Diclofenac

Base Information

• Chemical Name: Diclofenac
• CAS No.: 15307-86-5
• Molecular Formula: C14H11Cl2NO2
• Molecular Weight: 296.153
• Hs Code.: 2942000000
• European Community (EC) Number: 239-348-5
• UNII: 144O8QL0L1
• DSSTox Substance ID: DTXSID6022923
• Nikkaji Number: J8.557J
• Wikipedia: Diclofenac
• Wikidata: Q244408
• NCI Thesaurus Code: C28985
• RXCUI: 3355
• Pharos Ligand ID: MUDSKU2U2VCB
• Metabolomics Workbench ID: 42917
• ChEMBL ID: CHEMBL139
• Mol file: 15307-86-5.mol

Synonyms:Dichlofenal;Diclofenac;Diclofenac Potassium;Diclofenac Sodium;Diclofenac, Sodium;Diclonate P;Diclophenac;Dicrofenac;Feloran;GP 45,840;GP-45,840;GP45,840;Novapirina;Orthofen;Orthophen;Ortofen;Sodium Diclofenac;SR 38;SR-38;SR38;Voltaren;Voltarol

Chemical Property of Diclofenac

Chemical Property:

• Appearance/Colour: White to yellowish crystalline powder
• Vapor Pressure: 1.07E-09mmHg at 25°C
• Melting Point: 156-158oC
• Refractive Index: 1.66
• Boiling Point: 412 ºC at 760 mmHg
• PKA: pKa 4 (Uncertain)
• Flash Point: 203 ºC
• PSA: 49.33000
• Density: 1.431 g/cm³
• LogP: 4.43710
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility.: soluble in Methanol
• Water Solubility.: 1.278mg/L(30 oC)
• XLogP3: 4.4
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 4
• Exact Mass: 295.0166840
• Heavy Atom Count: 19
• Complexity: 304

Purity/Quality:

99%min ^*data from raw suppliers

DiclofenacAcid ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Drug Classes: Nonsteroidal Antiinflammatory Drugs
• Canonical SMILES: C1=CC=C(C(=C1)CC(=O)O)NC2=C(C=CC=C2Cl)Cl
• Recent ClinicalTrials: Topical Treatment for TMJ Arthralgia
• Recent EU Clinical Trials: Steroids and Non-steroidal Anti-inflammatory drugs in the Postoperative regime after trabeculectomy. An investigator-initiated randomized study (The SNAP study)
• Recent NIPH Clinical Trials: A clinical pharmacological study of HP-3150 in patients with low back pain
• Uses: Diclofenac possesses all of the properties unique to the series of propionic acid drugs, yet in terms of anti-inflammatory and analgesic strength it exceeds that of aspirin, analgin, and ibuprofen. It is used in acute rheumatism, rheumatoid arthritis, osteoarthritis, ankylosing spondylitis, arthrosis, back pain, neuralgia, and myalgia. It rarely causes side effects. The most common synonym is voltaren. prostaglandin synthetic inhibitor
• Indications: Diclofenac (Voltaren, Cataflam) is approved for use in rheumatoid arthritis, osteoarthritis, ankylosing spondylitis, dysmenorrhea, and topically for the treatment treatment of ocular inflammation and actinic keratosis. Diclofenac exhibits approximately equal selectivity for COX-1 and COX-2. The most common adverse reactions are GI disturbances and headache.A reversible elevation of serum transaminases occurs in 15% of patients.
• Therapeutic Function: Antiinflammatory
• Biological Functions: Diclofenac (Voltaren) is a phenylacetic acid derivative that is a potent inhibitor of COX and that has analgesic, antiinflammatory, and antipyretic effects. Its use is accompanied by side effects similar to those of other NSAIDs. Indications for the drug include rheumatoid arthritis, osteoarthritis, and ophthalmic inflammation (use of an ophthalmic preparation).
• Clinical Use: Diclofenac is synthesized from N-phenyl-2,6-dichloroaniline. It is available in 120 different countries and, perhaps, is the most widely used NSAID in the world. It was introduced in the United States in 1989 but was first marketed in Japan in 1974. It ranks among the top prescription drugs in the United States. Diclofenac possesses structural characteristics of both arylalkanoic acid and the anthranilic acid classes of anti-inflammatory drugs, and it displays anti-inflammatory, analgetic, and antipyretic properties.

Technology Process of Diclofenac

There total 38 articles about Diclofenac which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 100.0%

[2-(2,6-dichloro-phenylamino)-phenyl]-acetic acid diethylcarbamoylmethylcarbamoyloxymethyl ester (934548-15-9) → 2-amino-N,N-diethylacetamide (34105-57-2) + [2-(2,6-dichloroanilino)phenyl]acetic acid (15307-86-5)

Guidance literature:

With human plasma; In phosphate buffer; at 37 ℃; pH=7.4;

DOI:10.1002/ardp.200600145

Reference yield: 100.0%

[2-(2,6-dichloro-phenylamino)-phenyl]-acetic acid 1-diethylcarbamoyl-2-phenyl-ethylcarbamoyloxymethyl ester (934548-16-0) → [2-(2,6-dichloroanilino)phenyl]acetic acid (15307-86-5) + N-(phenylalanyl)-N,N-diethylamine (40847-09-4)

Guidance literature:

With human plasma; In phosphate buffer; at 37 ℃; pH=7.4;

DOI:10.1002/ardp.200600145

Reference yield: 95.0%

2,6-Dichlorophenol (87-65-0) + methyl 2-(2-(2-bromopropionamido)phenyl)acetate → [2-(2,6-dichloroanilino)phenyl]acetic acid (15307-86-5)

Guidance literature:

With potassium hydroxide; In dimethyl sulfoxide; at 60 - 100 ℃; for 8h; Temperature; Reagent/catalyst;

upstream raw materials:

diclofenac sodium

2-<(2,6-Dichlorphenacyl)amino>phenylessigsaeure-2-oxopropylester

2-<(2,6-dichlorophenyl)amino>-α-(methylthio)phenylacetic acid

aceclofenac

Downstream raw materials:

[2-(2,6-Dichloro-phenylamino)-phenyl]-acetic acid; compound with (S)-2-amino-5-guanidino-pentanoic acid

1-(2,6-dichlorophenyl)indolin-2-one

2-[(2,6-dichlorophenyl)amino]phenylacetic acid methyl ester

[2-(2,6-dichloroanilino)phenyl]acetate diethylene glycol

Refernces

• 1、 Castellari, Carlo,Ottani, Stefano. "Two monoclinic forms of diclofenac acid". . p. 794 - 797. Retrieved 1997.
• 2、 Iley, Jim,Mendes, Eduarda,Moreira, Rui,Souza, Sofia. "Cleavage of tertiary amidomethyl ester prodrugs of carboxylic acids by rat liver homogenates". . p. 201 - 205. Retrieved 1999.
• 3、 Hammond, Thomas G.,Meng, Xiaoli,Jenkins, Rosalind E.,Maggs, James L.,Castelazo, Anahi Santoyo,Regan, Sophie L.,Bennett, Stuart N.L.,Earnshaw, Caroline J.,Aithal, Guruprasad P.,Pande, Ira,Kenna, J. Gerry,Stachulski, Andrew V.,Park, B. Kevin,Williams, Dominic P.. "Mass spectrometric characterization of circulating covalent protein adducts derived from a drug Acyl glucuronide metabolite: Multiple albumin adductions in diclofenac patients". . p. 387 - 402. Retrieved 2014.
• 4、 Galisteo, Alberto,Jannus, Fatin,García-García, Amalia,Aheget, Houssam,Rojas, Sara,Lupia?ez, José A.,Rodríguez-Diéguez, Antonio,Reyes-Zurita, Fernando J.,Quílez Del Moral, José F.. "Diclofenac n-derivatives as therapeutic agents with anti-inflammatory and anti-cancer effect". . . Retrieved 2021/05/18.
• 5、 -. "Preparation method of diclofenac". Paragraph 0027-0124. . Retrieved 2019/09/13.