description Uses Mechanisms of action Clinical Application
ChemicalBook > CAS DataBase List > Diclofenac sodium

Diclofenac sodium

description Uses Mechanisms of action Clinical Application
Product Name
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;KROPLEX;Diacron
CBNumber
CB5474464
Molecular Formula
C14H10Cl2NNaO2
Formula Weight
318.13
MOL File
15307-79-6.mol
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Diclofenac sodium Property

Melting point:
288-290°C
Density 
0.781 g/cm3
storage temp. 
room temp
solubility 
H2O: 50 mg/mL
pka
4(at 25℃)
form 
White solid
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)
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Safety

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)
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Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Danger
Hazard statements

H301Toxic if swalloed

H372Causes damage to organs through prolonged or repeated exposure

H411Toxic to aquatic life with long lasting effects

Precautionary statements

P201Obtain special instructions before use.

P202Do not handle until all safety precautions have been read and understood.

P260Do not breathe dust/fume/gas/mist/vapours/spray.

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P273Avoid release to the environment.

P301+P310IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician.

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N-Bromosuccinimide Price

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

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

Diclofenac sodium Preparation Products And Raw materials

Raw materials

Ethanol Chloroacetyl chloride 2,6-Dichlorophenol 2-Chlorobenzoic acid Aniline 2,5-Dichloroaniline 2-Chlorotoluene

Preparation Products

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View Lastest Price from Diclofenac sodium manufacturers

WUHAN FORTUNA CHEMICAL CO., LTD
Product
Diclofenac sodium 15307-79-6
Price
US $1.00/KG
Min. Order
1KG
Purity
99%~101%,BP2010
Supply Ability
2ton/month
Release date
2021-06-09
HEBEI SHENGSUAN CHEMICAL INDUSTRY CO.,LTD
Product
Diclofenac sodium 15307-79-6
Price
US $99.00-66.00/kg
Min. Order
0.00100000kg
Purity
99%
Supply Ability
5000
Release date
2024-08-12
Henan Suikang Pharmaceutical Co.,Ltd.
Product
Diclofenac sodium 15307-79-6
Price
US $0.00-0.00/kg
Min. Order
1kg
Purity
99.0%
Supply Ability
1tons
Release date
2024-04-26

15307-79-6, Diclofenac sodiumRelated Search:

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

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  • 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