2-diphenylmethanesulfinylacetamide

• ChemBase编号: 625
• 分子式: C15H15NO2S
• 平均质量: 273.3501
• 单一同位素质量: 273.08234973
• SMILES: S(=O)(C(c1ccccc1)c1ccccc1)CC(=O)N
• Canonical SMILES: NC(=O)CS(=O)C(c1ccccc1)c1ccccc1
• InChI: InChI=1S/C15H15NO2S/c16-14(17)11-19(18)15(12-7-3-1-4-8-12)13-9-5-2-6-10-13/h1-10,15H,11H2,(H2,16,17)
• InChIKey: YFGHCGITMMYXAQ-UHFFFAOYSA-N

名称和登记号

名称

• IUPAC标准名: 2-diphenylmethanesulfinylacetamide
• IUPAC传统名: 2-diphenylmethanesulfinylacetamide; modafinil
• 商标名: Modiodal; Provigil; Sparlon
• 别名: Modafinil [USAN:INN]; Modafinilo [Spanish]; Modafinilum [Latin]; Moderateafinil; Modafinil; 2-[(Diphenylmethyl)sulfinyl]acetamide; 2-[(Diphenylmethyl)sulfinyl]-acetamide; Modafinil; 2-[(Diphenylmethyl)sulfinyl]acetamide; (±)-Modafinil; 2-(Benzhydrylsulfinyl)acetamide; CEP 1538; CRC 40476; CRL 40476; DEP 1538; Modaphonil; Modiodal; Provigil

登记号

• CAS号: 68693-11-8
• MDL号: MFCD00868082
• PubChem SID: 24897132; 46504648; 160964088
• PubChem CID: 4236

理论计算性质

JChem

• Acid pKa: 8.8397665
• 质子受体: 2
• 质子供体: 1
• LogD (pH = 5.5): 1.5326362
• LogD (pH = 7.4): 1.517359
• Log P: 1.5328344
• 摩尔折射率: 77.3886 cm^3
• 极化性: 30.265642 Å^3
• 极化表面积: 60.16 Å^2
• 可自由旋转的化学键: 5
• 里宾斯基五规则: true

ALOGPS 2.1

• Log P: 1.75
• LOG S: -2.64
• 溶解度: 6.22e-01 g/l

分子性质

理化性质

• 溶解度: Chloroform; DMSO; DMSO: >10 mg/mL; Slightly soluble
• 外观: white solid; White Solid
• 熔点: 154-157°C
• 疏水性(logP): 0.6

安全信息

• 保存条件: -20°C Freezer
• 保存注意事项: IRRITANT
• 德国WGK号: 3
• TSCA收录: false
• 个人保护装置: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• 毒品管制信息: USDEA Schedule IV

药理学性质

• 相关基因信息: rat ... Slc6a3(24898)

产品相关信息

• 纯度: ≥98% (HPLC); 95+%
• Empirical Formula (Hill Notation): C15H15NO2S

详细说明

DrugBank - DB00745

• Drug Groups: approved; investigational
• Description: Modafinil is a stimulant drug marketed as a 'wakefulness promoting agent' and is one of the stimulants used in the treatment of narcolepsy. Narcolepsy is caused by dysfunction of a family of wakefulness-promoting and sleep-suppressing peptides, the orexins, whose neurons are activated by modafinil. The prexin neuron activation is associated with psychoactivation and euphoria. The exact mechanism of action is unclear, although in vitro studies have shown it to inhibit the reuptake of dopamine by binding to the dopamine reuptake pump, and lead to an increase in extracellular dopamine. Modafinil activates glutamatergic circuits while inhibiting GABA.
• Indication: To improve wakefulness in patients with excessive daytime sleepiness (EDS) associated with narcolepsy.
• Pharmacology: Modafinil is a stimulant drug marketed as a 'wakefulness promoting agent' and is one of the stimulants used in the treatment of narcolepsy. Narcolepsy is caused by dysfunction of a family of wakefulness-promoting and sleep-suppressing peptides, the orexins, whose neurons are activated by modafinil. The prexin neuron activation is associated with psychoactivation and euphoria. Modafinil is not indicated for complaints of lack of energy or fatigue; but it appears to be very helpful for some patients. Also, it has been used in the treatment of hypersomnia, a disorder in which patients lack the capacity for meaningful sleep and may require ten or more hours per day. Recent studies have have found that modafinil may help recovering cocaine addicts fight their addiction.
• Affected Organisms: Humans and other mammals
• Biotransformation: Hepatic
• Absorption: Rapid following oral administration.
• Half Life: 23-215 hours
• Protein Binding: 60%
• Elimination: The major route of elimination is metabolism (~90%), primarily by the liver, with subsequent renal elimination of the metabolites.
• Distribution: * 0.9 L/kg
• References: Lindsay SE, Gudelsky GA, Heaton PC: Use of modafinil for the treatment of attention deficit/hyperactivity disorder. Ann Pharmacother. 2006 Oct;40(10):1829-33. Epub 2006 Sep 5. [Pubmed] ; Ishizuka T, Sakamoto Y, Sakurai T, Yamatodani A: Modafinil increases histamine release in the anterior hypothalamus of rats. Neurosci Lett. 2003 Mar 20;339(2):143-6. [Pubmed]
• External Links: Wikipedia; RxList; PDRhealth; Drugs.com

Sigma Aldrich - M6940

Biochem/physiol Actions
Modafinil is a central nervous system vigilance promoting agent, which posseses neuroprotective properties.
Other Notes
Tandem Mass Spectrometry data independently generated by Scripps Center for Metabolomics is available to view or download in PDF. M6940.pdf Tested metabolites are featured on Scripps Center for Metabolomics METLIN Metabolite Database. To learn more, visit sigma.com/metlin.

Toronto Research Chemicals - M482500

Modafinil is an α-1-adrenergic agonist. Modafinil is a CNS stimulant; psychostimulant that displays neuroprotective and antiparkinsonian activity in a primate model of Parkinson's disease.This is a controlled substance (stimulant).

参考文献

• Lindsay SE, Gudelsky GA, Heaton PC: Use of modafinil for the treatment of attention deficit/hyperactivity disorder. Ann Pharmacother. 2006 Oct;40(10):1829-33. Epub 2006 Sep 5. Pubmed
• Ishizuka T, Sakamoto Y, Sakurai T, Yamatodani A: Modafinil increases histamine release in the anterior hypothalamus of rats. Neurosci Lett. 2003 Mar 20;339(2):143-6. Pubmed
• Saletu, B., et al.: Int. J. Clin. Pharmacol. Res., 9, 183 (1989)
• Chemelli, R.M., et al.: Cell, 98, 437 (1989)
• Purnell, M., et al.: J. Sleep Res., 11, 219 (1989)
• Dinges, D., et al.: Curr. Med. Res. Opin., 22, 159 (1989)