Sulfasalazine
- CAS No.
- 599-79-1
- Chemical Name:
- Sulfasalazine
- Synonyms
- sasp;salicylazosulfapyridine;sulphasalazine;SSZ;azulfidine;sulfasalazin;SALAZOSULFAPYRIDINE;s.a.s.-500;salazopyrin;si-88
- CBNumber:
- CB0181156
- Molecular Formula:
- C18H14N4O5S
- Molecular Weight:
- 398.39
- MDL Number:
- MFCD00057363
- MOL File:
- 599-79-1.mol
| Melting point | 260-265 °C (dec.)(lit.) |
|---|---|
| Boiling point | 689.3±65.0 °C(Predicted) |
| Density | 1.3742 (rough estimate) |
| refractive index | 1.6000 (estimate) |
| storage temp. | Keep in dark place,Sealed in dry,Room Temperature |
| solubility | 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) |
| form | powder |
| color | Orange |
| Water Solubility | <0.1 g/100 mL at 25 ºC |
| Merck | 14,8942 |
| BRN | 356241 |
| BCS Class | 2,4 |
| Stability | 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 DataBase Reference | 599-79-1(CAS DataBase Reference) |
| FDA UNII | 3XC8GUZ6CB |
| IARC | 2B (Vol. 108) 2016 |
| Proposition 65 List | Sulfasalazine (salicylazosulfapyridine) |
| NCI Drug Dictionary | Azulfidine |
| ATC code | A07EC01 |
| EPA Substance Registry System | Salicylazosulfapyridine (599-79-1) |
SAFETY
Risk and Safety Statements
| Symbol(GHS) |  GHS08 |
|||||||||
|---|---|---|---|---|---|---|---|---|---|---|
| Signal word | Danger | |||||||||
| Hazard statements | H317-H334 | |||||||||
| Precautionary statements | P261-P272-P280-P284-P302+P352-P333+P313 | |||||||||
| Hazard Codes | Xn | |||||||||
| Risk Statements | 42/43 | |||||||||
| Safety Statements | 22-29/56-45 | |||||||||
| RIDADR | 3077 | |||||||||
| WGK Germany | 2 | |||||||||
| RTECS | VO6250000 | |||||||||
| F | 8 | |||||||||
| HS Code | 29350090 | |||||||||
| Toxicity | LD50 oral in rabbit: > 7500mg/kg | |||||||||
| NFPA 704 |
|
Sulfasalazine price More Price(33)
| Manufacturer | Product number | Product description | CAS number | Packaging | Price | Updated | Buy |
|---|---|---|---|---|---|---|---|
| Sigma-Aldrich | S0883 | Sulfasalazine analytical standard, ≥98% (HPLC) | 599-79-1 | 10g | $70.5 | 2024-03-01 | Buy |
| Sigma-Aldrich | 1636005 | Sulfasalazine United States Pharmacopeia (USP) Reference Standard | 599-79-1 | 125mg | $358 | 2024-03-01 | Buy |
| TCI Chemical | S0580 | Sulfasalazine >95.0%(HPLC)(T) | 599-79-1 | 25g | $98 | 2024-03-01 | Buy |
| Cayman Chemical | 15025 | Sulfasalazine ≥98% | 599-79-1 | 5g | $44 | 2024-03-01 | Buy |
| Cayman Chemical | 15025 | Sulfasalazine ≥98% | 599-79-1 | 10g | $63 | 2024-03-01 | Buy |
Sulfasalazine Chemical Properties,Uses,Production
Brand Name(s)
Azulfidine (Salazopyrin in Canada)
Description
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.
Chemical Properties
Brownish-Yellow Crystals
Uses
Sulfasalazine is an anti-inflammatory (gastrointestinal). Sulfasalazine has been used in granulomatous colitis.
Uses
An inhibitor of of GSH-H-transferase and NF-kB activation and an apoptosis inducer
Uses
anticolitis and Crohn's disease
Uses
Anti-inflammatory (gastrointestinal). Has been used in granulomatous colitis.
Uses
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]
Indications
Sulfasalazine (Azulfidine) was first introduced in 1940 as a treatment for rheumatoid arthritis. It was found that a number of patients with coexistent inflammatory bowel disease showed improvement of their GI symptoms, and the drug has subsequently been used for the treatment of patients with inflammatory bowel disease.
Indications
Sulfasalazine (Azulfidine) is approved for the treatment of rheumatoid arthritis and ulcerative colitis. It is also used to treat ankylosing spondylitis and Crohn’s disease. Comparisons of sulfasalazine with other DMARDs suggest that it is more effective than hydroxychloroquine, azathioprine, and oral gold compounds. It is at least as effective as intramuscular gold and penicillamine. It has a greater degree of toxicity than hydroxychloroquine but less than gold compounds and penicillamine. After 5 years, approximately 75% of patients have discontinued sulfasalazine therapy, primarily because of a lack of efficacy as opposed to intolerable side effects.
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.
General Description
Odorless yellow or brownish-yellow to orange powder. Tasteless.
General Description
Sulfasalazine (Azufidine) is an azo prodrug that is reducedby the bacterium present in the lower intestine to its activemetabolites, sulfapyridine and 5-aminosalicylic acid (5-ASA or mesalamine). It has been used for the treatment ofRA or ankylosing spondylitis, and inflammatory bowel diseases(IBDs) such as ulcerative colitis and Crohn disease.It is generally agreed that the therapeutic effects of sulfasalazinein treating IBDs are due mainly through its activemetabolite, 5-ASA. 5-ASA is believed to work, via similarmechanisms of action to the salicylates discussed earlier, byblocking prostaglandin synthesis in the lower intestine. On the other hand, because 5-ASA is completelyionized and very little of this metabolite can enter into systemiccirculation, the antirheumatic effects of sulfasalazinehave been attributed to its other active metabolite, sulfapyridine. In a more recent study, sulfasalazine and sulfapyridinewere found to inhibit 5-aminoimidazole-4-carboxamideribonucleotide transformylase, an enzyme involved in denovo purine biosynthesis. Sulfasalazine also inhibits neutrophilfunction, reduces immunoglobulin levels, and interfereswith T-cell function via suppression of NF-κB activation. Furthermore, like methotrexate, sulfasalazine hasalso been shown to inhibit osteoclastogenesis, thereby preventingbone erosion in arthritic patients.
It should be pointed out that approximately one third of thepatients treated long term with sulfasalazine discontinued thedrug because of dose-related adverse effects including nausea,dyspepsia, vomiting, headache, rash, gastric distress, especiallyin patients on a daily dosage of greater than 4 g (or aserum sulfapyridine levels above 50 mg/mL).
Air & Water Reactions
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.
Fire Hazard
Flash point data for Salicylazosulfapyridine are not available; however, Salicylazosulfapyridine is probably combustible.
Pharmaceutical Applications
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.
Pharmacology
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.
Pharmacokinetics
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 (Azulfidine) was first introduced in 1940 as a treatment for rheumatoid arthritis.
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.
Side effects
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.
Side effects
Mild to moderate side effects, including nausea, vomiting, abdominal pain, diarrhea, anorexia, and headache, occur in up to 33% of patients taking this drug. Skin rash and discoloration, fever, reversible male infertility, and liver enzyme elevation occur less frequently. Rare hematological abnormalities, such as agranulocytosis, aplastic anemia, hemolytic anemia, neutropenia, or other blood dyscrasias, can be fatal. Hypersensitivity reactions occur rarely.
Side effects
It is, however, responsible for most of sulfasalazine’s side effects, including sulfa allergic reactions. 5-ASA, the active metabolite, may inhibit the synthesis of mediators of inflammation.
Synthesis
Sulfasalazine, 5-[p-[(4,6-dimethyl-2-pyridinyl)sulfamoyl]phenylazo]salicylic acid (33.1.22), is a derivative of sulfapyridine drug described above and one of the few sulfanilamides in which the free amino group in the benzene ring is modified, and it is synthesized by an azo-coupling reaction of a diazo salt, which is synthesized by reacting sulfapyridine (33.1.21) with nitrous acid and salicylic acid alkaline media.
Veterinary Drugs and Treatments
Sulfasalazine is used for the treatment of inflammatory bowel disease in dogs and cats. It has also been suggested for adjunctive use in treating vasculitis in dogs.
Drug interactions
Potentially hazardous interactions with other drugs
Ciclosporin: may reduce ciclosporin levels.
Metabolism
After cleavage of the sulfasalazine molecule about 60 to
80% of available sulfapyridine is absorbed, and undergoes
extensive metabolism in the liver by acetylation,
hydroxylation, and glucuronidation.
Most of a dose of sulfasalazine is excreted in the urine.
Unchanged sulfasalazine accounts for 15% of the original
dose, sulfapyridine and its metabolites 60%, and 5-ASA
and its metabolites 20-33%.
storage
Store at RT
Mode of action
Sulfasalazine, and its metabolite 5-ASA, are poorly absorbed from the gut. Its main mode of action is therefore believed to be inside the intestine.
Bowel disease
In Crohn's disease and ulcerative colitis, it is thought to be an antinflammatory drug that is essentially providing topical relief inside the intestine. It does this via a number of mechanisms such as reducing the synthesis of inflammatory mediators known as eicosanoids and inflammatory cytokines. However, unlike glucocorticoids ( another class of drug used in the treatment in inflammatory bowel disease ), sulfasalazine is a mild immunosuppressant.
Arthritis
When treatment for arthritis is successful, pain, joint swelling and stiffness will be reduced and this may slow down or stop the development of joint damage. The precise reasons why sulfasalazine are effective in various forms of arthritis is not clearly understood. Because sulfasalazine and its metabolite 5-ASA are poorly absorbed into the bloodstream, it is surprising that the drug is effective against symptoms outside of the intestine. One possible explanation is that, given that ulcerative colitis produces arthritic symptoms, the arthritic symptoms are actually a product of unrecognized ulcerative colitis , which is effectively treated with sulfazalazine.
Precautions
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.
References
1) Peppercorn (1984),?Sulfasalazine. Pharmacology, clinical use, toxicity, and related drug development; Ann. Intern. Med.,?101?377 2) Wahl?et al. (1998),?Sulfasalazine: a potent and specific inhibitor of nuclear factor kappa B; J. Clin. Invest.,?101?1163 3) Sheldon?et al. (1988),?Effect of sulphasalazine and its metabolites on mitogen induced transformation of lymphocytes D clues to its clinical action?; Br. J. Rheumatol.,?27?344 4) Fujiwara?et al. (1990),?Inhibition of proliferation responses and interleukin 2 production by salazosulfapyridine and its metabolites; Jpn. J. Pharmacol.,?54?121 5) Chung and Sontheimer (2009),?Sulfasalazine inhibits the growth of primary brain tumors in dependent of nuclear factor-κB; J.Neurochem.,?110?182 6) Patel?et al. (2004),?Differentiation of substrate and non-substrate inhibitors of transport system Xc – :an obligate exchanger of L-glutamate and L-cystine; Neuropharmacol.,?46?273
Sulfasalazine Preparation Products And Raw materials
Raw materials
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Preparation Products
| Supplier | Tel | Country | ProdList | Advantage | |
|---|---|---|---|---|---|
| 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 |
| Shaanxi TNJONE Pharmaceutical Co., Ltd | +86-13474506593 +86-13474506593 | sarah@tnjone.com | China | 775 | 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 | 21695 | 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 | 8822 | 58 |
| Xiamen AmoyChem Co., Ltd | +86-592-6051114 +8618959220845 | sales@amoychem.com | China | 6387 | 58 |
View Lastest Price from Sulfasalazine manufacturers
| Image | Update time | Product | Price | Min. Order | Purity | Supply Ability | Manufacturer | |
|---|---|---|---|---|---|---|---|---|
 |
2024-04-07 | Sulfasalazine
599-79-1
|
US $0.00 / kg | 1kg | 99% | 1000kg | Shaanxi TNJONE Pharmaceutical Co., Ltd | |
 |
2023-12-19 | Sulfasalazine
599-79-1
|
US $85.00-75.00 / Kg/Bag | 1Kg/Bag | 98% | 2500kg/month | XI'AN TIANGUANGYUAN BIOTECH CO., LTD. | |
 |
2023-06-28 | Sulfasalazine
599-79-1
|
US $0.00-0.00 / Kg | 1Kg | 99%;USP/EP/CP | 1-10000kgs | Changzhou Rokechem Technology Co., Ltd. |
-
- Sulfasalazine
599-79-1
- US $0.00 / kg
- 99%
- Shaanxi TNJONE Pharmaceutical Co., Ltd
-
- Sulfasalazine
599-79-1
- US $85.00-75.00 / Kg/Bag
- 98%
- XI'AN TIANGUANGYUAN BIOTECH CO., LTD.
-
- Sulfasalazine
599-79-1
- US $0.00-0.00 / Kg
- 99%;USP/EP/CP
- Changzhou Rokechem Technology Co., Ltd.
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