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127-69-5 molecular structure
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4-amino-N-(dimethyl-1,2-oxazol-5-yl)benzene-1-sulfonamide

ChemBase ID: 148
Molecular Formular: C11H13N3O3S
Molecular Mass: 267.30422
Monoisotopic Mass: 267.06776229
SMILES and InChIs

SMILES:
S(=O)(=O)(Nc1onc(c1C)C)c1ccc(N)cc1
Canonical SMILES:
Nc1ccc(cc1)S(=O)(=O)Nc1onc(c1C)C
InChI:
InChI=1S/C11H13N3O3S/c1-7-8(2)13-17-11(7)14-18(15,16)10-5-3-9(12)4-6-10/h3-6,14H,12H2,1-2H3
InChIKey:
NHUHCSRWZMLRLA-UHFFFAOYSA-N

Cite this record

CBID:148 http://www.chembase.cn/molecule-148.html

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NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
IUPAC name
4-amino-N-(dimethyl-1,2-oxazol-5-yl)benzene-1-sulfonamide
IUPAC Traditional name
sulfisoxazole
4-amino-N-(dimethyl-1,2-oxazol-5-yl)benzene-1-sulfonamide
ganda
Brand Name
Accuzole
Alphazole
Amidoxal
Astrazolo
Azo Gantrisin
Azosulfizin
Bactesulf
Barazae
Chemouag
Cosoxazole
Dorsulfan
Dorsulfan Warthausen
Entusil
Entusul
G-Sox
Ganda
Gantrisin
Gantrisine
Gantrisona
Gantrosan
Isoxamin
J-Sul
Koro-Sulf
Neazolin
Neoxazol
Norilgan-S
Novazolo
Novosaxazole
Pancid
Renosulfan
Resoxol
Roxosul
Roxosul Tablets
Roxoxol
SI
Saxosozine
Sk-Soxazole
Sodizole
Sosol
Soxamide
Soxazole
Soxisol
Soxitabs
Soxo
Soxomide
Stansin
Sulbio
Sulfagan
Sulfagen
Sulfalar
Sulfapolar
Sulfasan
Sulfasol
Sulfazin
Sulfisin
Sulfizin
Sulfizol
Sulfizole
Sulfoxol
Suloxsol
Sulphafuraz
Sulsoxin
Thiasin
Tl-Azole
Unisulf
Urisoxin
Uritrisin
Urogan
V-Sul
Vagilia
Synonyms
Sulfadimethylisoxazole
Sulfafurazol
Sulfafurazole
Sulfaisoxazole
Sulfasoxazole
Sulfisoxazole Dialamine
Sulfisoxasole
Sulfisoxazol
Sulfisoxazole Diolamine
Sulphafurazol
Sulphafurazolum
Sulphafurazole
Sulphofurazole
Sulphisoxazol
Sulphaisoxazole
Sulfofurazole
Sulfisonazole
Sulfisoxazole
4-Amino-N-(3,4-dimethylisoxazol-5-yl)-benzenesulfonamide
Gantrisin Pediatric
5-Sulfanilamido-3,4-dimethyl-isoxazole
Accuzole
Amidoxal
4-Amino-N-(3,4-dimethyl-5-isoxazolyl)benzenesulfonamide
N1-(3,4-Dimethyl-5-isoxazolyl)sulfanilamide
N1-(3,4-Dimethyl-5-isoxazolyl)sulfanilamide
Sulfisoxazole
Sulfisoxazole
Gantrisin
Soxomide
Thiasin
Neoxazol
Sulfafurazole
4-氨基-N-(3,4-二甲基-5-异噁唑基)苯磺酰胺
N1-(3,4-二甲基-5-异噁唑基)磺胺
磺胺异噁唑
CAS Number
127-69-5
EC Number
204-858-9
MDL Number
MFCD00003150
Beilstein Number
6737262
PubChem SID
24899697
46505342
24870567
160963611
PubChem CID
5344

CALCULATED PROPERTIES

CALCULATED PROPERTIES

JChem ALOGPS 2.1
Acid pKa 5.804935  H Acceptors
H Donor LogD (pH = 5.5) 0.5794782 
LogD (pH = 7.4) -0.13589385  Log P 0.7306131 
Molar Refractivity 67.9186 cm3 Polarizability 25.915007 Å3
Polar Surface Area 98.22 Å2 Rotatable Bonds
Lipinski's Rule of Five true 
Log P 1.14  LOG S -2.93 
Solubility (Water) 3.13e-01 g/l 

PROPERTIES

PROPERTIES

Physical Property Safety Information Pharmacology Properties Product Information Bioassay(PubChem)
Solubility
0.13 mg/ml (25 oC) expand Show data source
Melting Point
197-199°C expand Show data source
Hydrophobicity(logP)
0.9 expand Show data source
Storage Condition
-20°C expand Show data source
2-8°C expand Show data source
Storage Warning
IRRITANT expand Show data source
RTECS
WO9100000 expand Show data source
European Hazard Symbols
Irritant Irritant (Xi) expand Show data source
MSDS Link
Download expand Show data source
Download expand Show data source
Download expand Show data source
Download expand Show data source
German water hazard class
2 expand Show data source
Risk Statements
36/37/38 expand Show data source
Safety Statements
26-36 expand Show data source
TSCA Listed
false expand Show data source
GHS Pictograms
GHS07 expand Show data source
GHS Signal Word
Warning expand Show data source
GHS Hazard statements
H315-H319-H335 expand Show data source
GHS Precautionary statements
P261-P305 + P351 + P338 expand Show data source
Personal Protective Equipment
dust mask type N95 (US), Eyeshields, Gloves expand Show data source
Storage Temperature
2-8°C expand Show data source
Gene Information
rat ... Ednra(24326) expand Show data source
Mechanism of Action
Folate antagonist expand Show data source
Restrict folate synthesis through competitive antagonism of PABA expand Show data source
Purity
≥99.0% expand Show data source
Grade
VETRANAL™, analytical standard expand Show data source
Salt Data
Free Base expand Show data source
Certificate of Analysis
Download expand Show data source
Application(s)
Antiseptic expand Show data source
Low acute toxicity expand Show data source
Protozoacide expand Show data source
Short-acting sulfonamide used for urinary tract infections. expand Show data source
Empirical Formula (Hill Notation)
C11H13N3O3S expand Show data source

DETAILS

DETAILS

DrugBank DrugBank MP Biomedicals MP Biomedicals Sigma Aldrich Sigma Aldrich Selleck Chemicals Selleck Chemicals
DrugBank - DB00263 external link
Item Information
Drug Groups approved
Description A short-acting sulfonamide antibacterial with activity against a wide range of gram- negative and gram-positive organisms. [PubChem]
Indication For the treatment of severe, repeated, or long-lasting urinary tract infections, meningococcal meningitis, acute otitis media, trachoma, inclusion conjunctivitis, nocardiosis, chancroid, toxoplasmosis, malaria and other bacterial infections.
Pharmacology Sulfisoxazole is a sulfonamide antibiotic. The sulfonamides are synthetic bacteriostatic antibiotics with a wide spectrum against most gram-positive and many gram-negative organisms. However, many strains of an individual species may be resistant. Sulfonamides inhibit multiplication of bacteria by acting as competitive inhibitors of p-aminobenzoic acid in the folic acid metabolism cycle. Bacterial sensitivity is the same for the various sulfonamides, and resistance to one sulfonamide indicates resistance to all. Most sulfonamides are readily absorbed orally. However, parenteral administration is difficult, since the soluble sulfonamide salts are highly alkaline and irritating to the tissues. The sulfonamides are widely distributed throughout all tissues. High levels are achieved in pleural, peritoneal, synovial, and ocular fluids. Although these drugs are no longer used to treat meningitis, CSF levels are high in meningeal infections. Their antibacterial action is inhibited by pus.
Toxicity LD50=6800 mg/kg (Orally in mice)
Affected Organisms
Enteric bacteria and other eubacteria
Elimination The mean urinary excretion recovery following oral administration of sulfisoxazole is 97% within 48 hours, of which 52% is intact drug, with the remaining as the N4-acetylated metabolite. It is excreted in human milk.
External Links
Wikipedia
Drugs.com
Sigma Aldrich - S6377 external link
Biochem/physiol Actions
Selective ETA antagonist.
Sigma Aldrich - 31739 external link
Legal Information
VETRANAL is a trademark of Sigma-Aldrich Co. LLC
Selleck Chemicals - S1916 external link
Research Area: Infection
Biological Activity:
Sulfisoxazole is a sulfonamide antibacterial with an oxazole substituent. It has antibiotic activity against a wide range of Gram-negative and Gram-positive organisms. It is sometimes given in combination with erythromycin or phenazopyridine. It is used locally in a 4% solution or ointment. [1]

REFERENCES

REFERENCES

From Suppliers Google Scholar IconGoogle Scholar PubMed iconPubMed Google Books IconGoogle Books
  • • http://en.wikipedia.org/wiki/Sulfafurazole
  • • Aldrich Library of 13C and 1H FT NMR Spectra, 1992, 3, 101A, (nmr)
  • • Hoeprich, P.D., Antimicrob. Agents Chemother., 1967, 697, (pharmacol)
  • • Rudy, B.C. et al., Anal. Profiles Drug Subst., 1973, 2, 487, (rev, synth)
  • • Manzo, R.H. et al., J. Pharm. Sci., 1973, 62, 152, (uv)
  • • IARC Monog., 1980, 24, 275; Suppl. 7, 347; Suppl. 6, 502, (rev, tox)
  • • Chatterjee, C. et al., Acta Cryst. B, 1982, 38, 1845, (cryst struct)
  • • Bult, A., Pharm. Weekbl., Sci. Ed., 1983, 5, 77, (cmr, tautom)
  • • Negwer, M., Organic-Chemical Drugs and their Synonyms, 6th edn., Akademie-Verlag, 1987, 1971
  • • Kirk-Othmer Encycl. Chem. Technol., 4th edn., Wiley, 1991, 2, 876, (rev)
  • • Martindale, The Extra Pharmacopoeia, 30th edn., Pharmaceutical Press, 1993, 207
  • • Lewis, R.J., Sax's Dangerous Properties of Industrial Materials, 8th edn., Van Nostrand Reinhold, 1992, SNN500
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PATENTS

PATENTS

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INTERNET

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