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599-79-1

599-79-1 structure
599-79-1 structure
Name sulfasalazine
Synonyms salazosulfapyridine
reupirin
sulcolon
2-Hydroxy-5-{[4-(2-pyridinylsulfamoyl)phenyl]diazenyl}benzoic acid
salisulf
EINECS 209-974-3
Salicylazosulfapyridine
2-Hydroxy-5-{[4-(pyridin-2-ylsulfamoyl)phenyl]diazenyl}benzoic acid
azopyrin
sas-500
si-88
MFCD00057363
sulfasalazine
rorasul
accucol
SSZ
sasp
Description Sulfasalazine is a drug for the treatment of rheumatoid arthritis and ulcerative colitis. Sulfasalazine is reported to suppress NF-κB activity.
Related Catalog
Target

RelA

Autophagy

In Vitro Treatment of SW620 colon cells with sulfasalazine inhibits TNFα-, LPS-, or phorbol ester-induced NFκB activation. NFκB–dependent transcription is inhibited by sulfasalazine at micro- to millimolar concentrations. TNFα-induced nuclear translocation of NFκB is prevented by sulfasalazine through inhibition of IκBα degradation[1]. Pre‐incubation with 5 mM of sulfasalazine alone significantly increases basal mRNA expression of all pro‐inflammatory cytokines with levels of IL‐6 mRNA increased by 80‐fold compared with vehicle control[2]. Once digested, sulfasalazine is cleaved into sulfapyridine and 5-aminosalicylic acid by colonic bacteria, and the latter, too, is reported to suppress NF-kappaB activity[3].
In Vivo At low doses (0.25 mM), SAS is able to suppress glioma growth by over 60% compared to untreated controls[3].
Cell Assay Sulfasalazine is dissolved in culture medium. SW620 cells are grown in Dulbecco’s modified Eagle medium, supplemented with 10% heat-inactivated FCS, 2 mmol/liter glutamine, and 1% (wt/vol) penicillin/streptomycin. SW620 cells are transfected with the 3xIgkBLuc reporter construct. After 18 h, cells are incubated with either medium alone or with sulfasalazine (0.1, 0.2, 0.5, 1, 2, 5 mM) before stimulation with TNFα, LPS, or PMA. Luciferase assay is performed[1].
Animal Admin Mice: Sulfasalazine is dissolved in 0.1 M NaOH, and then neutralized by titrating with 0.1 M HCl. U-87MG glioma cells are implanted into the cranium of a SCID mouse. After 7 days, animals are randomized into three groups of five animals each. One group receives 1 mL i.p. saline injections twice daily for 3 weeks. The two test groups receives 8 mg of sulfasalazine in 1 mL saline twice daily for 3 weeks. Tumor growth and animal health were monitored. After perfusion with 4% paraformaldehyde, mouse brains were collected, rinsed, and placed in 30% sucrose[3].
References

[1]. Wahl C, et al. Sulfasalazine: a potent and specific inhibitor of nuclear factor kappa B. J Clin Invest. 1998 Mar 1;101(5):1163-74.

[2]. Sykes L, et al. Sulfasalazine augments a pro-inflammatory response in interleukin-1β-stimulated amniocytes and myocytes. Immunology. 2015 Dec;146(4):630-44.

[3]. Chung WJ, et al. Sulfasalazine inhibits the growth of primary brain tumors independent of nuclear factor-kappaB. J Neurochem. 2009 Jul;110(1):182-93.

Density 1.5±0.1 g/cm3
Boiling Point 689.3±65.0 °C at 760 mmHg
Melting Point 260-265 °C (dec.)(lit.)
Molecular Formula C18H14N4O5S
Molecular Weight 398.393
Flash Point 370.7±34.3 °C
Exact Mass 398.068481
PSA 149.69000
LogP 3.18
Vapour Pressure 0.0±2.3 mmHg at 25°C
Index of Refraction 1.691
Storage condition Refrigerator
Water Solubility NH4OH 1 M: 50 mg/mL, clear, red | <0.1 g/100 mL at 25 ºC

CHEMICAL IDENTIFICATION

RTECS NUMBER :
VO6250000
CHEMICAL NAME :
Salicylic acid, 5-((p-(2-pyridylsulfamoyl)phenyl)azo)-
CAS REGISTRY NUMBER :
599-79-1
BEILSTEIN REFERENCE NO. :
0356241
LAST UPDATED :
199803
DATA ITEMS CITED :
38
MOLECULAR FORMULA :
C18-H14-N4-O5-S
MOLECULAR WEIGHT :
398.42
WISWESSER LINE NOTATION :
T6NJ BSWMR DNUNR DQ CVQ

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Human - man
DOSE/DURATION :
1286 mg/kg/30D-I
TOXIC EFFECTS :
Lungs, Thorax, or Respiration - other changes Blood - eosinophilia Blood - changes in cell count (unspecified)
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Human - woman
DOSE/DURATION :
570 mg/kg/11D-I
TOXIC EFFECTS :
Blood - leukopenia Blood - thrombocytopenia Blood - other changes
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Human - child
DOSE/DURATION :
3800 mg/kg/19D-I
TOXIC EFFECTS :
Liver - hepatitis (hepatocellular necrosis), diffuse
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Human - man
DOSE/DURATION :
7143 ug/kg
TOXIC EFFECTS :
Gastrointestinal - hypermotility, diarrhea Gastrointestinal - nausea or vomiting
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Human - man
DOSE/DURATION :
143 mg/kg/10D-I
TOXIC EFFECTS :
Blood - thrombocytopenia
TYPE OF TEST :
LDLo - Lowest published lethal dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Human - man
DOSE/DURATION :
3200 mg/kg/31D-I
TOXIC EFFECTS :
Blood - agranulocytosis Blood - other changes Skin and Appendages - dermatitis, allergic (after systemic exposure)
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Human
DOSE/DURATION :
429 mg/kg/10D-I
TOXIC EFFECTS :
Blood - other hemolysis with or without anemia
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Human - man
DOSE/DURATION :
357 mg/kg
TOXIC EFFECTS :
Behavioral - hallucinations, distorted perceptions Behavioral - headache
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Human - woman
DOSE/DURATION :
140 mg/kg/2W-I
TOXIC EFFECTS :
Behavioral - headache Gastrointestinal - hypermotility, diarrhea Nutritional and Gross Metabolic - body temperature increase
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Unreported
SPECIES OBSERVED :
Human - man
DOSE/DURATION :
1300 mg/kg/4W-I
TOXIC EFFECTS :
Behavioral - hallucinations, distorted perceptions Behavioral - ataxia Gastrointestinal - nausea or vomiting
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Unreported
SPECIES OBSERVED :
Human - woman
DOSE/DURATION :
2700 mg/kg/13W-I
TOXIC EFFECTS :
Skin and Appendages - dermatitis, other (after systemic exposure) Immunological Including Allergic - uncharacterized
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Rectal
SPECIES OBSERVED :
Human - man
DOSE/DURATION :
7143 ug/kg
TOXIC EFFECTS :
Gastrointestinal - hypermotility, diarrhea Gastrointestinal - nausea or vomiting
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
15600 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Subcutaneous
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
3870 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intravenous
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
1520 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
12500 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Subcutaneous
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
3 gm/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intravenous
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
1096 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - rabbit
DOSE/DURATION :
>7500 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
32400 mg/kg/16D-I
TOXIC EFFECTS :
Blood - changes in serum composition (e.g. TP, bilirubin, cholesterol) Endocrine - changes in thymus weight Nutritional and Gross Metabolic - weight loss or decreased weight gain
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
32400 mg/kg/16D-I
TOXIC EFFECTS :
Gastrointestinal - other changes
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
177 mg/kg/2Y-I
TOXIC EFFECTS :
Tumorigenic - Carcinogenic by RTECS criteria Kidney, Ureter, Bladder - tumors
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
141 mg/kg/2Y-I
TOXIC EFFECTS :
Tumorigenic - Carcinogenic by RTECS criteria Liver - tumors
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
DOSE :
8100 mg/kg
SEX/DURATION :
female 1-40 week(s) after conception
TOXIC EFFECTS :
Reproductive - Specific Developmental Abnormalities - craniofacial (including nose and tongue) Reproductive - Specific Developmental Abnormalities - cardiovascular (circulatory) system
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
DOSE :
5460 mg/kg
SEX/DURATION :
male 13 week(s) pre-mating
TOXIC EFFECTS :
Reproductive - Paternal Effects - spermatogenesis (incl. genetic material, sperm morphology, motility, and count)
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
DOSE :
8400 mg/kg
SEX/DURATION :
male 28 day(s) pre-mating
TOXIC EFFECTS :
Reproductive - Fertility - male fertility index (e.g. # males impregnating females per # males exposed to fertile nonpregnant females)
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
DOSE :
16800 mg/kg
SEX/DURATION :
male 28 day(s) pre-mating
TOXIC EFFECTS :
Reproductive - Fertility - pre-implantation mortality (e.g. reduction in number of implants per female; total number of implants per corpora lutea)
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
DOSE :
7 gm/kg
SEX/DURATION :
male 35 day(s) pre-mating
TOXIC EFFECTS :
Reproductive - Paternal Effects - spermatogenesis (incl. genetic material, sperm morphology, motility, and count)
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
DOSE :
8400 mg/kg
SEX/DURATION :
male 14 day(s) pre-mating
TOXIC EFFECTS :
Reproductive - Paternal Effects - testes, epididymis, sperm duct Reproductive - Fertility - male fertility index (e.g. # males impregnating females per # males exposed to fertile nonpregnant females)
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
DOSE :
43875 mg/kg
SEX/DURATION :
male 13 week(s) pre-mating
TOXIC EFFECTS :
Reproductive - Paternal Effects - testes, epididymis, sperm duct

MUTATION DATA

TEST SYSTEM :
Rodent - mouse
DOSE/DURATION :
5634 mg/kg
REFERENCE :
MUREAV Mutation Research. (Elsevier Science Pub. B.V., POB 211, 1000 AE Amsterdam, Netherlands) V.1- 1964- Volume(issue)/page/year: 283,53,1992 *** REVIEWS *** TOXICOLOGY REVIEW DPIRDU Dangerous Properties of Industrial Materials Report. (Van Nostrand Reinhold, 115 Fifth Ave., New York, NY 10003) V.1- 1981- Volume(issue)/page/year: 1(8),8,1981 *** NIOSH STANDARDS DEVELOPMENT AND SURVEILLANCE DATA *** NIOSH OCCUPATIONAL EXPOSURE SURVEY DATA : NOES - National Occupational Exposure Survey (1983) NOES Hazard Code - X5355 No. of Facilities: 48 (estimated) No. of Industries: 1 No. of Occupations: 1 No. of Employees: 704 (estimated) No. of Female Employees: 435 (estimated)
Symbol GHS08
GHS08
Signal Word Danger
Hazard Statements H317-H334
Precautionary Statements P261-P280-P284-P304 + P340-P333 + P313-P342 + P311
Personal Protective Equipment dust mask type N95 (US);Eyeshields;Faceshields;Gloves
Hazard Codes Xn: Harmful;
Risk Phrases R42/43
Safety Phrases S22-S29/56-S45
RIDADR NONH for all modes of transport
WGK Germany 2
RTECS VO6250000
HS Code 2935009090
144-83-2 structure

144-83-2

69-72-7 structure

69-72-7

~%

599-79-1 structure

599-79-1

Literature: Przemysl Chemiczny, , vol. 37, p. 162 Chem.Abstr., , p. 13727
Precursor  2

DownStream  2

HS Code 2935009090
Summary 2935009090 other sulphonamides VAT:17.0% Tax rebate rate:9.0% Supervision conditions:none MFN tariff:6.5% General tariff:35.0%
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