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Substance Name: Sulfasalazine [USAN:USP:INN:BAN]
RN: 599-79-1
UNII: 3XC8GUZ6CB
InChIKey: NCEXYHBECQHGNR-QZQOTICOSA-N

Note

  • A drug that is used in the management of inflammatory bowel diseases. Its activity is generally considered to lie in its metabolic breakdown product, 5-aminosalicylic acid (see MESALAMINE) released in the colon. (From Martindale, The Extra Pharmacopoeia, 30th ed, p907).

Molecular Formula

  • C18-H14-N4-O5-S

Molecular Weight

  • 398.3976
 

Classification Codes

  • Analgesics
  • Analgesics, Non-Narcotic
  • Anti-Infective Agents
  • Anti-Inflammatory Agents
  • Anti-Inflammatory Agents, Non-Steroidal
  • Antibacterial
  • Antirheumatic Agents
  • Drug / Therapeutic Agent
  • Gastrointestinal Agents
  • Human Data
  • Mutation Data
  • Peripheral Nervous System Agents
  • Reproductive Effect
  • Sensory System Agents
  • Tumor Data

Names and Synonyms

Name of Substance

  • Sulfasalazine
  • Sulfasalazine [USAN:USP:INN:BAN]

MeSH Heading

  • Sulfasalazine

Synonyms

  • 2-Hydroxy-5-((4-((2-pyridinylamino)sulfonyl)phenyl)azo)benzoic acid
  • 4-(Pyridyl-2-amidosulfonyl)-3'-carboxy-4'-hydroxyazobenzene
  • 5-((p-(2-Pyridylsulfamoyl)phenyl)azo)salicylic acid
  • 5-(4-(2-Pyridylsulfamoyl)phenylazo)-2-hydroxybenzoic acid
  • 5-(p-(2-Pyridylsulfamyl)phenylazo)salicylic acid
  • 5-22-08-00433 (Beilstein Handbook Reference)
  • Accucol
  • Asulfidine
  • Azopyrin
  • Azopyrine
  • Azosulfidin
  • Azulfidine
  • Azulfidine EN
  • Azulfidine EN-Tabs
  • Benzoic acid, 2-hydroxy-5-((4-((2-pyridinylamino)sulfonyl)phenyl)azo)-
  • Benzosulfa
  • BRN 0356241
  • CCRIS 4713
  • Colo-Pleon
  • EINECS 209-974-3
  • HSDB 3395
  • NSC 203730
  • NSC 667219
  • Reupirin
  • Rorasul
  • S.a.s.
  • S.A.S. 500
  • S.A.S.-500
  • Salazo-sulfapyridinum
  • Salazopiridazin
  • Salazopyridin
  • Salazopyrin
  • Salazosulfapiridina
  • Salazosulfapiridina [INN-Spanish]
  • Salazosulfapyridin
  • Salazosulfapyridine
  • Salazosulfapyridinum
  • Salazosulfapyridinum [INN-Latin]
  • Salicylazosulfapyridine
  • Salisulf
  • Sas-500
  • SASP
  • SI-88
  • Sulcolon
  • Sulfasalazina
  • Sulfasalazina [INN-Spanish]
  • Sulfasalazine
  • Sulfasalazinum
  • Sulfasalazinum [INN-Latin]
  • Sulfazalazine
  • Sulphasalazine
  • UNII-3XC8GUZ6CB
  • W-T Sasp Oral

Systematic Names

  • Benzoic acid, 2-hydroxy-5-((4-((2-pyridinylamino)sulfonyl)phenyl)azo)-
  • Salazosulfapyridine
  • Salicylazosulfapyridine
  • Salicylic acid, 5-((p-(2-pyridylsulfamoyl)phenyl)azo)-

Superlist Name

  • Salicylazosulfapyridine

Registry Numbers

CAS Registry Number

  • 599-79-1

FDA UNII

  • 3XC8GUZ6CB

System Generated Number

  • 0000599791

Structure Descriptors

InChI

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+

InChIKey

NCEXYHBECQHGNR-QZQOTICOSA-N

Smiles

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

Toxicity

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
child TDLo oral 3800mg/kg/19D (3800mg/kg) LIVER: "HEPATITIS (HEPATOCELLULAR NECROSIS), DIFFUSE" American Journal of Digestive Diseases. Vol. 23, Pg. 956, 1978.
human TDLo oral 429mg/kg/10D- (429mg/kg) BLOOD: OTHER HEMOLYSIS WITH OR WITHOUT ANEMIA New England Journal of Medicine. Vol. 289, Pg. 491, 1973.
man LDLo oral 3200mg/kg/31D (3200mg/kg) SKIN AND APPENDAGES (SKIN): "DERMATITIS, ALLERGIC: AFTER SYSTEMIC EXPOSURE"

BLOOD: OTHER CHANGES

BLOOD: AGRANULOCYTOSIS		 Journal of the Royal Society of Medicine. Vol. 73, Pg. 587, 1980.
man TDLo oral 7143ug/kg (7.143mg/kg) GASTROINTESTINAL: NAUSEA OR VOMITING

GASTROINTESTINAL: "HYPERMOTILITY, DIARRHEA"		 New England Journal of Medicine. Vol. 306, Pg. 409, 1982.
man TDLo oral 143mg/kg/10D- (143mg/kg) BLOOD: THROMBOCYTOPENIA Annals of Internal Medicine. Vol. 102, Pg. 277, 1985.
man TDLo oral 357mg/kg (357mg/kg) BEHAVIORAL: HEADACHE

BEHAVIORAL: "HALLUCINATIONS, DISTORTED PERCEPTIONS"		 Journal of Toxicology, Clinical Toxicology. Vol. 29, Pg. 543, 1991.
man TDLo oral 1286mg/kg/30D (1286mg/kg) BLOOD: CHANGES IN CELL COUNT (UNSPECIFIED)

BLOOD: EOSINOPHILIA

LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES		 Internal Medicine. Vol. 31, Pg. 108, 1992.
man TDLo oral 122gm/kg/8Y-I (122000mg/kg) VASCULAR: OTHER CHANGES

PERIPHERAL NERVE AND SENSATION: PARESTHESIS		 Postgraduate Medical Journal. Vol. 56, Pg. 106, 1980.
man TDLo rectal 7143ug/kg (7.143mg/kg) GASTROINTESTINAL: "HYPERMOTILITY, DIARRHEA"

GASTROINTESTINAL: NAUSEA OR VOMITING		 New England Journal of Medicine. Vol. 306, Pg. 409, 1982.
man TDLo unreported 1300mg/kg/4W- (1300mg/kg) BEHAVIORAL: ATAXIA

GASTROINTESTINAL: NAUSEA OR VOMITING

BEHAVIORAL: "HALLUCINATIONS, DISTORTED PERCEPTIONS"		 Practitioner. Vol. 204, Pg. 850, 1970.
mouse LD50 intravenous 1096mg/kg (1096mg/kg)   Drugs in Japan Vol. -, Pg. 420, 1990.
mouse LD50 oral 12500mg/kg (12500mg/kg)   Drugs in Japan Vol. -, Pg. 420, 1990.
mouse LD50 subcutaneous 3gm/kg (3000mg/kg)   Drugs in Japan Vol. -, Pg. 420, 1990.
rabbit LD50 oral > 7500mg/kg (7500mg/kg)   Iyakuhin Kenkyu. Study of Medical Supplies. Vol. 26, Pg. 953, 1995.
rat LD50 intravenous 1520mg/kg (1520mg/kg)   Drugs in Japan Vol. -, Pg. 420, 1990.
rat LD50 oral 15600mg/kg (15600mg/kg)   Drugs in Japan Vol. -, Pg. 420, 1990.
rat LD50 subcutaneous 3870mg/kg (3870mg/kg)   Drugs in Japan Vol. -, Pg. 420, 1990.
women LDLo unreported 840mg/kg/3W-I (840mg/kg) SKIN AND APPENDAGES (SKIN): "DERMATITIS, OTHER: AFTER SYSTEMIC EXPOSURE"

LIVER: "HEPATITIS (HEPATOCELLULAR NECROSIS), DIFFUSE"

IMMUNOLOGICAL INCLUDING ALLERGIC: INCREASED IMMUNE RESPONSE		 Therapie. Vol. 37, Pg. 315, 1982.
women TDLo oral 140mg/kg/2W-I (140mg/kg) BEHAVIORAL: HEADACHE

GASTROINTESTINAL: "HYPERMOTILITY, DIARRHEA"		 Lancet. Vol. 1, Pg. 917, 1984.
women TDLo oral 570mg/kg/11D- (570mg/kg) BLOOD: THROMBOCYTOPENIA

BLOOD: LEUKOPENIA

BLOOD: OTHER CHANGES		 Clinical and Experimental Dermatology. Vol. 19, Pg. 419, 1994.
women TDLo oral 700mg/kg/4W-I (700mg/kg) BLOOD: CHANGES IN LEUCOCYTE (WBC) COUNT

LIVER: LIVER FUNCTION TESTS IMPAIRED

BEHAVIORAL: EXCITEMENT		 Clinical and Experimental Rheumatology. Vol. 10, Pg. 427, 1992.
women TDLo unreported 2700mg/kg/13W (2700mg/kg) SKIN AND APPENDAGES (SKIN): "DERMATITIS, OTHER: AFTER SYSTEMIC EXPOSURE" British Medical Journal. Vol. 286, Pg. 1547, 1983.

Physical Properties

Physical Property Value Units Temp (deg C) Source
Melting Point 220 dec deg C   EXP
log P (octanol-water) 3.810 (none)   EST
Atmospheric OH Rate Constant 1.38E-11 cm3/molecule-sec 25 EST

Physical property data is provided to ChemIDplus by SRC, Inc.