クロルメザノン
Wikipedia preview
出典(authority):フリー百科事典『ウィキペディア(Wikipedia)』「2016/03/23 20:24:08」(JST)
[Wiki en表示]
"Trancopal" redirects here. For Trancopal Dolo, see Flupirtine.
Chlormezanone
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Systematic (IUPAC) name |
2-(4-chlorophenyl)-3-methyl-1,1-dioxo-1,3-thiazinan-4-one
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Clinical data |
AHFS/Drugs.com |
International Drug Names |
Routes of
administration |
Oral |
Legal status |
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Pharmacokinetic data |
Biological half-life |
40.5 hours |
Identifiers |
CAS Number |
80-77-3 Y |
ATC code |
M03BB02 (WHO) |
PubChem |
CID 2717 |
IUPHAR/BPS |
7323 |
DrugBank |
DB01178 Y |
ChemSpider |
2616 Y |
UNII |
GP568V9G19 Y |
KEGG |
D00268 Y |
ChEBI |
CHEBI:3619 Y |
ChEMBL |
CHEMBL1200714 N |
Chemical data |
Formula |
C11H12ClNO3S |
Molar mass |
273.737 g/mol |
SMILES
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O=S1(CCC(N(C)C1C2=CC=C(C=C2)Cl)=O)=O
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InChI
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InChI=1S/C11H12ClNO3S/c1-13-10(14)6-7-17(15,16)11(13)8-2-4-9(12)5-3-8/h2-5,11H,6-7H2,1H3 Y
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Key:WEQAYVWKMWHEJO-UHFFFAOYSA-N Y
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NY (what is this?) (verify) |
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.
Chemistry
- Sterling Drug Inc., US 3082209 (1958).
- 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.
- 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)
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5-HT1A agonists |
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GABAAR 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
- Carbamates
- Chlormezanone‡
- Ethanol
- Etifoxine; Herbs:
- Kava
- Skullcap
- Valerian
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α2δ VDCC blockers |
- Gabapentin
- Gabapentin enacarbil
- Phenibut
- Pregabalin
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Antidepressants |
- SSRIs
- SNRIs
- SARIs
- TCAs
- TeCAs
- MAOIs; Others: Agomelatine
- Bupropion
- Vilazodone
- Vortioxetine
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Sympatholytics |
- Beta blockers
- Clonidine
- Guanfacine
- Prazosin
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Others |
- Benzoctamine
- Cannabidiol
- Cycloserine
- Fabomotizole
- Hydroxyzine
- Kanna
- Lavender
- Lorpiprazole
- Mebicar
- Mepiprazole
- Nicotine
- Opipramol
- Oxaflozane‡
- Phenaglycodol
- Phenibut
- Picamilon
- Selank
- Tenoten
- Tiagabine
- Tofisopam
- Validolum
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Skeletal muscle relaxants (M03)
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Peripherally acting
(primarily antinicotinic,
NMJ block) |
Non-depolarizing
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Curare alkaloids
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- Alcuronium
- Dimethyltubocurarine
- Tubocurarine
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4° ammonium agents
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- ultra-short duration: Gantacurium
- short duration: Mivacurium
- Chandonium
- intermediate duration: Atracurium
- Cisatracurium
- Fazadinium
- Rocuronium
- Vecuronium
- long duration: Doxacurium
- Dimethyltubocurarine
- Pancuronium
- Pipecuronium
- Laudexium
- Gallamine
- unsorted: Hexafluronium (Hexafluorenium)
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Depolarizing
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- Choline derivatives: Suxamethonium (Succinylcholine)
- Polyalkylene derivatives: Hexamethonium
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ACh release inhibitors
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Centrally acting |
Carbamic acid esters
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- Carisoprodol
- Cyclarbamate
- Difebarbamate
- Febarbamate
- Meprobamate
- Phenprobamate
- Styramate
- Tybamate
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Benzodiazepines
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- Bromazepam
- Diazepam
- Clonazepam
- Flunitrazepam
- Lorazepam
- Nitrazepam
- Temazepam
- Tetrazepam
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Nonbenzodiazepines
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Thienodiazepines
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Quinazolines
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Anticholinergics
(Antimuscarinics)
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- Cyclobenzaprine
- Orphenadrine
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Other
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- Arbaclofen placarbil
- Baclofen
- Chlormezanone
- Chlorphenesin
- Chlorzoxazone
- Donepezil
- Eperisone
- Fenyramidol
- Flopropione
- Gabapentin
- GHB
- Mephenesin
- Mephenoxalone
- Metaxalone
- Methocarbamol
- Phenibut
- Pregabalin
- Pridinol
- Promoxolane
- Quinine
- Thiocolchicoside
- Tizanidine
- Tolperisone
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Directly acting |
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GABAA receptor positive allosteric modulators
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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
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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
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Benzodiazepines |
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Carbamates |
- Carisbamate
- Carisoprodol
- Clocental
- Cyclarbamate
- Difebarbamate
- Emylcamate
- Ethinamate
- Febarbamate
- Felbamate
- Hexapropymate
- Lorbamate
- Mebutamate
- Meprobamate
- Nisobamate
- Pentabamate
- Phenprobamate
- Procymate
- Styramate
- Tetrabamate
- Tybamate
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Flavonoids |
- 6-Methylapigenin
- Ampelopsin (dihydromyricetin)
- Apigenin
- Baicalein
- Baicalin
- Catechin
- EGC
- EGCG
- Hispidulin
- Linarin
- Luteolin
- Rc-OMe
- Skullcap constituents (e.g., baicalin)
- Wogonin
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Imidazoles |
- Etomidate
- Metomidate
- Propoxate
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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
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Monoureides |
- Acecarbromal
- Apronal (apronalide)
- Bromisoval
- Carbromal
- Capuride
- Ectylurea
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Neuroactive steroids |
- Acebrochol
- Allopregnanolone
- Alfadolone
- Alfaxalone
- 3α-Androstanediol
- Androstenol
- Androsterone
- Cholesterol
- DHDOC
- 3α-DHP
- 5α-DHP
- 5β-DHP
- Etiocholanolone
- Ganaxolone
- Hydroxydione
- Minaxolone
- Org 20599
- Org 21465
- Pregnanolone (eltanolone)
- Progesterone
- Renanolone
- SAGE-217
- SAGE-689
- THDOC
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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
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Phenols |
- Fospropofol
- Propofol
- Thymol
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Piperidinediones |
- Glutethimide
- Methyprylon
- Piperidione
- Pyrithyldione
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Pyrazolopyridines |
- Cartazolate
- Etazolate
- ICI-190,622
- Tracazolate
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Quinazolinones |
- Afloqualone
- Cloroqualone
- Diproqualone
- Etaqualone
- Mebroqualone
- Mecloqualone
- Methaqualone
- Methylmethaqualone
- Nitromethaqualone
- SL-164
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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
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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
- SAGE-547
- 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
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See also: GABAergics
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English Journal
- Erythema multiforme secondary to dimenhydrinate in a patient with previous similar reactions to pamabrom.
- Tan DS1, Sklar GE.
- The Annals of pharmacotherapy.Ann Pharmacother.2014 Mar;48(3):425-8. doi: 10.1177/1060028013518728. Epub 2014 Jan 6.
- OBJECTIVE: To report a case of erythema multiforme secondary to dimenhydrinate and pamabrom cross-sensitivity.CASE SUMMARY: A 22-year-old Chinese female presented with a complaint of lip mucosal ulceration with necrosis and stomatitis, worsening over the past 24 hours and associated with reduced ora
- PMID 24396093
- [Determination of chlormezanone in serum by gas chromatography].
- Chen ZR, Chen LM, Du SM.
- Zhonghua lao dong wei sheng zhi ye bing za zhi = Zhonghua laodong weisheng zhiyebing zazhi = Chinese journal of industrial hygiene and occupational diseases.Zhonghua Lao Dong Wei Sheng Zhi Ye Bing Za Zhi.2012 May;30(5):391-2.
- PMID 22804998
- Flupirtine in pain management: pharmacological properties and clinical use.
- Devulder J1.
- CNS drugs.CNS Drugs.2010 Oct;24(10):867-81. doi: 10.2165/11536230-000000000-00000.
- Flupirtine is a centrally acting, non-opioid analgesic that is available in a number of European countries for the treatment of a variety of pain states. The therapeutic benefits seen with flupirtine relate to its unique pharmacological properties. Flupirtine displays indirect NDMA receptor antagoni
- PMID 20839897
Japanese Journal
- Structure of Chlormezanone
- Analytical Sciences: X-ray Structure Analysis Online 21, X57-X58, 2005
- NAID 130004442638
Related Links
- Chlormezanone is a medicine available in a number of countries worldwide. A list of US medications equivalent to Chlormezanone is available on the Drugs.com website. ... In the US, Chlormezanone is a member of the drug class miscellaneous anxiolytics, sedatives and hypnotics
- forum Join the Word of the Day Mailing List For webmasters TheFreeDictionary Google Bing? Word / Article Starts with Ends with Text ... chlormezanone a nonbarbiturate sedative, used as a muscle relaxant and tranquilizer.