4-amino-N-(5-methyl-1,2-oxazol-3-yl)benzene-1-sulfonamide

• ChemBase ID: 888
• Molecular Formular: C10H11N3O3S
• Molecular Mass: 253.27764
• Monoisotopic Mass: 253.05211223
• SMILES: S(=O)(=O)(Nc1noc(c1)C)c1ccc(N)cc1
• Canonical SMILES: Nc1ccc(cc1)S(=O)(=O)Nc1noc(c1)C
• InChI: InChI=1S/C10H11N3O3S/c1-7-6-10(12-16-7)13-17(14,15)9-4-2-8(11)3-5-9/h2-6H,11H2,1H3,(H,12,13)
• InChIKey: JLKIGFTWXXRPMT-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 4-amino-N-(5-methyl-1,2-oxazol-3-yl)benzene-1-sulfonamide
• IUPAC Traditional name: 4-amino-N-(5-methyl-1,2-oxazol-3-yl)benzene-1-sulfonamide; sulfamethoxazole; trib
• Brand Name: Apo-Sulfamethoxazole; Azo Gantanol; Azo-Gantanol; Bactrimel; Gamazole; Gantanol; Gantanol-DS; Metoxal; Radonil; SIM; Septran; Simsinomin; Sinomin; Sulfamethalazole; Sulfamethoxazol; Sulfamethoxizole; Sulfamethylisoxazole; Sulfisomezole; Sulpha-Methoxizole; Sulphamethalazole; Sulphamethoxazol; Sulphamethoxazole; Sulphamethoxazole BP 98; Sulphamethylisoxazole; Sulphisomezole; Trib; Urobak
• Synonyms: Sulphamethoxazole; 4-[N-(5-Methylisoxazol-3-yl)sulphamoyl]aniline; 4-Amino-N-(5-methylisoxazol-3-yl)benzenesulphonamide; Gantanol; Gantanol DS; 4-Amino-N-(5-methyl-3-isoxazolyl)benzenesulfonamide; N1-(5-Methylisoxazol-3-yl)sulfanilamide; Sulfamethoxazole; 4-Amino-N-(5-methyl-3-isoxazolyl)-benzenesulfonamide; Sulfamethoxazole; 4-amino-N-(5-methylisoxazol-3-yl)benzenesulfonamide; 4-Amino-N-[5-methyl-3-isoxazolyl]benzenesulfonamide; N1-(5-methylisoxazol-3-yl)-4-aminobenzene-1-sulfonamide; 3-(p-Aminobenzenesulfonamido)-5-methylisoxazole; Sulfamethoxazole; 3-Sulfanilamido-5-methylisoxazole; 5-Methyl-3-sulfanilamidoisoxazole; MS 53; Radonil; Ro 4-2130; STX 608; Sinomin; Sulfamethalazole; Sulfamethoxazol; 4-amino-n-(5-methyl-3-isoxazolyl)benzenesulfonamide; 4-氨基-N-(5-甲基-3-异噁唑基)苯磺酰胺; N1-(5-甲基异噁唑基-3-基)磺胺; 新诺明

Database IDs

• CAS Number: 723-46-6
• EC Number: 211-963-3
• MDL Number: MFCD00010546
• Beilstein Number: 6732984
• PubChem SID: 24899752; 160964351; 46508111; 24870521
• PubChem CID: 5329

CALCULATED PROPERTIES

JChem

• Acid pKa: 6.1607323
• H Acceptors: 4
• H Donor: 2
• LogD (pH = 5.5): 0.71531755
• LogD (pH = 7.4): 9.2587294E-4
• Log P: 0.7905494
• Molar Refractivity: 64.4958 cm^3
• Polarizability: 24.161753 Å^3
• Polar Surface Area: 98.22 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 0.79
• LOG S: -2.74
• Solubility (Water): 4.59e-01 g/l

PROPERTIES

Physical Property

• Solubility: 610 mg/L; DMSO; Methanol
• Apperance: White Solid
• Melting Point: 166-169°C; 168-170°C
• Hydrophobicity(logP): 0.7

Safety Information

• Storage Condition: -20°C; Refrigerator, Under Inert Atmosphere; Room Temperature (15-30°C), Protect from light
• Storage Warning: IRRITANT; Irritant/Light Sensitive
• RTECS: WP0700000
• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 2
• Risk Statements: 36/37/38-43
• Safety Statements: 26-36
• TSCA Listed: false
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H315-H317-H319-H335
• GHS Precautionary statements: P261-P280-P305 + P351 + P338
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Faceshields, Gloves
• Storage Temperature: room temp

Pharmacology Properties

• Target: DNA/RNA
• Gene Information: rat ... Ednra(24326)
• Mechanism of Action: Folate antagonist; Folate synthesis inhibitor; Restrict folate synthesis through competitive antagonism of PABA

Product Information

• Purity: 95+%; 97%; 98%
• Grade: certified reference material; TraceCERT®; VETRANAL™, analytical standard
• Salt Data: Free Base
• Packaging: pkg of 1 g
• Shelf Life: (limited shelf life, expiry date on the label)
• Application(s): Sulfonamide bacteriostatic antibiotic; Used in treatment of respiratory and urinary tract infections
• Pharmacopeia Traceability: traceable to BP 314; traceable to PhEur S2100000; traceable to USP 1631001
• Empirical Formula (Hill Notation): C10H11N3O3S

DETAILS

MP Biomedicals - 02156711

(4-Amino-N-[5-methyl-3-
isoxazolyl]benzenesulfonamide)

DrugBank - DB01015

• Drug Groups: approved
• Description: A bacteriostatic antibacterial agent that interferes with folic acid synthesis in susceptible bacteria. Its broad spectrum of activity has been limited by the development of resistance. (From Martindale, The Extra Pharmacopoeia, 30th ed, p208)
• Indication: For the treatment bacterial infections causing bronchitis, prostatitis and urinary tract infections.
• Pharmacology: Sulfamethoxazole is a sulfonamide drug that inhibits bacterial synthesis of dihydrofolic acid by competing with para-aminobenzoic acid (PABA) for binding to dihydropteroate synthetase (dihydrofolate synthetase). Sulfamethoxazole is bacteriostatic in nature. Inhibition of dihydrofolic acid synthesis decreases the synthesis of bacterial nucleotides and DNA. Sulfamethoxazole is normally given in combination with Trimethoprim, a dihydrofolate reductase inhibitor, which inhibits the reduction of dihydrofolic acid to tetrahydrofolic acid. Studies have shown that bacterial resistance develops more slowly with the combination of the two drugs than with either Trimethoprim or Sulfamethoxazole alone.
• Toxicity: Sulfamethoxazole may cause nausea, vomiting, diarrhea and hypersensitivity reactions. Hematologic effects such as anemia, agranulocytosis, thrombocytopenia and hemolytic anemia in patients with glucose-6-phosphate dehydrogenase deficiency may also occur. Sulfamethoxazole may displace bilirubin from albumin binding sites causing jaundice or kernicterus in newborns.
• Affected Organisms: Gram negative and gram positive bacteria
• Biotransformation: Hepatic. The metabolism of sulfamethoxazole occurs predominately by N4-acetylation, although the glucuronide conjugate has been identified.
• Absorption: Rapidly absorbed following oral administration. Also well-absorbed topically.
• Half Life: 10 hours
• Protein Binding: 70%
• External Links: Wikipedia; RxList

Selleck Chemicals - S1915

Research Area: Infection
Biological Activity:
Sulfamethoxazole is a sulfonamide bacteriostatic antibiotic with an IC50 of 2.7 μM. Sulfamethoxazole is most often used as a part of synergistic combination with trimethoprim in a 5:1 ratio in co-trimoxazole. Sulfonamides 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. [1][2]

Sigma Aldrich - 76177

General description
Certified content by quantitative NMR incl. uncertainty and expiry are given in the certificate.Download your certificate at: http://www.sigma-aldrich.com.
Legal Information
TraceCERT is a registered trademark of Sigma-Aldrich Co. LLC

Sigma Aldrich - S7507

Biochem/physiol Actions
通过抑制二氢叶酸合成酶阻断二氢叶酸合成的磺胺类抗生素。 作用方式：在原核生物中抑制叶酸合成。 抗菌谱：革兰氏阳性菌、革兰氏阴性菌、衣原体 抗性机理：二氢叶酸合成酶或叶酸合成替代路径的改变。

Sigma Aldrich - PHR1126

General description
This certified reference material (CRM) is produced and certified in accordance with ISO/IEC 17025 and ISO Guide 34.
Other Notes
Values of analytes vary lot to lot.

Sigma Aldrich - 31737

Legal Information
VETRANAL is a trademark of Sigma-Aldrich Co. LLC

Toronto Research Chemicals - S699086

An antibacterial drug. Sulfonamide antibiotic that blocks the synthesis of dihydrofolic acid by inhibiting the enzyme dihydropteroate synthase.

REFERENCES

• http://en.wikipedia.org/wiki/Sulfamethoxazole
• Rudy, B.C., et al.: Anal. Profiles Drug Subs., 2, 467 (1973)
• Wormser, G.P., et al.: Drugs, 24, 459 (1973)
• Wharton, M., et al.: Ann. Intern. Med., 105, 37 (1973)
• U.K. Pat., 1959, 814276; CA, 55, 20091c, (synth)
• Fujimoto, M. et al., Chem. Pharm. Bull., 1962, 10, 572-575, (derivs)
• Iwai, I. et al., Chem. Pharm. Bull., 1966, 14, 1277, (synth)
• Rudy, B.C. et al., Anal. Profiles Drug Subst., 1973, 2, 467, (rev, synth, props)
• Brumfitt, W. et al., J. Infect. Dis., 1973, 128, 5778, (rev, pharmacol)
• Manzo, R.H. et al., J. Pharm. Sci., 1973, 62, 152, (uv)
• IARC Monog., 1980, 24, 285; Suppl. 7, 348; Suppl. 6, 502, (rev, tox)
• Bushby, S.R.M. et al., Handb. Exp. Pharmacol., 1983, 64, 75; 163; 185, (revs)
• Bult, A., Pharm. Weekbl., Sci. Ed., 1983, 5, 77, (cmr, tautom)
• Maury, L. et al., Can. J. Chem., 1985, 63, 3012, (cryst struct, ir, Raman)
• Negwer, M., Organic-Chemical Drugs and their Synonyms, 6th edn., Akademie-Verlag, 1987, 1514; 3212
• Kirk-Othmer Encycl. Chem. Technol., 4th edn., Wiley, 1991, 2, 876
• Martindale, The Extra Pharmacopoeia, 30th edn., Pharmaceutical Press, 1993, 208
• Lewis, R.J., Sax's Dangerous Properties of Industrial Materials, 8th edn., Van Nostrand Reinhold, 1992, SNK000