Sulfamethoxazole

Base Information

• Chemical Name: Sulfamethoxazole
• CAS No.: 723-46-6
• Deprecated CAS: 129378-89-8
• Molecular Formula: C10H11N3O3S
• Molecular Weight: 253.282
• Hs Code.: 29350090
• European Community (EC) Number: 211-963-3,656-929-2
• NSC Number: 757328,147832
• UNII: JE42381TNV
• DSSTox Substance ID: DTXSID8026064
• Nikkaji Number: J4.525J
• Wikipedia: Sulfamethoxazole
• Wikidata: Q415843
• NCI Thesaurus Code: C47737
• RXCUI: 10180
• Metabolomics Workbench ID: 43260
• ChEMBL ID: CHEMBL443
• Mol file: 723-46-6.mol

Synonyms:Gantanol;Sulfamethoxazole;Sulfamethylisoxazole;Sulfisomezole;Sulphamethoxazole

Chemical Property of Sulfamethoxazole

Chemical Property:

• Appearance/Colour: Crystals or white powder
• Melting Point: 166 °C
• Refractive Index: 1.6630 (estimate)
• Boiling Point: 482.1 °C at 760 mmHg
• PKA: pKa 5.60±0.05 (Uncertain)
• Flash Point: 245.4 °C
• PSA: 106.60000
• Density: 1.462 g/cm³
• LogP: 3.10100
• Storage Temp.: 0-6°C
• Sensitive.: Light Sensitive
• Solubility.: Practically insoluble in water, freely soluble in acetone, sparingly soluble in ethanol (96 per cent). It dissolves in dilute solutions of sodium hydroxide and in dilute acids.
• Water Solubility.: Soluble in ethanol or acetone. Very slightly soluble in water
• XLogP3: 0.9
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 3
• Exact Mass: 253.05211239
• Heavy Atom Count: 17
• Complexity: 346

Purity/Quality:

99.7% ^*data from raw suppliers

Sulfamethoxazole ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn, Xi
• Hazard Codes: Xi,Xn
• Statements: 36/37/38-43-22
• Safety Statements: 26-36-36/37/39-22

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CC1=CC(=NO1)NS(=O)(=O)C2=CC=C(C=C2)N
• Recent ClinicalTrials: Collaborative Urological Prosthetics Investigation Directive Research Group
• Recent EU Clinical Trials: A Multicenter, Open-Label, Evaluator-Blinded, Randomized Study to Evaluate the Safety and Tolerability of Single-Dose IV Oritavancin Versus Standard of Care for the Treatment of Pediatric Subjects with Acute Bacterial Skin And Skin Structure Infections
• Uses: As an antimicrobial agent, it is particularly effective in treating Staphylococcus aureus and E. coli. It is mainly used for the treatment of fowl cholera. It can be used as anti-infective drug and can be used for the treatment and prevention of acute and chronic urinary tract infections, respiratory infections, intestinal infections, Salmonella infections, children acute otitis media, and meningitis. An antibacterial drug. Sulfonamide antibiotic that blocks the synthesis of dihydrofolic acid by inhibiting the enzyme dihydropteroate synthase. antibacterial, antipneumocystis An antibacterial drug. Sulfonamide antibiotic that blocks the synthesis of dihydrofolic acid by inhibiting the enzyme dihydropteroate synthase.This compound is a contaminant of emerging concern (CECs).
• Production method: It can be produced from 5-methyl-isobutyl-3-carboxamide via degradation, condensation and hydrolysis successively. Use 5-methyl-isobutyl-3-carboxamide as raw materials, it is degraded into 5-methyl-isoxazol-3 amine under the action of sodium hypochlorite solution, then condense with para-acetamidophenoxymethyl chloride to generate 3-(p-acetamide benzenesulfonamido)-5-methylisoxazole with further hydrolysis under alkaline conditions to give 3-(p-amino benzenesulfonamido)-5-methylisoxazole.
• Description: Like sulfisoxazole, this drug is effective in treating infections caused by streptococci, gonococci, pneumococci, staphylococci as well as colon bacillus. Unlike sulfisoxazole, only about 70% of it binds with proteins in the plasma after oral administration, and it diffuses mostly to tissues and tissue fluids. However, since it is removed much slower than sulfisoxazole, it does not require frequent administration and is also the drug of choice for many systemic infections. Moreover, it is an ingredient of a combined drug named bactrim, biseptol, and so on (which will be examined later on), which has a fixed correlation with trimethoprim. Synonyms of this drug are gantanol, sinomin, sulfisomezole, and others.
• Clinical Use: Sulfamethoxazole is used only in combination with the diaminopyrimidine trimethoprim.

Technology Process of Sulfamethoxazole

There total 16 articles about Sulfamethoxazole which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 100.0%

N-acetylsulfamethoxazole (21312-10-7) → sulfamethoxazole (723-46-6)

Guidance literature:

With hydrogenchloride; In methanol; diethyl ether; at 75 ℃; for 0.25h; Microwave irradiation;

DOI:10.1021/ml400259d

Reference yield: 95.0%

5-methylisoxazol-3-ylamine (1072-67-9) + 4-aminobenzenesulfonyl chloride (24939-24-0) → sulfamethoxazole (723-46-6)

Guidance literature:

5-methylisoxazol-3-ylamine; With ammonium hydroxide; at 35 - 40 ℃; for 1h; Large scale;

4-aminobenzenesulfonyl chloride; at 15 - 20 ℃; for 4.5h; Large scale;

Reference yield: 60.0%

5-methylisoxazol-3-ylamine (1072-67-9) + p-acetylaminobenzenesulfonyl chloride (121-60-8) → sulfamethoxazole (723-46-6)

Guidance literature:

5-methylisoxazol-3-ylamine; p-acetylaminobenzenesulfonyl chloride; With pyridine; In tetrahydrofuran; at 20 ℃; Inert atmosphere;

With sodium hydroxide; for 2h; Inert atmosphere; Reflux;

DOI:10.1080/14756366.2020.1765166

upstream raw materials:

N-acetylsulfamethoxazole

N,N'-bis-(5-methyl-isoxazol-3-yl)-4,4'-diazenediyl-bis-benzenesulfonamide

2-butynenitrile

p-acetylaminobenzenesulfonyl chloride

Downstream raw materials:

N-(5-methyl-isoxazol-3-yl)-4-xanthen-9-ylamino-benzenesulfonamide

4-(4,6-Diamino-2-methyl-pyrimidin-5-ylazo)-N-(5-methyl-isoxazol-3-yl)-benzenesulfonamide

4-(4,6-Diamino-2-phenyl-pyrimidin-5-ylazo)-N-(5-methyl-isoxazol-3-yl)-benzenesulfonamide

N-(5-Methyl-isoxazol-3-yl)-4-[(5-nitro-1H-benzoimidazol-2-ylmethyl)-amino]-benzenesulfonamide

Refernces

• 1、 Al-Omar, Mohamed A.,Bhat, Mashooq A.,Khan, Azmat Ali,Naglah, Ahmed M.. "Synthesis of novel sulfamethaoxazole 4-thiazolidinone hybrids and their biological evaluation". . . Retrieved 2020/09/18.
• 2、 Ham, Won Seok,Hillenbrand, Julius,Jacq, Jér?me,Genicot, Christophe,Ritter, Tobias. "Divergent Late-Stage (Hetero)aryl C?H Amination by the Pyridinium Radical Cation". supporting information. p. 532 - 536. Retrieved 2019/01/04.