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 effects. 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. Due to increased sensitivity and potentially dangerous adverse events among elderly patients, it is recommended to avoid prescribing them as specified by the 2015 American Geriatrics Society Beers Criteria.[6] Individuals with an impaired liver also metabolize benzodiazepines more slowly. 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 and can lead to withdrawal symptoms.[This quote needs a citation] 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.[7][8] Equivalent doses of benzodiazepines differ as much as 20 fold.[9][10][11] Data in the table below is taken from the Ashton "Benzodiazepine Equivalency Table".[4][12][13][14] (hours)
hypnotic, muscle relaxant
4 (IV)
of active metabolite (hours)
Drug name
Common trade names[a]
Year approved (US FDA)
Approx. equivalent oral doses to 10 mg diazepam[b] (mg)
Time to peak onset of action
Adinazolam
Deracyn
Research chemical
1–2
3
anxiolytic, antidepressant
Alprazolam
Xanax, Helex, Xanor, Trankimazin, Onax, Alprox, Misar, Restyl, Solanax, Tafil, Neurol, Frontin, Kalma, Ksalol, Farmapram
1981
0.5
1–3[16]
11-13 [10–20][16]
anxiolytic, antidepressant[17] Bentazepam[c]
Thiadipona
1–3
2–4
anxiolytic
Bretazenil[18]
2.5
anxiolytic, anticonvulsant
Bromazepam
Lectopam, Lexaurin, Lexatin, Lexotanil, Lexotan, Bromam
1981
6
1–5
20–40
anxiolytic,
Bromazolam
Research chemical
anxiolytic
Brotizolam[d]
Lendormin, Dormex, Sintonal, Noctilan
0.5
0.5–2
4–5
hypnotic
Camazepam
Albego, Limpidon, Paxor
40[19]
1–3
6–11
anxiolytic
Chlordiazepoxide
Librium, Risolid, Elenium
1960
25
1.5–6
36–200
anxiolytic
Cinazepam
Levana
2–4
60
hypnotic, anxiolytic
Cinolazepam
Gerodorm
0.5–2
9
hypnotic
Clobazam
Onfi, Frisium, Urbanol
2011
20
1–5
8–60
anxiolytic, anticonvulsant
Clonazepam
Rivatril, Rivotril, Klonopin, Iktorivil, Paxam
1975
0.5
1–5
19.5–50
anticonvulsant, anxiolytic
Clonazolam
Research chemical
0.2
1–4
10–18
hypnotic, anticonvulsant
Clorazepate
Tranxene, Tranxilium
1972
20
Variable
32–152
anxiolytic, anticonvulsant
Clotiazepam[c]
Veratran, Clozan, Rize
1–3
4
anxiolytic
Cloxazolam
Sepazon, Olcadil
1.5[19]
2–5
55–77[19]
anxiolytic, anticonvulsant
Delorazepam
Dadumir
1–2
79<[20]
anxiolytic, amnesic
Deschloroetizolam[d]
Research chemical
anxiolytic
Diazepam
Antenex, Apaurin, Apzepam, Apozepam, Diazepan, Hexalid, Normabel, Pax, Stesolid, Stedon, Tranquirit, Valium, Vival, Valaxona
1963
10
1–1.5
32–205
anxiolytic, anticonvulsant, muscle relaxant, amnesic
Diclazepam[21]
Research chemical
1.5–3
42
anxiolytic, muscle relaxant
Estazolam
ProSom, Nuctalon
1990
2[19]
3–5
10–24
hypnotic, anxiolytic
Ethyl carfluzepate
Not approved
2
1–5
11–24
hypnotic
Etizolam[d]
Etilaam, Etizest, Pasaden, Depas
Often sold as a research chemical, but is approved for human use in many countries. Controlled substance in some US states, Canada, Germany, Austria, and others.[22][23]
2
1–3
5-7
anxiolytic, muscle relaxant, anticonvulsant
Ethyl loflazepate
Victan, Meilax, Ronlax
2[19]
2.5–3
73–119
anxiolytic
Flualprazolam
Research chemical
0.25
1-2
12-22
anxiolytic, hypnotic
Flubromazepam[24]
Research chemical
1.5–8
100–220
anxiolytic, hypnotic, amnesic, muscle relaxant, anticonvulsant
Flubromazolam
Research chemical
0.075
0.5-5
10-20[25]
hypnotic
Fluclotizolam[d]
Research chemical
anxiolytic
Flunitrazepam
Rohypnol, Hipnosedon, Vulbegal, Fluscand, Flunipam, Ronal, Rohydorm, Hypnodorm
1972
1
0.5–3
18–200
hypnotic
Flunitrazolam
Research chemical
0.125
0.5-1
5-13
hypnotic
Flurazepam
Dalmadorm, Dalmane, Fluzepam
1970
20
1–1.5
40–250
hypnotic
Flutazolam
Coreminal
10
1-3
47-100
hypnotic
Flutoprazepam
Restas
1984
2.5
0.5–9
87[26]
hypnotic, anticonvulsant, muscle relaxant
Halazepam
Paxipam
1981
40
3–6
15-35 [30-100]
anxiolytic
Ketazolam
Anxon
1980
20
2.5–6
30-100 [36-200]
anxiolytic
Loprazolam
Dormonoct
1983
1.5
2–4
6–20[27]
hypnotic
Lorazepam
Ativan, Orfidal, Lorenin, Lorsilan, Temesta, Tavor, Lorabenz
1971
1
2–4
10–20
anxiolytic, anticonvulsant, hypnotic, muscle relaxant[28][14][29] Lormetazepam
Loramet, Noctamid, Pronoctan
1984
1.5
0.5–2
10-12
hypnotic, anxiolytic
Meclonazepam
Research chemical
anxiolytic
Medazepam
Nobrium, Ansilan, Mezapam, Rudotel, Raporan
10
4-8
36–200
anxiolytic
Metizolam[d]
Research chemical
2–4
12
anxiolytic
Mexazolam
Melex, Sedoxil
1–2
anxiolytic
Midazolam
Dormicum, Flormidal, Versed, Hypnovel, Dormonid
1985
10 (oral)
0.5–1
1.8-6
hypnotic, anticonvulsant
Nifoxipam
Research chemical
hypnotic
Nimetazepam
Erimin
1984
5
0.5–3
14–30
hypnotic
Nitemazepam
Research chemical
2
0.5-5
10-27
hypnotic, anticonvulsant
Nitrazepam
Mogadon, Alodorm, Pacisyn, Dumolid, Nitrazadon
1965
10
0.5–7
17–48
hypnotic, anticonvulsant
Nitrazolam
Research chemical
hypnotic
Nordiazepam
Madar, Stilny
30–150
anxiolytic
Norflurazepam
Research chemical
5
47-100
hypnotic
Oxazepam
Seresta, Serax, Serenid, Serepax, Sobril, Oxabenz, Oxapax, Oxascand, Ox-Pam, Opamox, Alepam, Medopam, Murelax, Noripam, Purata
1965
30
3–4
4–11
anxiolytic
Phenazepam
Phenazepam, Phenzitat
Research chemical
1.5–4
60
anxiolytic, anticonvulsant
Pinazepam
Domar
40–100
anxiolytic
Prazepam
Lysanxia, Centrax
15
2–6
36–200
anxiolytic
Premazepam
Not approved
2–6
10–13
anxiolytic
Pyrazolam
Research chemical
1–1.5
16–18[30]
anxiolytic, amnesic
Quazepam
Doral
1985
20
1–5
39–120
hypnotic
Rilmazafone
Rhythmy
11
hypnotic
Temazepam
Restoril, Normison, Euhypnos, Temaze, Tenox
1981
20
0.5–3
4–11
hypnotic, anxiolytic, muscle relaxant
Tetrazepam
Myolastan
1–3
3–26
muscle relaxant, anxiolytic
Triazolam
Halcion, Rilamir
1980
0.25
0.5–2
2
hypnotic
Drug name
Common trade names
Year approved
Approx. equivalent oral doses to 10 mg diazepam (mg)
Time to peak onset of action (hours)
Elimination half-life of active metabolite (hours)
Therapeutic use
Atypical benzodiazepine receptor ligands
Drug name
Common trade names
Year approved (US FDA)
Elimination half-life
Therapeutic use
DMCM
anxiogenic, convulsant
Flumazenil[e]
Anexate, Lanexat, Mazicon, Romazicon
1
antidote
Eszopiclone§
Lunesta
2004
6
hypnotic
Zaleplon§
Sonata, Starnoc
1999
1
hypnotic
Zolpidem§
Ambien, Nytamel, Sanval, Stilnoct, Stilnox, Sublinox (Canada), Xolnox, Zoldem, Zolnod
1992
2.6
hypnotic
Zopiclone§
Imovane, Rhovane, Ximovan; Zileze; Zimoclone; Zimovane; Zopitan; Zorclone, Zopiklone
4–6
hypnotic
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.[36]
A large number of benzodiazepine derivatives have been synthesised and their structure-activity relationships explored in detail.[37][38] 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).[39][40][41][42][43][44] Other benzodiazepines are also listed for comparison purposes,[45][46][47] 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.)[48][49][50][51][52]
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.[53][54] 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 GABAA 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 GABAA 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 GABAA modulatory action of the classical benzodiazepines,[55] 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 GABAA receptors.
|
- Benzodiazepine
- Benzodiazepine dependence
- Benzodiazepine withdrawal syndrome
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