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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 02:51:42 UTC

HMDB ID

HMDB0014694

Secondary Accession Numbers

HMDB14694

Metabolite Identification

Common Name

Piroxicam

Description

Piroxicam is only found in individuals that have used or taken this drug. It is a cyclooxygenase inhibiting, non-steroidal anti-inflammatory agent (NSAID) that is well established in treating rheumatoid arthritis and osteoarthritis and used for musculoskeletal disorders, dysmenorrhea, and postoperative pain. Its long half-life enables it to be administered once daily. [PubChem]The antiinflammatory effect of Piroxicam may result from the reversible inhibition of cyclooxygenase, causing the peripheral inhibition of prostaglandin synthesis. The prostaglandins are produced by an enzyme called Cox-1. Piroxicam blocks the Cox-1 enzyme, resulting into the disruption of production of prostaglandins. Piroxicam also inhibits the migration of leukocytes into sites of inflammation and prevents the formation of thromboxane A2, an aggregating agent, by the platelets.

Structure

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

HMDB0014694
     RDKit          3D
Piroxicam
 36 38  0  0  0  0  0  0  0  0999 V2000
    0.1008   -2.2944    1.1696 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7692   -0.9902    1.0580 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.4237    0.0010    0.1146 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9401    0.1299   -0.3629 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1432    1.0138   -1.2674 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0758   -0.5747    0.0319 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3935   -0.4077   -0.4712 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8040    0.4680   -1.4364 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1184    0.5801   -1.8813 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0642   -0.2358   -1.3203 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6598   -1.1239   -0.3446 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3894   -1.1968    0.0505 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.3434    0.8656   -0.3718 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9134    1.8102   -1.3368 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7262    0.9347    0.0271 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6077    1.7438   -0.7309 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9584    1.6950   -0.4865 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4958    0.8731    0.4867 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6050    0.0907    1.2198 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2890    0.1348    0.9898 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1424   -0.6950    2.0756 S   0  0  0  0  0  6  0  0  0  0  0  0
    2.7333   -1.9438    2.6113 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7421    0.2890    3.1091 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0042   -3.0133    1.2963 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2801   -2.5868    0.1913 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5237   -2.3999    2.0426 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0225   -1.3309    0.7850 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0950    1.1224   -1.8997 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3704    1.2971   -2.6501 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0849   -0.1872   -1.6279 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4329   -1.7544    0.0780 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1932    2.7609   -1.3042 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1966    2.3947   -1.4989 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6376    2.3097   -1.0612 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5373    0.7978    0.7127 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9789   -0.5775    2.0025 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  4  6  1  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
  3 13  2  0
 13 14  1  0
 13 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 21 23  2  0
 21  2  1  0
 12  7  1  0
 20 15  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  6 27  1  0
  8 28  1  0
  9 29  1  0
 10 30  1  0
 11 31  1  0
 14 32  1  0
 16 33  1  0
 17 34  1  0
 18 35  1  0
 19 36  1  0
M  END

  Mrv0541 04191212132D          

 23 25  0  0  0  0            999 V2000
   -3.4179    0.7661    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1323    1.1786    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8468    0.7661    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8468   -0.0589    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1323   -0.4714    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4179   -0.0589    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7034   -0.4714    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9889   -0.0589    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9889    0.7661    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7034    1.1786    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2744    1.1786    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2744    2.0036    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5600    2.4161    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1545    3.6536    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5600    3.2411    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.1545    2.0036    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8690    2.4161    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8690    3.2411    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2744   -0.4714    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7034    2.0036    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5599    0.7661    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2868   -1.0548    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1200   -1.0548    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  6  2  0  0  0  0
  1 10  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
  9 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 15 13  2  0  0  0  0
 13 16  1  0  0  0  0
 14 15  1  0  0  0  0
 14 18  2  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
  8 19  1  0  0  0  0
 10 20  1  0  0  0  0
 11 21  2  0  0  0  0
  7 22  2  0  0  0  0
  7 23  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0014694

> <DATABASE_NAME>
hmdb

> <SMILES>
CN1C(C(=O)NC2=NC=CC=C2)=C(O)C2=C(C=CC=C2)S1(=O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C15H13N3O4S/c1-18-13(15(20)17-12-8-4-5-9-16-12)14(19)10-6-2-3-7-11(10)23(18,21)22/h2-9,19H,1H3,(H,16,17,20)

> <INCHI_KEY>
QYSPLQLAKJAUJT-UHFFFAOYSA-N

> <FORMULA>
C15H13N3O4S

> <MOLECULAR_WEIGHT>
331.346

> <EXACT_MASS>
331.062676609

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_AVERAGE_POLARIZABILITY>
32.27132005937933

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
4-hydroxy-2-methyl-1,1-dioxo-N-(pyridin-2-yl)-2H-1λ⁶,2-benzothiazine-3-carboxamide

> <ALOGPS_LOGP>
2.20

> <JCHEM_LOGP>
0.5998838320211013

> <ALOGPS_LOGS>
-3.37

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
11.734046266182963

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.760423459469111

> <JCHEM_PKA_STRONGEST_BASIC>
3.792497901770875

> <JCHEM_POLAR_SURFACE_AREA>
99.6

> <JCHEM_REFRACTIVITY>
87.0435

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.43e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
piroxicam

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0014694
     RDKit          3D
Piroxicam
 36 38  0  0  0  0  0  0  0  0999 V2000
    0.1008   -2.2944    1.1696 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7692   -0.9902    1.0580 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.4237    0.0010    0.1146 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9401    0.1299   -0.3629 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1432    1.0138   -1.2674 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0758   -0.5747    0.0319 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3935   -0.4077   -0.4712 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8040    0.4680   -1.4364 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1184    0.5801   -1.8813 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0642   -0.2358   -1.3203 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6598   -1.1239   -0.3446 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3894   -1.1968    0.0505 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.3434    0.8656   -0.3718 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9134    1.8102   -1.3368 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7262    0.9347    0.0271 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6077    1.7438   -0.7309 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9584    1.6950   -0.4865 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4958    0.8731    0.4867 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6050    0.0907    1.2198 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2890    0.1348    0.9898 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1424   -0.6950    2.0756 S   0  0  0  0  0  6  0  0  0  0  0  0
    2.7333   -1.9438    2.6113 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7421    0.2890    3.1091 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0042   -3.0133    1.2963 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2801   -2.5868    0.1913 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5237   -2.3999    2.0426 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0225   -1.3309    0.7850 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0950    1.1224   -1.8997 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3704    1.2971   -2.6501 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0849   -0.1872   -1.6279 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4329   -1.7544    0.0780 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1932    2.7609   -1.3042 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1966    2.3947   -1.4989 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6376    2.3097   -1.0612 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5373    0.7978    0.7127 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9789   -0.5775    2.0025 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  4  6  1  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
  3 13  2  0
 13 14  1  0
 13 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 21 23  2  0
 21  2  1  0
 12  7  1  0
 20 15  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  6 27  1  0
  8 28  1  0
  9 29  1  0
 10 30  1  0
 11 31  1  0
 14 32  1  0
 16 33  1  0
 17 34  1  0
 18 35  1  0
 19 36  1  0
M  END

HEADER    PROTEIN                                 19-APR-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   19-APR-12         0                                  
HETATM    1  C   UNK     0      -6.380   1.430   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -7.714   2.200   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -9.047   1.430   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -9.047  -0.110   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -7.714  -0.880   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -6.380  -0.110   0.000  0.00  0.00           C+0
HETATM    7  S   UNK     0      -5.046  -0.880   0.000  0.00  0.00           S+0
HETATM    8  N   UNK     0      -3.713  -0.110   0.000  0.00  0.00           N+0
HETATM    9  C   UNK     0      -3.713   1.430   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -5.046   2.200   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -2.379   2.200   0.000  0.00  0.00           C+0
HETATM   12  N   UNK     0      -2.379   3.740   0.000  0.00  0.00           N+0
HETATM   13  C   UNK     0      -1.045   4.510   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       0.288   6.820   0.000  0.00  0.00           C+0
HETATM   15  N   UNK     0      -1.045   6.050   0.000  0.00  0.00           N+0
HETATM   16  C   UNK     0       0.288   3.740   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       1.622   4.510   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       1.622   6.050   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -2.379  -0.880   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0      -5.046   3.740   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0      -1.045   1.430   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0      -6.135  -1.969   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0      -3.957  -1.969   0.000  0.00  0.00           O+0
CONECT    1    2    6   10                                                  
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    1    5    7                                                  
CONECT    7    6    8   22   23                                             
CONECT    8    7    9   19                                                  
CONECT    9    8   10   11                                                  
CONECT   10    1    9   20                                                  
CONECT   11    9   12   21                                                  
CONECT   12   11   13                                                       
CONECT   13   12   15   16                                                  
CONECT   14   15   18                                                       
CONECT   15   13   14                                                       
CONECT   16   13   17                                                       
CONECT   17   16   18                                                       
CONECT   18   14   17                                                       
CONECT   19    8                                                            
CONECT   20   10                                                            
CONECT   21   11                                                            
CONECT   22    7                                                            
CONECT   23    7                                                            
MASTER        0    0    0    0    0    0    0    0   23    0   50    0
END

COMPND    HMDB0014694
HETATM    1  C1  UNL     1       0.101  -2.294   1.170  1.00  0.00           C  
HETATM    2  N1  UNL     1       0.769  -0.990   1.058  1.00  0.00           N  
HETATM    3  C2  UNL     1       0.424   0.001   0.115  1.00  0.00           C  
HETATM    4  C3  UNL     1      -0.940   0.130  -0.363  1.00  0.00           C  
HETATM    5  O1  UNL     1      -1.143   1.014  -1.267  1.00  0.00           O  
HETATM    6  N2  UNL     1      -2.076  -0.575   0.032  1.00  0.00           N  
HETATM    7  C4  UNL     1      -3.393  -0.408  -0.471  1.00  0.00           C  
HETATM    8  C5  UNL     1      -3.804   0.468  -1.436  1.00  0.00           C  
HETATM    9  C6  UNL     1      -5.118   0.580  -1.881  1.00  0.00           C  
HETATM   10  C7  UNL     1      -6.064  -0.236  -1.320  1.00  0.00           C  
HETATM   11  C8  UNL     1      -5.660  -1.124  -0.345  1.00  0.00           C  
HETATM   12  N3  UNL     1      -4.389  -1.197   0.051  1.00  0.00           N  
HETATM   13  C9  UNL     1       1.343   0.866  -0.372  1.00  0.00           C  
HETATM   14  O2  UNL     1       0.913   1.810  -1.337  1.00  0.00           O  
HETATM   15  C10 UNL     1       2.726   0.935   0.027  1.00  0.00           C  
HETATM   16  C11 UNL     1       3.608   1.744  -0.731  1.00  0.00           C  
HETATM   17  C12 UNL     1       4.958   1.695  -0.486  1.00  0.00           C  
HETATM   18  C13 UNL     1       5.496   0.873   0.487  1.00  0.00           C  
HETATM   19  C14 UNL     1       4.605   0.091   1.220  1.00  0.00           C  
HETATM   20  C15 UNL     1       3.289   0.135   0.990  1.00  0.00           C  
HETATM   21  S1  UNL     1       2.142  -0.695   2.076  1.00  0.00           S  
HETATM   22  O3  UNL     1       2.733  -1.944   2.611  1.00  0.00           O  
HETATM   23  O4  UNL     1       1.742   0.289   3.109  1.00  0.00           O  
HETATM   24  H1  UNL     1       1.004  -3.013   1.296  1.00  0.00           H  
HETATM   25  H2  UNL     1      -0.280  -2.587   0.191  1.00  0.00           H  
HETATM   26  H3  UNL     1      -0.524  -2.400   2.043  1.00  0.00           H  
HETATM   27  H4  UNL     1      -2.022  -1.331   0.785  1.00  0.00           H  
HETATM   28  H5  UNL     1      -3.095   1.122  -1.900  1.00  0.00           H  
HETATM   29  H6  UNL     1      -5.370   1.297  -2.650  1.00  0.00           H  
HETATM   30  H7  UNL     1      -7.085  -0.187  -1.628  1.00  0.00           H  
HETATM   31  H8  UNL     1      -6.433  -1.754   0.078  1.00  0.00           H  
HETATM   32  H9  UNL     1       1.193   2.761  -1.304  1.00  0.00           H  
HETATM   33  H10 UNL     1       3.197   2.395  -1.499  1.00  0.00           H  
HETATM   34  H11 UNL     1       5.638   2.310  -1.061  1.00  0.00           H  
HETATM   35  H12 UNL     1       6.537   0.798   0.713  1.00  0.00           H  
HETATM   36  H13 UNL     1       4.979  -0.577   2.003  1.00  0.00           H  
CONECT    1    2   24   25   26
CONECT    2    3   21
CONECT    3    4   13   13
CONECT    4    5    5    6
CONECT    6    7   27
CONECT    7    8    8   12
CONECT    8    9   28
CONECT    9   10   10   29
CONECT   10   11   30
CONECT   11   12   12   31
CONECT   13   14   15
CONECT   14   32
CONECT   15   16   16   20
CONECT   16   17   33
CONECT   17   18   18   34
CONECT   18   19   35
CONECT   19   20   20   36
CONECT   20   21
CONECT   21   22   22   23   23
END

HMDB0014694
     RDKit          3D
Piroxicam
 36 38  0  0  0  0  0  0  0  0999 V2000
    0.1008   -2.2944    1.1696 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7692   -0.9902    1.0580 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.4237    0.0010    0.1146 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9401    0.1299   -0.3629 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1432    1.0138   -1.2674 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0758   -0.5747    0.0319 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3935   -0.4077   -0.4712 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8040    0.4680   -1.4364 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1184    0.5801   -1.8813 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0642   -0.2358   -1.3203 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6598   -1.1239   -0.3446 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3894   -1.1968    0.0505 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.3434    0.8656   -0.3718 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9134    1.8102   -1.3368 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7262    0.9347    0.0271 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6077    1.7438   -0.7309 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9584    1.6950   -0.4865 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4958    0.8731    0.4867 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6050    0.0907    1.2198 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2890    0.1348    0.9898 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1424   -0.6950    2.0756 S   0  0  0  0  0  6  0  0  0  0  0  0
    2.7333   -1.9438    2.6113 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7421    0.2890    3.1091 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0042   -3.0133    1.2963 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2801   -2.5868    0.1913 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5237   -2.3999    2.0426 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0225   -1.3309    0.7850 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0950    1.1224   -1.8997 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3704    1.2971   -2.6501 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0849   -0.1872   -1.6279 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4329   -1.7544    0.0780 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1932    2.7609   -1.3042 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1966    2.3947   -1.4989 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6376    2.3097   -1.0612 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5373    0.7978    0.7127 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9789   -0.5775    2.0025 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  4  6  1  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
  3 13  2  0
 13 14  1  0
 13 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 21 23  2  0
 21  2  1  0
 12  7  1  0
 20 15  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  6 27  1  0
  8 28  1  0
  9 29  1  0
 10 30  1  0
 11 31  1  0
 14 32  1  0
 16 33  1  0
 17 34  1  0
 18 35  1  0
 19 36  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
4-Hydroxy-2-methyl-N-(2-pyridyl)-2H-1,2-benzothiazin-3-caboxyamid-1,1-dioxid	ChEBI
Feldene	ChEBI
Piroxicamum	ChEBI
Pyroxycam	ChEBI
AK1015	HMDB

Chemical Formula

C₁₅H₁₃N₃O₄S

Average Molecular Weight

331.346

Monoisotopic Molecular Weight

331.062676609

IUPAC Name

4-hydroxy-2-methyl-1,1-dioxo-N-(pyridin-2-yl)-2H-1λ⁶,2-benzothiazine-3-carboxamide

Traditional Name

piroxicam

CAS Registry Number

36322-90-4

SMILES

CN1C(C(=O)NC2=NC=CC=C2)=C(O)C2=C(C=CC=C2)S1(=O)=O

InChI Identifier

InChI=1S/C15H13N3O4S/c1-18-13(15(20)17-12-8-4-5-9-16-12)14(19)10-6-2-3-7-11(10)23(18,21)22/h2-9,19H,1H3,(H,16,17,20)

InChI Key

QYSPLQLAKJAUJT-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as benzothiazines. These are organic compounds containing a benzene fused to a thiazine ring (a six-membered ring with four carbon atoms, one nitrogen atom and one sulfur atom).

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Benzothiazines

Sub Class

Not Available

Direct Parent

Benzothiazines

Alternative Parents

Substituents

Alpha-amino acid or derivatives
Benzothiazine
Ortho-thiazine
Pyridine
Organosulfonic acid amide
Benzenoid
Imidolactam
Organic sulfonic acid or derivatives
Organosulfonic acid or derivatives
Heteroaromatic compound
Secondary carboxylic acid amide
Carboxylic acid derivative
Carboximidic acid
Azacycle
Hydrocarbon derivative
Organic oxygen compound
Organic nitrogen compound
Organic oxide
Organooxygen compound
Organonitrogen compound
Carbonyl group
Organopnictogen compound
Organic zwitterion
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

monocarboxylic acid amide (CHEBI:8249 )
pyridines (CHEBI:8249 )
benzothiazine (CHEBI:8249 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 21059682)

Excreta

Biofluid or Excreta

Urine (PMID: 21059682)

Cellular substructure

Source

Exogenous

Exogenous (HMDB: HMDB0014694)

Process

Naturally occurring process

Biological process

Biochemical pathway

Drug action pathway

Piroxicam Action Pathway (PathBank: SMP0000077)

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	198 - 200 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	0.14 g/L	Not Available
LogP	3	Not Available

Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct Type	Data Source	CCS Value (Å²)	Reference
[M+H]+	CBM	170.9	30932474
[M+H]+	Not Available	170.677	http://allccs.zhulab.cn/database/detail?ID=AllCCS00000980

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.14 g/L	ALOGPS
logP	2.2	ALOGPS
logP	0.6	ChemAxon
logS	-3.4	ALOGPS
pKa (Strongest Acidic)	4.76	ChemAxon
pKa (Strongest Basic)	3.79	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	99.6 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	87.04 m³·mol⁻¹	ChemAxon
Polarizability	32.27 Å³	ChemAxon
Number of Rings	3	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]+	175.947	31661259
DarkChem	[M-H]-	170.992	31661259
DeepCCS	[M+H]+	168.644	30932474
DeepCCS	[M-H]-	166.286	30932474
DeepCCS	[M-2H]-	199.417	30932474
DeepCCS	[M+Na]+	174.737	30932474
AllCCS	[M+H]+	176.3	32859911
AllCCS	[M+H-H2O]+	172.9	32859911
AllCCS	[M+NH4]+	179.3	32859911
AllCCS	[M+Na]+	180.2	32859911
AllCCS	[M-H]-	172.7	32859911
AllCCS	[M+Na-2H]-	172.3	32859911
AllCCS	[M+HCOO]-	172.0	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Piroxicam	CN1C(C(=O)NC2=NC=CC=C2)=C(O)C2=C(C=CC=C2)S1(=O)=O	4575.1	Standard polar	33892256
Piroxicam	CN1C(C(=O)NC2=NC=CC=C2)=C(O)C2=C(C=CC=C2)S1(=O)=O	2558.7	Standard non polar	33892256
Piroxicam	CN1C(C(=O)NC2=NC=CC=C2)=C(O)C2=C(C=CC=C2)S1(=O)=O	2835.7	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Piroxicam,1TMS,isomer #1	CN1C(C(=O)NC2=CC=CC=N2)=C(O[Si](C)(C)C)C2=CC=CC=C2S1(=O)=O	2835.3	Semi standard non polar	33892256
Piroxicam,1TMS,isomer #2	CN1C(C(=O)N(C2=CC=CC=N2)[Si](C)(C)C)=C(O)C2=CC=CC=C2S1(=O)=O	2772.1	Semi standard non polar	33892256
Piroxicam,2TMS,isomer #1	CN1C(C(=O)N(C2=CC=CC=N2)[Si](C)(C)C)=C(O[Si](C)(C)C)C2=CC=CC=C2S1(=O)=O	2758.1	Semi standard non polar	33892256
Piroxicam,2TMS,isomer #1	CN1C(C(=O)N(C2=CC=CC=N2)[Si](C)(C)C)=C(O[Si](C)(C)C)C2=CC=CC=C2S1(=O)=O	2912.3	Standard non polar	33892256
Piroxicam,2TMS,isomer #1	CN1C(C(=O)N(C2=CC=CC=N2)[Si](C)(C)C)=C(O[Si](C)(C)C)C2=CC=CC=C2S1(=O)=O	3833.8	Standard polar	33892256
Piroxicam,1TBDMS,isomer #1	CN1C(C(=O)NC2=CC=CC=N2)=C(O[Si](C)(C)C(C)(C)C)C2=CC=CC=C2S1(=O)=O	3054.1	Semi standard non polar	33892256
Piroxicam,1TBDMS,isomer #2	CN1C(C(=O)N(C2=CC=CC=N2)[Si](C)(C)C(C)(C)C)=C(O)C2=CC=CC=C2S1(=O)=O	2995.4	Semi standard non polar	33892256
Piroxicam,2TBDMS,isomer #1	CN1C(C(=O)N(C2=CC=CC=N2)[Si](C)(C)C(C)(C)C)=C(O[Si](C)(C)C(C)(C)C)C2=CC=CC=C2S1(=O)=O	3149.5	Semi standard non polar	33892256
Piroxicam,2TBDMS,isomer #1	CN1C(C(=O)N(C2=CC=CC=N2)[Si](C)(C)C(C)(C)C)=C(O[Si](C)(C)C(C)(C)C)C2=CC=CC=C2S1(=O)=O	3375.6	Standard non polar	33892256
Piroxicam,2TBDMS,isomer #1	CN1C(C(=O)N(C2=CC=CC=N2)[Si](C)(C)C(C)(C)C)=C(O[Si](C)(C)C(C)(C)C)C2=CC=CC=C2S1(=O)=O	3894.1	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Piroxicam GC-MS (Non-derivatized) - 70eV, Positive	splash10-014i-3911000000-4ebab92e0a9daf942bf0	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Piroxicam GC-MS (1 TMS) - 70eV, Positive	splash10-014i-2911000000-0f09e215129357f2b76d	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Piroxicam GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Piroxicam 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 - Piroxicam LC-ESI-qTof , Positive-QTOF	splash10-1000-1698000000-9bfc929b8cee2ec1d841	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Piroxicam LC-ESI-qTof , Positive-QTOF	splash10-00dj-6911100000-64e355e5e08c884173b8	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Piroxicam LC-ESI-QQ , negative-QTOF	splash10-001i-0019000000-0d247806d6203409cc16	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Piroxicam LC-ESI-QQ , negative-QTOF	splash10-014j-0591000000-7d11d429795ac27fa093	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Piroxicam LC-ESI-QQ , negative-QTOF	splash10-000t-0910000000-42d97ebe5da8190aa202	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Piroxicam LC-ESI-QQ , negative-QTOF	splash10-001m-2900000000-32c34cd63ced296fee89	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Piroxicam LC-ESI-QQ , negative-QTOF	splash10-00kf-5900000000-1d4473d813b920140b81	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Piroxicam LC-ESI-QQ , positive-QTOF	splash10-00lr-0009000000-9e65aa6e4b407ea80734	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Piroxicam LC-ESI-QQ , positive-QTOF	splash10-000f-3984000000-e855ded4bfe08c600884	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Piroxicam LC-ESI-QQ , positive-QTOF	splash10-007c-3900000000-fb37337024398fe8044d	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Piroxicam LC-ESI-QQ , positive-QTOF	splash10-006t-9600000000-db1bff24de3a9b89b68d	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Piroxicam LC-ESI-QQ , positive-QTOF	splash10-00r2-9200000000-22caea8b3219419be51f	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Piroxicam LC-ESI-IT , positive-QTOF	splash10-01vk-6900000000-a75ce07d3bc58c9e773b	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Piroxicam , positive-QTOF	splash10-001i-5829000000-bfa87ed6f54b64fe3942	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Piroxicam , positive-QTOF	splash10-1000-1698000000-9bfc929b8cee2ec1d841	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Piroxicam , positive-QTOF	splash10-00dj-6911100000-64e355e5e08c884173b8	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Piroxicam 35V, Positive-QTOF	splash10-006t-6901000000-41ed9a5326f5d54c5f9f	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Piroxicam 35V, Negative-QTOF	splash10-00l2-0930000000-471bbc619da22cd3edf4	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Piroxicam 10V, Positive-QTOF	splash10-001i-1109000000-0a5f568ccd8ec0dd21ab	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Piroxicam 20V, Positive-QTOF	splash10-00ed-5914000000-f68896ad0dca3bacbe4c	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Piroxicam 40V, Positive-QTOF	splash10-00di-9700000000-1b72c24a77ff99dbce05	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Piroxicam 10V, Negative-QTOF	splash10-001i-2019000000-7caa2d44b7aec18e603d	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Piroxicam 20V, Negative-QTOF	splash10-000x-6339000000-58dcc57574d9e999f7b2	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Piroxicam 40V, Negative-QTOF	splash10-0006-9700000000-4282d1d0a308fb07b8c9	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Piroxicam 10V, Positive-QTOF	splash10-001i-0109000000-a10d4fec58f8f1308694	2021-09-22	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Extracellular
Membrane

Biospecimen Locations

Blood
Urine

Tissue Locations

Not Available

Pathways

Name	SMPDB/PathBank	KEGG
Piroxicam Action Pathway		Not Available

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 DB00554	21059682	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB00554	21059682	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB00554

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

10442653

KEGG Compound ID

C01608

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Piroxicam

METLIN ID

Not Available

PubChem Compound

54676228

PDB ID

Not Available

ChEBI ID

8249

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

Not Available

Showing metabocard for Piroxicam (HMDB0014694)

MOL for HMDB0014694 (Piroxicam)

3D MOL for HMDB0014694 (Piroxicam)

3D SDF for HMDB0014694 (Piroxicam)

3D-SDF for HMDB0014694 (Piroxicam)

PDB for HMDB0014694 (Piroxicam)

3D PDB for HMDB0014694 (Piroxicam)

SMILES for HMDB0014694 (Piroxicam)

INCHI for HMDB0014694 (Piroxicam)

Structure for HMDB0014694 (Piroxicam)

3D Structure for HMDB0014694 (Piroxicam)

Experimental Collision Cross Sections

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra