Sulfamethazine

Modify Date: 2024-01-02 06:24:35

Sulfamethazine Structure
Sulfamethazine structure
 Common Name Sulfamethazine
CAS Number 57-68-1 Molecular Weight 278.330
Density 1.4±0.1 g/cm3 Boiling Point 526.2±52.0 °C at 760 mmHg
Molecular Formula C12H14N4O2S Melting Point 197 °C
MSDS Chinese USA Flash Point 272.1±30.7 °C

 Use of Sulfamethazine


Sulfamethazine is a sulfonamide antibacterial.Target: AntibacterialSulfamethazine is an antibiotic used to treat bronchitis, prostatitis and urinary tract infections. Sulfamethazine blocks the synthesis of dihydrofolic acid by inhibiting dihydropteroate synthase. In addition, sulfamethazine is a structural analog and competitive antagonist of para-aminobenzoic acid (PABA) and can inhibit normal bacterial utilization of PABA for the synthesis of folic acid, which is an important metabolite in DNA synthesis [1, 2].

 Names

Name sulfamethazine
Synonym More Synonyms

 Sulfamethazine Biological Activity

Description Sulfamethazine is a sulfonamide antibacterial.Target: AntibacterialSulfamethazine is an antibiotic used to treat bronchitis, prostatitis and urinary tract infections. Sulfamethazine blocks the synthesis of dihydrofolic acid by inhibiting dihydropteroate synthase. In addition, sulfamethazine is a structural analog and competitive antagonist of para-aminobenzoic acid (PABA) and can inhibit normal bacterial utilization of PABA for the synthesis of folic acid, which is an important metabolite in DNA synthesis [1, 2].
Related Catalog
References

[1]. Perez, S., P. Eichhorn, and D.S. Aga, Evaluating the biodegradability of sulfamethazine, sulfamethoxazole, sulfathiazole, and trimethoprim at different stages of sewage treatment. Environ Toxicol Chem, 2005. 24(6): p. 1361-7.

[2]. Kaniou, S., et al., Photocatalytic oxidation of sulfamethazine. Chemosphere, 2005. 60(3): p. 372-80.

 Chemical & Physical Properties

Density 1.4±0.1 g/cm3
Boiling Point 526.2±52.0 °C at 760 mmHg
Melting Point 197 °C
Molecular Formula C12H14N4O2S
Molecular Weight 278.330
Flash Point 272.1±30.7 °C
Exact Mass 278.083740
PSA 106.35000
LogP 0.80
Vapour Pressure 0.0±1.4 mmHg at 25°C
Index of Refraction 1.644
Storage condition 2-8°C
Stability Stable, but light sensitive. Incompatible with strong oxidizing agents.
Water Solubility 150mg/100mL (29 ºC)

 Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :
WO9275000
CHEMICAL NAME :
Sulfanilamide, N(sup 1)-(4,6-dimethyl-2-pyrimidinyl)-
CAS REGISTRY NUMBER :
57-68-1
BEILSTEIN REFERENCE NO. :
0261304
LAST UPDATED :
199706
DATA ITEMS CITED :
19
MOLECULAR FORMULA :
C12-H14-N4-O2-S
MOLECULAR WEIGHT :
278.36
WISWESSER LINE NOTATION :
T6N CNJ BMSWR DZ& D1 F1

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Subcutaneous
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
2 gm/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
ABMGAJ Acta Biologica et Medica Germanica. (Berlin, Ger. Dem. Rep.) V.1-41, 1958-82. For publisher information, see BBIADT. Volume(issue)/page/year: 27,141,1971
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
50 gm/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
NIIRDN Drugs in Japan (Ethical Drugs). (Yakugyo Jiho Co., Ltd., Tokyo, Japan) Volume(issue)/page/year: 6,392,1982
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intraperitoneal
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
1060 mg/kg
TOXIC EFFECTS :
Behavioral - somnolence (general depressed activity) Lungs, Thorax, or Respiration - dyspnea
REFERENCE :
AITEAT Archivum Immunologiae et Therapiae Experimentalis. (Ars Polona, POB 1001, 00-068 Warsaw 1, Poland) V.10- 1962- Volume(issue)/page/year: 16,804,1968
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Subcutaneous
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
1440 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
ABMGAJ Acta Biologica et Medica Germanica. (Berlin, Ger. Dem. Rep.) V.1-41, 1958-82. For publisher information, see BBIADT. Volume(issue)/page/year: 27,141,1971
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intravenous
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
1776 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
HBTXAC "Handbook of Toxicology," 4 vols., Philadelphia, W.B. Saunders Co., 1956-59 Volume(issue)/page/year: 5,163,1959
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intravenous
SPECIES OBSERVED :
Rodent - rabbit
DOSE/DURATION :
2450 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
DIPHAH Dissertationes Pharmaceuticae. (Warsaw, Poland) V.1-17, 1949-65. For publisher information, see PJPPAA. Volume(issue)/page/year: 11,149,1959 ** OTHER MULTIPLE DOSE TOXICITY DATA **
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
52560 mg/kg/2Y-C
TOXIC EFFECTS :
Endocrine - changes in thyroid weight Blood - changes in serum composition (e.g. TP, bilirubin, cholesterol)
REFERENCE :
JTEHD6 Journal of Toxicology and Environmental Health. (Hemisphere Pub., 1025 Vermont Ave., NW, Washington, DC 20005) V.1- 1975/76- Volume(issue)/page/year: 22,175,1987 ** TUMORIGENIC DATA **
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
104 gm/kg/2Y-C
TOXIC EFFECTS :
Tumorigenic - Carcinogenic by RTECS criteria Endocrine - thyroid tumors
REFERENCE :
FCTOD7 Food and Chemical Toxicology. (Pergamon Press Inc., Maxwell House, Fairview Park, Elmsford, NY 10523) V.20- 1982- Volume(issue)/page/year: 28,157,1990
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Implant
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
5000 mg/kg
TOXIC EFFECTS :
Tumorigenic - equivocal tumorigenic agent by RTECS criteria Tumorigenic - tumor types after systemic administration not seen spontaneously
REFERENCE :
ACRAAX Acta Radiologica. (Stockholm, Sweden) V.1-58, 1921-62. For publisher information, see ACRDA8. Volume(issue)/page/year: 37,258,1952
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
419 gm/kg/2Y-C
TOXIC EFFECTS :
Tumorigenic - Carcinogenic by RTECS criteria Endocrine - thyroid tumors
REFERENCE :
FCTOD7 Food and Chemical Toxicology. (Pergamon Press Inc., Maxwell House, Fairview Park, Elmsford, NY 10523) V.20- 1982- Volume(issue)/page/year: 27,455,1989 ** REPRODUCTIVE DATA **
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
DOSE :
6850 mg/kg
SEX/DURATION :
female 6-15 day(s) after conception
TOXIC EFFECTS :
Reproductive - Specific Developmental Abnormalities - craniofacial (including nose and tongue) Reproductive - Specific Developmental Abnormalities - urogenital system
REFERENCE :
NTIS** National Technical Information Service. (Springfield, VA 22161) Formerly U.S. Clearinghouse for Scientific & Technical Information. Volume(issue)/page/year: PB83-151035
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
DOSE :
8650 mg/kg
SEX/DURATION :
female 6-15 day(s) after conception
TOXIC EFFECTS :
Reproductive - Effects on Embryo or Fetus - fetotoxicity (except death, e.g., stunted fetus)
REFERENCE :
NTIS** National Technical Information Service. (Springfield, VA 22161) Formerly U.S. Clearinghouse for Scientific & Technical Information. Volume(issue)/page/year: PB83-151035
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
DOSE :
46200 mg/kg
SEX/DURATION :
male 6 week(s) pre-mating
TOXIC EFFECTS :
Reproductive - Fertility - male fertility index (e.g. # males impregnating females per # males exposed to fertile nonpregnant females)
REFERENCE :
JRPFA4 Journal of Reproduction and Fertility. (Biochemical Soc. Book Depot, POB 32, Commerce Way, Colchester, Essex CO2 8HP, UK) V.1- 1960- Volume(issue)/page/year: 81,259,1987
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
DOSE :
25200 mg/kg
SEX/DURATION :
female 6-19 day(s) after conception
TOXIC EFFECTS :
Reproductive - Fertility - post-implantation mortality (e.g. dead and/or resorbed implants per total number of implants) Reproductive - Effects on Embryo or Fetus - fetal death
REFERENCE :
NTIS** National Technical Information Service. (Springfield, VA 22161) Formerly U.S. Clearinghouse for Scientific & Technical Information. Volume(issue)/page/year: PB85-105690 *** 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: 2(2),5,1982 TOXICOLOGY REVIEW FAATDF Fundamental and Applied Toxicology. (Academic Press, Inc., 1 E. First St., Duluth, MN 55802) V.1- 1981- Volume(issue)/page/year: 13,747,1989 *** NIOSH STANDARDS DEVELOPMENT AND SURVEILLANCE DATA *** NIOSH OCCUPATIONAL EXPOSURE SURVEY DATA : NOHS - National Occupational Hazard Survey (1974) NOHS Hazard Code - 83543 No. of Facilities: 1105 (estimated) No. of Industries: 6 No. of Occupations: 12 No. of Employees: 6918 (estimated) NOES - National Occupational Exposure Survey (1983) NOES Hazard Code - 83543 No. of Facilities: 1303 (estimated) No. of Industries: 4 No. of Occupations: 22 No. of Employees: 17376 (estimated) No. of Female Employees: 2625 (estimated)

 Safety Information

Personal Protective Equipment Eyeshields;Gloves;type N95 (US);type P1 (EN143) respirator filter
Hazard Codes Xi
Risk Phrases R36/37/38
Safety Phrases S23-S24/25
RIDADR NONH for all modes of transport
WGK Germany 2
RTECS WO9275000
HS Code 2935009090

 Synthetic Route

 Customs

HS Code 2935002000
Summary 2935002000. VAT:17.0%. Tax rebate rate:9.0%. Supervision conditions:A(certificate of inspection for goods inward). MFN tariff:6.5%. General tariff:35.0%

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 Synonyms

sulfadimidine
MFCD00006066
4-amino-N-(4,6-dimethylpyrimidin-2-yl)benzenesulfonamide
EINECS 200-346-4
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Related Compounds: More...
Sulfamethazine
35762-76-6
SULFAMETHAZINE)
8017-57-0
Sulfamethazine-D4
1020719-82-7
Sulfamethazine-13C6
77643-91-5
sulfamethazine sodium
1981-58-4
Sulfamethazine N-oxide
19250-31-8
N-Acetyl Sulfamethazine
100-90-3
N-Acetyl sulfamethazine-d4
1189891-99-3
methacryloyl sulfamethazine
59941-98-9
4-((Cyclohexylamino)methyl)benzoic acid hydrochloride
1158522-08-7
1-[(2,4-Dichlorophenyl)methyl]-N-(1,1-dimethylethyl)-2-methyl-1H-indole-3-methanamine
940364-43-2
Ethyl 3-amino-3-(naphthalen-2-YL)propanoate
403600-00-0
2-Methoxy-6-(pyrazol-1-yl)-benzonitrile
134104-43-1
1H-3-Benzazepin-7-ol, 8-chloro-2,3,4,5-tetrahydro-5-(3-iodophenyl)-3-methyl-, (S)-
131615-57-1
(4-Methyl-tetrahydro-furan-2-yl)-methanol
6906-52-1
N-(1-cyanocyclopentyl)-2-[4-(4-fluorobenzenesulfonyl)-1,4-diazepan-1-yl]acetamide
930439-75-1
4,5,6,7-Tetrahydrobenzo[d]isoxazole-3-carbaldehyde
1018584-77-4
tert-Butyl-DL-alanine
1375289-11-4
4-amino-N-[2-tert-butyl-1-(tetrahydro-2H-pyran-4-ylmethyl)-1H-benzimidazol-5-yl]-N-ethylbenzenesulfonamide
849349-65-1
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