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Diclofenac sodium

CAS No.
15307-79-6
Chemical Name:
Diclofenac sodium
Synonyms
DICLOFENAC SODIUM SALT;VOLTAREN;Solaraze;tsudohmin;SODIUM 2-(2,6-DICHLOROANILINO)PHENYLACETATE;N-(2,6-Dichlorophenyl)-o-aminophenylacetic acid sodium salt;Naclof;Voldal;gp45840;kriplex
CBNumber:
CB5474464
Molecular Formula:
C14H10Cl2NNaO2
Molecular Weight:
318.13
MDL Number:
MFCD00082251
MOL File:
15307-79-6.mol
Last updated:2024-03-12 17:20:04

Diclofenac sodium Properties

Melting point 288-290°C
Density 0.781 g/cm3
storage temp. room temp
solubility H2O: 50 mg/mL
form White solid
pka 4(at 25℃)
color White to Almost white
Water Solubility Soluble in water to 50mg/ml.
Merck 14,3081
BCS Class 2
Stability Stable.
InChI InChI=1S/C14H11Cl2NO2.Na/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);/q;+1/p-1
InChIKey KPHWPUGNDIVLNH-UHFFFAOYSA-M
SMILES C1(=CC=CC=C1CC([O-])=O)NC1=C(Cl)C=CC=C1Cl.[Na+]
CAS DataBase Reference 15307-79-6(CAS DataBase Reference)
NCI Dictionary of Cancer Terms diclofenac sodium; Voltaren
FDA UNII QTG126297Q
NCI Drug Dictionary diclofenac sodium

Pharmacokinetic data

Protein binding 99.7%
Excreted unchanged in urine <1%
Volume of distribution 0.12-0.17(L/kg)
Biological half-life 1-2 / Unchanged

SAFETY

Risk and Safety Statements

Symbol(GHS)  GHS hazard pictogramsGHS hazard pictogramsGHS hazard pictograms
GHS06,GHS08,GHS09
Signal word  Danger
Hazard statements  H301-H361d-H372-H411
Precautionary statements  P201-P202-P260-P264-P273-P301+P310
Hazard Codes  T,Xi
Risk Statements  25-36/37/38-63
Safety Statements  22-36/37-45-36-26-60-20
RIDADR  UN 2811 6.1/PG 3
WGK Germany  3
RTECS  AG6330000
HazardClass  6.1(b)
PackingGroup  III
HS Code  29224999
Toxicity LD50 in mice, rats (mg/kg): ~390, 150 orally (Krupp)
NFPA 704
0
2 0

Diclofenac sodium price More Price(38)

Manufacturer Product number Product description CAS number Packaging Price Updated Buy
Sigma-Aldrich 287840 Diclofenac Sodium - CAS 15307-79-6 - Calbiochem 15307-79-6 1G $56.2 2024-03-01 Buy
Sigma-Aldrich 1188800 Diclofenac sodium United States Pharmacopeia (USP) Reference Standard 15307-79-6 200mg $436 2024-03-01 Buy
TCI Chemical D2508 Diclofenac Sodium Salt >98.0%(HPLC)(N) 15307-79-6 25g $72 2024-03-01 Buy
Alfa Aesar J62609 Diclofenac sodium salt 15307-79-6 5g $39.1 2024-03-01 Buy
Alfa Aesar J62609 Diclofenac sodium salt 15307-79-6 25g $86.4 2024-03-01 Buy
Product number Packaging Price Buy
287840 1G $56.2 Buy
1188800 200mg $436 Buy
D2508 25g $72 Buy
J62609 5g $39.1 Buy
J62609 25g $86.4 Buy

Diclofenac sodium Chemical Properties,Uses,Production

description

Diclofenac Sodium (Diclofenac sodium) is the sodium salt form of diclofenac, a benzene acetic acid derivate and nonsteroidal anti-inflammatory drug (NSAID) with analgesic, antipyretic and anti-inflammatory activity. Diclofenac sodium is a non-selective reversible and competitive inhibitor of cyclooxygenase (COX), subsequently blocking the conversion of arachidonic acid into prostaglandin precursors. This leads to an inhibition of the formation of prostaglandins that are involved in pain, inflammation and fever.

Uses

Diclofenac is a phenylacetic acid derivative belonging to the class of the non-selective non-steroidal anti-inflammatory drugs (NSAIDs). It exhibits analgesic, antipyretic and anti-inflammatory activity. Due to its poor solubility, the parenteral formulation of diclofenac sodium (Voltarol ampoules) currently available in Europe contains the solvents propylene glycol and benzyl alcohol that allows intramuscular and intravenous administration. Diclofenac sodium has long been used to treat acute pain and inflammation, and is effective in various acute forms of pain.

Mechanisms of action

Putative mechanisms of action of diclofenac may include inhibition of leukotriene synthesis, inhibition of phospholipase A2, modulation of free arachidonic acid levels, stimulation of adenosine triphosphate-sensitive potassium channels via the L-arginine-nitric oxide-cyclic guanosine monophosphate pathway and centrally mediated and neuropathic mechanisms. Other emerging mechanisms of action may include inhibition of peroxisome proliferator activated receptor-c, reduction in plasma and synovial substance P and interleukin-6 levels, inhibition of the thromboxane-prostanoid receptor and inhibition of acid-sensing ion channels.

Clinical Application

Clinical trials have demonstrated the analgesic efficacy of diclofenac sodium in terms of relieving moderate to severe postoperative pain in patients undergoing dental surgery or minor orthopaedic surgery. Subcutaneous diclofenac sodium also effectively relieved moderate to severe neuropathic pain, related to cancer or not. Diclofenac sodium was generally well tolerated in clinical trials, with injection-site reactions among the most commonly reported adverse events.

Description

Diclofenac is a non-steroidal anti-inflammatory drug (NSAID) and COX inhibitor (IC50s = 0.9-2.7 and 1.5-20 μM, for human COX-1 and COX-2, respectively). It is also an active metabolite of diclofenac methyl ester and diclofenac amide . Diclofenac inhibits release of arachidonic acid (Item Nos. 90010 | 90010.1 | 10006607) induced by A23187 in isolated rat peritoneal neutrophils and macrophages (IC50s = 60 and 10 μM, respectively). Transdermal administration of diclofenac inhibits carrageenan-induced paw edema in rats. Formulations containing diclofenac have been used in the treatment of pain associated with osteoarthritis, rheumatoid arthritis, and ankylosing spondylitis.

Chemical Properties

Off-White Crystalline Solid

Originator

Voltaren,Fujisawa,Japan,1974

Uses

Diclofenac sodium is a nonsteroidal anti-inflammatory compound and cyclooxygenase (COX) inhibitor. Oxidation of diclofenac sodium produces the metabolite 4'-hydroxy diclofenac) which demonstrates specific inhibition of Cox-2. Inhibition of Cox by diclofenac and 4'-hydroxy diclofenac suppresses prostaglandin E2 synthesis, producing anti-inflammatory and analgesic effects. Diclofenac is also shown to stabilize the native tetrameric conformation of transthyretin (TTR) fibrils, preventing the formation of insoluble amyloidogenic TTR deposits. Diclofenac Sodium is a substrate of CYP2C9. It is also used as an inhibitor of Cox-1 and Cox-2.

Definition

ChEBI: Diclofenac sodium is the sodium salt of diclofenac. It contains a diclofenac(1-).

Manufacturing Process

Four grams of N-chloroacetyl-N-phenyl-2,6-dichloroaniline and 4 grams of aluminum chloride are well mixed together and heated for 2 hours at 160°C. The melt is cooled and poured onto about 50 grams of ice while it is still warm. The oil which separates is dissolved in 50 ml of chloroform, the chloroform solution is washed with 10 ml of water, dried over sodium sulfate and concentrated under 11 torr. The residue is distilled. The 1-(2,6- dichlorophenyl)-2-indolinone melts at 126°-127°C.
A solution of 186 grams of 1-(2,6-dichlorophenyl)-2-indolinone in 660 ml of ethanol and 660 ml of 2 N sodium hydroxide solution is refluxed for 4 hours. The solution is then cooled and left to stand for 4 hours at 0°-5°C. The crystals which form are filtered off and recrystallized from water. The sodium salt of 2-(2,6-dichloroanilino)-phenylacetic acid melts at 283°-285°C. The yield is 97% of theoretical, according to US Patent 3,558,690.

brand name

Solaraze (Bioglan); Voltaren (Novartis);Aflamin;Alfamin;Allvoran;Artren;Blesin;B-voltaren;Cgp 9194;Chlorgyl;Ct-diclo;Dichloronic;Diclo attritin;Diclo spondril;Diclo-attritin;Diclo-burg;Diclo-phlohont;Diclo-puren;Diclo-recip;Dicloreum;Diclo-spondyril;Diclo-wolf;Dolobasan;Dolotrem;Doragon;Duravolten;Duvavotten;Feloran;Fenoflam;Flogofenac;Flogogenac;Forgenac;Inflamac;Klast;Monoflam;Myogit;Neuro-effekton;Neurofenac;Neuro-voltaren;Neviodin;Olfen;Panamor;Rewodina;Rheumalgen;Rheumavincin-n;Seecoren;Shignol;Silino;Sofarin;Thicataren;Toryxil;Tsudomin;Voltarene.

Therapeutic Function

Antiinflammatory

World Health Organization (WHO)

The World Health Organization currently has no information to suggest that diclofenac is less safe than other widely available non-steroidal antiinflammatory substances of this type, or that children are particularly liable to react adversely. It is registered in many countries in several dosage forms, including a 12.5 mg suppository indicated for juvenile arthritis.

General Description

Pharmaceutical secondary standards for application in quality control, provide pharma laboratories and manufacturers with a convenient and cost-effective alternative to the preparation of in-house working standards.
Diclofenac is a derivative of benzeneacetic acid. It is categorized under the class of non-steroidal anti-inflammatory drugs (NSAIDs). It shows inflammatory, analgesic and antipyretic activities.

Biochem/physiol Actions

Standard NSAID and cyclooxygenase (COX) inhibitor. Major metabolites are 4′-hydroxydiclofenac and 5′-hydroxydiclofenac. Has been used as substrate selective for CYP2C9.

Clinical Use

Diclofenac sodium is indicated for the treatment of rheumatoid arthritis, osteoarthritis, and ankylosing spondylitis.

Side effects

The structure of diclofenac is a hybrid of a fenamate and an arylacetic acid. The compound is used as its sodium salt for the symptomatic relief of rheumatoid arthritis and osteoarthritis, including degenerative joint disease of the hip. The recommended dose is 75 – 150 mg/d which is clinically equivalent to 3.6g/d of aspirin. Gastrointestinal problems (ulceration and bleeding) and adverse CNS reactions (dizziness and headache) are the most commonly encountered adverse effects.

Synthesis

Synthesis: Acylation of N-phenyl-2,6- dichloroaniline with chloroacetyl chloride gives the corresponding chloroacetanilide, which is fused with aluminum chloride to give 1-(2,6- dichlorophenyl)-2-indolinone. Hydrolysis of the indolinone with dilute aqueous-alcoholic sodium hydroxide affords the desired sodium salt directly.
synthesis of Diclofenac sodium

Veterinary Drugs and Treatments

The equine topical cream (Surpass?) is labeled for the control of pain and inflammation associated with osteoarthritis in tarsal, carpal, metacarpophalangeal, metarsophalangeal, and proximal interphalangeal (hock, knee, fetlock, pastern) joints for use up to 10 days duration. While, theoretically, diclofenac could be used systemically (orally) in other veterinary species, there are approved and safer alternatives.

Drug interactions

Potentially hazardous interactions with other drugs
antagonism of hypotensive effect; increased risk of nephrotoxicity and hyperkalaemia.
Analgesics: avoid concomitant use of 2 or more NSAIDs, including aspirin (increased side effects); avoid with ketorolac (increased risk of side effects and haemorrhage).
Antibacterials: possibly increased risk of convulsions with quinolones; concentration reduced by rifampicin.
Anticoagulants: effects of coumarins and phenindione enhanced; possibly increased risk of bleeding with heparins, dabigatran and edoxaban - avoid long term use with edoxaban; increased risk of haemorrhage with IV diclofenac - avoid.
Antidepressants: increased risk of bleeding with SSRIs and venlaflaxine.
Antidiabetic agents: effects of sulphonylureas enhanced.
Antiepileptics: possibly increased phenytoin concentration.
Ciclosporin: may potentiate nephrotoxicity; concentration increased by ciclosporin.
Cytotoxics: reduced excretion of methotrexate; increased risk of bleeding with erlotinib.

Metabolism

Diclofenac undergoes first-pass metabolism and is It is then excreted in the form of glucuronide and sulfate conjugates, mainly in the urine (about 60%) but also in the bile (about 35%). then extensively metabolised to 4′-hydroxydiclofenac, 5-hydroxydiclofenac, 3′-hydroxydiclofenac, and 4′,5-dihydroxydiclofenac by glucuronidation of the intact molecule or more commonly by single and multiple hydroxylation followed by glucuronidation.

storage

Store at RT

15307-78-5
15307-79-6
Synthesis of Diclofenac sodium from DICLOFENAC METHYL ESTER
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View Lastest Price from Diclofenac sodium manufacturers

Image Update time Product Price Min. Order Purity Supply Ability Manufacturer
Diclofenac sodium pictures 2024-03-19 Diclofenac sodium
15307-79-6
US $14.00-10.00 / kg 1kg 99% 100Tons Hebei Dangtong Import and export Co LTD
Diclofenac sodium pictures 2024-03-16 Diclofenac sodium
15307-79-6
US $0.00 / KG 100g 98%+ 100kg WUHAN CIRCLE POWDER TECHNOLOGY CO.,LTD
Diclofenac sodium pictures 2024-03-15 Diclofenac sodium
15307-79-6
US $100.00 / kg 1kg 99.9% 20tons Hong Kong Excellence Biotechnology Co., Ltd.
  • Diclofenac sodium pictures
  • Diclofenac sodium
    15307-79-6
  • US $14.00-10.00 / kg
  • 99%
  • Hebei Dangtong Import and export Co LTD
  • Diclofenac sodium pictures
  • Diclofenac sodium
    15307-79-6
  • US $100.00 / kg
  • 99.9%
  • Hong Kong Excellence Biotechnology Co., Ltd.
2[(2,6-dichlorophenyl)amino]-benzeneaceticacimonosodium diclophenacsodium gp45840 huma-difenac kriplex o-(2,6-dichloroanilino)phenyl-aceticacimonosodiumsalt orthophen ortofen prophenatin 2-[(2,6-dichlorophenyl)amino]-benzeneacetic acid,sodium salt (1:1) 51.75/KG Diclofenac for system suitability AURORA KA-854 ECOFENAC DICLOFENAC SODIUM DICHRONIC DICLOFENAC SODIUM DMF NERIODIN VALETAN VOLTAROL DICLOFENAC SODIUM BP sodium [2-[(2,6-dichlorophenyl)amino]phenyl]acetate Diclofanic potassium DICLOFENAC SODIUM SALT USP BP JP EP Benzeneacetic acid, 2-(2,6-dichlorophenyl)amino-, monosodium salt DICLOFENACSODIUM,USP DICLOFENAC SODIUM /SODIUM 2-((2,6-DICHLOROPHENYL)AMINO)PHENYL)ACETATE DICLOFENAC-NA 2-([2,6-Dichlorophenyl] amino) benezeneacetic acid, monosodium salt Benzeneacetic acid, 2[(2,6-dichlorophenyl)amino]-, monosodium 2-[(2,6-dichlorophenyl)amino]phenylacetate sodium Diclofenac Sodium salt, Ph.Eur. 4th Ed. sodium(o-((2,6-dichlorophenyl)amino)phenyl)acetate sodium(o-(2,6-dichloroanilino)phenyl)acetate sodiumdiclofenac AKOS B020028 2-(2,6-DICHLOROANILINO)PHENYLACETIC ACID SODIUM SALT 2-[(2,6-DICHLOROPHENYL)AMINO]-BENZENEACETIC ACID MONOSODIUM SALT 2-[(2,6-DICHLOROPHENYL)AMINO]BENZENEACETIC ACID, NA 2-[(2,6-DICHLOROPHENYL)AMINO]-BENZENEACETIC ACID SODIUM SALT KROPLEX BENFOFEN OOTHECA MANTIDIS Diclofenac SodiuM EC pellets 32% DelphiMix Diacron Naclof Naclofen Novapirina Orthofen SorelMon Voldal Voltaren Ophtha Diclofenac sodiuM COS 2-(2,6-Dichloroanilino)phenylacetic Acid Sodium Salt Sodium 2-(2,6-Dichloroanilino)phenylacetate Diclofenac SodiuM SR pellets 32% Diclofenac SodiuM(EP/BP) Aceclofenac EP IMpurity A