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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-06 15:16:50 UTC

Update Date

2022-03-07 02:51:41 UTC

HMDB ID

HMDB0014649

Secondary Accession Numbers

HMDB14649

Metabolite Identification

Common Name

Nitazoxanide

Description

Nitazoxanide, also known by the brand name Alinia, is a synthetic nitrothiazolyl-salicylamide derivative and an anti-protozoal agent. It is approved for treatment of infectious diarrhea caused by Cryptosporidium parvum and Giardia lamblia in patients 1 year of age and older. Following oral administration it is rapidly hydrolyzed to its active metabolite, tizoxanide, which is 99% protein bound. Peak concentrations are observed 1-4 hours after administration. It is excreted in the urine, bile and feces. Untoward effects include abdominal pain, vomiting and diarrhea. [Wikipedia ]

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

HMDB0014649
     RDKit          3D
Nitazoxanide
 30 31  0  0  0  0  0  0  0  0999 V2000
    1.5278    3.2726   -1.1691 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1694    2.6311    0.1168 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9606    2.5099    1.0614 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1339    2.1194    0.3115 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4384    1.5195    1.5378 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5927    2.3768    2.6198 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8896    1.8979    3.8737 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0271    0.5464    4.0152 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8756   -0.2948    2.9498 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5726    0.1662    1.6554 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4687   -0.7860    0.5792 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6029   -2.0235    0.9141 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2375   -0.4675   -0.7610 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1502   -1.5309   -1.7578 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2659   -2.8289   -1.5780 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1605   -3.6384   -2.5791 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0729   -3.0990   -3.8168 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2268   -3.7623   -5.0640 N   0  0  0  0  0  4  0  0  0  0  0  0
    0.1470   -4.9969   -5.0918 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4580   -3.0899   -6.2274 O   0  0  0  0  0  1  0  0  0  0  0  0
    0.1252   -1.4158   -3.4365 S   0  0  0  0  0  0  0  0  0  0  0  0
    2.3407    4.0187   -1.0388 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6411    3.7987   -1.5864 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8603    2.5123   -1.8990 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4785    3.4483    2.4866 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0070    2.5745    4.7056 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2625    0.1774    5.0162 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9923   -1.3784    3.0972 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1225    0.4798   -1.1082 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2513   -4.7372   -2.4700 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  1  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 11 13  1  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 18 20  1  0
 17 21  1  0
 10  5  1  0
 21 14  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  6 25  1  0
  7 26  1  0
  8 27  1  0
  9 28  1  0
 13 29  1  0
 16 30  1  0
M  CHG  2  18   1  20  -1
M  END

507
  Mrv0541 02231214442D          

 21 22  0  0  0  0            999 V2000
    4.5550    0.9959    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791   -1.5516    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935   -0.3141    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -2.7891    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6606    3.2016    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
    3.5045    2.3617    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2224   -0.3141    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.8899    0.9959    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.3250    2.4480    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
    4.5080   -1.5516    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935   -1.9641    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080   -0.7266    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2224   -1.9641    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935   -2.7891    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2224   -2.7891    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2224    0.5109    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080   -3.2016    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8099    1.7805    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6350    1.7805    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -1.9641    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500   -1.5516    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1 16  1  0  0  0  0
  1 18  1  0  0  0  0
  2 11  1  0  0  0  0
  2 20  1  0  0  0  0
  3 12  2  0  0  0  0
  4 20  2  0  0  0  0
  5  9  1  0  0  0  0
  6  9  2  0  0  0  0
  7 12  1  0  0  0  0
  7 16  1  0  0  0  0
  8 16  2  0  0  0  0
  8 19  1  0  0  0  0
  9 18  1  0  0  0  0
 10 11  1  0  0  0  0
 10 12  1  0  0  0  0
 10 13  2  0  0  0  0
 11 14  2  0  0  0  0
 13 15  1  0  0  0  0
 14 17  1  0  0  0  0
 15 17  2  0  0  0  0
 18 19  2  0  0  0  0
 20 21  1  0  0  0  0
M  CHG  2   5  -1   9   1
M  END
> <DATABASE_ID>
HMDB0014649

> <DATABASE_NAME>
hmdb

> <SMILES>
CC(=O)OC1=CC=CC=C1C(=O)NC1=NC=C(S1)[N+]([O-])=O

> <INCHI_IDENTIFIER>
InChI=1S/C12H9N3O5S/c1-7(16)20-9-5-3-2-4-8(9)11(17)14-12-13-6-10(21-12)15(18)19/h2-6H,1H3,(H,13,14,17)

> <INCHI_KEY>
YQNQNVDNTFHQSW-UHFFFAOYSA-N

> <FORMULA>
C12H9N3O5S

> <MOLECULAR_WEIGHT>
307.282

> <EXACT_MASS>
307.026291103

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_AVERAGE_POLARIZABILITY>
27.5429801667647

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-[(5-nitro-1,3-thiazol-2-yl)carbamoyl]phenyl acetate

> <ALOGPS_LOGP>
2.14

> <JCHEM_LOGP>
2.121414542333333

> <ALOGPS_LOGS>
-4.61

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.299087339145986

> <JCHEM_PKA_STRONGEST_BASIC>
-4.1975087648445655

> <JCHEM_POLAR_SURFACE_AREA>
114.11000000000001

> <JCHEM_REFRACTIVITY>
73.89020000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
7.55e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
nitazoxanide

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0014649
     RDKit          3D
Nitazoxanide
 30 31  0  0  0  0  0  0  0  0999 V2000
    1.5278    3.2726   -1.1691 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1694    2.6311    0.1168 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9606    2.5099    1.0614 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1339    2.1194    0.3115 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4384    1.5195    1.5378 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5927    2.3768    2.6198 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8896    1.8979    3.8737 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0271    0.5464    4.0152 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8756   -0.2948    2.9498 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5726    0.1662    1.6554 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4687   -0.7860    0.5792 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6029   -2.0235    0.9141 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2375   -0.4675   -0.7610 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1502   -1.5309   -1.7578 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2659   -2.8289   -1.5780 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1605   -3.6384   -2.5791 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0729   -3.0990   -3.8168 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2268   -3.7623   -5.0640 N   0  0  0  0  0  4  0  0  0  0  0  0
    0.1470   -4.9969   -5.0918 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4580   -3.0899   -6.2274 O   0  0  0  0  0  1  0  0  0  0  0  0
    0.1252   -1.4158   -3.4365 S   0  0  0  0  0  0  0  0  0  0  0  0
    2.3407    4.0187   -1.0388 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6411    3.7987   -1.5864 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8603    2.5123   -1.8990 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4785    3.4483    2.4866 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0070    2.5745    4.7056 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2625    0.1774    5.0162 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9923   -1.3784    3.0972 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1225    0.4798   -1.1082 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2513   -4.7372   -2.4700 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  1  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 11 13  1  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 18 20  1  0
 17 21  1  0
 10  5  1  0
 21 14  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  6 25  1  0
  7 26  1  0
  8 27  1  0
  9 28  1  0
 13 29  1  0
 16 30  1  0
M  CHG  2  18   1  20  -1
M  END

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 507                                               
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  S   UNK     0       8.503   1.859   0.000  0.00  0.00           S+0
HETATM    2  O   UNK     0       5.748  -2.896   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0       7.081  -0.586   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0       4.414  -5.206   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0       8.700   5.976   0.000  0.00  0.00           O-1
HETATM    6  O   UNK     0       6.542   4.409   0.000  0.00  0.00           O+0
HETATM    7  N   UNK     0       9.748  -0.586   0.000  0.00  0.00           N+0
HETATM    8  N   UNK     0      10.994   1.859   0.000  0.00  0.00           N+0
HETATM    9  N   UNK     0       8.073   4.570   0.000  0.00  0.00           N+1
HETATM   10  C   UNK     0       8.415  -2.896   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       7.081  -3.666   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       8.415  -1.356   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       9.748  -3.666   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       7.081  -5.206   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       9.748  -5.206   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       9.748   0.954   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       8.415  -5.976   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       8.978   3.324   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      10.519   3.324   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       4.414  -3.666   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       3.080  -2.896   0.000  0.00  0.00           C+0
CONECT    1   16   18                                                       
CONECT    2   11   20                                                       
CONECT    3   12                                                            
CONECT    4   20                                                            
CONECT    5    9                                                            
CONECT    6    9                                                            
CONECT    7   12   16                                                       
CONECT    8   16   19                                                       
CONECT    9    5    6   18                                                  
CONECT   10   11   12   13                                                  
CONECT   11    2   10   14                                                  
CONECT   12    3    7   10                                                  
CONECT   13   10   15                                                       
CONECT   14   11   17                                                       
CONECT   15   13   17                                                       
CONECT   16    1    7    8                                                  
CONECT   17   14   15                                                       
CONECT   18    1    9   19                                                  
CONECT   19    8   18                                                       
CONECT   20    2    4   21                                                  
CONECT   21   20                                                            
MASTER        0    0    0    0    0    0    0    0   21    0   44    0
END

COMPND    HMDB0014649
HETATM    1  C1  UNL     1       1.528   3.273  -1.169  1.00  0.00           C  
HETATM    2  C2  UNL     1       1.169   2.631   0.117  1.00  0.00           C  
HETATM    3  O1  UNL     1       1.961   2.510   1.061  1.00  0.00           O  
HETATM    4  O2  UNL     1      -0.134   2.119   0.311  1.00  0.00           O  
HETATM    5  C3  UNL     1      -0.438   1.520   1.538  1.00  0.00           C  
HETATM    6  C4  UNL     1      -0.593   2.377   2.620  1.00  0.00           C  
HETATM    7  C5  UNL     1      -0.890   1.898   3.874  1.00  0.00           C  
HETATM    8  C6  UNL     1      -1.027   0.546   4.015  1.00  0.00           C  
HETATM    9  C7  UNL     1      -0.876  -0.295   2.950  1.00  0.00           C  
HETATM   10  C8  UNL     1      -0.573   0.166   1.655  1.00  0.00           C  
HETATM   11  C9  UNL     1      -0.469  -0.786   0.579  1.00  0.00           C  
HETATM   12  O3  UNL     1      -0.603  -2.023   0.914  1.00  0.00           O  
HETATM   13  N1  UNL     1      -0.238  -0.467  -0.761  1.00  0.00           N  
HETATM   14  C10 UNL     1      -0.150  -1.531  -1.758  1.00  0.00           C  
HETATM   15  N2  UNL     1      -0.266  -2.829  -1.578  1.00  0.00           N  
HETATM   16  C11 UNL     1      -0.161  -3.638  -2.579  1.00  0.00           C  
HETATM   17  C12 UNL     1       0.073  -3.099  -3.817  1.00  0.00           C  
HETATM   18  N3  UNL     1       0.227  -3.762  -5.064  1.00  0.00           N1+
HETATM   19  O4  UNL     1       0.147  -4.997  -5.092  1.00  0.00           O  
HETATM   20  O5  UNL     1       0.458  -3.090  -6.227  1.00  0.00           O1-
HETATM   21  S1  UNL     1       0.125  -1.416  -3.436  1.00  0.00           S  
HETATM   22  H1  UNL     1       2.341   4.019  -1.039  1.00  0.00           H  
HETATM   23  H2  UNL     1       0.641   3.799  -1.586  1.00  0.00           H  
HETATM   24  H3  UNL     1       1.860   2.512  -1.899  1.00  0.00           H  
HETATM   25  H4  UNL     1      -0.479   3.448   2.487  1.00  0.00           H  
HETATM   26  H5  UNL     1      -1.007   2.574   4.706  1.00  0.00           H  
HETATM   27  H6  UNL     1      -1.262   0.177   5.016  1.00  0.00           H  
HETATM   28  H7  UNL     1      -0.992  -1.378   3.097  1.00  0.00           H  
HETATM   29  H8  UNL     1      -0.123   0.480  -1.108  1.00  0.00           H  
HETATM   30  H9  UNL     1      -0.251  -4.737  -2.470  1.00  0.00           H  
CONECT    1    2   22   23   24
CONECT    2    3    3    4
CONECT    4    5
CONECT    5    6    6   10
CONECT    6    7   25
CONECT    7    8    8   26
CONECT    8    9   27
CONECT    9   10   10   28
CONECT   10   11
CONECT   11   12   12   13
CONECT   13   14   29
CONECT   14   15   15   21
CONECT   15   16
CONECT   16   17   17   30
CONECT   17   18   21
CONECT   18   19   19   20
END

HMDB0014649
     RDKit          3D
Nitazoxanide
 30 31  0  0  0  0  0  0  0  0999 V2000
    1.5278    3.2726   -1.1691 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1694    2.6311    0.1168 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9606    2.5099    1.0614 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1339    2.1194    0.3115 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4384    1.5195    1.5378 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5927    2.3768    2.6198 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8896    1.8979    3.8737 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0271    0.5464    4.0152 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8756   -0.2948    2.9498 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5726    0.1662    1.6554 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4687   -0.7860    0.5792 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6029   -2.0235    0.9141 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2375   -0.4675   -0.7610 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1502   -1.5309   -1.7578 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2659   -2.8289   -1.5780 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1605   -3.6384   -2.5791 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0729   -3.0990   -3.8168 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2268   -3.7623   -5.0640 N   0  0  0  0  0  4  0  0  0  0  0  0
    0.1470   -4.9969   -5.0918 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4580   -3.0899   -6.2274 O   0  0  0  0  0  1  0  0  0  0  0  0
    0.1252   -1.4158   -3.4365 S   0  0  0  0  0  0  0  0  0  0  0  0
    2.3407    4.0187   -1.0388 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6411    3.7987   -1.5864 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8603    2.5123   -1.8990 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4785    3.4483    2.4866 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0070    2.5745    4.7056 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2625    0.1774    5.0162 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9923   -1.3784    3.0972 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1225    0.4798   -1.1082 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2513   -4.7372   -2.4700 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  1  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 11 13  1  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 18 20  1  0
 17 21  1  0
 10  5  1  0
 21 14  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  6 25  1  0
  7 26  1  0
  8 27  1  0
  9 28  1  0
 13 29  1  0
 16 30  1  0
M  CHG  2  18   1  20  -1
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Alinia	Kegg
2-(Acetolyloxy)-N-(5-nitro-2-thiazolyl)benzamide	HMDB
2-Acetyloxy-N-[(5-nitro-2-thiazolyl)]benzamide	HMDB
Nitazoxanid	HMDB
Tizoxanide glucuronide	HMDB
Columbia brand 2 OF nitazoxanide	HMDB
Cryptaz	HMDB
Columbia brand 1 OF nitazoxanide	HMDB
Columbia brand 3 OF nitazoxanide	HMDB
Heliton	HMDB
NTZ	HMDB
Romark brand 1 OF nitazoxanide	HMDB
Colufase	HMDB
Daxon	HMDB
Romark brand 2 OF nitazoxanide	HMDB
Taenitaz	HMDB

Chemical Formula

C₁₂H₉N₃O₅S

Average Molecular Weight

307.282

Monoisotopic Molecular Weight

307.026291103

IUPAC Name

2-[(5-nitro-1,3-thiazol-2-yl)carbamoyl]phenyl acetate

Traditional Name

nitazoxanide

CAS Registry Number

55981-09-4

SMILES

CC(=O)OC1=CC=CC=C1C(=O)NC1=NC=C(S1)[N+]([O-])=O

InChI Identifier

InChI=1S/C12H9N3O5S/c1-7(16)20-9-5-3-2-4-8(9)11(17)14-12-13-6-10(21-12)15(18)19/h2-6H,1H3,(H,13,14,17)

InChI Key

YQNQNVDNTFHQSW-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as acylsalicylamides. These are o-acylated derivatives of salicylamide.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Benzoic acids and derivatives

Direct Parent

Acylsalicylamides

Alternative Parents

Substituents

Acylsalicylamide
Phenol ester
Benzamide
Phenoxy compound
Nitroaromatic compound
Benzoyl
Nitrothiazole
2,5-disubstituted 1,3-thiazole
Azole
Thiazole
Heteroaromatic compound
Organic nitro compound
Secondary carboxylic acid amide
Carboxamide group
Carboxylic acid ester
C-nitro compound
Organoheterocyclic compound
Organic 1,3-dipolar compound
Propargyl-type 1,3-dipolar organic compound
Allyl-type 1,3-dipolar organic compound
Azacycle
Carboxylic acid derivative
Organic oxoazanium
Monocarboxylic acid or derivatives
Organic nitrogen compound
Organic oxide
Organonitrogen compound
Organooxygen compound
Hydrocarbon derivative
Carbonyl group
Organopnictogen compound
Organic oxygen compound
Organic zwitterion
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

Not Available

Ontology

Not Available

Urine (PMID: 21059682)

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 21059682)

Cellular substructure

Membrane (HMDB: HMDB0014649)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	202 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	0.0076 g/L	Not Available
LogP	1.2	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.0076 g/L	ALOGPS
logP	2.14	ALOGPS
logP	2.12	ChemAxon
logS	-4.6	ALOGPS
pKa (Strongest Acidic)	8.3	ChemAxon
pKa (Strongest Basic)	-4.2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	114.11 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	73.89 m³·mol⁻¹	ChemAxon
Polarizability	27.54 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	168.635	31661259
DarkChem	[M-H]-	169.375	31661259
DeepCCS	[M+H]+	155.477	30932474
DeepCCS	[M-H]-	152.641	30932474
DeepCCS	[M-2H]-	187.662	30932474
DeepCCS	[M+Na]+	163.706	30932474
AllCCS	[M+H]+	165.2	32859911
AllCCS	[M+H-H2O]+	161.9	32859911
AllCCS	[M+NH4]+	168.3	32859911
AllCCS	[M+Na]+	169.2	32859911
AllCCS	[M-H]-	164.5	32859911
AllCCS	[M+Na-2H]-	164.0	32859911
AllCCS	[M+HCOO]-	163.6	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Nitazoxanide	CC(=O)OC1=CC=CC=C1C(=O)NC1=NC=C(S1)[N+]([O-])=O	3721.8	Standard polar	33892256
Nitazoxanide	CC(=O)OC1=CC=CC=C1C(=O)NC1=NC=C(S1)[N+]([O-])=O	2650.1	Standard non polar	33892256
Nitazoxanide	CC(=O)OC1=CC=CC=C1C(=O)NC1=NC=C(S1)[N+]([O-])=O	2682.5	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Nitazoxanide,1TMS,isomer #1	CC(=O)OC1=CC=CC=C1C(=O)N(C1=NC=C([N+](=O)[O-])S1)[Si](C)(C)C	2497.6	Semi standard non polar	33892256
Nitazoxanide,1TMS,isomer #1	CC(=O)OC1=CC=CC=C1C(=O)N(C1=NC=C([N+](=O)[O-])S1)[Si](C)(C)C	2457.8	Standard non polar	33892256
Nitazoxanide,1TMS,isomer #1	CC(=O)OC1=CC=CC=C1C(=O)N(C1=NC=C([N+](=O)[O-])S1)[Si](C)(C)C	3563.8	Standard polar	33892256
Nitazoxanide,1TBDMS,isomer #1	CC(=O)OC1=CC=CC=C1C(=O)N(C1=NC=C([N+](=O)[O-])S1)[Si](C)(C)C(C)(C)C	2734.3	Semi standard non polar	33892256
Nitazoxanide,1TBDMS,isomer #1	CC(=O)OC1=CC=CC=C1C(=O)N(C1=NC=C([N+](=O)[O-])S1)[Si](C)(C)C(C)(C)C	2661.1	Standard non polar	33892256
Nitazoxanide,1TBDMS,isomer #1	CC(=O)OC1=CC=CC=C1C(=O)N(C1=NC=C([N+](=O)[O-])S1)[Si](C)(C)C(C)(C)C	3578.7	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Nitazoxanide GC-MS (Non-derivatized) - 70eV, Positive	splash10-006x-9820000000-92fb5445f11125065e46	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Nitazoxanide GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Nitazoxanide GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental LC-MS/MS	LC-MS/MS Spectrum - Nitazoxanide LC-ESI-qTof , Positive-QTOF	splash10-01b9-1950000000-3d1aca26d9cbdaaab410	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Nitazoxanide , positive-QTOF	splash10-01b9-1950000000-3d1aca26d9cbdaaab410	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Nitazoxanide 35V, Positive-QTOF	splash10-00di-0900000000-1e121f0a39d98b11856b	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Nitazoxanide 35V, Negative-QTOF	splash10-0a4i-0229000000-53676b9ef27d67cc1750	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Nitazoxanide 10V, Positive-QTOF	splash10-0a4i-0009000000-2008214409594d8a4aa4	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Nitazoxanide 20V, Positive-QTOF	splash10-0a4i-1069000000-3e719ea5b05adffe4b69	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Nitazoxanide 40V, Positive-QTOF	splash10-002e-9210000000-c412f82070045302bd47	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Nitazoxanide 10V, Negative-QTOF	splash10-0a4i-2109000000-985c0c92983f75acb4b0	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Nitazoxanide 20V, Negative-QTOF	splash10-0a4i-9212000000-ebc430c35ab9200dcd18	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Nitazoxanide 40V, Negative-QTOF	splash10-0a4i-9010000000-0ec40f1534d5fe909654	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Nitazoxanide 10V, Positive-QTOF	splash10-01b9-0960000000-97c646f778e77a560b20	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Nitazoxanide 20V, Positive-QTOF	splash10-00di-0900000000-d727decb3e04530d2177	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Nitazoxanide 40V, Positive-QTOF	splash10-00di-1900000000-dc0087192f244a933bea	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Nitazoxanide 10V, Negative-QTOF	splash10-0a4i-0009000000-880114e27c1b22207ace	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Nitazoxanide 20V, Negative-QTOF	splash10-0a4i-2009000000-db39e69949f5cad9dc20	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Nitazoxanide 40V, Negative-QTOF	splash10-052f-9111000000-1bb86956f101434bfa18	2021-09-24	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Membrane (predicted from logP)

Biospecimen Locations

Blood
Urine

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB00507	21059682	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB00507	21059682	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB00507

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

38037

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Nitazoxanide

METLIN ID

Not Available

PubChem Compound

41684

PDB ID

NTI

ChEBI ID

438934

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Authors unspecified: Parasitic infections. Am J Transplant. 2004 Nov;4 Suppl 10:142-55. [PubMed:15504227 ]

Showing metabocard for Nitazoxanide (HMDB0014649)

MOL for HMDB0014649 (Nitazoxanide)

3D MOL for HMDB0014649 (Nitazoxanide)

3D SDF for HMDB0014649 (Nitazoxanide)

3D-SDF for HMDB0014649 (Nitazoxanide)

PDB for HMDB0014649 (Nitazoxanide)

3D PDB for HMDB0014649 (Nitazoxanide)

SMILES for HMDB0014649 (Nitazoxanide)

INCHI for HMDB0014649 (Nitazoxanide)

Structure for HMDB0014649 (Nitazoxanide)

3D Structure for HMDB0014649 (Nitazoxanide)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra