2-{2-[(2,6-dichlorophenyl)amino]phenyl}acetic acid

• ChemBase编号: 468
• 分子式: C14H11Cl2NO2
• 平均质量: 296.14864
• 单一同位素质量: 295.01668396
• SMILES: Clc1c(Nc2c(CC(=O)O)cccc2)c(Cl)ccc1
• Canonical SMILES: OC(=O)Cc1ccccc1Nc1c(Cl)cccc1Cl
• InChI: InChI=1S/C14H11Cl2NO2/c15-10-5-3-6-11(16)14(10)17-12-7-2-1-4-9(12)8-13(18)19/h1-7,17H,8H2,(H,18,19)
• InChIKey: DCOPUUMXTXDBNB-UHFFFAOYSA-N

名称和登记号

名称

• IUPAC标准名: 2-{2-[(2,6-dichlorophenyl)amino]phenyl}acetic acid
• IUPAC传统名: diclofenac
• 商标名: Allvoran; Apo-Diclo; Assaren; Benfofen; Cataflam; Delphimix; Dichlofenac; Dichronic; Diclo-Phlogont; Diclo-Puren; Diclobenin; Diclord; Dicloreum; Dolobasan; Duravolten; Ecofenac; Effekton; Kriplex; Neriodin; Novapirina; Novo-Difenac; Novo-Difenac SR; Nu-Diclo; Pennsaid; Primofenac; Prophenatin; Rhumalgan; Solaraze; Solaraze T; Tsudohmin; Valetan; Voldal; Voltaren; Voltaren Ophtha; Voltaren Ophthalmic; Voltaren Rapide; Voltaren SR; Voltaren-XR; Voltarol; Xenid; Dyloject; ProSorb-D
• 别名: Diclofenac Sodium; Diclofenac Potassium; Diclofenac Acid; ISV-205; Diclofenac; 2-{2-[(2,6-dichlorophenyl)amino]phenyl}acetic acid; 2-(2-((2,6-Dichlorophenyl)amino)phenyl)acetic acid

登记号

• CAS号: 15307-86-5
• MDL号: MFCD00056694; MFCD00451393
• PubChem SID: 46504644; 160963931
• PubChem CID: 3033

理论计算性质

JChem

• Acid pKa: 3.995652
• 质子受体: 3
• 质子供体: 2
• LogD (pH = 5.5): 2.7453504
• LogD (pH = 7.4): 1.0974493
• Log P: 4.2590094
• 摩尔折射率: 75.4614 cm^3
• 极化性: 29.034273 Å^3
• 极化表面积: 49.33 Å^2
• 可自由旋转的化学键: 4
• 里宾斯基五规则: true

ALOGPS 2.1

• Log P: 4.98
• LOG S: -4.82
• 溶解度: 4.47e-03 g/l

分子性质

理化性质

• 溶解度: 50 mg/mL (sodium salt) [Sigma Aldrich]
• 疏水性(logP): 3.9; 4.726

产品相关信息

• 纯度: 95%; 95+%

详细说明

DrugBank - DB00586

• Drug Groups: approved
• Description: A non-steroidal anti-inflammatory agent (NSAID) with antipyretic and analgesic actions. It is primarily available as the sodium salt. [PubChem]
• Indication: For the acute and chronic treatment of signs and symptoms of osteoarthritis and rheumatoid arthritis.
• Pharmacology: Diclofenac is an acetic acid nonsteroidal antiinflammatory drug (NSAID) with analgesic and antipyretic properties. Diclofenac is used to treat pain, dysmenorrhea, ocular inflammation, osteoarthritis, rheumatoid arthritis, ankylosing spondylitis, and actinic keratosis
• Toxicity: Symptoms of overdose include loss of consciousness, increased intracranial pressure, and aspiration pneumonitis. LD₅₀=390mg/kg (orally in mice)
• Affected Organisms: Humans and other mammals
• Biotransformation: Hepatic
• Absorption: Completely absorbed from the gastrointestinal tract.
• Half Life: 2 hours
• Protein Binding: More than 99%
• Elimination: Diclofenac is eliminated through metabolism and subsequent urinary and biliary excretion of the glucuronide and the sulfate conjugates of the metabolites. Little or no free unchanged diclofenac is excreted in the urine. Approximately 65% of the dose is excreted in the urine and approximately 35% in the bile as conjugates of unchanged diclofenac plus metabolites.
• Distribution: * 1.3 L/kg
• Clearance: * oral cl=622 mL/min [healthy]; * renal cl <1 mL/min [healthy]
• 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] ; Solomon DH, Avorn J, Sturmer T, Glynn RJ, Mogun H, Schneeweiss S: Cardiovascular outcomes in new users of coxibs and nonsteroidal antiinflammatory drugs: high-risk subgroups and time course of risk. Arthritis Rheum. 2006 May;54(5):1378-89. [Pubmed] ; FitzGerald GA, Patrono C: The coxibs, selective inhibitors of cyclooxygenase-2. N Engl J Med. 2001 Aug 9;345(6):433-42. [Pubmed] ; Graham DJ: COX-2 inhibitors, other NSAIDs, and cardiovascular risk: the seduction of common sense. JAMA. 2006 Oct 4;296(13):1653-6. Epub 2006 Sep 12. [Pubmed] ; Brater DC: Renal effects of cyclooxygyenase-2-selective inhibitors. J Pain Symptom Manage. 2002 Apr;23(4 Suppl):S15-20; discussion S21-3. [Pubmed] ; Sigma Aldrich [Link] ; Gan TJ: Diclofenac: an update on its mechanism of action and safety profile. Curr Med Res Opin. 2010 Jul;26(7):1715-31. [Pubmed]
• External Links: Wikipedia; RxList; Drugs.com

参考文献

• Sigma Aldrich Link
• 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
• Solomon DH, Avorn J, Sturmer T, Glynn RJ, Mogun H, Schneeweiss S: Cardiovascular outcomes in new users of coxibs and nonsteroidal antiinflammatory drugs: high-risk subgroups and time course of risk. Arthritis Rheum. 2006 May;54(5):1378-89. Pubmed
• FitzGerald GA, Patrono C: The coxibs, selective inhibitors of cyclooxygenase-2. N Engl J Med. 2001 Aug 9;345(6):433-42. Pubmed
• Graham DJ: COX-2 inhibitors, other NSAIDs, and cardiovascular risk: the seduction of common sense. JAMA. 2006 Oct 4;296(13):1653-6. Epub 2006 Sep 12. Pubmed
• Brater DC: Renal effects of cyclooxygyenase-2-selective inhibitors. J Pain Symptom Manage. 2002 Apr;23(4 Suppl):S15-20; discussion S21-3. Pubmed
• Gan TJ: Diclofenac: an update on its mechanism of action and safety profile. Curr Med Res Opin. 2010 Jul;26(7):1715-31. Pubmed