Salazosulfapyridin

Sulfasalazine Struktur
599-79-1
CAS-Nr.
599-79-1
Bezeichnung:
Salazosulfapyridin
Englisch Name:
Sulfasalazine
Synonyma:
sasp;salicylazosulfapyridine;sulphasalazine;SSZ;azulfidine;sulfasalazin;SALAZOSULFAPYRIDINE;s.a.s.-500;salazopyrin;si-88
CBNumber:
CB0181156
Summenformel:
C18H14N4O5S
Molgewicht:
398.39
MOL-Datei:
599-79-1.mol

Salazosulfapyridin Eigenschaften

Schmelzpunkt:
260-265 °C (dec.)(lit.)
Siedepunkt:
689.3±65.0 °C(Predicted)
Dichte
1.3742 (rough estimate)
Brechungsindex
1.6000 (estimate)
storage temp. 
Keep in dark place,Sealed in dry,Room Temperature
Löslichkeit
NH4OH 1 M: 50 mg/mL, clear, red
pka
pKa 0.6(H2O t = 20 I < 0.001) (Uncertain);2.4(H2O t = 20 I < 0.001) (Uncertain);9.7(H2O t = 20 I < 0.001) (Uncertain);11.8(H2O t = 20 I < 0.001) (Uncertain)
Aggregatzustand
powder
Farbe
Orange
Wasserlöslichkeit
<0.1 g/100 mL at 25 ºC
Merck 
14,8942
BRN 
356241
BCS Class
2,4
Stabilität:
Stable for 1 year from date of purchase as supplied. Solutions in DMSO may be stored at -20° for up to 1 month.
InChIKey
NCEXYHBECQHGNR-QZQOTICOSA-N
CAS Datenbank
599-79-1(CAS DataBase Reference)
IARC
2B (Vol. 108) 2016
EPA chemische Informationen
Salicylazosulfapyridine (599-79-1)
Sicherheit
  • Risiko- und Sicherheitserklärung
  • Gefahreninformationscode (GHS)
Kennzeichnung gefährlicher Xn
R-Sätze: 42/43
S-Sätze: 22-29/56-45
RIDADR  3077
WGK Germany  2
RTECS-Nr. VO6250000
8
HS Code  29350090
Giftige Stoffe Daten 599-79-1(Hazardous Substances Data)
Toxizität LD50 oral in rabbit: > 7500mg/kg
Bildanzeige (GHS) GHS hazard pictograms
Alarmwort Achtung
Gefahrenhinweise
Code Gefahrenhinweise Gefahrenklasse Abteilung Alarmwort Symbol P-Code
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
Sicherheit
P261 Einatmen von Staub vermeiden.
P272 Kontaminierte Arbeitskleidung nicht außerhalb des Arbeitsplatzes tragen.
P280 Schutzhandschuhe/Schutzkleidung/Augenschutz tragen.
P284 Atemschutz tragen.
P302+P352 BEI BERÜHRUNG MIT DER HAUT: Mit viel Wasser/... (Hersteller kann, falls zweckmäßig, ein Reinigungsmittel angeben oder, wenn Wasser eindeutig ungeeignet ist, ein alternatives Mittel empfehlen) waschen.
P333+P313 Bei Hautreizung oder -ausschlag: Ärztlichen Rat einholen/ärztliche Hilfe hinzuziehen.

Salazosulfapyridin Chemische Eigenschaften,Einsatz,Produktion Methoden

R-Sätze Betriebsanweisung:

R42/43:Sensibilisierung durch Einatmen und Hautkontakt möglich.

S-Sätze Betriebsanweisung:

S22:Staub nicht einatmen.
S29/56:Nicht in die Kanalisation gelangen lassen;dieses Produkt und seinen Behälter der Problemabfallentsorgung zuführen.
S45:Bei Unfall oder Unwohlsein sofort Arzt zuziehen (wenn möglich, dieses Etikett vorzeigen).

Beschreibung

Sulfasalazine (brand name Azulfidine in the U.S., Salazopyrin and Sulazine in Europe and Hong Kong) was developed in the 1950s specifically to treat rheumatoid arthritis. It was believed at the time that bacterial infections were the cause of rheumatoid arthritis. Sulfasalazine is a sulfa drug, (a derivative of mesalazine) and is formed by combining sulfa pyridine and salicylate with an azo bond. It may be abbreviated SSZ.

Chemische Eigenschaften

Brownish-Yellow Crystals

Verwenden

Sulfasalazine is an anti-inflammatory (gastrointestinal). Sulfasalazine has been used in granulomatous colitis.

Definition

ChEBI: An azobenzene consisting of diphenyldiazene having a carboxy substituent at the 4-position, a hydroxy substituent at the 3-position and a 2-pyridylaminosulphonyl substituent at the 4'-position.

Indications

Sulfasalazine is used in the treatment of inflammatory bowel disease, including ulcerative colitis and Crohn's disease. It is also indicated for use in rheumatoid arthritis and used in other types of inflammatory arthritis (e.g. psoriatic arthritis) where it has a beneficial effect. It is often well tolerated compared to other DMARDS.
In clinical trials for the treatment of chronic alcoholics, sulfasalazine has been found to reverse the scarring associated with cirrhosis of the liver .
Cells called myofibroblasts, which contribute to scar tissue in a diseased liver, also appear to secrete proteins that prevent the breakdown of the scar tissue. Sulfasalazine appears to retard this secretion.

Allgemeine Beschreibung

Odorless yellow or brownish-yellow to orange powder. Tasteless.

Air & Water Reaktionen

Light sensitive and may be sensitive to prolonged exposure to air. Dust can be explosive when suspended in air at specific concentrations. Insoluble in water.

Brandgefahr

Flash point data for Salicylazosulfapyridine are not available; however, Salicylazosulfapyridine is probably combustible.

Pharmazeutische Anwendungen

One of the earliest and most successful sulfonamides to be developed was sulfapyridine, which fell into disuse because of unwanted effects such as crystalluria. Later, a number of salicylazosulfonamides, developed because of their increased water solubility, showed anti-inflammatory properties; one of them, sulfasalazine (salicylazosulfapyridine), has come into general use for ulcerative colitis.
After oral administration, some intact compound is absorbed from the upper gastrointestinal tract, appearing in the blood in 1–2 h, but most is cleaved by colonic bacteria to yield sulfapyridine and 5-aminosalicylic acid (mesalamine, mesalazine). Controlled trials have confirmed the efficacy of 5-aminosalicylic acid alone in ulcerative colitis, the sulfonamide component merely acting as a carrier. Thus, in remarkable extension of the good fortune that attended the discovery of sulfanilamide as the unexpected active principle of Prontosil, a cleavage product appears to be responsible for the beneficial effect of sulfasalazine. Since most of the side effects associated with sulfasalazine are attributable to sulfapyridine, there seems little reason, other than cost, to use it in preference to mesalamine.
Sulfasalazine is also of benefit in Crohn’s disease and rheumatoid arthritis, but the role, if any, of sulfapyridine in the overall effect is unclear.

Mechanism of action

Sulfasalazine is composed of sulfapyridine and 5- ASA molecules linked by an azo bond. Sulfapyridine has no effect on the inflammatory bowel disease, and instillation of this agent into the colon does not heal colonic mucosa.

Pharmakologie

Sulfasalazine is a prodrug of which 70% is converted by colon bacteria to two active metabolites, sulfapyridine and 5-aminosalicylic acid (mesalamine). Sulfapyridine has antibacterial activities, and 5-aminosalicylic acid is antiinflammatory; however, these effects do not account for the ability of this drug to slow the processes of rheumatoid arthritis. Recent research suggests additional activities of sulfasalazine that may be relevant to these effects: its ability to increase adenosine levels, its inhibitory effects on IL-1 and TNF- release, and its inhibition of NF-κB.

Pharmakokinetik

sulfasalazine is poorly absorbed, with approximately 20% of the ingested sulfasalazine reaching the systemic circulation. The remainder of the ingested dose is metabolized by colonic bacteria into its components, sulfapyridine and mesalamine (5-ASA). Most of the sulfapyridine metabolized from sulfasalazine (60–80%) is absorbed in the colon following oral administration, and approximately 25% of the 5-ASA metabolized from sulfasalazine is absorbed in the colon.

Clinical Use

Sulfasalazine (2-hydroxy-5[[4-[(2-pyridinylamino)sulfonyl]phenyl]azo]benzoic acid or 5-[p-(2-pyridylsulfamoyl)phenylazo]salicylic acid) is a brownish yellow, odorlesspowder, slightly soluble in alcohol but practically insolublein water, ether, and benzene.
Sulfasalazine is broken down in the body to m-aminosalicylicacid and sulfapyridine. The drug is excreted throughthe kidneys and is detectable colorimetrically in the urine,producing an orange-yellow color when the urine is alkalineand no color when the urine is acid.

Nebenwirkungen

Sulfsalazine metabolizes to sulfa pyridine. Serum levels should be monitored every three months, and more frequently at the outset. Serum levels above 50 μg / l are associated with side effects. In rare cases, Sulfasalazine can cause severe depression in young males. It can also cause temporary infertility. Immune thrombocytopenia has been reported.
Sulfasalazine inhibits dihydrofolate reductase, and can cause folate deficiency and megaloblastic anemia.
Sulfasalazine can cause hemolytic anemia in people with G6PD deficiency.

Vorsichtsmaßnahmen

Sulfasalazine is contraindicated in individuals with hypersensitivityto salicylates, sulfonamides, sulfonylureas,and certain diuretics (furosemide, thiazides, andcarbonic anhydrase inhibitors). Because it can causekernicterus, sulfasalazine is contraindicated in infantsand children under 2 years of age. Sulfasalazine passesinto breast milk and is therefore contraindicated fornursing mothers. Similarly, pregnant women near termshould not use this drug, although it appears to be thesafest of the DMARDs during early pregnancy.Sulfasalazine can precipitate attacks of porphyria andshould not be used by individuals with bowel or urinaryobstruction.
Sulfasalazine can inhibit the absorption of cardiacglycosides and folic acid. It may displace certain drugs,including warfarin, phenytoin, methotrexate, tolbutamide,chlorpropamide, and oral sulfonylureas, fromtheir protein binding sites. Sulfasalazine can diminishthe effectiveness of penicillins and estrogen-containingoral contraceptives.

Salazosulfapyridin Upstream-Materialien And Downstream Produkte

Upstream-Materialien

Downstream Produkte


Salazosulfapyridin Anbieter Lieferant Produzent Hersteller Vertrieb Händler.

Global( 408)Lieferanten
Firmenname Telefon E-Mail Land Produktkatalog Edge Rate
XI'AN TIANGUANGYUAN BIOTECH CO., LTD.
+86-029-86333380 18829239519
sales06@tgybio.com China 962 58
Changzhou Rokechem Technology Co., Ltd.
18758118018
sales001@rokechem.com China 255 58
Capot Chemical Co.,Ltd.
571-85586718 +8613336195806
sales@capotchem.com China 29797 60
Henan Tianfu Chemical Co.,Ltd.
+86-0371-55170693 +86-19937530512
info@tianfuchem.com China 21700 55
career henan chemical co
+86-0371-86658258
sales@coreychem.com China 29914 58
Hubei Jusheng Technology Co.,Ltd.
18871490254
linda@hubeijusheng.com CHINA 28180 58
Accela ChemBio Inc.
(+1)-858-699-3322
info@accelachem.com United States 19965 58
Hebei Guanlang Biotechnology Co., Ltd.
+86-19930503282
alice@crovellbio.com China 8823 58
Xiamen AmoyChem Co., Ltd
+86-592-6051114 +8618959220845
sales@amoychem.com China 6387 58
Shanghai Longyu Biotechnology Co., Ltd.
+8615821988213
info@longyupharma.com China 2530 58

599-79-1(Salazosulfapyridin)Verwandte Suche:


  • SULFASALAZINE
  • LABOTEST-BB LT00772281
  • 5-(p-(2-pyridylsulfamoyl)phenylazo)salicylic acid
  • 5-[4-(2-PYRIDYLSULFAMOYL)PHENYLAZO]SALICYLIC ACID
  • Benzoic acid, 2-hydroxy-5-4-(2-pyridinylamino)sulfonylphenylazo-
  • SULFASALAZINE USP 26,EP 4
  • SULFASALAZINE(SASP)(NDC:55631-0130)
  • SALICYLAZOSULPHAPYRIDINE
  • SALICYLICACID,5-((PARA-(2-PYRIDYLSULFAMOYL)PHENYL)AZO)-
  • sulfasalazine,SASP
  • 2-Hydroxy-5-[4-(pyridin-2-ylsulfamoyl)phenyl]diazenyl-benzoic acid
  • Sulfasalazine (125 mg)
  • Sulfasalazine (125 mg)G3F0351.000mg/mg(dr)
  • Azulfidine EN
  • Colo-Pleo
  • NSC 667219
  • Sulfasalazine-d3
  • 2-hydroxy-5-[[4-[(2-pyridinylamino)sulfonyl]phenyl]azo]benzoic acid
  • 2-hydroxy-5-((4-((2-pyridinylamino)sulfonyl)phenyl)azo)-benzoicaci
  • 2-hydroxy-5-[[4-[(2-pyridinylamino)sulfonyl]phenyl]azo]-benzoicaci
  • 4-(pyridyl-2-amidosulfonyl)-3’-carboxy-4’-hydroxyazobenzene
  • 5-((p-(2-pyridylsulfamoyl)phenyl)azo)-salicylicaci
  • 5-(4-(2-pyridylsulfamoyl)phenylazo)-2-hydroxybenzoicacid
  • 5-(p-(2-pyridylsulfamyl)phenylazo)salicylicacid
  • accucol
  • asulfidine
  • azopyrin
  • azopyrine
  • azosulfidin
  • benzosulfa
  • colo-pleon
  • reupirin
  • rorasul
  • salazopyridin
  • salazosulfapyridin
  • salisulf
  • sas-500
  • si-88
  • sulcolon
  • w-tsasporal
  • (E)-2-hydroxy-5-((4-(N-(pyridin-2-yl)sulfaMoyl)phenyl)diazenyl)benzoic acid
  • 2-hydroxy-5-[2-[4-[(2-pyridinylamino)sulfonyl]phenyl]diazenyl]-benzoic acid
  • NCEXYHBECQHGNR-UHFFFAOYSA-N
  • Sulfasalazine, 95%, Anti-inflammatory
  • Sulfasalazine - SSZ
  • Sulfasalazine[Salazosulfapyridine]
  • Sulfasalazine>
  • Sulfasalazine CRS
  • Benzoic acid, 2-hydroxy-5-[2-[4-[(2-pyridinylamino)sulfonyl]phenyl]diazenyl]-
  • 2-Hydroxy-5-((4-(N-(pyridin-2-yl)sulfamoyl)phenyl)diazenyl)benzoic acid
  • Sulfasalazine USP/EP/BP
  • Sulfasalazine (NSC 667219)
  • Sulfasalazine D3 15N
  • Sulfasalazine (1636005)
  • salicylazosulfapyridine
  • SALAZOSULFAPYRIDINE
  • SSZ
  • azulfidine
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