CAS 80-77-3|Supotran|chlormezanone|Lobak|Chlormethazanone|Bisina|Myolespen|Dichloromezanone|Chlormezanonum [INN-Latin]|Chlormezanone|Suprotan|Rilaquil|Banabin|Chlormethazone|Clormetazanone|Rilax|Ban...

General Information

Structure

Molecular Formula

C₁₁H₁₂ClNO₃S

Molecular Mass

273.73588

Exact Mass

273.02264193

Charge

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

Canonic Smiles

CN1C(=O)CCS(=O)(=O)C1c1ccc(cc1)Cl

Isomeric Smiles

Clc1ccc(C2S(=O)(=O)CCC(=O)N2C)cc1

Calculated Properties

JChem

Acid pKa

19.072128

H Acceptors

H Donor

LogD (pH = 5.5)

0.9171674

LogD (pH = 7.4)

0.9171674

Log P

0.9171674

Molar Refractivity

64.88

Polarizability

26.133999

Polar Surface Area

54.45

Rotatable Bonds

Lipinski's Rule of Five

true

ALOGPS 2.1

Log P

0.84

LOG S

-2.23

Solubility (Water)

1.61e+00 g/l

Data Source

Names and Identifiers

Synonyms

DichloromezanoneChlormezanonum [INN-Latin]ChlormethazanoneChlormezanonedl-ChlormezanoneClormetazanoneChlormezanonChlormethazoneClormezanone [DCIT]Clormezanona [INN-Spanish]Chlormezanone [BAN:INN:JAN]ClormetazonDichloromethazanoneTrancopal2-(4-Chlorophenyl)-3-methyl-1,3-thiazinan-4-one 1,1-dioxide

Brand Name

SuprotanBisinaSupotranLobakMyolespenRilaquilBanabil-sintyalRilaxRillasolTrancopalBanabinRexanMio-SedMiorilaxTrancoteBanabin-syntyalMuskel-TrancopalBanabin-SintyalAlinamTransanateTranrilaxChlomedinonClorilaxRilassolRilasolMuskelPhenarolRilansylTanafol

IUPAC Traditional name

chlormezanone muskel

IUPAC name

2-(4-chlorophenyl)-3-methyl-1$l^{6},3-thiazinane-1,1,4-trione 2-(4-chlorophenyl)-3-methyl-1λ⁶,3-thiazinane-1,1,4-trione

Names and Identifiers

Registration numbers

CAS Number

Wikipedia Title

Chemspider ID

PubChem CID

DrugBank ID

CHEMBL

ATC CODE

Registration numbers

Properties

Physical Property

Hydrophobicity(logP)

1.3

Solubility

2500 mg/L (hardly soluble)

Product Information

Salt Data

Free Base

Certificate of Analysis

Download link

Purity

95+%

Pharmacology Properties

Half Life

40.5 hours

Admin Routes

Oral

Legal Status

Rx-only

Properties

Related Proteins

Molecular Spectra

No Data Available

Click here to submit data

Molecule Details

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approved; withdrawn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]

MP Biomedicals

02159741

Skeletal muscle relaxant.

Wikipedia

Chlormezanone

Molecule Details

References

PubChem Literature

From Data Sources

• Gautier V, Vincon G, Demotes-Mainard F, Albin H: [Pharmacokinetics of chlormezanone in healthy volunteers] Therapie. 1990 Jul-Aug;45(4):315-9. 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

References

Bioactivity

PubChem BioAssay

Bioactivity

Names and Identifiers

Synonyms

Brand Name

IUPAC Traditional name

chlormezanone muskel

IUPAC name

2-(4-chlorophenyl)-3-methyl-1$l^{6},3-thiazinane-1,1,4-trione 2-(4-chlorophenyl)-3-methyl-1λ⁶,3-thiazinane-1,1,4-trione

References

PubChem Literature

From Data Sources

• Gautier V, Vincon G, Demotes-Mainard F, Albin H: [Pharmacokinetics of chlormezanone in healthy volunteers] Therapie. 1990 Jul-Aug;45(4):315-9. 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

Bioactivity

PubChem BioAssay

Registration numbers

CAS Number

Wikipedia Title

Chemspider ID

PubChem CID

DrugBank ID

CHEMBL

ATC CODE

Properties

Physical Property

Hydrophobicity(logP)

1.3

Solubility

2500 mg/L (hardly soluble)

Product Information

Salt Data

Free Base

Certificate of Analysis

Download link

Purity

95+%

Pharmacology Properties

Half Life

40.5 hours

Admin Routes

Oral

Legal Status

Rx-only

Molecule Details

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

Affected Organisms

Humans and other mammals

References

• Seeling A, Oelschlager H, Rothley D: [Important pharmaceutical-chemical characteristics of the central muscle relaxant chlormezanone] Pharmazie. 2000 Apr;55(4):293-6. [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

MP Biomedicals

02159741

Skeletal muscle relaxant.

Wikipedia

Chlormezanone

Molecule

ID:1049