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Home > Encyclopedia > Sulfamethoxazole

Sulfamethoxazole

pharmaceutical raw materials
Sulfamethoxazole structure

Sulfamethoxazole 

structure
  • CAS No:

    723-46-6

  • Formula:

    C10H11N3O3S

  • Chemical Name:

    Sulfamethoxazole

  • Synonyms:

    Benzenesulfonamide,4-amino-N-(5-methyl-3-isoxazolyl)-;Sulfanilamide,N1-(5-methyl-3-isoxazolyl)-;4-Amino-N-(5-methyl-3-isoxazolyl)benzenesulfonamide;MS 53;Ro 4-2130;Gantanol;N1-(5-Methyl-3-isoxazolyl)sulfanilamide;5-Methyl-3-sulfanilamidoisoxazole;Sinomin;Sulfamethalazole;Sulfamethoxazole;3-Sulfanilamido-5-methylisoxazole;Sulfisomezole;Sulphamethoxazole;Radonil;Sulfamethoxazol;4-Amino-N-(5-methyl-3-isoxazolyl)benzensulfonamide;NSC 147832;STX 608;3-(p-Aminobenzenesulfonamido)-5-methylisoxazole;N-(5-Methylisoxazol-3-yl)-4-aminobenzenesulfonamide;129378-89-8

  • Categories:

    Organic Chemistry  >  Amides

Description

Sulfamethoxazole is a sulfonamide bacteriostatic antibiotic.Target: AntibacterialSulfonamides are structural analogs and competitive antagonists of para-aminobenzoic acid (PABA). They inhibit normal bacterial utilization of PABA for the synthesis of folic acid, an important metabolite in DNA synthesis. The effects seen are usually bacteriostatic in nature. Folic acid is not synthesized in humans, but is instead a dietary requirement. This allows for the selective toxicity to bacterial ce

Sulfamethoxazole Basic Attributes

253.27800

253.28

211-963-3

2935003000

Characteristics

106.60000

0.9

Crystals or white powder. (NTP, 1992)

1.4895 g/cm3

167 °C

482.1ºC at 760 mmHg

245.4ºC

1.641

Soluble in ethanol or acetone. Very slightly soluble in water

0-6ºC

6.93X10-8 mm Hg at 25 deg c (est)

LD50 orally in mice: 3662 mg/kg (Yamamoto)

Odorless

Bitter

Safety Information

NONH for all modes of transport

2

R22; R36/37/38

S22-S26-S36/37/39

WP0700000

Xn

Stable, but light sensitive. Incompatible with strong oxidizing agents.

P261-P280-P305 + P351 + P338

H315-H317-H319-H335

Sulfamethoxazole Use and Manufacturing

Methods of Manufacturing

4-Amino-N- (5-methvl-isoxazol-3-vl)-benzenesulphonamide (STX608, XDS01099); The solution of N- (5-methylisoxazol-3-yl)-4-acetamidobenzenesulphonamid (3.4 g, 11.5 mmol) in 10percent NaOH solution (15 mL) was stirred at 80°C for 1h, cooled to rt and neutralized to pH 6 with acetic acid. The precipitate was washed with water, dried in vacuo to yield off-white solid (2, 8 g, 96percent). Mp167-169°C (lit [29], 168-171°C) ; TLC single spot at Rf 0.39 (6percent methanol-DCM) ; HPLC purity > 99percent (tR 1.6 min in 4percent water- methanol) ;'H NMR (400 MHz, CD30D) : S 7.54 (2H, m, ArH), 6.63 (2H, m, ArH), 6.08 (1H, s, ArH), 2.30 (3H, s, CH3) ; FAB-MS 254 (MH+) ; FAB-HRMS calcd for C10H12N303S (MH+) 254.0599, found 254.0605.To the intermediate 2 (2.53 mmol) suspended in water (15 mL)was added NaOH (31.7 mmol) and refluxed for 4 h to generate a yellow solution. This was acidified to pH 5.5 at 70-80 °C with 2 MHCl. After cooling it to room temperature precipitates formed werecollected, washed with H2O and dried to obtain the compound 3. 4.3.1

Uses

Medication.

Computed Properties

Molecular Weight:253.28
XLogP3:0.9
Hydrogen Bond Donor Count:2
Hydrogen Bond Acceptor Count:6
Rotatable Bond Count:3
Exact Mass:253.05211239
Monoisotopic Mass:253.05211239
Topological Polar Surface Area:107
Heavy Atom Count:17
Complexity:346
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

Drug Function and Efficacy

After oral administration, it is completely absorbed from the gastrointestinal tract, and the peak blood concentration (Cmax) is reached 1 to 4 hours after taking the drug. It is mainly filtered through the glomeruli and secreted by the renal tubules, and the urine drug concentration is significantly higher than the blood drug concentration. It can be widely distributed in tissues and body fluids throughout the body, and can penetrate the blood-cerebrospinal fluid barrier to reach therapeutic concentrations. It can also cross the blood-placental barrier, enter the fetal blood circulation, and can be secreted into breast milk.

This ingredient has been used in drugs with the following functions (note: it does not mean that the ingredient itself has the following health functions)

Related Drugs

Registered Holders

  • EMCURE PHARMACEUTICALS LTD

    United States United States
    Active
  • Suzhou Sanray Pharmaceutical Co., Ltd.

    China China
    Active
  • Shanxi Shuangyan Pharmaceutical Co., Ltd.

    China China
    Active

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