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144-82-1 molecular structure
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4-amino-N-(5-methyl-1,3,4-thiadiazol-2-yl)benzene-1-sulfonamide

ChemBase ID: 458
Molecular Formular: C9H10N4O2S2
Molecular Mass: 270.3313
Monoisotopic Mass: 270.02451758
SMILES and InChIs

SMILES:
S(=O)(=O)(Nc1sc(nn1)C)c1ccc(N)cc1
Canonical SMILES:
Nc1ccc(cc1)S(=O)(=O)Nc1nnc(s1)C
InChI:
InChI=1S/C9H10N4O2S2/c1-6-11-12-9(16-6)13-17(14,15)8-4-2-7(10)3-5-8/h2-5H,10H2,1H3,(H,12,13)
InChIKey:
VACCAVUAMIDAGB-UHFFFAOYSA-N

Cite this record

CBID:458 http://www.chembase.cn/molecule-458.html

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NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
IUPAC name
4-amino-N-(5-methyl-1,3,4-thiadiazol-2-yl)benzene-1-sulfonamide
IUPAC Traditional name
sulfamethizole
Brand Name
Sulfamethizole [Usan:Inn:Jan]
Sulfamethizolum [INN-Latin]
Sulfamethylthiadiazole
Sulfametizol [INN-Spanish]
Sulfapyelon
Sulfstat
Sulfurine
Sulphamethizole
Sulphamethyltiadiazole
Tetracid
Thidicur
Thiosulfil
Thiosulfil Forte
Ultrasul
Urocydal
Urodiaton
Urolucosil
Urosulfin
Uroz
Ayerlucil
Famet
Lucosil
Methazol
Microsul
Proklar
Renasul
Rufol
Sulfamethiazole
Salimol
Solfametizolo [Dcit]
Sulamethizole
Sulfa Gram
Sulfamethazole
Sulfamethizol
Synonyms
Sulfamethizole
Sulfamethizol
Sulfamethizole
4-Amino-N-[5-methyl-1,3,4-thiadiazol-2-yl]benzenesulfonamide
4-Amino-N-(5-methyl-1,3,4-thiadiazol-2-yl)benzenesulfonamide
N1-(5-Methyl-1,3,4-thiadiazol-2-yl)sulfanilamide
Proklar
Sulfamethizole (Proklar)
4-氨基-N-(5-甲基-1,3,4-噻二唑-2-基)苯磺酰胺
N1-(5-甲基-1,3,4-噻二唑-2-基)磺胺
磺胺甲二唑
CAS Number
144-82-1
EC Number
205-641-1
MDL Number
MFCD00053363
Beilstein Number
255002
PubChem SID
24870514
160963921
24899662
46508656
PubChem CID
5328

CALCULATED PROPERTIES

CALCULATED PROPERTIES

JChem ALOGPS 2.1
Acid pKa 6.707642  H Acceptors
H Donor LogD (pH = 5.5) 0.19116575 
LogD (pH = 7.4) -0.364739  Log P 0.21434596 
Molar Refractivity 66.8358 cm3 Polarizability 25.134037 Å3
Polar Surface Area 97.97 Å2 Rotatable Bonds
Lipinski's Rule of Five true 
Log P 0.53  LOG S -2.65 
Solubility (Water) 6.11e-01 g/l 

PROPERTIES

PROPERTIES

Physical Property Safety Information Pharmacology Properties Product Information Bioassay(PubChem)
Solubility
1050 mg/L expand Show data source
Hydrophobicity(logP)
0.9 expand Show data source
Storage Condition
2-8°C expand Show data source
RTECS
WP0875000 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
German water hazard class
2 expand Show data source
Risk Statements
43 expand Show data source
Safety Statements
36/37 expand Show data source
GHS Pictograms
GHS07 expand Show data source
GHS Signal Word
Warning expand Show data source
GHS Hazard statements
H317 expand Show data source
GHS Precautionary statements
P280 expand Show data source
Personal Protective Equipment
dust mask type N95 (US), Eyeshields, Faceshields, Gloves expand Show data source
Storage Temperature
2-8°C expand Show data source
Target
Others expand Show data source
Purity
≥99% (HPLC) expand Show data source
98% 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
Suitability
suitable for 1694 per US EPA expand Show data source
Empirical Formula (Hill Notation)
C9H10N4O2S2 expand Show data source

DETAILS

DETAILS

MP Biomedicals MP Biomedicals DrugBank DrugBank Sigma Aldrich Sigma Aldrich
MP Biomedicals - 02156710 external link
Crystalline
Purity: 98%
DrugBank - DB00576 external link
Item Information
Drug Groups approved
Description A sulfathiazole antibacterial agent. [PubChem]
Indication For the treatment of urinary tract infection
Pharmacology Sulfamethizole 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.
Affected Organisms
Enteric bacteria and other eubacteria
Biotransformation Hepatic.
Absorption Rapidly absorbed.
Half Life 3-8 hours
Protein Binding 98-99%
References
Ratanajamit C, Skriver MV, Norgaard M, Jepsen P, Schonheyder HC, Sorensen HT: Adverse pregnancy outcome in users of sulfamethizole during pregnancy: a population-based observational study. J Antimicrob Chemother. 2003 Nov;52(5):837-41. Epub 2003 Sep 30. [Pubmed]
Kerrn MB, Frimodt-Moller N, Espersen F: Effects of sulfamethizole and amdinocillin against Escherichia coli strains (with various susceptibilities) in an ascending urinary tract infection mouse model. Antimicrob Agents Chemother. 2003 Mar;47(3):1002-9. [Pubmed]
Watanabe H, Hastings JW: Inhibition of bioluminescence in Photobacterium phosphoreum by sulfamethizole and its stimulation by thymine. Biochim Biophys Acta. 1990 Jun 26;1017(3):229-34. [Pubmed]
External Links
Wikipedia
Sigma Aldrich - 46842 external link
Legal Information
VETRANAL is a trademark of Sigma-Aldrich Co. LLC

REFERENCES

REFERENCES

From Suppliers Google Scholar IconGoogle Scholar PubMed iconPubMed Google Books IconGoogle Books
  • • Ratanajamit C, Skriver MV, Norgaard M, Jepsen P, Schonheyder HC, Sorensen HT: Adverse pregnancy outcome in users of sulfamethizole during pregnancy: a population-based observational study. J Antimicrob Chemother. 2003 Nov;52(5):837-41. Epub 2003 Sep 30. Pubmed
  • • Kerrn MB, Frimodt-Moller N, Espersen F: Effects of sulfamethizole and amdinocillin against Escherichia coli strains (with various susceptibilities) in an ascending urinary tract infection mouse model. Antimicrob Agents Chemother. 2003 Mar;47(3):1002-9. Pubmed
  • • Watanabe H, Hastings JW: Inhibition of bioluminescence in Photobacterium phosphoreum by sulfamethizole and its stimulation by thymine. Biochim Biophys Acta. 1990 Jun 26;1017(3):229-34. Pubmed
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