Motrazepam IC50 430nM 1-(methoxymethyl)-7-nitro-5-phenyl-1H-benzo[e] [1,4]diazepin-2(3H)-one 65764 29442-58-8 Ro08-9013 7.3716 Proflazepam 6.8539 / 140nM 7-chloro-1-(2,3-dihydroxypropyl)-5-(2-fluorophenyl)-1H-benzo[e] [1,4]diazepin-2(3H)-one 3050433 52829-30-8 Ro22-4683 6.5229 / 300nM 7-nitro-5-(2-fluorophenyl)-1-(t-butyl)-1H-benzo[e] [1,4]diazepin-2(3H)-one Ro15-8852 6.1391 / 726nM 5-(2-chlorophenyl)-4-methyl-7-nitro-4,5-dihydro-1H-benzo[e] [1,4]diazepin-2(3H)-one Chlorodiazepoxide 6.4535 / 352nM 7-chloro-2-methylamino-5-phenyl-3H-benzo[e] [1,4]diazepine-4-oxide 2712 58-25-3 Cyprazepam 7-chloro-N-(cyclopropylmethyl)-4-hydroxy-5-phenyl-3H-benzo[e] [1,4]diazepin-2-imine 27452 15687-07-7 Uldazepam 7-chloro-5-(2-chlorophenyl)-N-prop-2-enoxy-3H-benzo[e] [1,4]diazepin-2-amine 34274 28546-58-9 Demoxepam 6.5086 / 310nM 7-chloro-1,3-dihydro-5-phenyl-2H-benzo[e] [1,4]diazepin-2-one-4-oxide 13756 963-39-3 Medazepam IC50 870nM 7-chloro-5-phenyl-1-methyl-1H-benzo[e] [1,4]diazepine 4041 2898-12-6 Tuclazepam 7-chloro-5-(2-chlorophenyl)-2-(hydroxymethyl)-1-methyl-2,3-dihydro-1H-benzo[e] [1,4]diazepine 3050405 51037-88-8 Metaclazepam 7-bromo-5-(2-chlorophenyl)-2-(methoxymethyl)-1-methyl-2,3-dihydro-1H-benzo[e] [1,4]diazepine 71272 84031-17-4 Sulazepam 7-chloro-5-phenyl-1-methyl-1H-benzo[e] [1,4]diazepin-2(3H)-thione 17931 2898-13-7 Tetrazepam 7.4685 / 34nM 7-chloro-5-(cyclohexen-1-yl)-1-methyl-1H-benzo[e] [1,4]diazepin-2(3H)-one 25215 10379-14-3 Nortetrazepam IC50 34nM 7-chloro-5-(cyclohexen-1-yl)-1H-benzo[e] [1,4]diazepin-2(3H)-one 166581 10379-11-0 Menitrazepam 7-nitro-5-(cyclohexen-1-yl)-1-methyl-1H-benzo[e] [1,4]diazepin-2(3H)-one 189875 28781-64-8 Ro05-3328 7.0605 / 87nM 7-chloro-5-cyclohexyl-1H-benzo[e] [1,4]diazepin-2(3H)-one Clazolam 2-chloro-5-methyl-5,9,10,14b-tetrahydroisoquino[2,1-d] [1,4]benzodiazepin-6(7H)-one 24107 7492-29-7 Bromazepam 7.7447 / 18nM 7-bromo-5-(pyridin-2-yl)-1H-benzo[e] [1,4]diazepin-2(3H)-one 2441 1812-30-2 Methylbromazepam 7-bromo-5-(pyridin-2-yl)-1-methyl-1H-benzo[e] [1,4]diazepin-2(3H)-one 630183 1812-33-5 Ro05-5605 6.5376 Ro11-3129 8.1871 (+)-2-amino-N-[2-(2-chlorobenzoyl)-4-nitrophenyl]propanamide 21413751 65607-70-7 Ro03-7355 6.3768 Ro11-4878 8.4559 / 3.5nM 7-chloro-5-(2-fluorophenyl)-3-methyl-1H-benzo[e] [1,4]diazepin-2(3H)-one Meclonazepam 8.9208 / 1.2nM 7-nitro-5-(2-chlorophenyl)-3-methyl-1H-benzo[e] [1,4]diazepin-2(3H)-one 3033985 58662-84-3 Ro11-6896 8.1549 / 7nM 7-nitro-5-(2-fluorophenyl)-1,3-dimethyl-1H-benzo[e] [1,4]diazepin-2(3H)-one Ro06-7263 7.3098 / 49nM 1,7-dichloro-5-phenyl-3-methyl-1H-benzo[e] [1,4]diazepin-2(3H)-one Oxazepam 7.7447 / 18nM 7-chloro-3-hydroxy-5-phenyl-1H-benzo[e] [1,4]diazepin-2(3H)-one 4616 604-75-1 Temazepam 7.7959 / 16nM 7-chloro-3-hydroxy-5-phenyl-1-methyl-1H-benzo[e] [1,4]diazepin-2(3H)-one 5391 846-50-4 Lorazepam 8.4559 / 3.5nM 7-chloro-3-hydroxy-5-(2-chlorophenyl)-1H-benzo[e] [1,4]diazepin-2(3H)-one 3958 846-49-1 Lormetazepam 7-chloro-3-hydroxy-5-(2-chlorophenyl)-1-methyl-1H-benzo[e] [1,4]diazepin-2(3H)-one 13314 848-75-9 Flutemazepam 7-chloro-3-hydroxy-5-(2-fluorophenyl)-1-methyl-1H-benzo[e] [1,4]diazepin-2(3H)-one 40344 52391-89-6 Cinolazepam 7-chloro-3-hydroxy-5-(2-fluorophenyl)-1-(2-cyanoethyl)-1H-benzo[e] [1,4]diazepin-2(3H)-one 3033621 75696-02-5 Doxefazepam 7-chloro-3-hydroxy-5-(2-fluorophenyl)-1-(2-hydroxyethyl)-1H-benzo[e] [1,4]diazepin-2(3H)-one 38668 40762-15-0 Nifoxipam 7-nitro-3-hydroxy-5-(2-fluorophenyl)-1H-benzo[e] [1,4]diazepin-2(3H)-one 3058221 74723-10-7 Nitemazepam 7-nitro-3-hydroxy-5-phenyl-1-methyl-1H-benzo[e] [1,4]diazepin-2(3H)-one 3-Hydroxyphenazepam 7-bromo-3-hydroxy-5-(2-chlorophenyl)-1H-benzo[e] [1,4]diazepin-2(3H)-one 125820 70030-11-4 Cinazepam 7-bromo-3-succinyloxy-5-(2-chlorophenyl)-1H-benzo[e] [1,4]diazepin-2(3H)-one 629281 172986-25-3 Pivoxazepam 7-chloro-3-pivalyloxy-5-phenyl-1H-benzo[e] [1,4]diazepin-2(3H)-one 68722 55299-10-0 Camazepam 6.0458 7-chloro-1-methyl-2-oxo-5-phenyl-2,3-dihydro-1H-benzo[e] [1,4]diazepin-3-yl N,N-dimethylcarbamate 37367 36104-80-0 Clorazepate IC50 59nM 7-chloro-2-oxo-5-phenyl-1H-benzo[e] [1,4]diazepine-3-carboxylic acid 2809 23887-31-2 Nitrazepate 7-nitro-2-oxo-5-phenyl-1H-benzo[e] [1,4]diazepine-3-carboxylic acid 21740 5571-84-6 Ethyl carfluzepate ethyl 7-chloro-5-(2-fluorophenyl)-1-(methylcarbamoyl)-2-oxo-3H-benzo[e] [1,4]diazepine-3-carboxylate 68856 65400-85-3 Ethyl dirazepate ethyl 7-chloro-5-(2-chlorophenyl)-2-oxo-3H-benzo[e] [1,4]diazepine-3-carboxylate 208941 23980-14-5 Ethyl loflazepate ethyl 7-chloro-5-(2-fluorophenyl)-2-oxo-3H-benzo[e] [1,4]diazepine-3-carboxylate 3299 29177-84-2 Carburazepam 7-chloro-1-methyl-2-oxo-5-phenyl-1,2,3,5-tetrahydro-4H-benzo[e] [1,4]diazepine-4-carboxamide 68787 59009-93-7 Ro20-7078 8.2757 / 5.3nM 3,7-dichloro-5-(2-fluorophenyl)-1H-benzo[e] [1,4]diazepin-2(3H)-one Ro11-8125 IC50 37nM 5-(2-chlorophenyl)-1H-thieno[2,3-e] [1,4]diazepin-2(3H)-one Ro08-6739 IC50 70nM 7-chloro-5-phenyl-1H-thieno[2,3-e] [1,4]diazepin-2(3H)-one Ro08-9212 IC50 3.9nM 7-chloro-5-(2-chlorophenyl)-1H-thieno[2,3-e] [1,4]diazepin-2(3H)-one Ro10-2643 IC50 9.4nM 7-chloro-5-(2-chlorophenyl)-1H-thieno[3,2-e] [1,4]diazepin-2(3H)-one Clotiazepam 7-ethyl-5-(2-chlorophenyl)-1-methyl-1H-thieno[2,3-e] [1,4]diazepin-2(3H)-one 2811 33671-46-4 Bentazepam 5-phenyl-3,5a,6,7,8,9-hexahydro-2H-[1]benzothieno[2,3-e] [1,4]diazepin-2(3H)-one 34592 29462-18-8 Lopirazepam 7-chloro-5-(2-chlorophenyl)-3-hydroxy-1,3-dihydro-2H-pyrido[3,2-e] [1,4]diazepin-2-one 68672 42863-81-0 Clobazam 6.8861 / 130nM 7-chloro-1-methyl-5-phenyl-1H-1,5-benzodiazepine-2,4(3H,5H)-dione 2789 22316-47-8 Desmethylclobazam 6.6778 / 210nM 7-chloro-5-phenyl-1H-1,5-benzodiazepine-2,4(3H,5H)-dione Triflubazam 7-trifluoromethyl-1-methyl-5-phenyl-1H-1,5-benzodiazepine-2,4(3H,5H)-dione 2789 22316-47-8 Lofendazam 7-chloro-5-phenyl-1,3,4,5-tetrahydro-4H-1,5-benzodiazepin-4-one 71709 29176-29-2 Arfendazam ethyl 7-chloro-4-oxo-5-phenyl-2,3-dihydro-1,5-benzodiazepine-1-carboxylate 65803 37669-57-1 CP-1414S 8-nitro-1-phenyl-4-amino-3H-1,5-benzodiazepin-2-one 37594 36975-99-2 Oxazolam 10-chloro-2-methyl-11b-phenyl-2,3,7,11b-tetrahydrobenzo[f]oxazolo[3,2-d] [1,4]diazepin-6(5H)-one 62779 24143-17-7 Cloxazolam 10-chloro-11b-(2-chlorophenyl)-2,3,5,7-tetrahydro-[1,3]oxazolo[3,2-d] [1,4]benzodiazepin-6(5H)-one 2816 24166-13-0 Mexazolam 10-chloro-11b-(2-chlorophenyl)-3-methyl-2,3,7,11b-tetrahydro[1,3]oxazolo[3,2-d] [1,4]benzodiazepin-6(5H)-one 4177 31868-18-5 Flutazolam 10-chloro-11b-(2-fluorophenyl)-7-(2-hydroxyethyl)-3,5-dihydro-2H-[1,3]oxazolo[3,2-d] [1,4]benzodiazepin-6(5H)-one 3398 27060-91-9 Haloxazolam 10-bromo-11b-(2-fluorophenyl)-2,3,5,7-tetrahydro-[1,3]oxazolo[3,2-d] [1,4]benzodiazepin-6(5H)-one 3563 59128-97-1 Ketazolam 11-chloro-8,12b-dihydro-2,8-dimethyl-12b-phenyl-4H-[1,3]oxazino[3,2-d] [1,4]benzodiazepine-4,7(6H)-dione 33746 27223-35-4 U-35005 8.3665 / 4.3nM 6-(2-chlorophenyl)-1-methyl-4H-benzo[f] [1,2,4]triazolo[4,3-a] [1,4]diazepine 21680194 Estazolam 8.0706 / 8.5nM 8-chloro-6-phenyl-4H-benzo[f] [1,2,4]triazolo[4,3-a] [1,4]diazepine 3261 29975-16-4 Alprazolam 7.699 / 20nM 8-chloro-6-phenyl-1-methyl-4H-benzo[f] [1,2,4]triazolo[4,3-a] [1,4]diazepine 2118 28981-97-7 Triazolam 8.3979 / 4nM 8-chloro-6-(2-chlorophenyl)-1-methyl-4H-benzo[f] [1,2,4]triazolo[4,3-a] [1,4]diazepine 5556 28911-01-5 alpha-Hydroxytriazolam 8.3768 / 4.2nM 8-chloro-6-(2-chlorophenyl)-1-hydroxymethyl-4H-benzo[f] [1,2,4]triazolo[4,3-a] [1,4]diazepine 1963 37115-45-0 Flutriazolam 8-chloro-6-(2-fluorophenyl)-1-methyl-4H-benzo[f] [1,2,4]triazolo[4,3-a] [1,4]diazepine 10359044 28910-91-0 Desmethyltriazolam 8-chloro-6-(2-chlorophenyl)-4H-benzo[f] [1,2,4]triazolo[4,3-a] [1,4]diazepine 826660 42292-42-2 Nitrazolam 8-nitro-6-phenyl-1-methyl-4H-benzo[f] [1,2,4]triazolo[4,3-a] [1,4]diazepine 20317278 28910-99-8 Desmethylnitrazolam 8-nitro-6-phenyl-4H-benzo[f] [1,2,4]triazolo[4,3-a] [1,4]diazepine 20317280 30858-58-3 Clonazolam 8-nitro-6-(2-chlorophenyl)-1-methyl-4H-benzo[f] [1,2,4]triazolo[4,3-a] [1,4]diazepine 12317881 33887-02-4 Flunitrazolam 8-nitro-6-(2-fluorophenyl)-1-methyl-4H-benzo[f] [1,2,4]triazolo[4,3-a] [1,4]diazepine Flubromazolam 8-bromo-6-(2-fluorophenyl)-1-methyl-4H-benzo[f] [1,2,4]triazolo[4,3-a] [1,4]diazepine 21930924 612526-40-6 Phenazolam 8-bromo-6-(2-chlorophenyl)-1-methyl-4H-benzo[f] [1,2,4]triazolo[4,3-a] [1,4]diazepine 1032830 87213-50-1 Bromalprazolam 8-bromo-6-phenyl-1-methyl-4H-benzo[f] [1,2,4]triazolo[4,3-a] [1,4]diazepine 12562546 71368-80-4 Pyrazolam 8-bromo-6-(pyridin-2-yl)-1-methyl-4H-benzo[f] [1,2,4]triazolo[4,3-a] [1,4]diazepine 12562545 39243-02-2 Pyclazolam 8-chloro-6-(pyridin-2-yl)-1-methyl-4H-benzo[f] [1,2,4]triazolo[4,3-a] [1,4]diazepine 20368150 Pynazolam 8-nitro-6-(pyridin-2-yl)-1-methyl-4H-benzo[f] [1,2,4]triazolo[4,3-a] [1,4]diazepine 20368157 Pyeazolam 8-ethynyl-6-(pyridin-2-yl)-1-methyl-4H-benzo[f] [1,2,4]triazolo[4,3-a] [1,4]diazepine 71811108 1349115-59-8 Adinazolam 6.8697 / 135nM 8-chloro-6-phenyl-1-(N,N-dimethylaminomethyl)-4H-benzo[f] [1,2,4]triazolo[4,3-a] [1,4]diazepine 37632 37115-32-5 U-42352 8-chloro-6-phenyl-1-(N-methylaminomethyl)-4H-benzo[f] [1,2,4]triazolo[4,3-a] [1,4]diazepine 119094 37115-33-6 Fluadinazolam 8-chloro-6-(2-fluorophenyl)-1-(N,N-dimethylaminomethyl)-4H-benzo[f] [1,2,4]triazolo[4,3-a] [1,4]diazepine 21537253 Rilmazolam (LS-188,599) 8-chloro-6-(2-chlorophenyl)-N,N-dimethyl-4H-1,2,4-triazolo[1,5-a] [1,4]benzodiazepine-2-carboxamide 148494 50330-59-1 U-43465 F 7.9431 Ro11-5073 8.4815 / 3.3nM 8-chloro-6-(2-fluorophenyl)-1,4-dimethyl-4H-benzo[f] [1,2,4]triazolo[4,3-a] [1,4]diazepine Ro11-6679 8.3979 / 4nM 8-nitro-6-(2-fluorophenyl)-1,4-dimethyl-4H-benzo[f] [1,2,4]triazolo[4,3-a] [1,4]diazepine Ro17-4582 8.4559 / 3.5nM 4-(2-chlorophenyl)-9-methyl-6H-thieno[3,2-f] [1,2,4]triazolo[4,3-a] [1,4]diazepine Etizolam 8.5086 / 3.1nM 2-ethyl-4-(2-chlorophenyl)-9-methyl-6H-thieno[3,2-f] [1,2,4]triazolo[4,3-a] [1,4]diazepine 3307 40054-69-1 Deschloroetizolam 2-ethyl-4-phenyl-9-methyl-6H-thieno[3,2-f] [1,2,4]triazolo[4,3-a] [1,4]diazepine 827322 40054-73-7 Desmethyletizolam 2-ethyl-4-(2-chlorophenyl)-6H-thieno[3,2-f] [1,2,4]triazolo[4,3-a] [1,4]diazepine 12434325 40054-68-0 Fluetizolam 2-ethyl-4-(2-fluorophenyl)-9-methyl-6H-thieno[3,2-f] [1,2,4]triazolo[4,3-a] [1,4]diazepine 12434320 40054-88-4 Nitizolam 2-nitro-4-(2-chlorophenyl)-9-methyl-6H-thieno[3,2-f] [1,2,4]triazolo[4,3-a] [1,4]diazepine 70600959 Ro11-1465 8.8539 / 1.4nM 2-chloro-4-(2-chlorophenyl)-9-methyl-4H-thieno[3,2-f] [1,2,4]triazolo[4,3-a] [1,4]diazepine 3041455 54123-06-7 Brotizolam 8.9208 2-bromo-4-(2-chlorophenyl)-9-methyl-6H-thieno[3,2-f] [1,2,4]triazolo[4,3-a] [1,4]diazepine 2451 57801-81-7 Flubrotizolam (LS-152,574) 2-bromo-4-(2-fluorophenyl)-9-methyl-6H-thieno[3,2-f] [1,2,4]triazolo[4,3-a] [1,4]diazepine 3044878 57801-95-3 Ciclotizolam 2-bromo-4-(2-chlorophenyl)-9-cyclohexyl-6H-thieno[3,2-f] [1,2,4]triazolo[4,3-a] [1,4]diazepine 71949 58765-21-2 Zapizolam 8-chloro-6-(2-chlorophenyl)-4H-pyrido[2,3-f] [1,2,4]triazolo[4,3-a] [1,4]diazepine 68832 64098-32-4 Ro14-1636 8.8239 Ro11-7800 8.5376 / 2.9nM (2-chloro-4-(2-chlorophenyl)-6H-thieno[3,2-f] [1,2,4]triazolo[4,3-a] [1,4]diazepin-9-yl)methanamine Midazolam 8.3188 / 4.8nM 8-chloro-6-(2-fluorophenyl)-1-methyl-4H-imidazo[1,5-a] [1,4]benzodiazepine 4192 59467-70-8 alpha-Hydroxymidazolam 8.3468 / 4.5nM 8-chloro-6-(2-fluorophenyl)-1-hydroxymethyl-4H-imidazo[1,5-a] [1,4]benzodiazepine 107917 59468-90-5 Ro22-0284 8-chloro-6-(2-fluorophenyl)-1-hydroxymethyl-4-hydroxy-4H-imidazo[1,5-a] [1,4]benzodiazepine 10316307 64740-68-7 Climazolam 8-chloro-6-(2-chlorophenyl)-1-methyl-4H-imidazo[1,5-a] [1,4]benzodiazepine 68790 59467-77-5 Remimazolam methyl 3-[(4S)-8-bromo-1-methyl-6-(pyridin-2-yl)-4H-imidazo[1,2-a] [1,4]benzodiazepin-4-yl]propanoate 9824461 308242-62-8 Ro15-8670 7.8239 / 15nM ethyl 8-chloro-6-phenyl-4H-benzo[f]imidazo[1,5-a] [1,4]diazepine-3-carboxylate Ro16-0529 7.8539 / 14nM tert-butyl 7-chloro-6-phenyl-4H-benzo[f]imidazo[1,5-a] [1,4]diazepine-3-carboxylate Ro21-5205 8.1308 / 7.4nM methyl 8-chloro-6-(2-fluorophenyl)-4H-benzo[f]imidazo[1,5-a] [1,4]diazepine-3-carboxylate SH-053-R-CH3-2'F ethyl (4R)-8-ethynyl-6-(2-fluorophenyl)-4-methyl-4H-benzo[f]imidazo[1,5-a] [1,4]diazepine-3-carboxylate 11574585 872874-14-1 Ro22-1892 7.9208 / 12nM 8-chloro-6-(2-fluorophenyl)-3-(isopropoxycarbonyl)-4H-benzo[f]imidazo[1,5-a] [1,4]diazepine 5-oxide Ro22-0992 7.8861 / 13nM 8-chloro-6-(2-chlorophenyl)-4H-benzo[f]imidazo[1,5-a] [1,4]diazepine-3-carboxylic acid Ro21-8137 8.4559 / 3.5nM 8-chloro-6-(2-fluorophenyl)-4H-benzo[f]imidazo[1,5-a] [1,4]diazepine-3-carboxamide Ro21-8384 8.4202 8-chloro-6-(2-chlorophenyl)-4H-benzo[f]imidazo[1,5-a] [1,4]diazepine-3-carboxamide 162997 63176-94-3 Imidazenil 8-fluoro-6-(2-bromophenyl)-4H-benzo[f]imidazo[1,5-a] [1,4]diazepine-3-carboxamide 119194 151271-08-8 Ro23-0364 6-(2-chlorophenyl)-4H-benzo[f]imidazo[1,5-a] [1,4]diazepine-3-carboxamide 194998 113066-25-4 Ro21-8482 7.585 / 26nM 8-chloro-6-(2-chlorophenyl)-1-[(dimethylamino)methyl]-4H-benzo[f]imidazo[1,5-a] [1,4]diazepine-3-carboxamide Loprazolam 8.2007 (2Z)-6-(2-chlorophenyl)-2-[(4-methyl-1-piperazinyl)methylene]-8-nitro-2,4-dihydro-1H-imidazo[1,2-a] [1,4]benzodiazepin-1-one 3033860 61197-73-7 Fluloprazolam (2Z)-6-(2-fluorophenyl)-2-[(4-methyl-1-piperazinyl)methylene]-8-nitro-2,4-dihydro-1H-imidazo[1,2-a] [1,4]benzodiazepin-1-one 12371485 Ro14-1359 7.1549 / 70nM 7-chloro-5-(2-fluorophenyl)-1H-benzo[b]azepin-2(3H)-one Ro15-8867 7.6021 / 25nM 7-nitro-5-(2-chlorophenyl)-1H-benzo[b]azepin-2(3H)-one Ro14-7187 6.3872 / 410nM 1-methyl-6-phenyl-4H-benzo[f] [1,2,4]triazolo[4,3-a]azepine 85687871 Ro13-9868 7.3768 / 42nM 8-chloro-1-methyl-6-phenyl-4H-benzo[f] [1,2,4]triazolo[4,3-a]azepine Ro14-5921 7.7212 / 19nM 8-chloro-6-(2-fluorophenyl)-4H-benzo[f] [1,2,4]triazolo[4,3-a]azepine 20449965 Ro14-0304 8.1871 / 6.5nM 8-chloro-6-(2-fluorophenyl)-1-methyl-4H-benzo[f] [1,2,4]triazolo[4,3-a]azepine 20449964 Ro14-2652 8.2518 / 5.6nM (8-chloro-6-(2-fluorophenyl)-4H-benzo[f] [1,2,4]triazolo[4,3-a]azepin-1-yl)methanamine Ro15-9270 8.301 / 5nM 6-(2-chlorophenyl)-1-methyl-8-nitro-4H-benzo[f] [1,2,4]triazolo[4,3-a]azepine 20450010 Ro14-0609 7.6126 / 24.4nM 8-chloro-6-(2-fluorophenyl)-5,6-dihydro-4H-benzo[f] [1,2,4]triazolo[4,3-a]azepine Ro15-2201 8.8239 / 1.5nM methyl 6-phenyl-4H-benzo[f]imidazo[1,5-a]azepine-3-carboxylate Ro15-0791 8.6021 / 2.5nM ethyl 6-phenyl-4H-benzo[f]imidazo[1,5-a]azepine-3-carboxylate Ro15-2200 8.3768 / 4.2nM ethyl 6-(2-fluorophenyl)-4H-benzo[f]imidazo[1,5-a]azepine-3-carboxylate Ro14-3929 7.7959 / 16nM ethyl 8-chloro-6-(2-fluorophenyl)-4H-benzo[f]imidazo[1,5-a]azepine-3-carboxylate Ro14-3930 7.8239 / 15nM 8-chloro-6-(2-fluorophenyl)-4H-benzo[f]imidazo[1,5-a]azepine-3-carboxamide Ro14-5568 6.6383 / 230nM 8-chloro-6-(2-fluorophenyl)-4H-benzo[f]imidazo[1,5-a]azepine Ro22-1274 7.1249 / 75nM 8-chloro-1-(2-fluorophenyl)-3H-benzo[c]azepine 13271760 89376-31-8 Ro22-1251 7.9586 / 11nM 9-chloro-2-methyl-7-phenyl-5H-benzo[c]pyrimido[4,5-e]azepine Ro22-1366 8.3979 / 4nM 9-chloro-7-(2-fluorophenyl)-2-methyl-5H-benzo[c]pyrimido[4,5-e]azepine Ro22-2038 8.5528 / 2.8nM 9-chloro-7-(2-fluorophenyl)-5H-benzo[c]pyrimido[4,5-e]azepin-2-amine Ro22-3245 8.5528 / 2.8nM 9-chloro-7-(2-chlorophenyl)-5H-benzo[c]pyrimido[4,5-e]azepine Ro22-3148 6.3768 / 420nM 6-phenyl-2,4-dihydrobenzo[c] [1,2,3]triazolo[4,5-e]azepine Ro22-3147 8.284 / 5.2nM 6-(2-chlorophenyl)-2,4-dihydrobenzo[c] [1,2,3]triazolo[4,5-e]azepine Ro22-0780 7.9586 / 11nM 8-chloro-6-phenyl-2,4-dihydrobenzo[c] [1,2,3]triazolo[4,5-e]azepine Ro22-2466 8.7212 / 1.9nM 8-chloro-6-(2-fluorophenyl)-2,4-dihydrobenzo[c] [1,2,3]triazolo[4,5-e]azepine Ro22-2468 8.6021 Ro22-8515 8-chloro-6-(2-chlorophenyl)-1,4-dihydropyrrolo[3,4-d] [2]benzazepin-3(2H)-one 145981 Ro14-5974 8.1938 / 6.4nM ethyl 9-oxo-11,12,13,13a-tetrahydro-9H-benzo[e]imidazo[5,1-c]pyrrolo[1,2-a] [1,4]diazepine-1-carboxylate 10041121 88552-32-3 Ro15-4941 8.7696 / 1.7nM (S)-ethyl 8-chloro-9-oxo-11,12,13,13a-tetrahydro-9H-benzo[e]imidazo[5,1-c]pyrrolo[1,2-a] [1,4]diazepine-1-carboxylate Ro14-5975 7.2076 / 62nM (S)-ethyl 7-chloro-9-oxo-11,12,13,13a-tetrahydro-9H-benzo[e]imidazo[5,1-c]pyrrolo[1,2-a] [1,4]diazepine-1-carboxylate Ro16-3607 7.3372 / 46nM (S)-tert-butyl 8-methoxy-9-oxo-11,12,13,13a-tetrahydro-9H-benzo[e]imidazo[5,1-c]pyrrolo[1,2-a] [1,4]diazepine-1-carboxylate Ro16-6624 8 / 10nM (S)-tert-butyl 8-ethyl-9-oxo-11,12,13,13a-tetrahydro-9H-benzo[e]imidazo[5,1-c]pyrrolo[1,2-a] [1,4]diazepine-1-carboxylate Ro16-3774 8.4949 / 3.2nM (S)-tert-butyl 8-methyl-9-oxo-11,12,13,13a-tetrahydro-9H-benzo[e]imidazo[5,1-c]pyrrolo[1,2-a] [1,4]diazepine-1-carboxylate Ro16-0071 8.4949 / 3.2nM (S)-tert-butyl 9-oxo-11,12,13,13a-tetrahydro-9H-benzo[e]imidazo[5,1-c]pyrrolo[1,2-a] [1,4]diazepine-1-carboxylate Ro16-5824 8.4685 / 3.4nM (S)-tert-butyl 8-(methylthio)-9-oxo-11,12,13,13a-tetrahydro-9H-benzo[e]imidazo[5,1-c]pyrrolo[1,2-a] [1,4]diazepine-1-carboxylate Ro16-8912 8.2076 / 6.2nM (S)-tert-butyl 8-fluoro-9-oxo-11,12,13,13a-tetrahydro-9H-benzo[e]imidazo[5,1-c]pyrrolo[1,2-a] [1,4]diazepine-1-carboxylate Ro16-4261 8.1135 / 7.7nM (S)-tert-butyl 7-fluoro-9-oxo-11,12,13,13a-tetrahydro-9H-benzo[e]imidazo[5,1-c]pyrrolo[1,2-a] [1,4]diazepine-1-carboxylate Ro16-0075 8.6021 Ro16-6127 8.5086 / 3.1nM (S)-tert-butyl 8-chloro-7-fluoro-9-oxo-11,12,13,13a-tetrahydro-9H-benzo[e]imidazo[5,1-c]pyrrolo[1,2-a] [1,4]diazepine-1-carboxylate Ro16-3058 7.0458 Bretazenil 8.6576 (S)-tert-butyl 8-bromo-9-oxo-11,12,13,13a-tetrahydro-9H-imidazo[1,5-a]pyrrolo[2,1-c] [1,4]benzodiazepine-1-carboxylate 107926 84379-13-5 EVT-201 7-chloro-3-(5-[(dimethylamino)methyl]-1,2,4-oxadiazol-3-yl)-5-methyl-4,5-dihydro-6H-imidazo[1,5-a] [1,4]benzodiazepin-6-one 9885841 308239-86-3 FG-8205 7-chloro-5-methyl-3-(5-propan-2-yl-1,2,4-oxadiazol-3-yl)-4H-imidazo[1,5-a] [1,4]benzodiazepin-6-one 129710 122384-14-9 L-655,708 ethyl (13aS)-7-methoxy-9-oxo-11,12,13,13a-tetrahydro-9H-imidazo[1,5-a]pyrrolo[2,1-c] [1,4]benzodiazepine-1-carboxylate 5311203 130477-52-0 PWZ-029 8-chloro-3-(methoxymethyl)-5-methyl-4H-imidazo[1,5-a] [1,4]benzodiazepin-6-one 9971547 Ro48-6791 8-fluoro-5-methyl-3-(5-[(dipropylamino)methyl]-1,2,4-oxadiazol-3-yl)-4H-imidazo[1,5-a] [1,4]benzodiazepin-6-one 9953485 172407-17-9 Ro48-8684 8-fluoro-5-methyl-3-(5-[(dipropylamino)methyl]-1,3-oxazol-2-yl)-4H-imidazo[1,5-a] [1,4]benzodiazepin-6-one 9866317 Ro4938581 3-bromo-10-(difluoromethyl)-9H-benzo[f]imidazo[1,5-a] [1,2,4]triazolo[1,5-d] [1,4]diazepine 11624499 Ro16-6605 8.6778 Ro16-6048 8.4815 / 3.3nM (S)-tert-butyl 9-oxo-8-(trifluoromethyl)-11,12,13,13a-tetrahydro-9H-benzo[e]imidazo[5,1-c]pyrrolo[1,2-a] [1,4]diazepine-1-carboxylate Ro16-6950 8.5528 / 2.8nM (S)-tert-butyl 8-nitro-9-oxo-11,12,13,13a-tetrahydro-9H-benzo[e]imidazo[5,1-c]pyrrolo[1,2-a] [1,4]diazepine-1-carboxylate Ro16-4019 8.8539 / 1.4nM (S)-propyl 8-chloro-9-oxo-11,12,13,13a-tetrahydro-9H-benzo[e]imidazo[5,1-c]pyrrolo[1,2-a] [1,4]diazepine-1-carboxylate Ro16-3031 8.6021 / 2.5nM (S)-isopropyl 8-chloro-9-oxo-11,12,13,13a-tetrahydro-9H-benzo[e]imidazo[5,1-c]pyrrolo[1,2-a] [1,4]diazepine-1-carboxylate Ro16-9906 8.7696 / 1.7nM (S)-allyl 8-chloro-9-oxo-11,12,13,13a-tetrahydro-9H-benzo[e]imidazo[5,1-c]pyrrolo[1,2-a] [1,4]diazepine-1-carboxylate Ro16-7081 8.585 Ro16-7082 8.2007 / 6.3nM (S)-isobutyl 8-chloro-9-oxo-11,12,13,13a-tetrahydro-9H-benzo[e]imidazo[5,1-c]pyrrolo[1,2-a] [1,4]diazepine-1-carboxylate Ro16-7083 8.5376 / 2.9nM (13aS)-sec-butyl 8-chloro-9-oxo-11,12,13,13a-tetrahydro-9H-benzo[e]imidazo[5,1-c]pyrrolo[1,2-a] [1,4]diazepine-1-carboxylate Ro16-9918 8.6383 / 2.3nM (S)-cyclopropylmethyl 8-chloro-9-oxo-11,12,13,13a-tetrahydro-9H-benzo[e]imidazo[5,1-c]pyrrolo[1,2-a] [1,4]diazepine-1-carboxylate Ro16-4020 8.585 Ro16-6654 8.3979 / 4nM (S)-cyclohexyl 8-chloro-9-oxo-11,12,13,13a-tetrahydro-9H-benzo[e]imidazo[5,1-c]pyrrolo[1,2-a] [1,4]diazepine-1-carboxylate Ro17-3206 8.4685 Ro17-3207 8.284 Ro16-4021 8.8239 Ro17-1302 8.2757 / 5.3nM (S)-phenyl 8-chloro-9-oxo-11,12,13,13a-tetrahydro-9H-benzo[e]imidazo[5,1-c]pyrrolo[1,2-a] [1,4]diazepine-1-carboxylate Ro15-2427 IC50 >1000nM 5-methyl-6-oxo-5,6-dihydro-4H-benzo[f]imidazo[1,5-a] [1,4]diazepine-3-carboxamide Ro14-7437 8.5229 / 3nM ethyl 5-methyl-6-oxo-4H-imidazo[1,5-a] [1,4]benzodiazepine-3-carboxylate 127597 83210-63-3 Ro15-3505 8.5686 / 2.7nM ethyl 7-chloro-5-methyl-6-oxo-5,6-dihydro-4H-benzo[f]imidazo[1,5-a] [1,4]diazepine-3-carboxylate Ro15-1310 8.1675 / 6.8nM ethyl 8-chloro-5-methyl-6-oxo-5,6-dihydro-4H-benzo[f]imidazo[1,5-a] [1,4]diazepine-3-carboxylate 114888 78756-33-9 Ro15-1746 IC50 >1000nM ethyl 9-chloro-5-methyl-6-oxo-5,6-dihydro-4H-benzo[f]imidazo[1,5-a] [1,4]diazepine-3-carboxylate Ro15-3237 IC50 >1000nM ethyl 10-chloro-5-methyl-6-oxo-5,6-dihydro-4H-benzo[f]imidazo[1,5-a] [1,4]diazepine-3-carboxylate Ro15-5623 8.699 Flumazenil 8.6021 ethyl 8-fluoro-5-methyl-6-oxo-5,6-dihydro-4H-benzo[f]imidazo[1,5-a] [1,4]diazepine-3-carboxylate 3373 78755-81-4 Ro15-4513 ethyl 8-azido-5-methyl-6-oxo-5,6-dihydro-4H-benzo[f]imidazo[1,5-a] [1,4]diazepine-3-carboxylate 5081 91917-65-6 Sarmazenil ethyl 7-chloro-5-methyl-6-oxo-5,6-dihydro-4H-benzo[f]imidazo[1,5-a] [1,4]diazepine-3-carboxylate 71231 78771-13-8 Iomazenil ethyl 7-iodo-5-methyl-6-oxo-5,6-dihydro-4H-benzo[f]imidazo[1,5-a] [1,4]diazepine-3-carboxylate 10251042 127985-21-1 Ro17-9741 8.6198 / 2.4nM (S)-methyl 8-chloro-9-oxo-9,11,12,12a-tetrahydroazeto[1,2-a]benzo[e]imidazo[5,1-c] [1,4]diazepine-1-carboxylate Ro16-0858 8.8861 ethyl 8-chloro-9-oxo-12,12a-dihydro-9H,11H-azeto[1,2-a]benzo[e]imidazo[5,1-c] [1,4]diazepine-1-carboxylate Ro16-0153 8.2757 tert-butyl 8-chloro-9-oxo-12,12a-dihydro-9H,11H-azeto[2,1-c]benzo[e]imidazo[1,5-a] [1,4]diazepine-1-carboxylate Ro17-1812 8.8861 (S)-cyclopropylmethyl 8-chloro-9-oxo-9,11,12,12a-tetrahydroazeto[1,2-a]benzo[e]imidazo[5,1-c] [1,4]diazepine-1-carboxylate 146197 90450-01-4 Ro17-3211 8.62 Ro17-3401 9.0458 Ro17-3620 8.2924 Ro16-9351 8.4318 Ro16-9905 8.9208 Ro17-1338 9 Zopiclone 7.5086 6-(5-chloropyridin-2-yl)-7-oxo-6,7-dihydro-5H-pyrrolo[3,4-b]pyrazin-5-yl 4-methylpiperazine-1-carboxylate 5735 43200-80-2 Suriclone 8.6778 [6-(7-chloro- 1,8-naphthyridin-2-yl)- 5-oxo- 3,7-dihydro- 2H-[1,4]dithiino[2,3-c]pyrrol- 7-yl]4-methylpiperazine- 1-carboxylate 40903 53813-83-5 CL-218,872 6.9208 3-methyl-6-[3-(trifluoromethyl)phenyl]-[1,2,4]triazolo[3,4-f]pyridazine 107950 66548-69-4 GBLD-345 9 2-(4-aminophenyl)-3-methoxy-N-[(3-methoxyphenyl)methyl]imidazo[2,1-f]pyridazin-6-amine 4602899 122479-08-7

See also

• Benzodiazepine
• Benzodiazepine dependence
• Benzodiazepine withdrawal syndrome

References

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Further reading

• Gitlow, Stuart (1 October 2006). Substance Use Disorders: A Practical Guide (2nd ed.). USA: Lippincott Williams and Wilkins. p. 110. ISBN 978-0-7817-6998-3.
• Galanter, Marc; Kleber, Herbert D. (1 July 2008). The American Psychiatric Publishing Textbook of Substance Abuse Treatment (4th ed.). United States of America: American Psychiatric Publishing Inc. p. 216. ISBN 978-1-58562-276-4.