CAS 599-79-1|sulfasalazine

Introduction：Basic information about CAS 599-79-1|sulfasalazine, including its chemical name, molecular formula, synonyms, physicochemical properties, and safety information, etc.

Table of Contents

1. Names
2. sulfasalazine BiologicalActivity
3. Chemical & Physical Properties
4. Toxicological Information
CHEMICAL IDENTIFICATION
HEALTH HAZARD DATA
ACUTE TOXICITY DATA
MUTATION DATA
5. Safety Information
6. Customs
7. Articles70
8. Synonyms

Common Name	sulfasalazine
CAS Number	599-79-1	Molecular Weight	398.393
Density	1.5±0.1 g/cm3	Boiling Point	689.3±65.0 °C at 760 mmHg
Molecular Formula	C₁₈H₁₄N₄O₅S	Melting Point	260-265 °C (dec.)(lit.)
MSDS	ChineseUSA	Flash Point	370.7±34.3 °C
Symbol	GHS08	Signal Word	Danger

Names

Name	sulfasalazine
Synonym	More Synonyms

sulfasalazine BiologicalActivity

Description	Sulfasalazine is a drug for the treatment of rheumatoid arthritis and ulcerative colitis. Sulfasalazine is reported to suppress NF-κB activity.
Related Catalog	Signaling Pathways >>Autophagy >>AutophagySignaling Pathways >>NF-κB >>NF-κBResearch Areas >>Inflammation/Immunology
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.

Chemical & Physical Properties

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
InChIKey	NCEXYHBECQHGNR-UHFFFAOYSA-N
SMILES	O=C(O)c1cc(N=Nc2ccc(S(=O)(=O)Nc3ccccn3)cc2)ccc1O
Storage condition	Refrigerator
Water Solubility	NH4OH 1 M: 50 mg/mL, clear, red \| <0.1 g/100 mL at 25 ºC

Toxicological Information

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)

Safety Information

Symbol	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

Customs

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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Synonyms

salazosulfapyridine

reupirin

sulcolon

2-Hydroxy-5-{[4-(2-pyridinylsulfamoyl)phenyl]diazenyl}benzoic acid

Benzoic acid, 2-hydroxy-5-((4-((2-pyridinylamino)sulfonyl)phenyl)azo)-

salisulf

EINECS 209-974-3

Salicylazosulfapyridine

2-Hydroxy-5-{[4-(pyridin-2-ylsulfamoyl)phenyl]diazenyl}benzoic acid

azopyrin

sas-500

benzoic acid, 2-hydroxy-5-[2-[4-[(2-pyridinylamino)sulfonyl]phenyl]diazenyl]-

si-88

MFCD00057363

sulfasalazine

rorasul

accucol

benzoic acid, 2-hydroxy-5-[[4-[(2-pyridinylamino)sulfonyl]phenyl]azo]-

SSZ

sasp

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