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S0883

Sigma-Aldrich

Sulfasalazine

97.0-101.5%

Synonym(s):

2-Hydroxy-5-{{4-[(2-pyridinylamino)sulfonyl]phenyl}azo}benzoic acid, 5-[4-(2-Pyridylsulfamoyl)phenylazo]salicylic acid, Salicylazosulfapyridine

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About This Item

Empirical Formula (Hill Notation):
C18H14N4O5S
CAS Number:
599-79-1
Molecular Weight:
398.39
Beilstein:
356241
EC Number:
209-974-3
MDL number:
MFCD00057363
UNSPSC Code:
41116107
PubChem Substance ID:
329824182
NACRES:
NA.24

Quality Level

200

Assay

97.0-101.5%

form

powder

technique(s)

HPLC: suitable
gas chromatography (GC): suitable

mp

260-265 °C (dec.) (lit.)

application(s)

forensics and toxicology
pharmaceutical (small molecule)

Mode of action

DNA synthesis | interferes
enzyme | inhibits

SMILES string

OC(=O)c1cc(ccc1O)\N=N\c2ccc(cc2)S(=O)(=O)Nc3ccccn3

InChI

1S/C18H14N4O5S/c23-16-9-6-13(11-15(16)18(24)25)21-20-12-4-7-14(8-5-12)28(26,27)22-17-3-1-2-10-19-17/h1-11,23H,(H,19,22)(H,24,25)/b21-20+

InChI key

NCEXYHBECQHGNR-QZQOTICOSA-N

Gene Information

human ... ALOX5(240) , PTGS1(5742) , PTGS2(5743)

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General description

Chemical structure: sulfonamide
Sulfasalazine (SSZ) belongs to the sulfonamide class of drugs, which can be metabolized into 5-aminosalicylic acid and sulfapyridine. SSZ is obtained as a reaction product of an antibacterial agent (sulfapyridine) and an anti-inflammatory agent (salicylic acid).

Application

Refer to the product′s Certificate of Analysis for more information on a suitable instrument technique. Contact Technical Service for further support.
Sulfasalazine has been used as an analytical standard in clinical studies:
  • For investigating its therapeutic potential in patients suffering from multiple sclerosis (MS).
  • For studying its role as an antiarthritic agent via inhibition of the cartilage degeneration and pain associated with progression of osteoarthritis in the rat, which is used as the test animal.

It may also be used as an analytical reference standard for the quantification of the analyte in biological samples and aqueous samples using enzyme-linked immunosorbent assay (ELISA) and spectrofluorimetic technique.



Pictograms

Health hazardEnvironment
GHS08,GHS09

Signal Word

Danger

Hazard Statements

H317,H334,H351,H361f,H411

Hazard Classifications

Aquatic Chronic 2 - Carc. 2 - Repr. 2 - Resp. Sens. 1 - Skin Sens. 1

Storage Class Code

11 - Combustible Solids

WGK

WGK 2

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
0000400805
0000400805
0000322548
0000310553
0000336876

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Handbook of Drug Interactions: A Clinical and Forensic Guid (2004)
Maarten Boers et al.
Annals of the rheumatic diseases, 72(3), 406-409 (2012-11-17)
Treatment of rheumatoid arthritis (RA) with tumour necrosis factor (TNF) antagonists changes the relationship between disease activity and progression of radiological joint damage ('disconnect'): patients who have little or no response of disease activity still show reductions in damage progression.
Johan A Karlsson et al.
Annals of the rheumatic diseases, 72(12), 1927-1933 (2012-12-01)
To compare EuroQol 5-Dimensions (EQ-5D) utility and quality-adjusted life-years (QALYs) in patients with early, methotrexate (MTX) refractory rheumatoid arthritis (RA), randomised to addition of infliximab (IFX) or sulfasalazine and hydroxychloroquine (SSZ+HCQ). RA-patients with symptoms <1 year were enrolled between 2002
M van den Broek et al.
Clinical and experimental rheumatology, 30(4 Suppl 73), S35-S38 (2012-10-20)
Targeted treatment is effective in the short term in achieving low disease activity or even remission in patients with rheumatoid arthritis (RA). The benefits of long-term targeted treatment are discussed based on the BeSt study results. The BeSt study has
Irene E van der Horst-Bruinsma et al.
Annals of the rheumatic diseases, 72(7), 1221-1224 (2012-12-25)
To examine the impact (if any) of gender on the clinical, functional and patient-reported outcomes of treatment using data pooled from four controlled clinical trials. Study data were pooled from four clinical control trials in which 1283 adult patients with
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