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Showing NP-Card for sulfamethizole (NP0285699)

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Record Information
Version2.0
Created at2022-09-09 13:58:55 UTC
Updated at2022-09-09 13:58:55 UTC
NP-MRD IDNP0285699
Secondary Accession NumbersNone
Natural Product Identification
Common Namesulfamethizole
DescriptionSulfamethizole, also known as rufol or thiosulfil, belongs to the class of organic compounds known as aminobenzenesulfonamides. These are organic compounds containing a benzenesulfonamide moiety with an amine group attached to the benzene ring. Sulfamethizole is a drug which is used for the treatment of urinary tract infection. Sulfamethizole is a moderately basic compound (based on its pKa). sulfamethizole is found in Apis cerana. sulfamethizole was first documented in 1990 (PMID: 2372557). A sulfonamide consisting of a 1,3,4-thiadiazole nucleus with a methyl substituent at C-5 and a 4-aminobenzenesulfonamido group at C-2 (PMID: 12604534) (PMID: 14519675) (PMID: 17180970).
Structure
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MOL3D MOLSDFPDBSMILESInChI

MOL for NP0285699 (sulfamethizole)

576
  Mrv0541 02231214472D          

 17 18  0  0  0  0            999 V2000
    2.4751    0.6631    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    3.9433    1.5651    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500    0.6631    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3001    0.6631    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4751    1.4882    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.2758    2.7212    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.4751   -2.6369    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.0828    2.8927    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.4751   -0.1619    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7606   -0.5744    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1895   -0.5744    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4751   -1.8119    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7606   -1.3994    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1895   -1.3994    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1895    1.9007    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4953    2.1782    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3158    2.0920    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  3  2  0  0  0  0
  1  4  2  0  0  0  0
  1  5  1  0  0  0  0
  1  9  1  0  0  0  0
  2 15  1  0  0  0  0
  2 16  1  0  0  0  0
  5 15  1  0  0  0  0
  6  8  1  0  0  0  0
  6 15  2  0  0  0  0
  7 12  1  0  0  0  0
  8 16  2  0  0  0  0
  9 10  2  0  0  0  0
  9 11  1  0  0  0  0
 10 13  1  0  0  0  0
 11 14  2  0  0  0  0
 12 13  2  0  0  0  0
 12 14  1  0  0  0  0
 16 17  1  0  0  0  0
M  END
Download

3D MOL for NP0285699 (sulfamethizole)

     RDKit          3D

 27 28  0  0  0  0  0  0  0  0999 V2000
    4.3460   -1.8950   -0.1944 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5568   -0.6427   -0.4281 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7397    0.3112   -1.3325 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.9646    1.3040   -1.3795 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.9582    1.3943   -0.5168 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9799    2.4314   -0.4060 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2613    2.4084    0.7578 S   0  0  0  0  0  6  0  0  0  0  0  0
    0.3753    2.4043    2.1260 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1076    3.6322    0.6079 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2809    1.0327    0.5283 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1104   -0.1284    1.2310 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9618   -1.1827    0.9828 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9802   -1.1216    0.0571 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8157   -2.2490   -0.1422 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1439    0.0493   -0.6439 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2981    1.1063   -0.4022 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1662   -0.0322    0.3895 S   0  0  0  0  0  0  0  0  0  0  0  0
    5.3306   -1.6004    0.2181 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5003   -2.4222   -1.1346 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8246   -2.4911    0.5871 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0395    3.2401   -1.0790 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3239   -0.2438    1.9869 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8311   -2.1165    1.5420 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3141   -2.3340   -1.0564 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9511   -2.9845    0.5736 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9369    0.1130   -1.3722 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4647    2.0167   -0.9819 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  7  9  2  0
  7 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 13 15  1  0
 15 16  2  0
  5 17  1  0
 17  2  1  0
 16 10  1  0
  1 18  1  0
  1 19  1  0
  1 20  1  0
  6 21  1  0
 11 22  1  0
 12 23  1  0
 14 24  1  0
 14 25  1  0
 15 26  1  0
 16 27  1  0
M  END
Download

3D SDF for NP0285699 (sulfamethizole)

576
  Mrv0541 02231214472D          

 17 18  0  0  0  0            999 V2000
    2.4751    0.6631    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    3.9433    1.5651    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500    0.6631    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3001    0.6631    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4751    1.4882    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.2758    2.7212    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.4751   -2.6369    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.0828    2.8927    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.4751   -0.1619    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7606   -0.5744    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1895   -0.5744    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4751   -1.8119    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7606   -1.3994    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1895   -1.3994    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1895    1.9007    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4953    2.1782    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3158    2.0920    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  3  2  0  0  0  0
  1  4  2  0  0  0  0
  1  5  1  0  0  0  0
  1  9  1  0  0  0  0
  2 15  1  0  0  0  0
  2 16  1  0  0  0  0
  5 15  1  0  0  0  0
  6  8  1  0  0  0  0
  6 15  2  0  0  0  0
  7 12  1  0  0  0  0
  8 16  2  0  0  0  0
  9 10  2  0  0  0  0
  9 11  1  0  0  0  0
 10 13  1  0  0  0  0
 11 14  2  0  0  0  0
 12 13  2  0  0  0  0
 12 14  1  0  0  0  0
 16 17  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0285699

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1=NN=C(NS(=O)(=O)C2=CC=C(N)C=C2)S1

> <INCHI_IDENTIFIER>
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)

> <INCHI_KEY>
VACCAVUAMIDAGB-UHFFFAOYSA-N

> <FORMULA>
C9H10N4O2S2

> <MOLECULAR_WEIGHT>
270.331

> <EXACT_MASS>
270.024516964

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_AVERAGE_POLARIZABILITY>
26.264209134273333

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
4-amino-N-(5-methyl-1,3,4-thiadiazol-2-yl)benzene-1-sulfonamide

> <ALOGPS_LOGP>
0.53

> <JCHEM_LOGP>
0.21434596466666644

> <ALOGPS_LOGS>
-2.65

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
6.707642187543112

> <JCHEM_PKA_STRONGEST_BASIC>
1.951757408153643

> <JCHEM_POLAR_SURFACE_AREA>
97.97

> <JCHEM_REFRACTIVITY>
66.8358

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.11e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
sulfamethizole

> <JCHEM_VEBER_RULE>
0

$$$$
Download

3D-SDF for NP0285699 (sulfamethizole)

Download
PDB for NP0285699 (sulfamethizole)
HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 576                                               
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  S   UNK     0       4.620   1.238   0.000  0.00  0.00           S+0
HETATM    2  S   UNK     0       7.361   2.922   0.000  0.00  0.00           S+0
HETATM    3  O   UNK     0       3.080   1.238   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0       6.160   1.238   0.000  0.00  0.00           O+0
HETATM    5  N   UNK     0       4.620   2.778   0.000  0.00  0.00           N+0
HETATM    6  N   UNK     0       6.115   5.080   0.000  0.00  0.00           N+0
HETATM    7  N   UNK     0       4.620  -4.922   0.000  0.00  0.00           N+0
HETATM    8  N   UNK     0       7.621   5.400   0.000  0.00  0.00           N+0
HETATM    9  C   UNK     0       4.620  -0.302   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       3.286  -1.072   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.954  -1.072   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.620  -3.382   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       3.286  -2.612   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       5.954  -2.612   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       5.954   3.548   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       8.391   4.066   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       9.923   3.905   0.000  0.00  0.00           C+0
CONECT    1    3    4    5    9                                             
CONECT    2   15   16                                                       
CONECT    3    1                                                            
CONECT    4    1                                                            
CONECT    5    1   15                                                       
CONECT    6    8   15                                                       
CONECT    7   12                                                            
CONECT    8    6   16                                                       
CONECT    9    1   10   11                                                  
CONECT   10    9   13                                                       
CONECT   11    9   14                                                       
CONECT   12    7   13   14                                                  
CONECT   13   10   12                                                       
CONECT   14   11   12                                                       
CONECT   15    2    5    6                                                  
CONECT   16    2    8   17                                                  
CONECT   17   16                                                            
MASTER        0    0    0    0    0    0    0    0   17    0   36    0
END

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3D PDB for NP0285699 (sulfamethizole)
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SMILES for NP0285699 (sulfamethizole)
CC1=NN=C(NS(=O)(=O)C2=CC=C(N)C=C2)S1
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INCHI for NP0285699 (sulfamethizole)
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)
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View in JSmol
Synonyms
ValueSource
RufolChEBI
SulfamethizolChEBI
SulfamethizolumChEBI
SulfamethylthiadiazoleChEBI
SulfametizolChEBI
SulphamethazoleChEBI
SulphamethiozoleChEBI
ThiosulfilKegg
SulphamethizolGenerator
SulphamethizolumGenerator
SulphamethylthiadiazoleGenerator
SulphametizolGenerator
SulfamethazoleGenerator
SulfamethiozoleGenerator
ThiosulphilGenerator
SulphamethizoleGenerator
Urgo brand OF sulfamethizoleHMDB
FNA brand OF sulfamethizoleHMDB
FNA, sulfamethizolHMDB
Sulfamethizol fnaHMDB
Wyeth brand OF sulfamethizoleHMDB
Chemical FormulaC9H10N4O2S2
Average Mass270.3310 Da
Monoisotopic Mass270.02452 Da
IUPAC Name4-amino-N-(5-methyl-1,3,4-thiadiazol-2-yl)benzene-1-sulfonamide
Traditional Namesulfamethizole
CAS Registry NumberNot Available
SMILES
CC1=NN=C(NS(=O)(=O)C2=CC=C(N)C=C2)S1
InChI Identifier
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)
InChI KeyVACCAVUAMIDAGB-UHFFFAOYSA-N
Experimental Spectra
Not Available
Predicted Spectra
Spectrum TypeDescriptionDepositor IDDepositor OrganizationDepositorDeposition DateView
1D NMR13C NMR Spectrum (1D, 25 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 252 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 50 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 75 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 101 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 126 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 151 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 176 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 201 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 226 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Apis ceranaLOTUS Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as aminobenzenesulfonamides. These are organic compounds containing a benzenesulfonamide moiety with an amine group attached to the benzene ring.
KingdomOrganic compounds  
Super ClassBenzenoids  
ClassBenzene and substituted derivatives  
Sub ClassBenzenesulfonamides  
Direct ParentAminobenzenesulfonamides  
Alternative Parents
Substituents
  • Aminobenzenesulfonamide
    • 

  • Benzenesulfonyl group
    • 

  • Aniline or substituted anilines
    • 

  • Organosulfonic acid amide
    • 

  • Azole
    • 

  • Organic sulfonic acid or derivatives
    • 

  • Organosulfonic acid or derivatives
    • 

  • Sulfonyl
    • 

  • Thiadiazole
    • 

  • Aminosulfonyl compound
    • 

  • Heteroaromatic compound
    • 

  • Organoheterocyclic compound
    • 

  • Azacycle
    • 

  • Organonitrogen compound
    • 

  • Amine
    • 

  • Organic oxygen compound
    • 

  • Organic nitrogen compound
    • 

  • Organosulfur compound
    • 

  • Organopnictogen compound
    • 

  • Primary amine
    • 

  • Hydrocarbon derivative
    • 

  • Organic oxide
    • 

  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP0.53ALOGPS
logP0.21ChemAxon
logS-2.6ALOGPS
pKa (Strongest Acidic)6.71ChemAxon
pKa (Strongest Basic)1.95ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area97.97 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity66.84 m³·mol⁻¹ChemAxon
Polarizability26.26 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0014715  
DrugBank IDDB00576  
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID5137  
KEGG Compound IDC08050  
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkSulfamethizole  
METLIN IDNot Available
PubChem Compound5328  
PDB IDNot Available
ChEBI ID9331  
Good Scents IDNot Available
References
General References
  1. 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. doi:  10.1016/0005-2728(90)90189-b. [PubMed:2372557  ] 
  2. 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. doi:  10.1128/AAC.47.3.1002-1009.2003. [PubMed:12604534  ] 
  3. 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. doi: 10.1093/jac/dkg438. Epub 2003  Sep 30. [PubMed:14519675  ] 
  4. Sharma VK, Mishra SK, Nesnas N: Oxidation of sulfonamide antimicrobials by ferrate(VI) [Fe(VI)O4(2-)]. Environ Sci Technol. 2006 Dec 1;40(23):7222-7. doi: 10.1021/es060351z. [PubMed:17180970  ] 
  5. LOTUS database [Link]