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Identification
NameChlormezanone
Accession NumberDB01178  (APRD00865)
TypeSmall Molecule
GroupsApproved, Withdrawn
Description

A non-benzodiazepine that is used in the management of anxiety. It has been suggested for use in the treatment of muscle spasm. [PubChem]

Structure
Thumb
Synonyms
(+-)-Chlormezanone
(±)-chlormezanone
2-(P-Chlorophenyl)tetrahydro-3-methyl-4H-1,3-thiazin-4-one 1,1-dioxide
2-(P-Chlorphenyl)-3-methyl-1,3-perhydrothiazin-4-on-1,1-dioxide
Chlormethazanone
Chlormezanona
Chlormezanone
Chlormezanonum
Clormezanona
External Identifiers Not Available
Prescription ProductsNot Available
Generic Prescription ProductsNot Available
Over the Counter ProductsNot Available
International Brands
NameCompany
FenaprimNot Available
TrancopalWinthropSreon
Brand mixturesNot Available
SaltsNot Available
Categories
UNIIGP568V9G19
CAS number80-77-3
WeightAverage: 273.736
Monoisotopic: 273.022641652
Chemical FormulaC11H12ClNO3S
InChI KeyInChIKey=WEQAYVWKMWHEJO-UHFFFAOYSA-N
InChI
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
IUPAC Name
2-(4-chlorophenyl)-3-methyl-1λ⁶,3-thiazinane-1,1,4-trione
SMILES
CN1C(C2=CC=C(Cl)C=C2)S(=O)(=O)CCC1=O
Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as chlorobenzenes. These are compounds containing one or more chlorine atoms attached to a benzene moiety.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassHalobenzenes
Direct ParentChlorobenzenes
Alternative Parents
Substituents
  • Chlorobenzene
  • 1,3-thiazinane
  • Aryl halide
  • Aryl chloride
  • Tertiary carboxylic acid amide
  • Sulfone
  • Tertiary amine
  • Lactam
  • Carboxamide group
  • Azacycle
  • Organoheterocyclic compound
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Organochloride
  • Organohalogen compound
  • Carbonyl group
  • Amine
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External DescriptorsNot Available
Pharmacology
IndicationUsed in the management of anxiety and in the treatment of muscle spasm.
PharmacodynamicsChlormezanone is a non-benzodiazepine muscle relaxant. It was discontinued worldwide in 1996 by its manufacturer due to confirmed serious and rare cutaneous reactions (toxic epidermal necrolysis).
Mechanism of actionChlormezanone binds to central benzodiazepine receptors which interact allosterically with GABA receptors. This potentiates the effects of the inhibitory neurotransmitter GABA, increasing the inhibition of the ascending reticular activating system and blocking the cortical and limbic arousal that occurs following stimulation of the reticular pathways.
AbsorptionNot Available
Volume of distributionNot Available
Protein bindingNot Available
MetabolismNot Available
Route of eliminationNot Available
Half lifeNot Available
ClearanceNot Available
ToxicitySymptoms of overdose include drowsiness, weakness, nausea, dizziness, abdominal pain, cerebral oedema and renal tubular necrosis, hyperglycaemia and hypoglycaemia, liver damage, encephalopathy, coma and death.
Affected organisms
  • Humans and other mammals
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9167
Blood Brain Barrier+0.9383
Caco-2 permeable-0.5597
P-glycoprotein substrateNon-substrate0.6347
P-glycoprotein inhibitor INon-inhibitor0.6885
P-glycoprotein inhibitor IINon-inhibitor0.9959
Renal organic cation transporterNon-inhibitor0.7164
CYP450 2C9 substrateNon-substrate0.6022
CYP450 2D6 substrateNon-substrate0.7983
CYP450 3A4 substrateSubstrate0.6616
CYP450 1A2 substrateNon-inhibitor0.9045
CYP450 2C9 inhibitorNon-inhibitor0.9071
CYP450 2D6 inhibitorNon-inhibitor0.9231
CYP450 2C19 inhibitorNon-inhibitor0.9025
CYP450 3A4 inhibitorNon-inhibitor0.9375
CYP450 inhibitory promiscuityHigh CYP Inhibitory Promiscuity0.5186
Ames testNon AMES toxic0.6263
CarcinogenicityNon-carcinogens0.7622
BiodegradationNot ready biodegradable0.6329
Rat acute toxicity2.6246 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9892
hERG inhibition (predictor II)Non-inhibitor0.7018
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397 )
Pharmacoeconomics
ManufacturersNot Available
PackagersNot Available
Dosage formsNot Available
PricesNot Available
PatentsNot Available
Properties
StateSolid
Experimental Properties
PropertyValueSource
melting point116.2-118.6Merck Index 2072
water solubility2500 mg/L (at 25 °C)MERCK INDEX (1996)
logP1.3Not Available
Predicted Properties
PropertyValueSource
Water Solubility1.61 mg/mLALOGPS
logP0.84ALOGPS
logP0.92ChemAxon
logS-2.2ALOGPS
pKa (Strongest Acidic)19.07ChemAxon
pKa (Strongest Basic)-2.5ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area54.45 Å2ChemAxon
Rotatable Bond Count1ChemAxon
Refractivity64.88 m3·mol-1ChemAxon
Polarizability25.89 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Not Available
Spectra
Spectrum TypeDescriptionSplash Key
MSMass Spectrum (Electron Ionization)splash10-rz30000000-6c729f1a3c9cb4241b45View in MoNA
1D NMR1H NMR SpectrumNot Available
1D NMR13C NMR SpectrumNot Available
References
Synthesis ReferenceNot Available
General References
  1. Wollina U, Hipler UC, Seeling A, Oelschlager H: Investigations of interactions of chlormezanone racemate and its enantiomers on human keratinocytes and human leucoytes in vitro. Skin Pharmacol Physiol. 2005 May-Jun;18(3):132-8. Pubmed
  2. Seeling A, Oelschlager H, Rothley D: [Important pharmaceutical-chemical characteristics of the central muscle relaxant chlormezanone] Pharmazie. 2000 Apr;55(4):293-6. Pubmed
  3. Oelschlager H, Klinger W, Rothley D, Seeling A, Bockhard H, Hofmann B, Machts H, Riederer H, Rackur H: [Cleavage and biotransformation of the central muscle relaxant chlormezanone] Pharmazie. 1998 Sep;53(9):620-4. Pubmed
  4. Gautier V, Vincon G, Demotes-Mainard F, Albin H: [Pharmacokinetics of chlormezanone in healthy volunteers] Therapie. 1990 Jul-Aug;45(4):315-9. Pubmed
External Links
ATC CodesM03BB02
AHFS CodesNot Available
PDB EntriesNot Available
FDA labelNot Available
MSDSNot Available
Interactions
Drug Interactions
Drug
AlmotriptanThe risk or severity of adverse effects can be increased when Almotriptan is combined with Chlormezanone.
AminophyllineThe therapeutic efficacy of Chlormezanone can be decreased when used in combination with Aminophylline.
AmitriptylineThe risk or severity of adverse effects can be increased when Amitriptyline is combined with Chlormezanone.
AmoxapineThe risk or severity of adverse effects can be increased when Amoxapine is combined with Chlormezanone.
AmphetamineChlormezanone may decrease the stimulatory activities of Amphetamine.
BenzphetamineChlormezanone may decrease the stimulatory activities of Benzphetamine.
BuspironeThe risk or severity of adverse effects can be increased when Buspirone is combined with Chlormezanone.
CabergolineThe risk or severity of adverse effects can be increased when Cabergoline is combined with Chlormezanone.
CitalopramThe risk or severity of adverse effects can be increased when Citalopram is combined with Chlormezanone.
ClomipramineThe risk or severity of adverse effects can be increased when Clomipramine is combined with Chlormezanone.
ClozapineThe risk or severity of adverse effects can be increased when Chlormezanone is combined with Clozapine.
CyclobenzaprineThe risk or severity of adverse effects can be increased when Cyclobenzaprine is combined with Chlormezanone.
DesipramineThe risk or severity of adverse effects can be increased when Desipramine is combined with Chlormezanone.
DesvenlafaxineThe risk or severity of adverse effects can be increased when Desvenlafaxine is combined with Chlormezanone.
DextroamphetamineChlormezanone may decrease the stimulatory activities of Dextroamphetamine.
DextromethorphanThe risk or severity of adverse effects can be increased when Dextromethorphan is combined with Chlormezanone.
DihydroergotamineThe risk or severity of adverse effects can be increased when Dihydroergotamine is combined with Chlormezanone.
DonepezilDonepezil may increase the central neurotoxic activities of Chlormezanone.
DoxepinThe risk or severity of adverse effects can be increased when Doxepin is combined with Chlormezanone.
DuloxetineThe risk or severity of adverse effects can be increased when Duloxetine is combined with Chlormezanone.
DyphyllineThe therapeutic efficacy of Chlormezanone can be decreased when used in combination with Dyphylline.
EletriptanThe risk or severity of adverse effects can be increased when Eletriptan is combined with Chlormezanone.
Ergoloid mesylateThe risk or severity of adverse effects can be increased when Ergoloid mesylate is combined with Chlormezanone.
ErgonovineThe risk or severity of adverse effects can be increased when Ergonovine is combined with Chlormezanone.
ErgotamineThe risk or severity of adverse effects can be increased when Ergotamine is combined with Chlormezanone.
EscitalopramThe risk or severity of adverse effects can be increased when Escitalopram is combined with Chlormezanone.
FentanylThe risk or severity of adverse effects can be increased when Fentanyl is combined with Chlormezanone.
FluoxetineThe risk or severity of adverse effects can be increased when Fluoxetine is combined with Chlormezanone.
FluvoxamineThe risk or severity of adverse effects can be increased when Fluvoxamine is combined with Chlormezanone.
FosphenytoinThe serum concentration of Fosphenytoin can be increased when it is combined with Chlormezanone.
FrovatriptanThe risk or severity of adverse effects can be increased when Frovatriptan is combined with Chlormezanone.
GalantamineGalantamine may increase the central neurotoxic activities of Chlormezanone.
Gamma Hydroxybutyric AcidChlormezanone may increase the central nervous system depressant (CNS depressant) activities of Gamma Hydroxybutyric Acid.
ImipramineThe risk or severity of adverse effects can be increased when Imipramine is combined with Chlormezanone.
IsocarboxazidThe risk or severity of adverse effects can be increased when Isocarboxazid is combined with Chlormezanone.
LevomilnacipranThe risk or severity of adverse effects can be increased when Levomilnacipran is combined with Chlormezanone.
LinezolidThe risk or severity of adverse effects can be increased when Linezolid is combined with Chlormezanone.
LisdexamfetamineChlormezanone may decrease the stimulatory activities of Lisdexamfetamine.
LithiumLithium may increase the neurotoxic activities of Chlormezanone.
LorcaserinThe risk or severity of adverse effects can be increased when Lorcaserin is combined with Chlormezanone.
MaprotilineThe risk or severity of adverse effects can be increased when Maprotiline is combined with Chlormezanone.
MethadoneThe risk or severity of adverse effects can be increased when Methadone is combined with Chlormezanone.
MethamphetamineChlormezanone may decrease the stimulatory activities of Methamphetamine.
MethylphenidateThe risk or severity of adverse effects can be increased when Chlormezanone is combined with Methylphenidate.
MetoclopramideThe risk or severity of adverse effects can be increased when Metoclopramide is combined with Chlormezanone.
MetyrosineThe risk or severity of adverse effects can be increased when Metyrosine is combined with Chlormezanone.
MilnacipranThe risk or severity of adverse effects can be increased when Milnacipran is combined with Chlormezanone.
MoclobemideThe risk or severity of adverse effects can be increased when Moclobemide is combined with Chlormezanone.
NaratriptanThe risk or severity of adverse effects can be increased when Naratriptan is combined with Chlormezanone.
NefazodoneThe risk or severity of adverse effects can be increased when Nefazodone is combined with Chlormezanone.
NortriptylineThe risk or severity of adverse effects can be increased when Nortriptyline is combined with Chlormezanone.
OlanzapineThe risk or severity of adverse effects can be increased when Olanzapine is combined with Chlormezanone.
ParoxetineThe risk or severity of adverse effects can be increased when Paroxetine is combined with Chlormezanone.
PethidineThe risk or severity of adverse effects can be increased when Pethidine is combined with Chlormezanone.
PhendimetrazineChlormezanone may decrease the stimulatory activities of Phendimetrazine.
PhenelzineThe risk or severity of adverse effects can be increased when Phenelzine is combined with Chlormezanone.
PhentermineChlormezanone may decrease the stimulatory activities of Phentermine.
PhenytoinThe serum concentration of Phenytoin can be increased when it is combined with Chlormezanone.
ProcarbazineThe risk or severity of adverse effects can be increased when Procarbazine is combined with Chlormezanone.
PromethazineThe risk or severity of adverse effects can be increased when Promethazine is combined with Chlormezanone.
ProtriptylineThe risk or severity of adverse effects can be increased when Protriptyline is combined with Chlormezanone.
QuinagolideThe therapeutic efficacy of Quinagolide can be decreased when used in combination with Chlormezanone.
RasagilineThe risk or severity of adverse effects can be increased when Rasagiline is combined with Chlormezanone.
RivastigmineRivastigmine may increase the central neurotoxic activities of Chlormezanone.
RizatriptanThe risk or severity of adverse effects can be increased when Rizatriptan is combined with Chlormezanone.
SelegilineThe risk or severity of adverse effects can be increased when Selegiline is combined with Chlormezanone.
SertralineThe risk or severity of adverse effects can be increased when Sertraline is combined with Chlormezanone.
Sodium oxybateChlormezanone may increase the central nervous system depressant (CNS depressant) activities of Sodium oxybate.
SumatriptanThe risk or severity of adverse effects can be increased when Sumatriptan is combined with Chlormezanone.
Tedizolid PhosphateThe risk or severity of adverse effects can be increased when Tedizolid Phosphate is combined with Chlormezanone.
TeduglutideThe serum concentration of Chlormezanone can be increased when it is combined with Teduglutide.
TetrabenazineThe risk or severity of adverse effects can be increased when Tetrabenazine is combined with Chlormezanone.
TheophyllineThe therapeutic efficacy of Chlormezanone can be decreased when used in combination with Theophylline.
TramadolThe risk or severity of adverse effects can be increased when Tramadol is combined with Chlormezanone.
TranylcypromineThe risk or severity of adverse effects can be increased when Tranylcypromine is combined with Chlormezanone.
TrazodoneThe risk or severity of adverse effects can be increased when Trazodone is combined with Chlormezanone.
TrimipramineThe risk or severity of adverse effects can be increased when Trimipramine is combined with Chlormezanone.
VenlafaxineThe risk or severity of adverse effects can be increased when Venlafaxine is combined with Chlormezanone.
VilazodoneThe risk or severity of adverse effects can be increased when Vilazodone is combined with Chlormezanone.
VortioxetineThe risk or severity of adverse effects can be increased when Vortioxetine is combined with Chlormezanone.
ZolmitriptanThe risk or severity of adverse effects can be increased when Zolmitriptan is combined with Chlormezanone.
Food InteractionsNot Available

Targets

1. Translocator protein

Kind: Protein

Organism: Human

Pharmacological action: yes

Actions: agonist

Components

Name UniProt ID Details
Translocator protein P30536 Details

References:

  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. Pubmed
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. Pubmed
  3. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. Pubmed

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Drug created on June 13, 2005 07:24 / Updated on January 11, 2014 08:14