ChemicalBook
Chinese Japanese Germany Korea

Sulfasalazine

Brand Name(s)
Sulfasalazine
Sulfasalazine structure
CAS No.
599-79-1
Chemical Name:
Sulfasalazine
Synonyms
SSZ;sasp;si-88;accucol;rorasul;sas-500;azopyrin;reupirin;salisulf;sulcolon
CBNumber:
CB0181156
Molecular Formula:
C18H14N4O5S
Formula Weight:
398.4
MOL File:
599-79-1.mol

Sulfasalazine Properties

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. 
Refrigerator
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
Water Solubility 
<0.1 g/100 mL at 25 ºC
Merck 
14,8942
BRN 
356241
InChIKey
NCEXYHBECQHGNR-QZQOTICOSA-N
CAS DataBase Reference
599-79-1(CAS DataBase Reference)
FDA UNII
3XC8GUZ6CB
Proposition 65 List
Sulfasalazine (salicylazosulfapyridine)
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-P280-P284-P304+P340-P342+P311-P333+P313
Hazard Codes  Xn
Risk Statements  42/43
Safety Statements  22-29/56-45
RIDADR  3077
WGK Germany  2
RTECS  VO6250000
8
HS Code  29350090
Toxicity LD50 oral in rabbit: > 7500mg/kg

Sulfasalazine price More Price(7)

Manufacturer Product number Product description CAS number Packaging Price Updated Buy
Sigma-Aldrich S0883 Sulfasalazine analytical standard, ≥98% (HPLC) 599-79-1 10g $52.6 2019-12-02 Buy
Sigma-Aldrich 1636005 Sulfasalazine United States Pharmacopeia (USP) Reference Standard 599-79-1 125mg $286.65 2019-12-02 Buy
TCI Chemical S0580 Sulfasalazine >95.0%(HPLC)(T) 599-79-1 25g $85 2020-06-24 Buy
Cayman Chemical 15025 Sulfasalazine ≥98% 599-79-1 5g $35 2020-06-24 Buy
Cayman Chemical 15025 Sulfasalazine ≥98% 599-79-1 10g $50 2020-06-24 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

Anti-inflammatory (gastrointestinal). Has been used in granulomatous colitis.

Uses

anticolitis and Crohn's disease

Uses

Sulfasalazine is an anti-inflammatory (gastrointestinal). Sulfasalazine 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]

Uses

An inhibitor of of GSH-H-transferase and NF-kB activation and an apoptosis inducer

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.

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 (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.

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.

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

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.

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.

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.

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.

Sulfasalazine Preparation Products And Raw materials

Raw materials

Preparation Products


Sulfasalazine Suppliers

Global( 246)Suppliers
Supplier Tel Fax Email Country ProdList Advantage
Henan DaKen Chemical CO.,LTD.
+86-371-55531817
info@dakenchem.com CHINA 21837 58
Henan Tianfu Chemical Co.,Ltd.
0371-55170693
0371-55170693 info@tianfuchem.com CHINA 22625 55
career henan chemical co
+86-371-86658258
sales@coreychem.com CHINA 30043 58
Jinan Jianfeng Chemical Co., Ltd
15562555968
info@pharmachemm.com CHINA 304 58
Chemwill Asia Co.,Ltd.
86-21-51086038
86-21-51861608 chemwill_asia@126.com;sales@chemwill.com;chemwill@hotmail.com;chemwill@gmail.com CHINA 23977 58
Hubei Jusheng Technology Co.,Ltd.
86-18871470254
027-59599243 linda@hubeijusheng.com CHINA 28231 58
Accela ChemBio Inc.
(+1)-858-699-3322
(+1)-858-876-1948 info@accelachem.com United States 19988 58
QUALITY CONTROL CHEMICALS INC.
(323) 306-3136
(626) 453-0409 orders@qcchemical.com United States 8406 58
Xiamen AmoyChem Co., Ltd
+86 592-605 1114
sales@amoychem.com CHINA 6371 58
Chongqing Chemdad Co., Ltd
+86-13650506873
sales@chemdad.com CHINA 35434 58

View Lastest Price from Sulfasalazine manufacturers

Image Release date Product Price Min. Order Purity Supply Ability Manufacturer
2020-04-30 Sulfasalazine
599-79-1
US $0.10 / KG 1KG 99.0% 1000 tons Shaanxi Dideu Medichem Co. Ltd
2018-12-21 Salicylazosulfapyridine
599-79-1
US $7.00 / kg 1kg 99% 100kg career henan chemical co
2018-08-20 Salicylazosulfapyridine
599-79-1
US $1.00 / KG 1KG 98% 100KG career henan chemical co

599-79-1(Sulfasalazine)Related Search:


Copyright 2017 © ChemicalBook. All rights reserved