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15307-79-6

15307-79-6 Structure

15307-79-6 Structure
IdentificationMore
[Name]

Diclofenac sodium
[CAS]

15307-79-6
[Synonyms]

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
AKOS B020028
AURORA KA-854
BENFOFEN
DICHRONIC
DICLOFENAC SODIUM
DICLOFENAC SODIUM DMF
DICLOFENAC SODIUM SALT
ECOFENAC
KROPLEX
NERIODIN
SODIUM 2-(2,6-DICHLOROANILINO)PHENYLACETATE
VALETAN
VOLTAREN
VOLTAROL
(o-(2,6-dichloroanilino)phenyl)aceticacidmonosodiumsalt
(o-(2,6-dichloroanilino)phenyl)aceticacidsodiumsalt
[EINECS(EC#)]

239-346-4
[Molecular Formula]

C14H10Cl2NNaO2
[MDL Number]

MFCD00082251
[Molecular Weight]

318.13
[MOL File]

15307-79-6.mol
Chemical PropertiesBack Directory
[Appearance]

Off-White Crystalline Solid
[Melting point ]

288-290°C
[mp ]

288-290°C
[density ]

0.781 g/cm3
[storage temp. ]

room temp
[solubility ]

H2O: 50 mg/mL
[pka]

4(at 25℃)
[form ]

White solid
[Stability:]

Stable.
[Water Solubility ]

Soluble in water to 50mg/ml.
[Usage]

A nonsteroidal anti-inflammatory compound and cyclooxygenase (COX) inhibitor
[Merck ]

3081
[InChIKey]

KPHWPUGNDIVLNH-UHFFFAOYSA-M
[CAS DataBase Reference]

15307-79-6(CAS DataBase Reference)
Safety DataBack Directory
[Hazard Codes ]

T,Xi
[Risk Statements ]

R25:Toxic if swallowed.
R36/37/38:Irritating to eyes, respiratory system and skin .
[Safety Statements ]

S22:Do not breathe dust .
S36/37:Wear suitable protective clothing and gloves .
S45:In case of accident or if you feel unwell, seek medical advice immediately (show label where possible) .
S36:Wear suitable protective clothing .
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
[RIDADR ]

UN 2811 6.1/PG 3
[WGK Germany ]

3
[RTECS ]

AG6330000
[HazardClass ]

6.1(b)
[PackingGroup ]

III
[HS Code ]

29224900
[Toxicity]

LD50 in mice, rats (mg/kg): ~390, 150 orally (Krupp)
Raw materials And Preparation ProductsBack Directory
【Raw materials】

Ethanol-->Aniline-->Chloroacetyl chloride-->2-Chlorobenzoic acid-->2-Chlorotoluene-->2,6-Dichlorophenol-->2,5-Dichloroaniline-->2,6-Dichloroaniline-->Sodium hydroxide-->Aluminum chloride
【Preparation Products】

1-(2,6-Dichlorophenyl)indolin-2-one-->DICLOFENAC METHYL ESTER-->Oxindole
Material Safety Data Sheet(MSDS)Back Directory
[msds information]

2-[(2,6-Dichlorophenyl)amino]benzeneacetic acid sodium salt(15307-79-6).msds
Questions And AnswerBack Directory
[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.

Hazard InformationBack Directory
[Chemical Properties]

Off-White Crystalline Solid
[Originator]

Voltaren,Fujisawa,Japan,1974
[Definition]

ChEBI: The sodium salt of diclofenac.
[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.
[Clinical Use]

Diclofenac sodium is indicated for the treatment of rheumatoid arthritis, osteoarthritis, and ankylosing spondylitis.
[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.
Spectrum DetailBack Directory
[Spectrum Detail]

Diclofenac sodium(15307-79-6) 1H NMR
Diclofenac sodium(15307-79-6) IR1
Diclofenac sodium(15307-79-6) IR2
Well-known Reagent Company Product InformationBack Directory
[Sigma Aldrich]

15307-79-6(sigmaaldrich)
[TCI AMERICA]

Diclofenac Sodium Salt,>98.0%(LC)(T)(15307-79-6)
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