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

• ChemBase编号: 1049
• 分子式: C11H12ClNO3S
• 平均质量: 273.73588
• 单一同位素质量: 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

名称和登记号

名称

• IUPAC标准名: 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传统名: chlormezanone; muskel
• 商标名: 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
• 别名: 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

登记号

• CAS号: 80-77-3
• EC号: 201-307-4
• MDL号: MFCD00143951
• PubChem SID: 160964512; 46505352
• PubChem CID: 2717
• CHEBI ID: 3619
• ATC码: M03BB02
• CHEMBL: 1200714
• Chemspider ID: 2616
• DrugBank ID: DB01178
• KEGG ID: D00268
• 美国药典/FDA物质标识码: GP568V9G19
• 维基百科标题: Chlormezanone

理论计算性质

JChem

• Acid pKa: 19.072128
• 质子受体: 3
• 质子供体: 0
• LogD (pH = 5.5): 0.9171674
• LogD (pH = 7.4): 0.9171674
• Log P: 0.9171674
• 摩尔折射率: 64.88 cm^3
• 极化性: 26.133999 Å^3
• 极化表面积: 54.45 Å^2
• 可自由旋转的化学键: 1
• 里宾斯基五规则: true

ALOGPS 2.1

• Log P: 0.84
• LOG S: -2.23
• 溶解度: 1.61e+00 g/l

分子性质

理化性质

• 溶解度: 2500 mg/L (hardly soluble)
• 疏水性(logP): 1.3

安全信息

• 保存条件: -20°C; Room Temperature (15-30°C)
• RTECS编号: XJ1050000
• 欧盟危险性物质标志: 有害性(Harmful) (Xn)
• 危险公开号: R:22
• 安全公开号: S:36/37/39

药理学性质

• 给药途径: Oral
• 半衰期: 40.5 hours
• 法定药品分级: Rx-only

产品相关信息

• 纯度: 95+%
• 成盐信息: Free Base

详细说明

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• Drug Groups: approved; withdrawn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]

参考文献

• 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