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Diclofenac sodium

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CAS:15307-79-6
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Related articles

  • What is Diclofenac sodium?
  • Diclofenac is a phenylacetic acid derivative belonging to the class of the non-selective non-steroidal anti-inflammatory drugs....
  • Feb 11,2020
Diclofenac sodium Basic information
description Uses Mechanisms of action Clinical Application
Product Name:Diclofenac sodium
Synonyms:2[(2,6-dichlorophenyl)amino]-benzeneaceticacimonosodium;diclophenacsodium;gp45840;huma-difenac;kriplex;o-(2,6-dichloroanilino)phenyl-aceticacimonosodiumsalt;orthophen;ortofen
CAS:15307-79-6
MF:C14H10Cl2NNaO2
MW:318.13
EINECS:239-346-4
Product Categories:Other APIs;VOLATREN;Amines;Aromatics;Heterocycles;Organics;Active Pharmaceutical Ingredients;Intermediates & Fine Chemicals;Pharmaceuticals;Steroids;Lipid signaling;API's;15307-79-6
Mol File:15307-79-6.mol
Diclofenac sodium Structure
Diclofenac sodium Chemical Properties
Melting point 288-290°C
density 0.781 g/cm3
storage temp. room temp
solubility H2O: 50 mg/mL
form White solid
pka4(at 25℃)
color White to Almost white
Water Solubility Soluble in water to 50mg/ml.
Merck 14,3081
BCS Class2
Stability:Stable.
InChIInChI=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
InChIKeyKPHWPUGNDIVLNH-UHFFFAOYSA-M
SMILESC1(=CC=CC=C1CC([O-])=O)NC1=C(Cl)C=CC=C1Cl.[Na+]
CAS DataBase Reference15307-79-6(CAS DataBase Reference)
Safety Information
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
ToxicityLD50 in mice, rats (mg/kg): ~390, 150 orally (Krupp)
MSDS Information
Diclofenac sodium Usage And Synthesis
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.

DescriptionDiclofenac 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 PropertiesOff-White Crystalline Solid
OriginatorVoltaren,Fujisawa,Japan,1974
UsesDiclofenac 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.
DefinitionChEBI: Diclofenac sodium is the sodium salt of diclofenac. It contains a diclofenac(1-).
Manufacturing ProcessFour 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 nameSolaraze (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 FunctionAntiinflammatory
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 DescriptionPharmaceutical 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 ActionsStandard NSAID and cyclooxygenase (COX) inhibitor. Major metabolites are 4′-hydroxydiclofenac and 5′-hydroxydiclofenac. Has been used as substrate selective for CYP2C9.
Clinical UseDiclofenac sodium is indicated for the treatment of rheumatoid arthritis, osteoarthritis, and ankylosing spondylitis.
Side effectsThe 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.
SynthesisSynthesis: 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 TreatmentsThe 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 interactionsPotentially 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.
MetabolismDiclofenac 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.
storageStore at RT
Tag:Diclofenac sodium(15307-79-6) Related Product Information
Dichloromethylphenylsilane 3,4'-DIAMINODIPHENYLMETHANE Sodium citrate Sodium chlorite Sodium chloride Sodium benzoate Sulfanilic acid Aniline Sodium hydroxide Sodium bicarbonate 4-Aminobenzoic acid Sodium acetate Phenylphosphonic dichloride 1-(2,6-Dichlorophenyl)-2-indolinone Glycine 6-Aminocaproic acid Sodium sulfate 8-CHLOROADENOSINE-3',5'-CYCLIC MONOPHOSPHOROTHIOATE, RP-ISOMER SODIUM SALT Diclofenac Sodium Salt