N-(4-ethoxyphenyl)acetamide

• ChemBase编号: 3432
• 分子式: C10H13NO2
• 平均质量: 179.21572
• 单一同位素质量: 179.09462866
• SMILES: O(c1ccc(NC(=O)C)cc1)CC
• Canonical SMILES: CCOc1ccc(cc1)NC(=O)C
• InChI: InChI=1S/C10H13NO2/c1-3-13-10-6-4-9(5-7-10)11-8(2)12/h4-7H,3H2,1-2H3,(H,11,12)
• InChIKey: CPJSUEIXXCENMM-UHFFFAOYSA-N

名称和登记号

名称

• IUPAC标准名: N-(4-ethoxyphenyl)acetamide
• IUPAC传统名: phenacetin
• 商标名: Contradouleur; Achrocidin; Codempiral; Commotional; Contradol
• 别名: 4'-乙氧基乙酰苯胺; N-(4-乙氧苯基)乙酰胺; 乙酰乙氧基苯胺; 乙酰对氨基苯乙醚; 对乙氧基乙酰苯胺; 对乙酰乙氧基苯胺; 非那西丁; Acetophenetidin; Acetophenetidine; Acetophenetin; Acetphenetidin; Phenacetin; 4-Acetophenetidide; Phenacetin; 4'-Ethoxyacetanilide; 4-(Acetylamino)phenetole; 4-Ethoxy-1-acetylaminobenzene; 4-Ethoxyacetanilide; 4'-Ethoxyacetanilide; Aceto-4-phenetidine; Fenidina; Fenina; Kalmin; N-Acetyl-4-ethoxyaniline; N-Acetyl-p-ethoxyaniline; N-Acetyl-p-phenetidine; NSC 7651; Pertonal; Phenacetine; Phenazetin; Phenedina; Phenidin; Phenin; p-Ethoxyacetanilide; 1-Acetyl-p-phenetidin; 4′-Ethoxyacetanilide; N-(4-Ethoxyphenyl)acetamide; p-Acetophenetidide; Phenacetin; N-(4-ethoxyphenyl)acetamide

登记号

• CAS号: 62-44-2
• EC号: 200-533-0
• MDL号: MFCD00009094
• Beilstein号: 1869238
• 默克索引号: 147204
• PubChem SID: 160966871; 24890660; 46507394; 24854118; 24887192
• PubChem CID: 4754

理论计算性质

JChem

• Acid pKa: 14.978987
• 质子受体: 2
• 质子供体: 1
• LogD (pH = 5.5): 1.4100928
• LogD (pH = 7.4): 1.4100928
• Log P: 1.4100928
• 摩尔折射率: 52.1328 cm^3
• 极化性: 19.564053 Å^3
• 极化表面积: 38.33 Å^2
• 可自由旋转的化学键: 3
• 里宾斯基五规则: true

ALOGPS 2.1

• Log P: 1.62
• LOG S: -2.0
• 溶解度: 1.78e+00 g/l

分子性质

理化性质

• 溶解度: Chloroform; Methanol
• 外观: White Solid
• 熔点: 133-136 °C(lit.); 134-136°C; 135-137°C

安全信息

• 保存条件: -20°C; Refrigerator
• 保存注意事项: Hygroscopic
• RTECS编号: AM4375000
• 欧盟危险性物质标志: 有毒(Toxic) (T)
• 德国WGK号: 3
• 危险公开号: 45-22
• 安全公开号: 53-20-36-45; 53-45
• TSCA收录: 是
• GHS危险品标识: GHS07; GHS08
• GHS警示词: Danger
• GHS危险声明: H302-H350; H350-H302
• GHS警示性声明: P201-P308 + P313; P281-P264-P301+P312-P308+P313-P405-P501A
• 个人保护装置: Eyeshields, full-face particle respirator type N100 (US), Gloves, respirator cartridge type N100 (US), type P1 (EN143) respirator filter, type P3 (EN 143) respirator cartridges
• 保存温度: 2-8°C

产品相关信息

• 纯度: ≥98.0% (HPLC); 97%
• 成盐信息: Free Base
• Pharmacopeia Traceability: traceable to USP 1514008
• 线性分子式: CH3CONHC6H4OC2H5

详细说明

DrugBank - DB03783

• Drug Groups: experimental; withdrawn
• Description: Phenacetin was withdrawn from the Canadian market in June 1973 due to concerns regarding nephropathy (damage to or disease of the kidney).
• Indication: Used principally as an analgesic.
• Pharmacology: Phenacetin was the first NSAID and fever reducer to go on the market. Its analgesic effects are due to its actions on the sensory tracts of the spinal cord. In addition, phenacetin has a depressant action of the heart, where it acts as a negative inotrope. It is an antipyretic, acting on the brain to decrease the temperature set point. It is also used to treat rheumatoid arthritis (subacute type), intercostal neuralgia, and some forms of ataxia. [Wikipedia]
• Affected Organisms: Humans and other mammals
• References: Dubach UC, Rosner B, Sturmer T: An epidemiologic study of abuse of analgesic drugs. Effects of phenacetin and salicylate on mortality and cardiovascular morbidity (1968 to 1987) N Engl J Med. 1991 Jan 17;324(3):155-60. [Pubmed] ; Cochran AJ, Lawson DH, Linton AL: Renal papillary necrosis following phenacetin excess. Scott Med J. 1967 Jul;12(7):246-50. [Pubmed] ; TAN GH, RABBINO MD, HOPPER J Jr: IS PHENACETIN A NEPHROTOXIN?A REPORT ON TWENTY-THREE USERS OF THE DRUG. Calif Med. 1964 Aug;101:73-7. [Pubmed] ; Brix AE: Renal papillary necrosis. Toxicol Pathol. 2002 Nov-Dec;30(6):672-4. [Pubmed]
• External Links: Wikipedia

DrugBank - DB08243

Drug information: experimental

Selleck Chemicals - S2577

Research Area: Inflammation
Biological Activity:
Phenacetin is a non-opioid analgesic without anti-inflammatory properties. Its analgesic effects are due to its actions on the sensory tracts of the spinal cord. In addition, phenacetin has a depressant action on the heart, where it acts as a negative inotrope. Phenacetin is an antipyretic, acting on the brain to decrease the temperature set point. Phenacetin is also used to treat rheumatoid arthritis (subacute type) and intercostal neuralgia. [1][2]References on Phenacetin[1] http://en.wikipedia.org/wiki/Phenacetin, , [2] N Engl J Med. , 1991 Jan 17, 324(3):155-60

Sigma Aldrich - A2500

Biochem/physiol Actions
CYP1A2 和 CYP2D6 的底物。

Sigma Aldrich - 235830

Biochem/physiol Actions
CYP1A2 和 CYP2D6 的底物。
包装
5, 500 g in glass bottle

Sigma Aldrich - 77440

Biochem/physiol Actions
CYP1A2 和 CYP2D6 的底物。
包装
1 kg in poly bottle
50, 250 g in poly bottle

Sigma Aldrich - 44207

Biochem/physiol Actions
CYP1A2 和 CYP2D6 的底物。

Toronto Research Chemicals - P294580

Analgesic, antipyretic. Component of APC tablets, analgesic mixture also containing aspirin and caffeine. Phenacetin is reasonably anticipated to be a human carcinogen; analgesic mixtures containing Phenacetin are listed as known human carcinogens.

参考文献

• Dubach UC, Rosner B, Sturmer T: An epidemiologic study of abuse of analgesic drugs. Effects of phenacetin and salicylate on mortality and cardiovascular morbidity (1968 to 1987) N Engl J Med. 1991 Jan 17;324(3):155-60. Pubmed
• Brix AE: Renal papillary necrosis. Toxicol Pathol. 2002 Nov-Dec;30(6):672-4. Pubmed
• Cochran AJ, Lawson DH, Linton AL: Renal papillary necrosis following phenacetin excess. Scott Med J. 1967 Jul;12(7):246-50. Pubmed
• TAN GH, RABBINO MD, HOPPER J Jr: IS PHENACETIN A NEPHROTOXIN?A REPORT ON TWENTY-THREE USERS OF THE DRUG. Calif Med. 1964 Aug;101:73-7. Pubmed
• Boyd, et al.: Toxicol. Appl. Pharmacol., 1, 240 (1959)
• Dubach, C.U., et al.: N. Engl. J. Med., 308, 357 (1959)