2-methyl-2-({[(propan-2-yl)carbamoyl]oxy}methyl)pentyl carbamate

• ChemBase编号: 278
• 分子式: C12H24N2O4
• 平均质量: 260.32996
• 单一同位素质量: 260.17360726
• SMILES: O(CC(CCC)(COC(=O)N)C)C(=O)NC(C)C
• Canonical SMILES: CCCC(COC(=O)N)(COC(=O)NC(C)C)C
• InChI: InChI=1S/C12H24N2O4/c1-5-6-12(4,7-17-10(13)15)8-18-11(16)14-9(2)3/h9H,5-8H2,1-4H3,(H2,13,15)(H,14,16)
• InChIKey: OFZCIYFFPZCNJE-UHFFFAOYSA-N

名称和登记号

名称

• IUPAC标准名: 2-methyl-2-({[(propan-2-yl)carbamoyl]oxy}methyl)pentyl carbamate; 2-[(carbamoyloxy)methyl]-2-methylpentyl N-(propan-2-yl)carbamate
• IUPAC传统名: 2-{[(isopropylcarbamoyl)oxy]methyl}-2-methylpentyl carbamate; carisoprodol
• 商标名: Artifar; Caridolin; Chinchen; Fibrosona; Flexagilt; Flexagit; Flexidon; Listaflex; Meprodat; Muslax; Neotica; Scutamil-C; Skutamil; Soma; Carisoma; Mioartrina; Miolisodal; Mioratrina; Flexartal; Atonalyt; Nospasm; Relasom; Somanil; Apesan; Arusal; Flexal; Mioril; Sanoma
• 别名: N-(1-Methylethyl)carbamic Acid 2-[[(Aminocarbonyl)oxy]methyl]-2-methylpentyl Ester; Domarax; N-Isopropyl-2-methyl-2-propyl-1,3-propanediol Dicarbamate; Flexal; NIH 10966; NSC 172124; Somalgit; Stialgin; 2-methyl-2-({[(propan-2-yl)carbamoyl]oxy}methyl)pentyl carbamate; Sanoma; Isoprothane; Isoprotane; Isomeprobamate; Carisoprodatum; Carisoprodate; Carisoprodol; 1-Methylethyl)carbamic acid 2-[[(aminocarbonyl)oxy]-methyl]-2-methylpentyl ester; Carisoprodol

登记号

• CAS号: 78-44-4
• EC号: 201-118-7
• MDL号: MFCD00057661
• PubChem SID: 24278083; 46506377; 160963741
• PubChem CID: 2576
• CHEBI ID: 3419
• ATC码: M03BA02
• CHEMBL: 1233
• Chemspider ID: 2478
• DrugBank ID: DB00395
• KEGG ID: D00768
• 美国药典/FDA物质标识码: 21925K482H
• 维基百科标题: Carisoprodol
• Medline Plus: a682578

理论计算性质

JChem

• Acid pKa: 15.057489
• 质子受体: 2
• 质子供体: 2
• LogD (pH = 5.5): 1.9243119
• LogD (pH = 7.4): 1.9243119
• Log P: 1.9243119
• 摩尔折射率: 67.1008 cm^3
• 极化性: 26.694498 Å^3
• 极化表面积: 90.65 Å^2
• 可自由旋转的化学键: 9
• 里宾斯基五规则: true

ALOGPS 2.1

• Log P: 1.76
• LOG S: -2.52
• 溶解度: 7.92e-01 g/l

分子性质

理化性质

• 溶解度: 0.3 mg/ml; Chloroform; DMSO; ethanol: soluble
• 外观: Off-White Low Melting Solid
• 熔点: 90-94°C
• 疏水性(logP): 2.1; 2.341

安全信息

• 保存条件: -20°C; Refrigerator; Room Temperature (15-30°C)
• RTECS编号: FB3325000
• 欧盟危险性物质标志: 有害性(Harmful) (Xn)
• 德国WGK号: 3
• 危险公开号: 22; R:22-36/37/38
• 安全公开号: 36; S:25-26-36/37/39
• GHS危险品标识: GHS07
• GHS警示词: Warning
• GHS危险声明: H302
• 个人保护装置: dust mask type N95 (US), Eyeshields, Gloves
• 毒品管制信息: USDEA Schedule IV
• 保存温度: 2-8°C

药理学性质

• 给药途径: Oral
• 排泄: Renal
• 半衰期: 2 hours
• 代谢: Hepatic (CYP2C19-mediated)
• 蛋白结合率: 60%
• 法定药品分级: Schedule IV (US)
• 妊娠期药物分类: C

产品相关信息

• 纯度: 95%
• 成盐信息: Free Base

详细说明

DrugBank - DB00395

• Drug Groups: approved
• Description: A centrally acting skeletal muscle relaxant whose mechanism of action is not completely understood but may be related to its sedative actions. It is used as an adjunct in the symptomatic treatment of musculoskeletal conditions associated with painful muscle spasm. (From Martindale, The Extra Pharmacopoeia, 30th ed, p1202)
• Indication: For the relief of discomfort associated with acute, painful, musculoskeletal conditions.
• Pharmacology: Carisoprodol is used as a skeletal muscle relaxant. One of its metabolites, meprobamate, is available as an anxiolytic agent.
• Toxicity: Symptoms of overdose include drowsiness, giddiness, nausea, indigestion, or rash. Other adverse effects attributed to therapeutic use of carisoprodol include dizziness, irritability, insomnia, diplopia, temporary loss of vision, ataxia, weakness, headache, and dysarthria. Non-CNS adverse effects include gastrointestinal complaints, tachycardia, and postural hypotension. Patients sensitive to sulfites or tartrazine may experience wheezing, allergic rashes including erythema multiforme, or anaphylaxis after using some preparations of carisoprodol which contain such additives
• Affected Organisms: Humans and other mammals
• Biotransformation: Hepatic. Metabolized in the liver via the cytochrome P450 oxidase isozyme CYP2C19.
• Half Life: 8 hours
• Protein Binding: 60%
• Elimination: Carisoprodol is eliminated by both renal and non-renal routes.
• Clearance: * oral cl=0.772 L/hour/kg [Women]; * oral cl=0.38 L/hour/kg [Men]
• References: Toth PP, Urtis J: Commonly used muscle relaxant therapies for acute low back pain: a review of carisoprodol, cyclobenzaprine hydrochloride, and metaxalone. Clin Ther. 2004 Sep;26(9):1355-67. [Pubmed] ; Chou R, Peterson K, Helfand M: Comparative efficacy and safety of skeletal muscle relaxants for spasticity and musculoskeletal conditions: a systematic review. J Pain Symptom Manage. 2004 Aug;28(2):140-75. [Pubmed] ; Littrell RA, Hayes LR, Stillner V: Carisoprodol (Soma): a new and cautious perspective on an old agent. South Med J. 1993 Jul;86(7):753-6. [Pubmed]
• External Links: Wikipedia; RxList; Drugs.com

Selleck Chemicals - S2049

Research Area: Neurological Disease
Biological Activity:

Sigma Aldrich - C8759

Biochem/physiol Actions
Metabolite of meprobamate that is a skeletal muscle relaxant, reduces muscle spasm by depression of brainstem neurons.
Other Notes
Tandem Mass Spectrometry data independently generated by Scripps Center for Metabolomics is available to view or download in PDF. C8759.pdf Tested metabolites are featured on Scripps Center for Metabolomics METLIN Metabolite Database. To learn more, visit sigma.com/metlin.

Toronto Research Chemicals - C183580

Muscle relaxant (skeletal).

参考文献

• Toth PP, Urtis J: Commonly used muscle relaxant therapies for acute low back pain: a review of carisoprodol, cyclobenzaprine hydrochloride, and metaxalone. Clin Ther. 2004 Sep;26(9):1355-67. Pubmed
• Littrell RA, Hayes LR, Stillner V: Carisoprodol (Soma): a new and cautious perspective on an old agent. South Med J. 1993 Jul;86(7):753-6. Pubmed
• Chou R, Peterson K, Helfand M: Comparative efficacy and safety of skeletal muscle relaxants for spasticity and musculoskeletal conditions: a systematic review. J Pain Symptom Manage. 2004 Aug;28(2):140-75. Pubmed
• Musso, D., et al.: J. Med. Chem. 46, 399 (2003)
• Newman, P., et al.: Eur. J. Clin. Pharm., 23, 31 (1982).