2-(4-chlorophenyl)-3-methyl-1$l^{6},3-thiazinane-1,1,4-trione

• ChemBase ID: 1049
• Molecular Formular: C11H12ClNO3S
• Molecular Mass: 273.73588
• Monoisotopic Mass: 273.02264193
• SMILES: Clc1ccc(C2S(=O)(=O)CCC(=O)N2C)cc1
• Canonical SMILES: CN1C(=O)CCS(=O)(=O)C1c1ccc(cc1)Cl
• 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
• InChIKey: WEQAYVWKMWHEJO-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-(4-chlorophenyl)-3-methyl-1$l^{6},3-thiazinane-1,1,4-trione; 2-(4-chlorophenyl)-3-methyl-1λ^6,3-thiazinane-1,1,4-trione
• IUPAC Traditional name: chlormezanone; muskel
• Brand Name: Alinam; Banabil-sintyal; Banabin; Banabin-Sintyal; Banabin-syntyal; Bisina; Chlomedinon; Clorilax; Lobak; Mio-Sed; Miorilax; Muskel; Muskel-Trancopal; Myolespen; Phenarol; Rexan; Rilansyl; Rilaquil; Rilasol; Rilassol; Rilax; Rillasol; Supotran; Suprotan; Tanafol; Trancopal; Trancote; Tranrilax; Transanate
• Synonyms: Chlormezanone [BAN:INN:JAN]; Chlormezanon; Chlormezanonum [INN-Latin]; Chlormethazanone; Chlormethazone; Clormetazanone; Clormetazon; Clormezanona [INN-Spanish]; Clormezanone [DCIT]; Dichloromethazanone; Dichloromezanone; dl-Chlormezanone; Chlormezanone; Trancopal; 2-(4-Chlorophenyl)-3-methyl-1,3-thiazinan-4-one 1,1-dioxide

Database IDs

• CAS Number: 80-77-3
• EC Number: 201-307-4
• MDL Number: MFCD00143951
• PubChem SID: 160964512; 46505352
• PubChem CID: 2717
• CHEBI ID: 3619
• ATC CODE: M03BB02
• CHEMBL: 1200714
• Chemspider ID: 2616
• DrugBank ID: DB01178
• KEGG ID: D00268
• Unique Ingredient Identifier: GP568V9G19
• Wikipedia Title: Chlormezanone

CALCULATED PROPERTIES

JChem

• Acid pKa: 19.072128
• H Acceptors: 3
• H Donor: 0
• LogD (pH = 5.5): 0.9171674
• LogD (pH = 7.4): 0.9171674
• Log P: 0.9171674
• Molar Refractivity: 64.88 cm^3
• Polarizability: 26.133999 Å^3
• Polar Surface Area: 54.45 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 0.84
• LOG S: -2.23
• Solubility (Water): 1.61e+00 g/l

PROPERTIES

Physical Property

• Solubility: 2500 mg/L (hardly soluble)
• Hydrophobicity(logP): 1.3

Safety Information

• Storage Condition: -20°C; Room Temperature (15-30°C)
• RTECS: XJ1050000
• European Hazard Symbols: Harmful (Xn)
• Risk Statements: R:22
• Safety Statements: S:36/37/39

Pharmacology Properties

• Admin Routes: Oral
• Half Life: 40.5 hours
• Legal Status: Rx-only

Product Information

• Purity: 95+%
• Salt Data: Free Base

DETAILS

MP Biomedicals - 02159741

Skeletal muscle relaxant.

DrugBank - DB01178

• Drug Groups: approved; 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]
• Indication: Used in the management of anxiety and in the treatment of muscle spasm.
• Pharmacology: Chlormezanone 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).
• Toxicity: Symptoms 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
• References: 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] ; Seeling A, Oelschlager H, Rothley D: [Important pharmaceutical-chemical characteristics of the central muscle relaxant chlormezanone] Pharmazie. 2000 Apr;55(4):293-6. [Pubmed] ; 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] ; 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: Wikipedia

Selleck Chemicals - S2021

Research Area: Neurological Disease
Biological Activity:
Chlormezanone(Trancopal)，a non-benzodiazepine that is used in the management of anxiety. It has been suggested for use in the treatment of muscle spasm. Chlormezanone 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. [1]

REFERENCES

• 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
• Gautier V, Vincon G, Demotes-Mainard F, Albin H: [Pharmacokinetics of chlormezanone in healthy volunteers] Therapie. 1990 Jul-Aug;45(4):315-9. Pubmed
• 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
• Seeling A, Oelschlager H, Rothley D: [Important pharmaceutical-chemical characteristics of the central muscle relaxant chlormezanone] Pharmazie. 2000 Apr;55(4):293-6. Pubmed
• http://www.drugbank.ca/drugs/DB01178