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Substance Name: Sulfamethazine [USP]
RN: 57-68-1
UNII: 48U51W007F
InChIKey: ASWVTGNCAZCNNR-UHFFFAOYSA-N

Note

  • A sulfanilamide anti-infective agent. It has a spectrum of antimicrobial action similar to other sulfonamides.

Molecular Formula

  • C12-H14-N4-O2-S

Molecular Weight

  • 278.3346
 

Classification Codes

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

Names and Synonyms

Results Name

  • Sulfamethazine [USP]

Name of Substance

  • Sulfadimidine [INN:BAN]
  • Sulfamethazine
  • Sulfamethazine [USP]

MeSH Heading

  • Sulfamethazine

Synonyms

  • (p-Aminobenzolsulfonyl)-2-amino-4,6-dimethylpyrimidin
  • (p-Aminobenzolsulfonyl)-2-amino-4,6-dimethylpyrimidin [German]
  • 2-(p-Aminobenzenesulfonamido)-4,6-dimethylpyrimidine
  • 2-Sulfanilamido-4,6-dimethylpyrimidine
  • 4,6-Dimethyl-2-sulfanilamidopyrimidine
  • 4-Amino-N-(2,6-dimethyl-4-pyrimidinyl)benzenesulfonamide
  • 5-25-10-00250 (Beilstein Handbook Reference)
  • 6-(4'-Aminobenzol-sulfonamido)-2,4-dimethylpyrimidin
  • 6-(4'-Aminobenzol-sulfonamido)-2,4-dimethylpyrimidin [German]
  • A-502
  • AI3-26817
  • Azolmetazin
  • Benzenesulfonamide, 4-amino-N-(2,6-dimethyl-4-pyrimidinyl)-
  • Benzenesulfonamide, 4-amino-N-(4,6-dimethyl-2-pyrimidinyl)-
  • BN 2409
  • BRN 0261304
  • Calfspan Tablets
  • CCRIS 3701
  • Cremomethazine
  • Diazil
  • Diazil (the sulfanilamide)
  • Diazyl
  • Diazyl (VAN)
  • Dimezathine
  • Dimidin-R
  • EINECS 200-346-4
  • Hava-Span
  • HSDB 4157
  • Intradine
  • Kelametazine
  • Mermeth
  • Metazin
  • N(1)-(4,6-Dimethyl-2-pyrimidinyl)sulfanilamide
  • N(1)-(4,6-Dimethyl-2-pyrimidyl)sulfanilamide
  • N(sup 1)-(4,6-Dimethyl-2-pyrimidinyl)sulfanilamide
  • N(sup 1)-(4,6-Dimethyl-2-pyrimidyl)sulfanilamide
  • N-(4,6-Dimethyl-2-pyrimidyl)sulfanilamide
  • NCI-C56600
  • Neasina
  • Neazina
  • NSC 67457
  • Pirmazin
  • SA III
  • Sentry aq mardel biospheres maracyn plus
  • Solfadimidina
  • Solfadimidina [DCIT]
  • Spanbolet
  • Sulfa-Isodimerazine
  • Sulfadimerazine
  • Sulfadimesin
  • Sulfadimesine
  • Sulfadimethyldiazine
  • Sulfadimethylpyrimidine
  • Sulfadimezin
  • Sulfadimezine
  • Sulfadimezinum
  • Sulfadimidin
  • Sulfadimidina
  • Sulfadimidina [INN-Spanish]
  • Sulfadimidine
  • Sulfadimidine [INN:BAN]
  • Sulfadimidinum
  • Sulfadimidinum [INN-Latin]
  • Sulfadine
  • Sulfametazina
  • Sulfametazina [Italian]
  • Sulfametazyny
  • Sulfametazyny [Polish]
  • Sulfamethazine
  • Sulfamethiazine
  • Sulfamezathine
  • Sulfanilamide, N(1)-(4,6-dimethyl-2-pyrimidinyl)-
  • Sulfanilamide, N(sup1)-(2,6-dimethyl-4-pyrimidinyl)-
  • Sulfanilamide, N(sup1)-(4,6-dimethyl-2-pyrimidinyl)-
  • SulfaSURE SR Bolus
  • Sulfodimesin
  • Sulfodimezine
  • Sulka S Boluses
  • Sulphadimethylpyrimidine
  • Sulphadimidine
  • Sulphamethasine
  • Sulphamethazine
  • Sulphamezathine
  • Sulphamidine
  • Sulphodimezine
  • Superseptil
  • Superseptyl
  • UNII-48U51W007F
  • Vertolan

Systematic Names

  • 4-Amino-N-(4,6-dimethyl-2-pyrimidinyl)benzenesulfonamide
  • Benzenesulfonamide, 4-amino-N-(4,6-dimethyl-2-pyrimidinyl)-
  • Sulfadimidine
  • Sulfanilamide, N(sup 1)-(4,6-dimethyl-2-pyrimidinyl)-
  • Sulfanilamide, N1-(4,6-dimethyl-2-pyrimidinyl)-

Superlist Name

  • Sulfamethazine

Mixture Name

  • Tylan 40 sulfa-G

Registry Numbers

CAS Registry Number

  • 57-68-1

FDA UNII

  • 48U51W007F

System Generated Number

  • 0000057681

Structure Descriptors

InChI

1S/C12H14N4O2S/c1-8-7-9(2)15-12(14-8)16-19(17,18)11-5-3-10(13)4-6-11/h3-7H,13H2,1-2H3,(H,14,15,16)

InChIKey

ASWVTGNCAZCNNR-UHFFFAOYSA-N

Smiles

Cc1cc(nc(n1)NS(=O)(=O)c2ccc(cc2)N)C

Toxicity

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
mouse LD50 intraperitoneal 1060mg/kg (1060mg/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

LUNGS, THORAX, OR RESPIRATION: DYSPNEA
Archivum Immunologiae et Therapiae Experimentalis. Vol. 16, Pg. 804, 1968.
mouse LD50 intravenous 1776mg/kg (1776mg/kg)   "Handbook of Toxicology," 4 vols., Philadelphia, W.B. Saunders Co., 1956-59Vol. 5, Pg. 163, 1959.
mouse LD50 oral 50gm/kg (50000mg/kg)   Drugs in Japan Vol. 6, Pg. 392, 1982.
mouse LD50 subcutaneous 1440mg/kg (1440mg/kg)   Acta Biologica et Medica Germanica. Vol. 27, Pg. 141, 1971.
rabbit LD50 intravenous 2450mg/kg (2450mg/kg)   Dissertationes Pharmaceuticae. Vol. 11, Pg. 149, 1959.
rat LD50 subcutaneous 2gm/kg (2000mg/kg)   Acta Biologica et Medica Germanica. Vol. 27, Pg. 141, 1971.

Physical Properties

Physical Property Value Units Temp (deg C) Source
Melting Point 198.5 deg C   EXP
pKa Dissociation Constant 7.59 (none)   EXP
log P (octanol-water) 0.89 (none)   EXP
Water Solubility 1500 mg/L 29 EXP
Vapor Pressure 8.62E-09 mm Hg 25 EST
Henry's Law Constant 3.05E-13 atm-m3/mole 25 EST
Atmospheric OH Rate Constant 5.76E-11 cm3/molecule-sec 25 EST

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