(o-(-2,6-Dichloranilino)phenyl)-essigsäure, Natrium-Salz

Bezeichnung:(o-(-2,6-Dichloranilino)phenyl)-essigsäure, Natrium-Salz

CAS-Nr15307-79-6

Englisch Name:Diclofenac sodium

CBNumberCB5474464

SummenformelC14H10Cl2NNaO2

Molgewicht318.13

MOL-Datei15307-79-6.mol

Synonyma

Natrium-[2-[(2,6-dichlorphenyl)amino]phenyl]acetat

(o-(-2,6-Dichloranilino)phenyl)-essigsäure, Natrium-Salz

(o-(-2,6-Dichloranilino)phenyl)-essigsäure, Natrium-Salz physikalisch-chemischer Eigenschaften

Schmelzpunkt	288-290°C
Dichte	0.781 g/cm3
storage temp.	room temp
Löslichkeit	H₂O: 50 mg/mL
Aggregatzustand	White solid
pka	4(at 25℃)
Farbe	White to Almost white
Wasserlöslichkeit	Soluble in water to 50mg/ml.
Merck	14,3081
BCS Class	2
Stabilität	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 Datenbank	15307-79-6(CAS DataBase Reference)

Sicherheit

Kennzeichnung gefährlicher	T,Xi
R-Sätze:	25-36/37/38-63
S-Sätze:	22-36/37-45-36-26-60-20
RIDADR	UN 2811 6.1/PG 3
WGK Germany	3
RTECS-Nr.	AG6330000
HazardClass	6.1(b)
PackingGroup	III
HS Code	29224999
Toxizität	LD50 in mice, rats (mg/kg): ~390, 150 orally (Krupp)

Gefahreninformationscode (GHS)

Diclofenac sodium Chemische Eigenschaften,Einsatz,Produktion Methoden

R-Sätze Betriebsanweisung:
R25:Giftig beim Verschlucken.
R36/37/38:Reizt die Augen, die Atmungsorgane und die Haut.
S-Sätze Betriebsanweisung:
S22:Staub nicht einatmen.
S36/37:Bei der Arbeit geeignete Schutzhandschuhe und Schutzkleidung tragen.
S45:Bei Unfall oder Unwohlsein sofort Arzt zuziehen (wenn möglich, dieses Etikett vorzeigen).
S36:DE: Bei der Arbeit geeignete Schutzkleidung tragen.
S26:Bei Berührung mit den Augen sofort gründlich mit Wasser abspülen und Arzt konsultieren.
Beschreibung
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.
Chemische Eigenschaften
Off-White Crystalline Solid
Originator
Voltaren,Fujisawa,Japan,1974
Verwenden
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.
Trademarks
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
Weltgesundheitsorganisation (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.
Allgemeine Beschreibung
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.
Nebenwirkungen
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.
Synthese
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.
Arzneimittelwechselwirkung
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.
Stoffwechsel
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.
Lager
Store at RT

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(o-(-2,6-Dichloranilino)phenyl)-essigsäure, Natrium-Salz Anbieter Lieferant Produzent Hersteller Vertrieb Händler.

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