"Trancopal" redirects here. For Trancopal Dolo, see Flupirtine .
Chlormezanone (marketed under the brandname Trancopal or Fenaprim ) is a drug used as an anxiolytic and a muscle relaxant .
Its use was discontinued in many countries from 1996 on, due to rare but serious cases of toxic epidermal necrolysis .
Synthesis [ ] Sterling Drug Inc., US 3082209
Surrey, A. R.; Webb, W. G.; Gesler, R. M. (1958). "Central Nervous System Depressants. The Preparation of Some 2-Aryl-4-metathiazanones". Journal of the American Chemical Society . 80 (13): 3469. doi :10.1021/ja01546a065 . References [ ] Wollina U, Hipler U, Seeling A, Oelschlager H (2005). "Investigations of interactions of chlormezanone racemate and its enantiomers on human keratinocytes and human leucoytes in vitro". Skin Pharmacol Physiol . 18 (3): 132–138. doi :10.1159/000084910 . PMID 15897685 . S2CID 36642315 . Seeling A, Oelschläger H, Rothley D (2000). "Important pharmaceutical-chemical characteristics of the central muscle relaxant chlormezanone". Pharmazie . 55 (4): 293–6. PMID 10798243 . Oelschläger H, Klinger W, Rothley D, Seeling A, Bockhard H, Hofmann B, Machts H, Riederer H, Rackur H (1998). "[Cleavage and biotransformation of the central muscle relaxant chlormezanone]". Pharmazie . 53 (9): 620–4. PMID 9770210 . Gautier V, Vincon G, Demotes-Mainard F, Albin H (1990). "[Pharmacokinetics of chlormezanone in healthy volunteers] (original in French)". Pharmazie . 45 (4): 315–9. PMID 2399514 .
Anxiolytics (N05B )
5-HT1A R agonists GABAA R PAMs
Benzodiazepines :Adinazolam Alprazolam Bromazepam Camazepam Chlordiazepoxide Clobazam Clonazepam Clorazepate Clotiazepam Cloxazolam Diazepam # Ethyl loflazepate Etizolam Fludiazepam Halazepam Ketazolam Lorazepam # Medazepam Nordazepam Oxazepam Pinazepam Prazepam ; Others: Alpidem ‡ Barbiturates (e.g., phenobarbital )Carisoprodol Carbamates (e.g., meprobamate )Chlormezanone ‡ Ethanol (alcohol) Etifoxine Imepitoin ; Herbs: Kava Skullcap Valerian Gabapentinoids (α2 δ VDCC blockers )
Gabapentin Gabapentin enacarbil Phenibut Pregabalin Antidepressants
SSRIs escitalopram )SNRIs duloxetine )SARIs trazodone )TCAs clomipramine # )TeCAs mirtazapine )MAOIs phenelzine ); Others: Agomelatine Bupropion Tianeptine Vilazodone Vortioxetine Sympatholytics (Antiadrenergics )
Alpha-1 blockers (e.g., prazosin )Alpha-2 agonists (e.g., clonidine , dexmedetomidine , guanfacine )Beta blockers (e.g., propranolol ) Others
Benzoctamine Cannabidiol Cycloserine Fabomotizole Hydroxyzine Kanna Lavender Lorpiprazole Mebicar Mepiprazole Nicotine Opipramol Oxaflozane ‡ Phenaglycodol Phenibut Picamilon Selank Tiagabine Tofisopam Validolum
# WHO-EM ‡ Withdrawn from marketClinical trials :
† Phase III § Never to phase III
Skeletal muscle relaxants (M03 )
Peripherally acting antinicotinic ,NMJ block )
Non-depolarizing
Curare alkaloids 4° ammonium agents
ultra-short duration: Gantacurium intermediate duration: Atracurium Cisatracurium Fazadinium Rocuronium Vecuronium long duration: Doxacurium Dimethyltubocurarine Pancuronium Pipecuronium Laudexium Gallamine
Depolarizing
Choline derivatives :Suxamethonium (Succinylcholine) ACh release inhibitors
Centrally acting
Carbamic acid estersBenzodiazepines
Bromazepam Diazepam Clonazepam Flunitrazepam Lorazepam Nitrazepam Temazepam Tetrazepam Nonbenzodiazepines Thienodiazepines Quinazolines Anticholinergics Antimuscarinics )
Cyclobenzaprine Orphenadrine Other
Directly acting
GABA A receptor positive modulatorsAlcohols
Butanol Chloralodol Chlorobutanol (cloretone) Ethanol (alcohol) (alcoholic drink )Ethchlorvynol Isobutanol Isopropanol Menthol Methanol Methylpentynol Pentanol Petrichloral Propanol tert -Butanol (2M2P)tert -Pentanol (2M2B)Tribromoethanol Trichloroethanol Triclofos Trifluoroethanol Barbiturates Benzodiazepines Carbamates Flavonoids
Ampelopsin (dihydromyricetin) Apigenin Baicalein Baicalin Catechin EGC EGCG Hispidulin Luteolin Skullcap constituents (e.g., baicalin )Wogonin Imidazoles Kava constituents
Desmethoxyyangonin Kavain Methysticin Yangonin Monoureides Neuroactive steroids Nonbenzodiazepines Phenols
Fospropofol Propofol Thymol Piperidinediones Pyrazolopyridines Quinazolinones 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 Avermectins (e.g., ivermectin )Bromide compounds (e.g., lithium bromide , potassium bromide , sodium bromide )Carbamazepine Chloralose Chlormezanone Clomethiazole DEABL Dihydroergolines (e.g., dihydroergocryptine , , dihydroergotamine , ergoloid (dihydroergotoxine) )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 Niacinamide Org 25,435 Phenytoin Propanidid Retigabine (ezogabine) Safranal Seproxetine Stiripentol (e.g., sulfonmethane (sulfonal) , tetronal , trional )
Terpenoids (e.g., borneol )Topiramate Valerian constituents (e.g., isovaleric acid , isovaleramide , valerenic acid , )Unsorted benzodiazepine site positive modulators: α-Pinene See also: Receptor/signaling modulators • GABA receptor modulators • GABA metabolism/transport modulators
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