Sulfamethoxazole

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Names

[ CAS No. ]:
723-46-6

[ Name ]:
Sulfamethoxazole

[Synonym ]:
MFCD00010546
N1-(5-methylisoxazol-3-yl)-4-aminobenzene-1-sulfonamide
SEPTRA
Sulfamethoxazole
4-Amino-N-(5-methyl-1,2-oxazol-3-yl)benzenesulfonamide
Benzenesulfonamide, 4-amino-N-(5-methyl-3-isoxazolyl)-
BACTRIM
Sulphamethoxazole
EINECS 211-963-3
Septrin
Gantanol
Sinomin

Chemical & Physical Properties

[ Density]:
1.5±0.1 g/cm3

[ Boiling Point ]:
482.1±55.0 °C at 760 mmHg

[ Melting Point ]:
166 °C

[ Molecular Formula ]:
C10H11N3O3S

[ Molecular Weight ]:
253.278

[ Flash Point ]:
245.4±31.5 °C

[ Exact Mass ]:
253.052109

[ PSA ]:
106.60000

[ LogP ]:
0.89

[ Vapour Pressure ]:
0.0±1.2 mmHg at 25°C

[ Index of Refraction ]:
1.641

[ Storage condition ]:
0-6°C

[ Stability ]:
Stable, but light sensitive. Incompatible with strong oxidizing agents.

MSDS

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :
WP0700000
CHEMICAL NAME :
Sulfanilamide, N'-(5-methyl-3-isoxazolyl)-
CAS REGISTRY NUMBER :
723-46-6
BEILSTEIN REFERENCE NO. :
0226453
LAST UPDATED :
199706
DATA ITEMS CITED :
20
MOLECULAR FORMULA :
C10-H11-N3-O3-S
MOLECULAR WEIGHT :
253.30
WISWESSER LINE NOTATION :
T5NOJ C1 EMSWR DZ

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Human - woman
DOSE/DURATION :
160 mg/kg/10D-I
TOXIC EFFECTS :
Endocrine - hypoglycemia
REFERENCE :
AIMDAP Archives of Internal Medicine. (AMA, 535 N. Dearborn St., Chicago, IL 60610) V.1- 1908- Volume(issue)/page/year: 143,827,1983
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
6200 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
TXAPA9 Toxicology and Applied Pharmacology. (Academic Press, Inc., 1 E. First St., Duluth, MN 55802) V.1- 1959- Volume(issue)/page/year: 18,185,1971
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intraperitoneal
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
2690 mg/kg
TOXIC EFFECTS :
Behavioral - somnolence (general depressed activity) Behavioral - convulsions or effect on seizure threshold Lungs, Thorax, or Respiration - dyspnea
REFERENCE :
NKRZAZ Chemotherapy (Tokyo). (Nippon Kagaku Ryoho Gakkai, 2-20-8 Kamiosaki, Shinagawa-Ku, Tokyo 141, Japan) V.1- 1953- Volume(issue)/page/year: 21,175,1973
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Subcutaneous
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
>5 gm/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
NKRZAZ Chemotherapy (Tokyo). (Nippon Kagaku Ryoho Gakkai, 2-20-8 Kamiosaki, Shinagawa-Ku, Tokyo 141, Japan) V.1- 1953- Volume(issue)/page/year: 21,175,1973
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
2300 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
CMTRAG Chemotherapia. (Basel, Switzerland) V.1-12, 1960-67. For publisher information, see CHTHBK. Volume(issue)/page/year: 8,63,1964
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intraperitoneal
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
2300 mg/kg
TOXIC EFFECTS :
Behavioral - somnolence (general depressed activity) Behavioral - convulsions or effect on seizure threshold Lungs, Thorax, or Respiration - dyspnea
REFERENCE :
NKRZAZ Chemotherapy (Tokyo). (Nippon Kagaku Ryoho Gakkai, 2-20-8 Kamiosaki, Shinagawa-Ku, Tokyo 141, Japan) V.1- 1953- Volume(issue)/page/year: 21,175,1973
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Subcutaneous
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
>5 gm/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
NKRZAZ Chemotherapy (Tokyo). (Nippon Kagaku Ryoho Gakkai, 2-20-8 Kamiosaki, Shinagawa-Ku, Tokyo 141, Japan) V.1- 1953- Volume(issue)/page/year: 21,175,1973
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intravenous
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
1460 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
85IRAK "Modern Pharmaceuticals of Japan, V," Tokyo, Japan Pharmaceutical, Medical and Dental Supply Exporters' Assoc., 1975 Volume(issue)/page/year: -,105,1975
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Unreported
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
5 gm/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
CMTRAG Chemotherapia. (Basel, Switzerland) V.1-12, 1960-67. For publisher information, see CHTHBK. Volume(issue)/page/year: 6,273,1963
TYPE OF TEST :
LDLo - Lowest published lethal dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Mammal - dog
DOSE/DURATION :
3 gm/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
12ZWAM "Experimental Chemotherapy, Volume II," Schnitzer, R.J., and F. Hawking, eds. Academic Press, New York, 1964 Volume(issue)/page/year: 2,249,1964 ** OTHER MULTIPLE DOSE TOXICITY DATA **
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
67500 mg/kg/30D-I
TOXIC EFFECTS :
Endocrine - changes in thyroid weight Blood - normocytic anemia Nutritional and Gross Metabolic - weight loss or decreased weight gain
REFERENCE :
NKRZAZ Chemotherapy (Tokyo). (Nippon Kagaku Ryoho Gakkai, 2-20-8 Kamiosaki, Shinagawa-Ku, Tokyo 141, Japan) V.1- 1953- Volume(issue)/page/year: 21,175,1973 ** TUMORIGENIC DATA **
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
21 gm/kg/60W-C
TOXIC EFFECTS :
Tumorigenic - equivocal tumorigenic agent by RTECS criteria Lungs, Thorax, or Respiration - tumors Endocrine - thyroid tumors
REFERENCE :
TXAPA9 Toxicology and Applied Pharmacology. (Academic Press, Inc., 1 E. First St., Duluth, MN 55802) V.1- 1959- Volume(issue)/page/year: 24,351,1973 *** REVIEWS *** IARC Cancer Review:Animal Limited Evidence IMEMDT IARC Monographs on the Evaluation of Carcinogenic Risk of Chemicals to Man. (WHO Publications Centre USA, 49 Sheridan Ave., Albany, NY 12210) V.1- 1972- Volume(issue)/page/year: 24,285,1980 IARC Cancer Review:Human Inadequate Evidence IMEMDT IARC Monographs on the Evaluation of Carcinogenic Risk of Chemicals to Man. (WHO Publications Centre USA, 49 Sheridan Ave., Albany, NY 12210) V.1- 1972- Volume(issue)/page/year: 24,285,1980 IARC Cancer Review:Group 3 IMSUDL IARC Monographs, Supplement. (WHO Publications Centre USA, 49 Sheridan Ave., Albany, NY 12210) No.1- 1979- Volume(issue)/page/year: 7,348,1987 TOXICOLOGY REVIEW HFHBAG Hartford Hospital Bulletin. (Hartford Hospital, 80 Seymour St., Hartford, CT 06115) V.1- 1938/39- Volume(issue)/page/year: 29,364,1974 *** NIOSH STANDARDS DEVELOPMENT AND SURVEILLANCE DATA *** NIOSH OCCUPATIONAL EXPOSURE SURVEY DATA : NOHS - National Occupational Hazard Survey (1974) NOHS Hazard Code - 81525 No. of Facilities: 58 (estimated) No. of Industries: 1 No. of Occupations: 2 No. of Employees: 230 (estimated) NOES - National Occupational Exposure Survey (1983) NOES Hazard Code - X2070 No. of Facilities: 88 (estimated) No. of Industries: 2 No. of Occupations: 2 No. of Employees: 4250 (estimated) No. of Female Employees: 4016 (estimated) NOES - National Occupational Exposure Survey (1983) NOES Hazard Code - 81525 No. of Facilities: 853 (estimated) No. of Industries: 3 No. of Occupations: 9 No. of Employees: 17028 (estimated) No. of Female Employees: 11965 (estimated)

Safety Information

[ Symbol ]:

GHS07

[ Signal Word ]:
Warning

[ Hazard Statements ]:
H315-H317-H319-H335

[ Precautionary Statements ]:
P261-P280-P305 + P351 + P338

[ Personal Protective Equipment ]:
dust mask type N95 (US);Eyeshields;Faceshields;Gloves

[ Hazard Codes ]:
Xn:Harmful

[ Risk Phrases ]:
R22;R36/37/38

[ Safety Phrases ]:
S26-S36-S36/37/39-S22

[ RIDADR ]:
NONH for all modes of transport

[ WGK Germany ]:
2

[ RTECS ]:
WP0700000

[ HS Code ]:
2935003000

Synthetic Route

Precursor & DownStream

Precursor

  • N4-Acetylsulfamethoxazole
  • 4-Nitro Sulfamethoxazole
  • nosyl chloride
  • 4-Acetamidobenzenesulfonyl chloride
  • N-Hydroxy Sulfamethoxazole
  • 3-Amino-5-methylisoxazole
  • 4-isocyanatobenzenesulfonyl chloride
  • but-2-ynenitrile

DownStream

  • 4-hydroxy-N-(5-methyl-1,2-oxazol-3-yl)benzenesulfonamide
  • N4-Acetylsulfamethoxazole
  • 4-[2-(3,5-dioxo-1,2-diphenyl-pyrazolidin-4-ylidene)hydrazinyl]-N-(5-methyloxazol-3-yl)benzenesulfonamide

Customs

[ HS Code ]: 2935003000

[ Summary ]:
HS:2935003000 4-amino-n-(5-methylisoxazol-3-yl)benzenesulfonamide VAT:17.0% Tax rebate rate:9.0% Supervision conditions:none MFN tariff:6.5% General tariff:35.0%

Articles

Sorption affinities of sulfamethoxazole and carbamazepine to two sorbents under co-sorption systems.

Environ. Pollut. 194 , 203-9, (2014)

The Kd of sulfamethoxazole (SMX) on activated carbon (AC) was larger than that of SMX on single-walled carbon nanotubes (SC), but the competition of SMX with carbamazepine (CBZ) for adsorption sites w...

Fast determination of 22 sulfonamides from chicken breast muscle using core-shell nanoring amino-functionalized superparamagnetic molecularly imprinted polymer followed by liquid chromatography-tandem mass spectrometry.

J. Chromatogr. A. 1345 , 17-28, (2014)

A novel, simple and sensitive method was developed for the simultaneous determination of 22 sulfonamides (SAs) in chicken breast muscle by using the dispersive micro-solid-phase extraction (d-μ-SPE) p...

Supported liquid membrane-protected molecularly imprinted beads for micro-solid phase extraction of sulfonamides in environmental waters.

J. Chromatogr. A. 1357 , 158-64, (2014)

In this work, molecularly imprinted polymer (MIP) beads have been prepared and evaluated for the development of a supported liquid membrane-protected micro-solid phase extraction method for the analys...


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Related Compounds

  • sulfamethoxazole
  • sulfamethoxazole
  • Sulfamethoxazole
  • Sulfamethoxazole D4
  • SulfaMethoxazole-13C6
  • Nitrosulfamethoxazole
  • 4-((Cyclohexylamino)methyl)benzoic acid hydrochloride
  • 1-(2-Fluorophenyl)-1,3,8-triazaspiro[4.5]decan-4-one
  • 1-[(2,4-Dichlorophenyl)methyl]-N-(1,1-dimethylethyl)-2-methyl-1H-indole-3-methanamine
  • 1-methyl-3,4-dihydro-1H-2-benzopyran-1-carbaldehyde
  • 2-Methoxy-6-(pyrazol-1-yl)-benzonitrile
  • 1-(2-Methyl-1,3-dithian-2-yl)propan-1-ol
  • N-(2,3-dihydro-1,4-benzodioxin-6-yl)-2-(morpholin-4-yl)acetamide; oxalic acid
  • 2,5-difluoro-N-(1-(thiophen-2-ylsulfonyl)-1,2,3,4-tetrahydroquinolin-7-yl)benzenesulfonamide
  • 1H-3-Benzazepin-7-ol, 8-chloro-2,3,4,5-tetrahydro-5-(3-iodophenyl)-3-methyl-, (S)-
  • (4-Methyl-tetrahydro-furan-2-yl)-methanol