Sulfasalazine
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Sulfasalazine
structure -
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CAS No:
599-79-1
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Formula:
C18H14N4O5S
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Chemical Name:
Sulfasalazine
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Synonyms:
Benzoic acid,2-hydroxy-5-[2-[4-[(2-pyridinylamino)sulfonyl]phenyl]diazenyl]-;Salicylic acid,5-[[p-(2-pyridylsulfamoyl)phenyl]azo]-;Benzoic acid,2-hydroxy-5-[[4-[(2-pyridinylamino)sulfonyl]phenyl]azo]-;2-Hydroxy-5-[2-[4-[(2-pyridinylamino)sulfonyl]phenyl]diazenyl]benzoic acid;Azopyrin;Azopyrine;Azulfidine;5-[p-(2-Pyridylsulfamoyl)phenylazo]salicylic acid;5-[4-(2-Pyridylsulfamyl)phenylazo]-2-hydroxybenzoic acid;5-[p-(2-Pyridylsulfamyl)phenylazo]salicylic acid;Salazopyrin;Sulphasalazine;Salazosulfapyridine;Salicylazosulfapyridine;Sulfasalazine;Sulfasalazin;Salazosulfapyridin;Benzosulfa;Reupirin;Salazopyridin;Salisulf;Salazopyrine;2-Hydroxy-5-((4-((2-pyridinylamino)sulfonyl)phenyl)azo)benzoic acid;Colo-Pleon;NSC 203730;NSC 667219;Azulfidine EN;Azulfin;Sulazine;2-Hydroxy-5-((4-(N-(pyridin-2-yl)sulfamoyl)phenyl)diazenyl)benzoic acid
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Categories:
Active Pharmaceutical Ingredients > Synthetic Anti-infective Drugs
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CAS No:
Description
Sulfasalazine is a drug for the treatment of rheumatoid arthritis and ulcerative colitis. Sulfasalazine is reported to suppress NF-κB activity.
Characteristics
150
2.5
Salicylazosulfapyridine appears as odorless yellow or brownish-yellow to orange powder. Tasteless. (NTP, 1992) It is a sulfa drug used as an antibiotic.
1.5±0.1 g/cm3
220 °C
689.3°C at 760 mmHg
370.7±34.3 °C
1.691
H2O: <0.1 g/100 mL at 25 ºC;NH4OH 1 M: 50 mg/mL, clear, red
Refrigerator
2.3X10-14 mm Hg at 25 °C (est)
LD50 oral in rabbit: > 7500mg/kg
Odorless
Tasteless
Safety Information
3077
2
42/43
22-29/56-45
VO6250000
Xn
Stable under recommended storage conditions.
P261-P280-P284-P304 + P340-P333 + P313-P342 + P311
H317-H334
Sulfasalazine Use and Manufacturing
Add 2.9 g of 5-aminosalicylic acid to 50 ml of water at 20 to 25 ° C, and add hydrochloric acid to adjust the pH to 3 to stir.Dissolve, heat up to 30 ~ 35 ° C insulation. Add 10 ml of 4-nitrososulfonate 5 g of methanol to the mixture at 30-35 ° C.The reaction was kept warm until the temperature was 50 ° C until the reaction was completed. After the heat preservation, the mixture was cooled to 0 ° C for suction filtration, and the dried baking material was dried to obtain 7 g of sulfasalazine.92.5percent.into the reaction bottle placed Salicylic acid and partialsodium hydroxide with a material amount of 1.3(with the material amount ofSulfapyridine is 1). After the temperature was controlled to 7 ° C, A wasgradually dropped into the above reaction bottle and simultaneously theremaining sodium hydroxide solution was dropped to control the pH of thereaction solution to 10 to initiate the reaction. The amount of sodiumhydroxide used is 4 (based on the material amount of Sulfapyridine is 1).after1.5h of reaction the reaction was stopped. In to the reaction mixture acetonewas added then the pH was adjusted to 3 with the addition of acid, and thetemperature was refluxed for a period of time. And then cooled to 30 ° C toprecipitate crystals. The crystals were filtered off and the crystals werewashed several times to obtain sulfasalazine. The yield of this example was 94.9percent, and the purity was 98.6percent by HPLC.
Sulfasalazine is a prodrug of the anti-inflammatory agent 5-aminosalicylic acid that is covalently linked to the antibiotic sulfapyridine by an azo bond. This bond is rapidly cleaved by bacteria in the terminal ileum and colon, thus releasing the active anti-inflammatory component. It has long been used in treatment of inflammatory bowel disease and rheumatoid arthritis because of its ability to induce T lymphocyte apoptosis, modulate inflammatory mediators from both cyclooxygenase/5-lipoxygenase pathways and NF-κB signaling pathways, attenuate transcription of proinflammatory cytokines, and activate PPARγ.[Cayman Chemical]
Computed Properties
Molecular Weight:398.4
XLogP3:-0.7
Hydrogen Bond Donor Count:3
Hydrogen Bond Acceptor Count:9
Rotatable Bond Count:6
Exact Mass:398.06849073
Monoisotopic Mass:398.06849073
Topological Polar Surface Area:150
Heavy Atom Count:28
Complexity:657
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes
Drug Function and Efficacy
Anti-inflammatory drugs. A pharmacological experiment on a rat immune ulcerative colitis model was conducted to compare the effects of anal suppositories and oral tablets in the treatment of colitis. The results showed that the therapeutic effect of anal suppositories was significantly better than oral administration.
Registered Holders
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VALENS MOLECULES PRIVATE LIMITED
Active
India
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Zhejiang Jiuzhou Pharmaceutical Co., Ltd.
Active
China
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Taicang Shenzhou Biopharmaceutical Co., Ltd.
Active
China
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