Sulfanilamide

Modify Date: 2024-01-01 19:06:16

Sulfanilamide Structure
Sulfanilamide structure
 Common Name Sulfanilamide
CAS Number 63-74-1 Molecular Weight 172.205
Density 1.4±0.1 g/cm3 Boiling Point 400.5±47.0 °C at 760 mmHg
Molecular Formula C6H8N2O2S Melting Point 164-166 °C(lit.)
MSDS Chinese USA Flash Point 196.0±29.3 °C

 Use of Sulfanilamide


Sulfanilamide is a competitive inhibitor for bacterial enzyme dihydropteroate synthetase with IC50 of 320 μM.Target: dihydropteroate synthetase; AntibacterialSulfanilamide containing the sulfonamide functional group displays inhibitory activity for dihydropteroate synthetase partially purified from Escherichia coli which normally uses para-aminobenzoic acid (PABA) for synthesizing the necessary folic acid acting as a coenzyme in the synthesis of purine, pyrimidine and other amino acids, exhibiting an IC 50 of 320 μM for dihydropteroate synthetasea and Km of 2.5 uM for PABA [1]. Sulfanilamide shows IC50 of 286.8 μg/mL for recombinant S. cerevisiae strains with wild-type FOL1 genes, but the single mutation 55Trp to 55Ala or 57Pro to 57Ser within the putative active site of the fungal DHPS confers resistance to Sulfanilamide with IC50 of >800 μg/mL [2]. Administration of Sulfanilamide with the dosage of 100 mg/kg/day is effective in the prevention of P. carinii infection in the immunosuppressed rat model. When the dosage of sulfaguanidine and Sulfanilamide reduced to 10 mg/kg/day, breakthrough P. carinii infection occurs in the rats [3].

 Names

Name sulfanilamide
Synonym More Synonyms

 Sulfanilamide Biological Activity

Description Sulfanilamide is a competitive inhibitor for bacterial enzyme dihydropteroate synthetase with IC50 of 320 μM.Target: dihydropteroate synthetase; AntibacterialSulfanilamide containing the sulfonamide functional group displays inhibitory activity for dihydropteroate synthetase partially purified from Escherichia coli which normally uses para-aminobenzoic acid (PABA) for synthesizing the necessary folic acid acting as a coenzyme in the synthesis of purine, pyrimidine and other amino acids, exhibiting an IC 50 of 320 μM for dihydropteroate synthetasea and Km of 2.5 uM for PABA [1]. Sulfanilamide shows IC50 of 286.8 μg/mL for recombinant S. cerevisiae strains with wild-type FOL1 genes, but the single mutation 55Trp to 55Ala or 57Pro to 57Ser within the putative active site of the fungal DHPS confers resistance to Sulfanilamide with IC50 of >800 μg/mL [2]. Administration of Sulfanilamide with the dosage of 100 mg/kg/day is effective in the prevention of P. carinii infection in the immunosuppressed rat model. When the dosage of sulfaguanidine and Sulfanilamide reduced to 10 mg/kg/day, breakthrough P. carinii infection occurs in the rats [3].
Related Catalog
References

[1]. McCullough, J.L. and T.H. Maren, Inhibition of dihydropteroate synthetase from Escherichia coli by sulfones and sulfonamides. Antimicrob Agents Chemother, 1973. 3(6): p. 665-9.

[2]. Meneau, I., et al., Pneumocystis jiroveci dihydropteroate synthase polymorphisms confer resistance to sulfadoxine and sulfanilamide in Saccharomyces cerevisiae. Antimicrob Agents Chemother, 2004. 48(7): p. 2610-6.

[3]. Hughes, W.T. and J. Killmar, Monodrug efficacies of sulfonamides in prophylaxis for Pneumocystis carinii pneumonia. Antimicrob Agents Chemother, 1996. 40(4): p. 962-5.

 Chemical & Physical Properties

Density 1.4±0.1 g/cm3
Boiling Point 400.5±47.0 °C at 760 mmHg
Melting Point 164-166 °C(lit.)
Molecular Formula C6H8N2O2S
Molecular Weight 172.205
Flash Point 196.0±29.3 °C
Exact Mass 172.030655
PSA 94.56000
LogP -0.72
Vapour Pressure 0.0±0.9 mmHg at 25°C
Index of Refraction 1.628
Water Solubility 7.5 g/L at 25 ºC

 Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :
WO8400000
CHEMICAL NAME :
Sulfanilamide
CAS REGISTRY NUMBER :
63-74-1
BEILSTEIN REFERENCE NO. :
0511852
LAST UPDATED :
199701
DATA ITEMS CITED :
30
MOLECULAR FORMULA :
C6-H8-N2-O2-S
MOLECULAR WEIGHT :
172.22
WISWESSER LINE NOTATION :
ZSWR DZ

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
3900 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intravenous
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
1400 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
3 gm/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intraperitoneal
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
5 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Subcutaneous
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
2900 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intravenous
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
500 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Mammal - dog
DOSE/DURATION :
2 gm/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - rabbit
DOSE/DURATION :
1300 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - guinea pig
DOSE/DURATION :
3130 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
180 gm/kg/90D-I
TOXIC EFFECTS :
Blood - changes in spleen Nutritional and Gross Metabolic - weight loss or decreased weight gain Related to Chronic Data - death
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
82200 mg/kg/39W-I
TOXIC EFFECTS :
Nutritional and Gross Metabolic - other changes
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Mammal - dog
DOSE/DURATION :
60 gm/kg/30D-I
TOXIC EFFECTS :
Related to Chronic Data - death
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Subcutaneous
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
135 mg/kg/9W-I
TOXIC EFFECTS :
Tumorigenic - Carcinogenic by RTECS criteria Tumorigenic - tumors at site of application
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Unreported
DOSE :
974 mg/kg
SEX/DURATION :
female 34-37 week(s) after conception
TOXIC EFFECTS :
Reproductive - Specific Developmental Abnormalities - blood and lymphatic systems (including spleen and marrow)
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
DOSE :
22 mg/kg
SEX/DURATION :
female 1-22 day(s) after conception
TOXIC EFFECTS :
Reproductive - Effects on Newborn - live birth index (measured after birth) Reproductive - Effects on Newborn - viability index (e.g., # alive at day 4 per # born alive) Reproductive - Effects on Newborn - weaning or lactation index (e.g., # alive at weaning per # alive at day 4)
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
DOSE :
22 mg/kg
SEX/DURATION :
female 1-22 day(s) after conception
TOXIC EFFECTS :
Reproductive - Effects on Newborn - growth statistics (e.g.%, reduced weight gain)
TYPE OF TEST :
Cytogenetic analysis

MUTATION DATA

TYPE OF TEST :
DNA damage
TEST SYSTEM :
Rodent - rat Liver
DOSE/DURATION :
30 umol/L
REFERENCE :
SinJF# Personal Communication from J.F. Sina, Merck Institute for Therapeutic Research, West Point, PA 19486, Oct. 26, 1982 Volume(issue)/page/year: 26OCT1982 *** REVIEWS *** TOXICOLOGY REVIEW JMSHAO Journal of the Mount Sinai Hospital (New York). (New York, NY) V.1-36, 1934-69. For publisher information, see MSJMAZ. Volume(issue)/page/year: 10,343,1943 TOXICOLOGY REVIEW PCNAA8 Pediatric Clinics of North America. (W.B. Saunders Co., W. Washington Sq., Philadelphia, PA 19105) V.1- 1954- Volume(issue)/page/year: 8,413,1961 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(6),13,1982 *** NIOSH STANDARDS DEVELOPMENT AND SURVEILLANCE DATA *** NIOSH OCCUPATIONAL EXPOSURE SURVEY DATA : NOHS - National Occupational Hazard Survey (1974) NOHS Hazard Code - 84382 No. of Facilities: 149 (estimated) No. of Industries: 3 No. of Occupations: 9 No. of Employees: 3565 (estimated) NOES - National Occupational Exposure Survey (1983) NOES Hazard Code - 84382 No. of Facilities: 654 (estimated) No. of Industries: 6 No. of Occupations: 11 No. of Employees: 6529 (estimated) No. of Female Employees: 3131 (estimated)

 Safety Information

Personal Protective Equipment Eyeshields;Gloves;type N95 (US);type P1 (EN143) respirator filter
Hazard Codes Xn
Risk Phrases R40
Safety Phrases S24/25
RIDADR NONH for all modes of transport
WGK Germany 3
RTECS WO8400000
HS Code 2935009090

 Synthetic Route

 Customs

HS Code 2935009090
Summary 2935009090 other sulphonamides VAT:17.0% Tax rebate rate:9.0% Supervision conditions:none MFN tariff:6.5% General tariff:35.0%

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 Synonyms

EINECS 200-563-4
Sulphonamide
Sulfamine
MFCD00007939
Sulfanilamide
Sulfonylamide
4-aminobenzene sulfonic acid amide
4-aminobenzene sulfonamide
4-aminobenzenesulfonamide
Bacteramid
Streptasol
p-Aminobenzenesulfonamide
para-aminobenzenesulfonamide
4-aminophenylsulfonamide
Sulphanilamide
p-aminophenylsulfonamide
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