N4-Acetylsulfamethoxazole

Names

[ Name ]:
N4-Acetylsulfamethoxazole

[Synonym ]:
Sulfamethoxazole impurity A
N-Acetyl Sulfamethoxazole
N4-Acetylsulfamethoxazole
N-[4-[(5-methyl-1,2-oxazol-3-yl)sulfamoyl]phenyl]acetamide
N-{4-{[(5-Methyl-3-isoxazolyl)amino]sulfonyl}phenyl}acetamide Sulfisomezole-N4-acetate
Sulfamethoxazole EP Impurity A

Biological Activity

[Description]:

N4-Acetylsulfamethoxazole (Acetylsulfamethoxazole) is a metabolite of Sulfamethoxazole (HY-B0322). Sulfamethoxazole is a sulfonamide bacteriostatic antibiotic, used for bacterial infections[1].

[Related Catalog]:

Research Areas >> Infection

Research Areas >> Metabolic Disease

Signaling Pathways >> Anti-infection >> Bacterial

[References]

[1]. https://pubchem.ncbi.nlm.nih.gov/compound/Acetylsulfamethoxazole

Chemical & Physical Properties

[ Density]:
1.448g/cm3

[ Melting Point ]:
222ºC dec.

[ Molecular Formula ]:
C₁₂H₁₃N₃O₄S

[ Molecular Weight ]:
295.31400

[ Exact Mass ]:
295.06300

[ PSA ]:
109.68000

[ LogP ]:
2.96900

[ Index of Refraction ]:
1.622

[ Storage condition ]:
Refrigerator

MSDS

Click to get detail MSDS

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: AE4935000

CHEMICAL NAME :: Acetanilide, 4'-((5-methyl-3-isoxazolyl)sulfamoyl)-

CAS REGISTRY NUMBER :: 21312-10-7

BEILSTEIN REFERENCE NO. :: 0285801

LAST UPDATED :: 199612

DATA ITEMS CITED :: 6

MOLECULAR FORMULA :: C12-H13-N3-O4-S

MOLECULAR WEIGHT :: 295.34

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 :: 8400 mg/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: -,27,1990

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 2690 mg/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: -,27,1990

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 :: NIIRDN Drugs in Japan (Ethical Drugs). (Yakugyo Jiho Co., Ltd., Tokyo, Japan) Volume(issue)/page/year: -,27,1990

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 3471 mg/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: -,27,1990

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 2300 mg/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: -,27,1990

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 :: NIIRDN Drugs in Japan (Ethical Drugs). (Yakugyo Jiho Co., Ltd., Tokyo, Japan) Volume(issue)/page/year: -,27,1990

Safety Information

[ RIDADR ]:
NONH for all modes of transport

[ HS Code ]:
2935009090

Synthetic Route

Click to get detail 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%

Articles

Excretion rates of sulfamethoxazole and N4-acetyl-sulfamethoxazole by fresh water turtles Pseudemys scripta elegans.

Vet. Q. 6(3) , 169-73, (1984)

Sulfamethoxazole and N4-acetylsulfamethoxazole are excreted by fresh water turtles Pseudemys scripta elegans in a biphasic mode, characterized half-lives of 5 and 100 min. Acetylation and deacetylatio...

Multiple-dose pharmacokinetics of 12 milligrams of trimethoprim and 60 milligrams of sulfamethoxazole per kilogram of body weight per day in healthy volunteers.

Antimicrob. Agents Chemother. 37(3) , 448-52, (1993)

The disposition of 12 mg of trimethoprim and 60 mg of sulfamethoxazole per kg of body weight in six healthy male volunteers is described. The daily dose was evenly divided and administered orally ever...

Sampling the lipogenic hepatic acetyl-CoA pool in vivo in the rat. Comparison of xenobiotic probe to values predicted from isotopomeric distribution in circulating lipids and measurement of lipogenesis and acetyl-CoA dilution.

J. Biol. Chem. 266(17) , 10912-9, (1991)

The acetylation of xenobiotics may provide a means for sampling hepatic cytosolic acetyl-CoA in vivo for isotopic studies of lipogenesis. Here, we test the accuracy of acetylated-sulfamethoxazole (SMX...