Sulindac

Sulindac Struktur
38194-50-2
CAS-Nr.
38194-50-2
Bezeichnung:
Sulindac
Englisch Name:
Sulindac
Synonyma:
Aclin;Sudac;Saldac;MK-231;ReuMyl;AFLODAC;Imbaral;mobilin;SULINOL;sulinac
CBNumber:
CB3740374
Summenformel:
C20H17FO3S
Molgewicht:
356.41
MOL-Datei:
38194-50-2.mol

Sulindac Eigenschaften

Schmelzpunkt:
182-185°C
Siedepunkt:
581.6±50.0 °C(Predicted)
Dichte
1.2581 (estimate)
storage temp. 
Sealed in dry,Store in freezer, under -20°C
Löslichkeit
Very slightly soluble in water, soluble in methylene chloride, sparingly soluble in ethanol (96 per cent). It dissolves in dilute solutions of alkali hydroxides.
pka
pKa (25°) 4.7
Farbe
Light yellow to Brown
Wasserlöslichkeit
Soluble in water, methanol, ethanol.
maximale Wellenlänge (λmax)
327nm(0.05mol/L methanolic HCl)(lit.)
Merck 
14,8982
CAS Datenbank
38194-50-2(CAS DataBase Reference)
NIST chemische Informationen
Sulindac(38194-50-2)
EPA chemische Informationen
1H-Indene-3-acetic acid, 5-fluoro-2-methyl-1-[[4-(methylsulfinyl)phenyl]methylene]-, (1Z)- (38194-50-2)
Sicherheit
  • Risiko- und Sicherheitserklärung
  • Gefahreninformationscode (GHS)
Kennzeichnung gefährlicher Xn
R-Sätze: 22-63-42/43
S-Sätze: -
RIDADR  3249
WGK Germany  3
RTECS-Nr. NK8226000
HazardClass  6.1(b)
PackingGroup  III
HS Code  29309090
Bildanzeige (GHS) GHS hazard pictogramsGHS hazard pictograms
Alarmwort Achtung
Gefahrenhinweise
Code Gefahrenhinweise Gefahrenklasse Abteilung Alarmwort Symbol P-Code
H301 Giftig bei Verschlucken. Akute Toxizität oral Kategorie 3 Achtung P264, P270, P301+P310, P321, P330,P405, P501
H317 Kann allergische Hautreaktionen verursachen. Sensibilisierung der Haut Kategorie 1A Warnung P261, P272, P280, P302+P352,P333+P313, P321, P363, P501
H334 Kann bei Einatmen Allergie, asthmaartige Symptome oder Atembeschwerden verursachen. Sensibilisierung der Atemwege Kategorie 1 Achtung P261, P285, P304+P341, P342+P311,P501
H361 Kann vermutlich die Fruchtbarkeit beeinträchtigen oder das Kind im Mutterleib schädigen. Reproduktionstoxizität Kategorie 2 Warnung P201, P202, P281, P308+P313, P405,P501
Sicherheit
P261 Einatmen von Staub vermeiden.
P280 Schutzhandschuhe/Schutzkleidung/Augenschutz tragen.
P284 Atemschutz tragen.
P304+P340 BEI EINATMEN: Die Person an die frische Luft bringen und für ungehinderte Atmung sorgen.
P342+P311 Bei Symptomen der Atemwege: GIFTINFORMATIONSZENTRUM/Arzt/... (geeignete Stelle für medizinische Notfallversorgung vom Hersteller/Lieferanten anzugeben) anrufen.

Sulindac Chemische Eigenschaften,Einsatz,Produktion Methoden

R-Sätze Betriebsanweisung:

R22:Gesundheitsschädlich beim Verschlucken.
R63:Kann das Kind im Mutterleib möglicherweise schädigen.
R42/43:Sensibilisierung durch Einatmen und Hautkontakt möglich.

Beschreibung

Many non-steroidal anti-inflammatory drugs (NSAIDs) are potent but non-selective inhibitors of both COX-1 and COX-2 in humans. Sulindac is one of the older NSAIDs, an isostere of indomethacin developed before the inducible form of COX-2 was discovered. Although a number of NSAIDs have been found to protect against digestive tract cancers, sulindac has an extensive epidemiology documenting reduced human colorectal cancer. In murine models, sulindac was found not only to inhibit the enzymatic activity of polyp-associated COX-2, but also to downregulate the expression of colonic COX-2 protein to control levels.

Chemische Eigenschaften

Yellow Crystalline Solid

Verwenden

Sulindac is a non-steroidal anti-inflammatory drug.

Definition

ChEBI: A monocarboxylic acid that is 1-benzylidene-1H-indene which is substituted at positions 2, 3, and 5 by methyl, carboxymethyl, and fluorine respectively, and in which the phenyl group of the benzylidene moiety is substituted at the ara position by a methylsulfinyl group. It is a prodrug for the corresponding sulfide, a non-steroidal anti-inflammatory drug, used particularly in the treatment of acute and chronic inflammatory conditions.

Indications

Sulindac (Clinoril) is chemically related to indomethacin and is generally used for the same indications. It is a prodrug that is metabolized to an active sulfide metabolite and an inactive metabolite. The most frequently reported side effects are GI pain, nausea, diarrhea, and constipation. The incidence of these effects is lower than for indomethacin, presumably because sulindac is a prodrug and thus the active metabolite is not highly concentrated at the gastric mucosa. As with indomethacin, a rather high incidence of CNS side effects (dizziness, headache) also occurs.

Allgemeine Beschreibung

Sulindac, (Z)-5-fluoro-2-methyl-1-([p-(methylsulfinyl)phenyl]methylene)-1H-indene-3-acetic acid (Clinoril), isan NSAID prodrug that contains a chiral sulfoxide moietybut is marketed as the racemate because it undergoes invivo reduction by the hepatic enzymes into its achiral, activemetabolite, methyl sulfide that exhibits potent andnonselective COX inhibition similar to indomethacin.
The parent sulfoxide has a plasma half-life of 8 hours, andthe active methyl sulfide metabolite is 16.4 hours. The morepolar and inactive sulfoxide is virtually the only form excretedinto the renal tubules, thus sulindac is believed to haveminimal nephrotoxicity associated with indomethacin. Thelong half-life of sulindac is caused by the extensive enterohepaticcirculation and reactivation of the inactive sulfoxideexcreted. Coadministration of aspirin is contraindicated becauseit considerably reduces the sulfide blood levels. Carefulmonitoring of patients with a history of ulcers is recommended.Gastric bleeding, nausea, diarrhea, dizziness, andother adverse effects have been noted with sulindac, but witha lower frequency than with aspirin. Sulindac is recommendedfor RA, OA, and ankylosing spondylitis.

Biologische Aktivität

Prodrug. Metabolizes to sulindac sulfide, a cyclooxgenase inhibitor that represses ras signaling, and sulindac sulfone, an antitumor agent, following oral administration in vivo . Widely used anti-inflammatory agent.

Pharmakokinetik

Sulindac is well absorbed on oral administration (90%), reaches peak plasma levels within 2 to 4 hours, and being acidic (pKa = 4.5), is highly bound to serum proteins (93%). The metabolism of sulindac plays a major role in its actions, because all of the pharmacological activity is associated with its major metabolite. Sulindac is, in fact, a pro-drug, the sulfoxide function being reduced to the active sulfide metabolite. Sulindac is absorbed as the sulfoxide, which is not an inhibitor of prostaglandin biosynthesis in the GI tract. Prostaglandins exert a protective effect in the GI tract, and inhibition of their synthesis here leads to many of the GI side effects noted for most NSAIDs. Once sulindac enters the circulatory system, it is reduced to the sulfide, which is an inhibitor of prostaglandin biosynthesis in the joints. Thus, sulindac produces less GI side effects, such as bleeding, ulcerations, and so on, than indomethacin and many other NSAIDs. In addition, the active metabolite has a plasma half-life approximately twice that of the parent compound (~16 hours versus 8 hours), which favorably affects the dosing schedule. In addition to the sulfide metabolite, sulindac is oxidized to the corresponding sulfone, which is inactive. A minor product results from hydroxylation of the benzylidene function and the methyl group at the 2-position. Glucuronides of several metabolites also are found. Sulindac as well as the sulfide and the sulfone metabolites are all highly protein-bound. Despite the fact that the sulfide metabolite is a major activation product and is found in high concentration in human plasma, it is not found in human urine, perhaps because of its high degree of protein binding.

Clinical Use

Sulindac is indicated for long-term use in the treatment of rheumatoid arthritis, osteoarthritis, ankylosing spondylitis, and acute gouty arthritis. The usual maximum dosage is 400 mg/day, with starting doses recommended at 150 mg twice a day. It is recommended that sulindac be administered with food.

Nebenwirkungen

Whereas the toxicity of sulindac is lower than that observed for indomethacin and other NSAIDs, the spectrum of adverse reactions is very similar. The most frequent side effects reported are associated with irritation of the GI tract (e.g., nausea, dyspepsia, and diarrhea), although these effects generally are mild. Effects on the CNS (e.g., dizziness and headache) are less common. Dermatological effects are less frequently encountered.

Sulindac Upstream-Materialien And Downstream Produkte

Upstream-Materialien

Downstream Produkte


Sulindac Anbieter Lieferant Produzent Hersteller Vertrieb Händler.

Global( 341)Lieferanten
Firmenname Telefon E-Mail Land Produktkatalog Edge Rate
Hebei Mojin Biotechnology Co., Ltd
+8613288715578
sales@hbmojin.com China 12452 58
Xiamen Wonderful Bio Technology Co., Ltd.
+8613043004613
Sara@xmwonderfulbio.com China 305 58
Capot Chemical Co.,Ltd.
571-85586718 +8613336195806
sales@capotchem.com China 29797 60
Shanghai Bojing Chemical Co.,Ltd.
+86-86-02137122233 +8613795318958
bj1@bj-chem.com China 297 55
Henan Tianfu Chemical Co.,Ltd.
+86-0371-55170693 +86-19937530512
info@tianfuchem.com China 21700 55
Nanjing ChemLin Chemical Industry Co., Ltd.
025-83697070
product@chemlin.com.cn CHINA 3012 60
ATK CHEMICAL COMPANY LIMITED
+undefined-21-51877795
ivan@atkchemical.com China 32480 60
Shanghai Zheyan Biotech Co., Ltd.
18017610038
zheyansh@163.com CHINA 3620 58
career henan chemical co
+86-0371-86658258
sales@coreychem.com China 29914 58
Hebei Guanlang Biotechnology Co., Ltd.
+86-19930503282
alice@crovellbio.com China 8823 58

38194-50-2(Sulindac)Verwandte Suche:


  • Sulindac Solution, 100ppm
  • Sulindac SynonyMs (Z)-5-Fluoro-2-Methyl-1-[p-(Methylsulfinyl)benzylidene]indene-3-acetic acid
  • 1h-indene-3-aceticacid,5-fluoro-2-methyl-1-((4-(methylsulfinyl)phenyl)methyle
  • Aclin
  • arthrocine
  • (z)-5-fluoro-2-methyl-1-((p-(methylsulfinyl)phenyl)methylene)-1h-indene-3-ac
  • sulindacsulfoxide
  • (Z)-5-FLUORO-2-METHYL-1-[P-(METHYLSULFINYL)BENZYLIDENE]INDENE-3-ACETIC ACID
  • 5-FLUORO-2-METHYL-1Z-[[4(METHYLSILFUNYL)PHENYL]METHYLENE]-1H-INDENE-3-ACETIC ACID
  • AFLODAC
  • ALGOCETIL
  • AKOS NCG1-0019
  • (1Z)-5-FLUORO-2-METHYL-1-[[4-(METHYLSULFINYL)PHENYL]METHYLENE]-1H-INDENE-3-ACETIC ACID
  • LABOTEST-BB LT00772301
  • SULINDAC, USP
  • (1Z)-5-Fluoro-2-methyl-1-[(4-(methylsulfinyl)phenyl]methylene]-1H-indene-3-acetic Acid, MK-231, Aflodac, Algocetil, Sulinol, Sulreuma
  • 1H-Indene-3-acetic acid, 5-fluoro-2-methyl-1-4-(methylsulfinyl)phenylmethylene-, (1Z)-
  • SULINDAC(RG)
  • NO-SULINDAC
  • Saldac
  • (Z)-5-Fluoro-2-methyl-1-[[4-(methylsulfinyl)phenyl]methylene]-1H-indene-3-acetic acid
  • Arthrobid
  • Arthroeine
  • Artribid
  • Citireuma:Clinoril
  • Clisundac
  • Imbaral
  • Reumofil
  • Sudac
  • Sulinol:S1ureuma
  • 5-Fluoro-2-methyl-1-[[4-(methylsulfinyl)phenyl]methylene]-1H-indene-3-acetic acid
  • cis-5-Fluoro-2-methyl-1-[(p-methylsulfinyl)benzylidenyl]indene-3-acetic acid
  • cis-5-fluoro-2-methyl-1-((4-(methylsulfinyl)phenyl)methylene)-1h-indene-3-ac
  • cis-sulindac
  • clinoril
  • Clusinol
  • mobilin
  • SULINOL
  • SULINDAC
  • SULREUMA
  • MK-231
  • Citireuma
  • Sulindac,(Z)-5-Fluoro-2-methyl-1-[p-(methylsulfinyl)benzylidene]indene-3-acetic acid
  • Sulindac (200 mg)
  • 2-[(1E)-5-fluoro-1-({4-[(R)-Methanesulfinyl]phenyl}Methylidene)-2-Methyl-1H-inden-3-yl]acetic acid
  • Sulindac(Clinoril)
  • ReuMyl
  • SULINDAC API
  • Sulindac E IsoMer
  • (Z)-2-(5-Fluoro-2-Methyl-1-(4-(Methylsulfinyl)benzylidene)-1H-inden-3-yl)acetic acid
  • (Z)-2-(3-(4-(methylsulfinyl)benzylidene)-6-fluoro-2-methyl-3H-inden-1-yl)acetic acid
  • {5-Fluoro-2-methyl-1-[4-(methylsulfinyl)benzylidene]-1H-inden-3-yl}acetic acid
  • Sulindac,Clinoril,Imbaron,Sudac,Sulinol,Artribid,Sudac,Zulida,Lyndak.
  • Sulindac, 98%, a COX inhibitor
  • 2-[(3Z)-6-fluoro-2-methyl-3-[[4-[(R)-methylsulfinyl]phenyl]methylidene]-1-indenyl]acetate
  • Sulindac Z
  • Sulindac CRS
  • (Z)-5-Fluoro-2-methyl-1-[(p-methylsulfinyl)benzylidene]-1H-indene-3-acetic Acid
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