5-chloro-2,3-dihydro-1,3-benzoxazol-2-one

• ChemBase编号: 240
• 分子式: C7H4ClNO2
• 平均质量: 169.56516
• 单一同位素质量: 168.99305605
• SMILES: Clc1cc2[nH]c(=O)oc2cc1
• Canonical SMILES: Clc1ccc2c(c1)[nH]c(=O)o2
• InChI: InChI=1S/C7H4ClNO2/c8-4-1-2-6-5(3-4)9-7(10)11-6/h1-3H,(H,9,10)
• InChIKey: TZFWDZFKRBELIQ-UHFFFAOYSA-N

名称和登记号

名称

• IUPAC标准名: 5-chloro-2,3-dihydro-1,3-benzoxazol-2-one
• IUPAC传统名: chlorzoxazone; 5-chloro-3H-1,3-benzoxazol-2-one
• 商标名: Biomioran; EZE-DS; Escoflex; Flexazone; Mioran; Miotran; Myoflexin; Myoflexine; Neoflex; Paraflex; Parafon Forte Dsc; Pathorysin; Relaxazone; Remular; Remular-S; Solaxin; Strifon Forte Dsc; Usaf Ma-10
• 别名: 5-氯-2(3H)-苯并噁唑酮; Chloroxazone; Chlorzoxazon; Chlorzoxane; Chlorzoxazone; 5-Chloro-1,3-benzoxazol-2(3H)-one; 5-Chloro-3H-benzoxazol-2-one; 5-Chloro-2,3-dihydro-2-oxo-1,3-benzoxazole; 5-Chloro-1,3-benzoxazol-2(3H)-one 99%; 5-Chloro-2(3H)-benzoxazolone; Chlorzoxazone; 5-Chloro-2-hydroxybenzoxazole; 5-Chloro-2-benzoxazolinone; Chlorzoxazone; 5-Chloro-2(3H)-benzoxazolone; 5-chloro-2(3h)-benzoxazolone

登记号

• CAS号: 95-25-0
• EC号: 202-403-9
• MDL号: MFCD00005717
• 默克索引号: 142194
• PubChem SID: 24277702; 160963703; 46507755
• PubChem CID: 2733

理论计算性质

JChem

• Acid pKa: 9.39075
• 质子受体: 2
• 质子供体: 1
• LogD (pH = 5.5): 1.9356183
• LogD (pH = 7.4): 1.9314784
• Log P: 1.9356713
• 摩尔折射率: 41.069 cm^3
• 极化性: 15.259254 Å^3
• 极化表面积: 38.33 Å^2
• 可自由旋转的化学键: 0
• 里宾斯基五规则: true

ALOGPS 2.1

• Log P: 2.09
• LOG S: -1.76
• 溶解度: 2.96e+00 g/l

分子性质

理化性质

• 溶解度: 1000 mg/L
• 熔点: 184 - 186°C; 189-192°C; 191-192 °C(lit.); 191-192°C
• 疏水性(logP): 1.6; 1.871

安全信息

• 保存条件: Room Temperature (15-30°C)
• 保存注意事项: Harmful/Irritant; IRRITANT
• RTECS编号: DM5250000
• 欧盟危险性物质标志: X; 有害性(Harmful) (Xn)
• 德国WGK号: 3
• 危险公开号: 22-36/37/38; R:22-36/37/38
• 安全公开号: 26-36; 26-36/37; S:25-26-36/37/39
• TSCA收录: false; 是
• GHS危险品标识: GHS06; GHS07
• GHS警示词: Warning
• GHS危险声明: H301-H315-H319-H335; H302-H315-H319-H335
• GHS警示性声明: P261-P301+P310-P305+P351+P338-P302+P352-P405-P501A; P261-P305 + P351 + P338
• 个人保护装置: dust mask type N95 (US), Eyeshields, Gloves

药理学性质

• 作用靶点: Others

产品相关信息

• 纯度: 95%; 97%; 98%; 99%
• 成盐信息: Free Base

详细说明

MP Biomedicals - 02154979

(5-Chloro-2-hydroxybenzoxazole) Crystalline

DrugBank - DB00356

• Drug Groups: approved
• Description: A centrally acting central muscle relaxant with sedative properties. It is claimed to inhibit muscle spasm by exerting an effect primarily at the level of the spinal cord and subcortical areas of the brain. (From Martindale, The Extra Pharmacopoea, 30th ed, p1202)
• Indication: For the relief of discomfort associated with acute painful musculoskeletal conditions.
• Pharmacology: Chlorzoxazone, a synthetic compound, inhibits antigen-induced bronchospasms and, hence, is used to treat asthma and allergic rhinitis. Chlorzoxazone is used as an ophthalmic solution to treat conjunctivitis and is taken orally to treat systemic mastocytosis and ulcerative colitis. Chlorzoxazone is also a centrally-acting agent for painful musculoskeletal conditions. Data available from animal experiments as well as human study indicate that chlorzoxazone acts primarily at the level of the spinal cord and subcortical areas of the brain where it inhibits multisynaptic reflex a.c. involved in producing and maintaining skeletal muscle spasm of varied etiology. The clinical result is a reduction of the skeletal muscle spasm with relief of pain and increased mobility of the involved muscles.
• Toxicity: Oral, mouse: LD₅₀ = 440 mg/kg; Oral, rat: LD₅₀ = 763 mg/kg; Symptoms of overdose include diarrhea, dizziness, drowsiness, headache, light-headedness, nausea, and vomiting.
• Affected Organisms: Humans and other mammals
• Biotransformation: Chlorzoxazone is rapidly metabolized in the liver and is excreted in the urine, primarily in a conjugated form as the glucuronide.
• Protein Binding: 13-18%
• Elimination: Chlorzoxazone is rapidly metabolized and is excreted in the urine, primarily in a conjugated form as the glucuronide.
• References: Dong DL, Luan Y, Feng TM, Fan CL, Yue P, Sun ZJ, Gu RM, Yang BF: Chlorzoxazone inhibits contraction of rat thoracic aorta. Eur J Pharmacol. 2006 Sep 18;545(2-3):161-6. Epub 2006 Jun 29. [Pubmed] ; Park JY, Kim KA, Park PW, Ha JM: Effect of high-dose aspirin on CYP2E1 activity in healthy subjects measured using chlorzoxazone as a probe. J Clin Pharmacol. 2006 Jan;46(1):109-14. [Pubmed] ; Wan J, Ernstgard L, Song BJ, Shoaf SE: Chlorzoxazone metabolism is increased in fasted Sprague-Dawley rats. J Pharm Pharmacol. 2006 Jan;58(1):51-61. [Pubmed]
• External Links: Wikipedia; RxList; PDRhealth; Drugs.com

Sigma Aldrich - C4397

Biochem/physiol Actions
Chlorzoxazone is a skeletal muscle relaxant.

参考文献

• Dong DL, Luan Y, Feng TM, Fan CL, Yue P, Sun ZJ, Gu RM, Yang BF: Chlorzoxazone inhibits contraction of rat thoracic aorta. Eur J Pharmacol. 2006 Sep 18;545(2-3):161-6. Epub 2006 Jun 29. Pubmed
• Park JY, Kim KA, Park PW, Ha JM: Effect of high-dose aspirin on CYP2E1 activity in healthy subjects measured using chlorzoxazone as a probe. J Clin Pharmacol. 2006 Jan;46(1):109-14. Pubmed
• Wan J, Ernstgard L, Song BJ, Shoaf SE: Chlorzoxazone metabolism is increased in fasted Sprague-Dawley rats. J Pharm Pharmacol. 2006 Jan;58(1):51-61. Pubmed