Sulfasalazine | CAS#599-79-1

MedKoo Cat#: 318775 | Name: Sulfasalazine

Description:

WARNING: This product is for research use only, not for human or veterinary use.

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 liver cirrhosis.

Chemical Structure

Sulfasalazine

CAS#599-79-1

Theoretical Analysis

MedKoo Cat#: 318775

Name: Sulfasalazine

CAS#: 599-79-1

Chemical Formula: C18H14N4O5S

Exact Mass: 398.0680

Molecular Weight: 398.39

Elemental Analysis: C, 54.27; H, 3.54; N, 14.06; O, 20.08; S, 8.05

Price and Availability

Size	Price	Availability
1g	USD 110.00	Ready to ship
2g	USD 180.00	Ready to ship
5g	USD 350.00	Ready to ship
10g	USD 550.00	Ready to ship
20g	USD 850.00	Ready to ship

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Related CAS #

No Data

Synonym

NSC203730; NSC-203730 NSC 203730; Sulfasalazine; Reupirin; Rorasul; Azopyrin; NSC 667219;

IUPAC/Chemical Name

(E)-2-hydroxy-5-((4-(N-(pyridin-2-yl)sulfamoyl)phenyl)diazenyl)benzoic acid

InChi Key

NCEXYHBECQHGNR-QZQOTICOSA-N

InChi Code

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+

SMILES Code

O=C(O)C1=CC(/N=N/C2=CC=C(S(=O)(NC3=NC=CC=C3)=O)C=C2)=CC=C1O

Appearance

Solid powder

Purity

>98% (or refer to the Certificate of Analysis)

Shipping Condition

Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition

Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility

Soluble in DMSO, DMF, and PBS (pH 7.2)

Shelf Life

>2 years if stored properly

Drug Formulation

This drug may be formulated in DMSO

Stock Solution Storage

0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code

2934.99.9001

More Info

Product Data

Product Data

Certificate of Analysis

View CoA: current batch, Lot#TCI80913

Safety Data Sheet (SDS)

View Safety Data Sheet (SDS)

Instruction

View handling instruction

Biological target:

Sulfasalazine is an inhibitor of nuclear factor kappa B (NF-κB), TGF-β and COX-2.

In vitro activity:

The expression of both sepiapterin reductase mRNA and sepiapterin reductase protein was significantly higher in neuroblastoma cell lines without MYCN amplification. Sulfasalazine inhibited sepiapterin reductase enzyme activity in vitro and exhibited anti-proliferative activity in a large number of neuroblastoma cell lines derived from high-risk tumors. Reference: Biochem Pharmacol. 2019 Apr;162:237-249. https://pubmed.ncbi.nlm.nih.gov/30639262/

In vivo activity:

Sulfasalazine resolved joint stiffness in a rabbit model of arthrofibrosis. Stiffness in immobilized joints treated with blank pellets (control) was significantly higher than in non-immobilized, untreated joints (normal), and higher than in immobilized joints treated with sulfasalazine. Intimal thickness was significantly lower than control in the normal and sulfasalazine-treated group. Sulfasalazine significantly inhibited contractile activity. Reference: J Orthop Res. 2020 Mar;38(3):629-638. https://pubmed.ncbi.nlm.nih.gov/31692083/

	Solvent	mg/mL	mM
Solubility
	DMSO	75.0	188.16
	DMF	30.0	75.30
	PBS (pH 7.2)	0.2	0.50

Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 398.39 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Concentration / Solvent Volume / Mass	1 mg	5 mg	10 mg
1 mM	1.15 mL	5.76 mL	11.51 mL
5 mM	0.23 mL	1.15 mL	2.3 mL
10 mM	0.12 mL	0.58 mL	1.15 mL
50 mM	0.02 mL	0.12 mL	0.23 mL

Formulation protocol:

1. Mooney MR, Geerts D, Kort EJ, Bachmann AS. Anti-tumor effect of sulfasalazine in neuroblastoma. Biochem Pharmacol. 2019 Apr;162:237-249. doi: 10.1016/j.bcp.2019.01.007. Epub 2019 Jan 9. PMID: 30639262. 2. Takatani-Nakase T, Ikushima C, Sakitani M, Nakase I. Regulatory network of ferroptosis and autophagy by targeting oxidative stress defense using sulfasalazine in triple-negative breast cancer. Life Sci. 2024 Feb 15;339:122411. doi: 10.1016/j.lfs.2023.122411. Epub 2024 Jan 5. PMID: 38184272. 3. Sun S, Guo C, Gao T, Ma D, Su X, Pang Q, Zhang R. Hypoxia Enhances Glioma Resistance to Sulfasalazine-Induced Ferroptosis by Upregulating SLC7A11 via PI3K/AKT/HIF-1α Axis. Oxid Med Cell Longev. 2022 Nov 18;2022:7862430. doi: 10.1155/2022/7862430. PMID: 36439690; PMCID: PMC9699746. 4. Atluri K, Brouillette MJ, Seol D, Khorsand B, Sander E, Salem AK, Fredericks D, Petersen E, Smith S, Fowler TP, Martin JA. Sulfasalazine Resolves Joint Stiffness in a Rabbit Model of Arthrofibrosis. J Orthop Res. 2020 Mar;38(3):629-638. doi: 10.1002/jor.24499. Epub 2019 Nov 11. PMID: 31692083.

In vitro protocol:

In vivo protocol:

1. Sun S, Guo C, Gao T, Ma D, Su X, Pang Q, Zhang R. Hypoxia Enhances Glioma Resistance to Sulfasalazine-Induced Ferroptosis by Upregulating SLC7A11 via PI3K/AKT/HIF-1α Axis. Oxid Med Cell Longev. 2022 Nov 18;2022:7862430. doi: 10.1155/2022/7862430. PMID: 36439690; PMCID: PMC9699746. 2. Atluri K, Brouillette MJ, Seol D, Khorsand B, Sander E, Salem AK, Fredericks D, Petersen E, Smith S, Fowler TP, Martin JA. Sulfasalazine Resolves Joint Stiffness in a Rabbit Model of Arthrofibrosis. J Orthop Res. 2020 Mar;38(3):629-638. doi: 10.1002/jor.24499. Epub 2019 Nov 11. PMID: 31692083.

1: Chen J, Lin S, Liu C. Sulfasalazine for ankylosing spondylitis. Cochrane Database Syst Rev. 2014 Nov 27;11:CD004800. doi: 10.1002/14651858.CD004800.pub3. Review. PubMed PMID: 25427435. 2: Salouage I, El Aïdli S, Cherif F, Kastalli S, Zaiem A, Daghfous R. Sulfasalazine-induced aseptic meningitis with positive rechallenge: a case report and review of the literature. Therapie. 2013 Nov-Dec;68(6):423-6. doi: 10.2515/therapie/2013065. Epub 2013 Dec 20. Review. PubMed PMID: 24356191. 3: Linares V, Alonso V, Domingo JL. Oxidative stress as a mechanism underlying sulfasalazine-induced toxicity. Expert Opin Drug Saf. 2011 Mar;10(2):253-63. doi: 10.1517/14740338.2011.529898. Epub 2011 Jan 10. Review. PubMed PMID: 21219240. 4: Marks WH. Tripterygium wilfordii Hook F. versus Sulfasalazine in the treatment of rheumatoid arthritis: a well-designed clinical trial of a botanical demonstrating effectiveness. Fitoterapia. 2011 Jan;82(1):85-7. doi: 10.1016/j.fitote.2010.11.024. Epub 2010 Nov 30. Review. PubMed PMID: 21126560. 5: Nikfar S, Rahimi R, Rezaie A, Abdollahi M. A meta-analysis of the efficacy of sulfasalazine in comparison with 5-aminosalicylates in the induction of improvement and maintenance of remission in patients with ulcerative colitis. Dig Dis Sci. 2009 Jun;54(6):1157-70. doi: 10.1007/s10620-008-0481-x. Epub 2008 Sep 4. Review. PubMed PMID: 18770034. 6: Dale J, Alcorn N, Capell H, Madhok R. Combination therapy for rheumatoid arthritis: methotrexate and sulfasalazine together or with other DMARDs. Nat Clin Pract Rheumatol. 2007 Aug;3(8):450-8; quiz, following 478. Review. PubMed PMID: 17664952. 7: Chen J, Liu C. Is sulfasalazine effective in ankylosing spondylitis? A systematic review of randomized controlled trials. J Rheumatol. 2006 Apr;33(4):722-31. Review. PubMed PMID: 16583475. 8: Avdeev VG, Fomin VV, Popova EN, Iurkevich LIu, Osipenko VI, Sokolina IA, Popova IA. [Tubular-interstitial nephritis and fibrosing alveolitis induced by sulfasalazine in ulcerative colitis]. Ter Arkh. 2006;78(1):77-9. Review. Russian. PubMed PMID: 16512452. 9: Plosker GL, Croom KF. Sulfasalazine: a review of its use in the management of rheumatoid arthritis. Drugs. 2005;65(13):1825-49. Review. Erratum in: Drugs. 2005;65(18):2591. PubMed PMID: 16114981. 10: Chen J, Liu C. Sulfasalazine for ankylosing spondylitis. Cochrane Database Syst Rev. 2005 Apr 18;(2):CD004800. Review. Update in: Cochrane Database Syst Rev. 2014;11:CD004800. PubMed PMID: 15846731. 11: Michel F, Navellou JC, Ferraud D, Toussirot E, Wendling D. DRESS syndrome in a patient on sulfasalazine for rheumatoid arthritis. Joint Bone Spine. 2005 Jan;72(1):82-5. Review. PubMed PMID: 15681256. 12: Halmos B, Anastopoulos HT, Schnipper LE, Ballesteros E. Extreme lymphoplasmacytosis and hepatic failure associated with sulfasalazine hypersensitivity reaction and a concurrent EBV infection--case report and review of the literature. Ann Hematol. 2004 Apr;83(4):242-6. Epub 2003 Sep 12. Review. PubMed PMID: 13680174. 13: Wolf R, Matz H, Orion E, Tüzün B, Tüzün Y. Miscellaneous treatments, I: sulfasalazine and pentoxifylline: unapproved uses, dosages, or indications. Clin Dermatol. 2002 Sep-Oct;20(5):531-46. Review. PubMed PMID: 12435524. 14: Braun J, Sieper J. [New and old therapeutic options in ankylosing spondylitis--is there an indication for sulfasalazine?]. Z Rheumatol. 2002 Apr;61(2):151-8. Review. German. PubMed PMID: 12056292. 15: Gerster JC, Hohl D. Nail lesions in psoriatic arthritis: recovery with sulfasalazine treatment. Ann Rheum Dis. 2002 Mar;61(3):277. Review. PubMed PMID: 11830442; PubMed Central PMCID: PMC1754037. 16: Suarez-Almazor ME, Belseck E, Shea B, Wells G, Tugwell P. Sulfasalazine for rheumatoid arthritis. Cochrane Database Syst Rev. 2000;(2):CD000958. Review. PubMed PMID: 10796400. 17: Hoshino J, Sugawara K, Ishikawa S, Hayami Y, Sakurazawa T, Tanaka T, Yamamoto N, Hashimoto M, Yamamoto T, Hoshihara Y. [A case of ulcerative colitis with folate deficient megaloblastic anemia induced by sulfasalazine]. Nihon Shokakibyo Gakkai Zasshi. 1999 Jul;96(7):840-5. Review. Japanese. PubMed PMID: 10434561. 18: Sáez J, Gómez A, Santos G, García C, Griño P, Quílez C. [A vertiginous syndrome due to sulfasalazine]. Gastroenterol Hepatol. 1999 Apr;22(4):207-8. Review. Spanish. PubMed PMID: 10349796. 19: Furst DE. The combination of methotrexate, sulfasalazine and hydroxychloroquine is highly effective in rheumatoid arthritis. Clin Exp Rheumatol. 1999 Jan-Feb;17(1):39-40. Review. PubMed PMID: 10084027. 20: O'Dell JR. Triple therapy with methotrexate, sulfasalazine, and hydroxychloroquine in patients with rheumatoid arthritis. Rheum Dis Clin North Am. 1998 Aug;24(3):465-77. Review. PubMed PMID: 9710881.

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Description:

Chemical Structure

Theoretical Analysis

Price and Availability

Preparing Stock Solutions

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