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Substance Name: Sulfamethoxazole [USAN:USP:INN:BAN:JAN]
RN: 723-46-6
UNII: JE42381TNV
InChIKey: JLKIGFTWXXRPMT-UHFFFAOYSA-N

Note

  • A bacteriostatic antibacterial agent that interferes with folic acid synthesis in susceptible bacteria. Its broad spectrum of activity has been limited by the development of resistance. (From Martindale, The Extra Pharmacopoeia, 30th ed, p208)

Molecular Formula

  • C10-H11-N3-O3-S

Molecular Weight

  • 253.2809
 

Classification Codes

Classification Codes

  • Anti-Infective Agents
  • Antibacterial
  • Drug / Therapeutic Agent
  • Human Data
  • Tumor Data

Superlist Classification Code

  • Overall Carcinogenic Evaluation: Group 3

Names and Synonyms

Name of Substance

  • Sulfamethoxazole
  • Sulfamethoxazole [USAN:USP:INN:BAN:JAN]

MeSH Heading

  • Sulfamethoxazole

Synonyms

  • 3-(p-Aminophenylsulfonamido)-5-methylisoxazole
  • 3-(para-Aminophenylsulphonamido)-5-methylisoxazole
  • 3-Sulfanilamido-5-methylisoxazole
  • 3-Sulphanilamido-5-methylisoxazole
  • 4-27-00-04685 (Beilstein Handbook Reference)
  • 4-Amino-N-(5-methyl-3-isoxazolyl)benzenesulfonamide
  • 5-Methyl-3-sulfanilamidoisoxazole
  • 5-Methyl-3-sulfanylamidoisoxazole
  • 5-Methyl-3-sulphanil-amidoisoxazole
  • A047
  • Azo-gantanol
  • Bactrim
  • Bactrimel
  • Benzenesulfonamide, 4-amino-N-(5-methyl-3-isoxazolyl)-
  • BRN 0226453
  • CCRIS 567
  • EINECS 211-963-3
  • Gamazole
  • Gantanol
  • Gantanol-DS
  • HSDB 3186
  • Metoxal
  • MS 53
  • N'-(5-Methyl-3-isoxazolyl)sulfanilamide
  • N'-(5-Methylisoxazol-3-yl)sulphanilamide
  • N(sup 1)-(5-Methyl-3-isoxazolyl)sulfanilamide
  • N(sup 1)-(5-Methyl-3-isoxazolyl)sulphanilamide
  • N1-(5-Methyl-3-isoxazolyl)sulfanilamide
  • NSC 147832
  • Radonil
  • Ro 4-2130
  • Simsinomin
  • Sinomin
  • Solfametossazolo
  • Solfametossazolo [DCIT]
  • Sulfamethoxazol
  • Sulfamethoxazole
  • Sulfamethoxazolum
  • Sulfamethoxazolum [INN-Latin]
  • Sulfamethoxizole
  • Sulfamethylisoxazole
  • Sulfametoxazol
  • Sulfametoxazol [INN-Spanish]
  • Sulfanilamide, N(1)-(5-methyl-3-isoxazolyl)-
  • Sulfisomezole
  • Sulpha-methoxizole
  • Sulphamethoxazol
  • Sulphamethoxazole
  • Sulphamethylisoxazole
  • UNII-JE42381TNV
  • Urobak

Systematic Names

  • Benzenesulfonamide, 4-amino-N-(5-methyl-3-isoxazolyl)-
  • Sulfamethoxazole
  • Sulfanilamide, N'-(5-methyl-3-isoxazolyl)-
  • Sulfanilamide, N1-(5-methyl-3-isoxazolyl)- (8CI)

Superlist Name

  • Sulfamethoxazole

Mixture Names

  • Azo gantanol
  • Bactrim
  • Cotrim
  • Septra
  • SMZ/TMP
  • Sulfatrim

Registry Numbers

CAS Registry Number

  • 723-46-6

FDA UNII

  • JE42381TNV

Other Registry Number

  • 129378-89-8

System Generated Number

  • 0000723466

Structure Descriptors

InChI

1S/C10H11N3O3S/c1-7-6-10(12-16-7)13-17(14,15)9-4-2-8(11)3-5-9/h2-6H,11H2,1H3,(H,12,13)

InChIKey

JLKIGFTWXXRPMT-UHFFFAOYSA-N

Smiles

c1(S(=O)(=O)Nc2cc(on2)C)ccc(cc1)N

Toxicity

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
dog LDLo oral 3gm/kg (3000mg/kg)   "Experimental Chemotherapy, Volume II," Schnitzer, R.J., and F. Hawking, eds. Academic Press New York, 1964Vol. 2, Pg. 249, 1964.
mouse LD50 intraperitoneal 2300mg/kg (2300mg/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

LUNGS, THORAX, OR RESPIRATION: DYSPNEA

BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD
Chemotherapy Vol. 21, Pg. 175, 1973.
mouse LD50 intravenous 1460mg/kg (1460mg/kg)   "Modern Pharmaceuticals of Japan, V," Tokyo, Japan Pharmaceutical, Medical and Dental Supply Exporters' Assoc., 1975Vol. -, Pg. 105, 1975.
mouse LD50 oral 2300mg/kg (2300mg/kg)   Chemotherapia. Vol. 8, Pg. 63, 1964.
mouse LD50 subcutaneous > 5gm/kg (5000mg/kg)   Chemotherapy Vol. 21, Pg. 175, 1973.
mouse LD50 unreported 5gm/kg (5000mg/kg)   Chemotherapia. Vol. 6, Pg. 273, 1963.
rat LD50 intraperitoneal 2690mg/kg (2690mg/kg) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

LUNGS, THORAX, OR RESPIRATION: DYSPNEA
Chemotherapy Vol. 21, Pg. 175, 1973.
rat LD50 oral 6200mg/kg (6200mg/kg)   Toxicology and Applied Pharmacology. Vol. 18, Pg. 185, 1971.
rat LD50 subcutaneous > 5gm/kg (5000mg/kg)   Chemotherapy Vol. 21, Pg. 175, 1973.
women TDLo oral 160mg/kg/10D- (160mg/kg) ENDOCRINE: HYPOGLYCEMIA Archives of Internal Medicine. Vol. 143, Pg. 827, 1983.

Physical Properties

Physical Property Value Units Temp (deg C) Source
Melting Point 167 deg C   EXP
log P (octanol-water) 0.89 (none)   EXP
Water Solubility 610 mg/L 37 EXP
Vapor Pressure 6.93E-08 mm Hg 25 EST
Henry's Law Constant 6.42E-13 atm-m3/mole 25 EST
Atmospheric OH Rate Constant 2.00E-10 cm3/molecule-sec 25 EST

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