2-(6-methoxynaphthalen-2-yl)propanoic acid

• ChemBase编号: 667
• 分子式: C14H14O3
• 平均质量: 230.25916
• 单一同位素质量: 230.09429431
• SMILES: O(c1cc2c(cc(C(C)C(=O)O)cc2)cc1)C
• Canonical SMILES: COc1ccc2c(c1)ccc(c2)C(C(=O)O)C
• InChI: InChI=1S/C14H14O3/c1-9(14(15)16)10-3-4-12-8-13(17-2)6-5-11(12)7-10/h3-9H,1-2H3,(H,15,16)
• InChIKey: CMWTZPSULFXXJA-UHFFFAOYSA-N

名称和登记号

名称

• IUPAC标准名: 2-(6-methoxynaphthalen-2-yl)propanoic acid
• IUPAC传统名: naprosyn
• 商标名: Aleve; Anaprox; Bonyl; DL Naproxen; DL-Naproxen; Diocodal; Dysmenalgit; Ec-naprosyn; Equiproxen; Floginax; Laraflex; Laser; Mnpa; Naixan; Naprelan; Napren; Naprium; Naprius; Naprosine; Naprosyn; Naprosyne; Naproxen Sodium; Naprux; Naxen; Naxyn; Niaxan; Nycopren; Panoxen; Pranoxen; Prexan; Proxen; Proxine; Reuxen; Veradol; Xenar
• 别名: (RS)-Naproxen; (+/-)-2-(6-Methoxy-2-naphthalenyl)propionic Acid; (+/-)-2-(6-Methoxy-2-naphthyl)propionic Acid; (+/-)-6-Methoxy-α-methyl-2-naphthaleneacetic Acid; (+/-)-Naproxen; 2-(6-Methoxy-2-naphthyl)propanoic Acid; dl-Naproxen; rac-Naproxen; (RS)-Naproxen-d3; (+/-)-2-(6-Methoxy-2-naphthalenyl)propionic Acid-d3; (+/-)-2-(6-Methoxy-2-naphthyl)propionic Acid-d3; (+/-)-6-Methoxy-α-(methyl-d3)-2-naphthaleneacetic Acid; (+/-)-Naproxen-d3; 2-(6-Methoxy-2-naphthyl)propanoic Acid-d3; dl-Naproxen-d3; rac Naproxen-d3; Naproxen; 2-(6-Methoxynaphthalen-2-yl)propanoic acid; (+)-2-(6-methoxy-2-naphthyl)-propionic acid; S(+)-6-methoxy-α-methyl-2-naphthaleneacetic acid); [S(+)-2-(6-Methoxy-2-naphthyl)propionic acid]

登记号

• CAS号: 23981-80-8; 22204-53-1
• EC号: 244-838-7
• MDL号: MFCD00439456
• PubChem SID: 160964130
• PubChem CID: 1302

理论计算性质

JChem

• Acid pKa: 4.1903534
• 质子受体: 3
• 质子供体: 1
• LogD (pH = 5.5): 1.6579665
• LogD (pH = 7.4): -0.054211214
• Log P: 2.985786
• 摩尔折射率: 64.8535 cm^3
• 极化性: 26.3861 Å^3
• 极化表面积: 46.53 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: 3.29
• LOG S: -3.65
• 溶解度: 5.11e-02 g/l

分子性质

理化性质

• 溶解度: 15.9 mg/L; Chloroform; Methanol
• 外观: Off-White Solid; White Solid
• 熔点: 154-154°C; 156-157°C; 157-158°C
• 疏水性(logP): 2.8

安全信息

• 保存条件: -20°C Freezer; Refrigerator; Room Temperature (15-30°C)
• RTECS编号: UF5275000
• 欧盟危险性物质标志: 有害性(Harmful) (Xn)
• 危险公开号: R:22-36/37/38
• 安全公开号: S:25-26-36/37/39

产品相关信息

• 纯度: 95+%; 97%

详细说明

MP Biomedicals - 02190247

Pharmacological agent that reportedly may show activity through ability to inhibit prostaglandin biosynthesis.

DrugBank - DB00788

• Drug Groups: approved
• Description: An anti-inflammatory agent with analgesic and antipyretic properties. Both the acid and its sodium salt are used in the treatment of rheumatoid arthritis and other rheumatic or musculoskeletal disorders, dysmenorrhea, and acute gout. [PubChem]
• Indication: For the treatment of rheumatoid arthritis, osteoarthritis, ankylosing spondylitis, tendinitis, bursitis, and acute gout. Also for the relief of mild to moderate pain and the treatment of primary dysmenorrhea.
• Pharmacology: Naproxen is a member of the arylacetic acid group of nonsteroidal anti-inflammatory drugs (NSAIDs). Naproxen has analgesic and antipyretic properties. As with other NSAIDs, its mode of action is not fully understood; however, its ability to inhibit prostaglandin synthesis may be involved in the anti-inflammatory effect.
• Toxicity: ORAL (LD₅₀): Acute: 248 mg/kg [Rat]. 360 mg/kg [Mouse]. Symptoms of overdose include drowsiness, heartburn, indigestion, nausea, and vomiting.
• Affected Organisms: Humans and other mammals
• Biotransformation: Naproxen is extensively metabolized to 6-0-desmethyl naproxen and both parent and metabolites do not induce metabolizing enzymes.
• Absorption: Naproxen itself is rapidly and completely absorbed from the GI tract with an in vivo bioavailability of 95%. Although naproxen itself is well absorbed, the sodium salt form is more rapidly absorbed resulting in higher peak plasma levels for a given dose. Food causes a slight decrease in the rate absorption.
• Half Life: The observed terminal elimination half-life is approximately 15 hours.
• Protein Binding: At therapeutic levels naproxen is greater than 99% albumin-bound.
• References: Kearney PM, Baigent C, Godwin J, Halls H, Emberson JR, Patrono C: Do selective cyclo-oxygenase-2 inhibitors and traditional non-steroidal anti-inflammatory drugs increase the risk of atherothrombosis? Meta-analysis of randomised trials. BMJ. 2006 Jun 3;332(7553):1302-8. [Pubmed] ; Zhang J, Ding EL, Song Y: Adverse effects of cyclooxygenase 2 inhibitors on renal and arrhythmia events: meta-analysis of randomized trials. JAMA. 2006 Oct 4;296(13):1619-32. Epub 2006 Sep 12. [Pubmed]
• External Links: Wikipedia; RxList; PDRhealth; Drugs.com

Toronto Research Chemicals - N377527

Labelled Naproxen. An anti-inflammatory, analgesic, antipyretic. A non-steroidal anti-inflammatory.

Toronto Research Chemicals - N377526

An anti-inflammatory, analgesic, antipyretic. A non-steroidal anti-inflammatory.

参考文献

• Tomlinson, et al., Biochem. Biophys. Res. Commun. , 46 : 552 (1972).
• Kearney PM, Baigent C, Godwin J, Halls H, Emberson JR, Patrono C: Do selective cyclo-oxygenase-2 inhibitors and traditional non-steroidal anti-inflammatory drugs increase the risk of atherothrombosis? Meta-analysis of randomised trials. BMJ. 2006 Jun 3;332(7553):1302-8. Pubmed
• Zhang J, Ding EL, Song Y: Adverse effects of cyclooxygenase 2 inhibitors on renal and arrhythmia events: meta-analysis of randomized trials. JAMA. 2006 Oct 4;296(13):1619-32. Epub 2006 Sep 12. Pubmed
• Harrison, I.T., et al.: J. Med. Chem., 13, 203 (1970)
• Harrison, I.T., et al.: J. Med. Chem., 13, 203 (1970)