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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (5) Show 5 proteins XML

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-06 15:16:51 UTC

Update Date

2022-03-07 02:51:49 UTC

HMDB ID

HMDB0015007

Secondary Accession Numbers

HMDB15007

Metabolite Identification

Common Name

Dorzolamide

Description

Dorzolamide is only found in individuals that have used or taken this drug. It is a carbonic anhydrase (CA) inhibitor. It is used in ophthalmic solutions (Trusopt) to lower intraocular pressure (IOP) in open-angle glaucoma and ocular hypertension.Dorzolamide is a sulfonamide and a highly specific carbonic anhydrase II (CA-II) inhibitor, which is the main CA isoenzyme involved in aqueous humor secretion. Inhibition of CA-II in the ciliary processes of the eye decreases aqueous humor secretion, presumably by slowing the formation of bicarbonate ions with subsequent reduction in sodium and fluid transport. Dorzolamide also accumulates in red blood cells as a result of CA-II binding, as CA-II is found predominantly in erythrocytes. However, sufficient CA-II activity remains so that adverse effects due to systemic CA inhibition are not observed.

Structure

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

HMDB0015007
     RDKit          3D
Dorzolamide
 35 36  0  0  0  0  0  0  0  0999 V2000
   -2.1967    3.3346    0.6129 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5534    2.1484   -0.1296 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5193    1.0298    0.7033 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9586   -0.1792    0.3303 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.5497   -0.7919   -0.9239 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4223   -2.2759   -0.9849 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.7176   -3.0115   -0.7841 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1262   -2.8741    0.0746 S   0  0  0  0  0  6  0  0  0  0  0  0
   -0.6746   -3.2544    1.4377 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5698   -4.0577   -0.4849 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0038   -1.5188    0.2457 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7029   -1.3297    0.3247 S   0  0  0  0  0  0  0  0  0  0  0  0
    2.7731    0.3534    0.5241 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2153    1.3650    0.6909 S   0  0  0  0  0  6  0  0  0  0  0  0
    5.1446    1.1294   -0.7704 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.9565    0.8828    1.8887 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7908    2.7823    0.8178 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4578    0.7323    0.5242 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5267   -0.2333    0.3787 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6625    4.0125   -0.1341 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3979    3.9235    1.1323 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8936    2.9798    1.3858 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5675    2.4828   -0.4499 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1680    2.0174   -1.0625 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9856    1.0940    1.6250 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3257   -0.9348    1.1386 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6187   -0.5311   -0.9258 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1071   -0.2754   -1.8117 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0868   -2.5265   -2.0349 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0096   -3.1167    0.2648 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5642   -4.0377   -1.2273 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4707   -2.5296   -1.4321 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1603    1.2889   -0.5907 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0369    0.1053   -1.0156 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2377    1.8159    0.6621 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  1  0
  5  6  1  0
  6  7  1  0
  6  8  1  0
  8  9  2  0
  8 10  2  0
  8 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 14 16  2  0
 14 17  2  0
 13 18  2  0
 18 19  1  0
 19  4  1  0
 19 11  2  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
  2 23  1  0
  2 24  1  0
  3 25  1  0
  4 26  1  1
  5 27  1  0
  5 28  1  0
  6 29  1  6
  7 30  1  0
  7 31  1  0
  7 32  1  0
 15 33  1  0
 15 34  1  0
 18 35  1  0
M  END


  Mrv0541 04191212152D          

 19 20  0  0  1  0            999 V2000
   16.8537   -6.8636    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.8537   -6.0579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.1375   -7.2933    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   17.6415   -7.1322    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   16.1375   -5.6460    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   17.6415   -5.7893    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.4213   -6.8636    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   15.7257   -7.9916    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.5135   -7.9916    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.1071   -6.4697    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.4213   -6.0579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.1375   -4.8045    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.7230   -7.2933    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.9307   -6.4697    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   19.3425   -7.1859    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   18.9307   -5.6460    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.6469   -6.0758    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.4182   -4.3995    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7072   -4.8202    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0  0  0  0
  3  1  1  0  0  0  0
  4  1  1  0  0  0  0
  5  2  1  0  0  0  0
  6  2  1  0  0  0  0
  7  3  1  0  0  0  0
  8  3  2  0  0  0  0
  9  3  2  0  0  0  0
 10  4  1  0  0  0  0
 11  5  1  0  0  0  0
  5 12  1  6  0  0  0
 10  6  2  0  0  0  0
  7 13  1  1  0  0  0
 11  7  1  0  0  0  0
 14 10  1  0  0  0  0
 15 14  1  0  0  0  0
 16 14  2  0  0  0  0
 17 14  2  0  0  0  0
 12 18  1  0  0  0  0
 18 19  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0015007

> <DATABASE_NAME>
hmdb

> <SMILES>
CCN[C@H]1C[C@H](C)S(=O)(=O)C2=C1C=C(S2)S(N)(=O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C10H16N2O4S3/c1-3-12-8-4-6(2)18(13,14)10-7(8)5-9(17-10)19(11,15)16/h5-6,8,12H,3-4H2,1-2H3,(H2,11,15,16)/t6-,8-/m0/s1

> <INCHI_KEY>
IAVUPMFITXYVAF-XPUUQOCRSA-N

> <FORMULA>
C10H16N2O4S3

> <MOLECULAR_WEIGHT>
324.44

> <EXACT_MASS>
324.02721908

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_AVERAGE_POLARIZABILITY>
31.55452028867875

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2S,4S)-4-(ethylamino)-2-methyl-1,1-dioxo-2H,3H,4H-1λ⁶-thieno[2,3-b]thiopyran-6-sulfonamide

> <ALOGPS_LOGP>
-0.50

> <JCHEM_LOGP>
-0.15111351272826437

> <ALOGPS_LOGS>
-2.67

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
19.427629743617562

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.184278107455052

> <JCHEM_PKA_STRONGEST_BASIC>
7.1401997858992345

> <JCHEM_POLAR_SURFACE_AREA>
106.32999999999998

> <JCHEM_REFRACTIVITY>
72.46110000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.99e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
dorzolamide

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0015007
     RDKit          3D
Dorzolamide
 35 36  0  0  0  0  0  0  0  0999 V2000
   -2.1967    3.3346    0.6129 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5534    2.1484   -0.1296 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5193    1.0298    0.7033 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9586   -0.1792    0.3303 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.5497   -0.7919   -0.9239 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4223   -2.2759   -0.9849 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.7176   -3.0115   -0.7841 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1262   -2.8741    0.0746 S   0  0  0  0  0  6  0  0  0  0  0  0
   -0.6746   -3.2544    1.4377 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5698   -4.0577   -0.4849 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0038   -1.5188    0.2457 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7029   -1.3297    0.3247 S   0  0  0  0  0  0  0  0  0  0  0  0
    2.7731    0.3534    0.5241 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2153    1.3650    0.6909 S   0  0  0  0  0  6  0  0  0  0  0  0
    5.1446    1.1294   -0.7704 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.9565    0.8828    1.8887 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7908    2.7823    0.8178 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4578    0.7323    0.5242 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5267   -0.2333    0.3787 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6625    4.0125   -0.1341 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3979    3.9235    1.1323 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8936    2.9798    1.3858 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5675    2.4828   -0.4499 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1680    2.0174   -1.0625 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9856    1.0940    1.6250 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3257   -0.9348    1.1386 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6187   -0.5311   -0.9258 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1071   -0.2754   -1.8117 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0868   -2.5265   -2.0349 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0096   -3.1167    0.2648 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5642   -4.0377   -1.2273 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4707   -2.5296   -1.4321 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1603    1.2889   -0.5907 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0369    0.1053   -1.0156 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2377    1.8159    0.6621 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  1  0
  5  6  1  0
  6  7  1  0
  6  8  1  0
  8  9  2  0
  8 10  2  0
  8 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 14 16  2  0
 14 17  2  0
 13 18  2  0
 18 19  1  0
 19  4  1  0
 19 11  2  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
  2 23  1  0
  2 24  1  0
  3 25  1  0
  4 26  1  1
  5 27  1  0
  5 28  1  0
  6 29  1  6
  7 30  1  0
  7 31  1  0
  7 32  1  0
 15 33  1  0
 15 34  1  0
 18 35  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      31.460 -12.812   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      31.460 -11.308   0.000  0.00  0.00           C+0
HETATM    3  S   UNK     0      30.123 -13.614   0.000  0.00  0.00           S+0
HETATM    4  S   UNK     0      32.931 -13.313   0.000  0.00  0.00           S+0
HETATM    5  C   UNK     0      30.123 -10.539   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      32.931 -10.807   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      28.786 -12.812   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0      29.355 -14.918   0.000  0.00  0.00           O+0
HETATM    9  O   UNK     0      30.825 -14.918   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0      33.800 -12.077   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      28.786 -11.308   0.000  0.00  0.00           C+0
HETATM   12  N   UNK     0      30.123  -8.968   0.000  0.00  0.00           N+0
HETATM   13  C   UNK     0      27.483 -13.614   0.000  0.00  0.00           C+0
HETATM   14  S   UNK     0      35.337 -12.077   0.000  0.00  0.00           S+0
HETATM   15  N   UNK     0      36.106 -13.414   0.000  0.00  0.00           N+0
HETATM   16  O   UNK     0      35.337 -10.539   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0      36.674 -11.341   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0      28.781  -8.212   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      27.453  -8.998   0.000  0.00  0.00           C+0
CONECT    1    2    3    4                                                  
CONECT    2    1    5    6                                                  
CONECT    3    1    7    8    9                                             
CONECT    4    1   10                                                       
CONECT    5    2   11   12                                                  
CONECT    6    2   10                                                       
CONECT    7    3   13   11                                                  
CONECT    8    3                                                            
CONECT    9    3                                                            
CONECT   10    4    6   14                                                  
CONECT   11    5    7                                                       
CONECT   12    5   18                                                       
CONECT   13    7                                                            
CONECT   14   10   15   16   17                                             
CONECT   15   14                                                            
CONECT   16   14                                                            
CONECT   17   14                                                            
CONECT   18   12   19                                                       
CONECT   19   18                                                            
MASTER        0    0    0    0    0    0    0    0   19    0   40    0
END

COMPND    HMDB0015007
HETATM    1  C1  UNL     1      -2.197   3.335   0.613  1.00  0.00           C  
HETATM    2  C2  UNL     1      -1.553   2.148  -0.130  1.00  0.00           C  
HETATM    3  N1  UNL     1      -1.519   1.030   0.703  1.00  0.00           N  
HETATM    4  C3  UNL     1      -0.959  -0.179   0.330  1.00  0.00           C  
HETATM    5  C4  UNL     1      -1.550  -0.792  -0.924  1.00  0.00           C  
HETATM    6  C5  UNL     1      -1.422  -2.276  -0.985  1.00  0.00           C  
HETATM    7  C6  UNL     1      -2.718  -3.012  -0.784  1.00  0.00           C  
HETATM    8  S1  UNL     1      -0.126  -2.874   0.075  1.00  0.00           S  
HETATM    9  O1  UNL     1      -0.675  -3.254   1.438  1.00  0.00           O  
HETATM   10  O2  UNL     1       0.570  -4.058  -0.485  1.00  0.00           O  
HETATM   11  C7  UNL     1       1.004  -1.519   0.246  1.00  0.00           C  
HETATM   12  S2  UNL     1       2.703  -1.330   0.325  1.00  0.00           S  
HETATM   13  C8  UNL     1       2.773   0.353   0.524  1.00  0.00           C  
HETATM   14  S3  UNL     1       4.215   1.365   0.691  1.00  0.00           S  
HETATM   15  N2  UNL     1       5.145   1.129  -0.770  1.00  0.00           N  
HETATM   16  O3  UNL     1       4.956   0.883   1.889  1.00  0.00           O  
HETATM   17  O4  UNL     1       3.791   2.782   0.818  1.00  0.00           O  
HETATM   18  C9  UNL     1       1.458   0.732   0.524  1.00  0.00           C  
HETATM   19  C10 UNL     1       0.527  -0.233   0.379  1.00  0.00           C  
HETATM   20  H1  UNL     1      -2.662   4.013  -0.134  1.00  0.00           H  
HETATM   21  H2  UNL     1      -1.398   3.923   1.132  1.00  0.00           H  
HETATM   22  H3  UNL     1      -2.894   2.980   1.386  1.00  0.00           H  
HETATM   23  H4  UNL     1      -0.568   2.483  -0.450  1.00  0.00           H  
HETATM   24  H5  UNL     1      -2.168   2.017  -1.063  1.00  0.00           H  
HETATM   25  H6  UNL     1      -1.986   1.094   1.625  1.00  0.00           H  
HETATM   26  H7  UNL     1      -1.326  -0.935   1.139  1.00  0.00           H  
HETATM   27  H8  UNL     1      -2.619  -0.531  -0.926  1.00  0.00           H  
HETATM   28  H9  UNL     1      -1.107  -0.275  -1.812  1.00  0.00           H  
HETATM   29  H10 UNL     1      -1.087  -2.527  -2.035  1.00  0.00           H  
HETATM   30  H11 UNL     1      -3.010  -3.117   0.265  1.00  0.00           H  
HETATM   31  H12 UNL     1      -2.564  -4.038  -1.227  1.00  0.00           H  
HETATM   32  H13 UNL     1      -3.471  -2.530  -1.432  1.00  0.00           H  
HETATM   33  H14 UNL     1       6.160   1.289  -0.591  1.00  0.00           H  
HETATM   34  H15 UNL     1       5.037   0.105  -1.016  1.00  0.00           H  
HETATM   35  H16 UNL     1       1.238   1.816   0.662  1.00  0.00           H  
CONECT    1    2   20   21   22
CONECT    2    3   23   24
CONECT    3    4   25
CONECT    4    5   19   26
CONECT    5    6   27   28
CONECT    6    7    8   29
CONECT    7   30   31   32
CONECT    8    9    9   10   10
CONECT    8   11
CONECT   11   12   19   19
CONECT   12   13
CONECT   13   14   18   18
CONECT   14   15   16   16   17
CONECT   14   17
CONECT   15   33   34
CONECT   18   19   35
END

HMDB0015007
     RDKit          3D
Dorzolamide
 35 36  0  0  0  0  0  0  0  0999 V2000
   -2.1967    3.3346    0.6129 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5534    2.1484   -0.1296 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5193    1.0298    0.7033 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9586   -0.1792    0.3303 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.5497   -0.7919   -0.9239 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4223   -2.2759   -0.9849 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.7176   -3.0115   -0.7841 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1262   -2.8741    0.0746 S   0  0  0  0  0  6  0  0  0  0  0  0
   -0.6746   -3.2544    1.4377 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5698   -4.0577   -0.4849 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0038   -1.5188    0.2457 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7029   -1.3297    0.3247 S   0  0  0  0  0  0  0  0  0  0  0  0
    2.7731    0.3534    0.5241 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2153    1.3650    0.6909 S   0  0  0  0  0  6  0  0  0  0  0  0
    5.1446    1.1294   -0.7704 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.9565    0.8828    1.8887 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7908    2.7823    0.8178 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4578    0.7323    0.5242 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5267   -0.2333    0.3787 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6625    4.0125   -0.1341 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3979    3.9235    1.1323 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8936    2.9798    1.3858 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5675    2.4828   -0.4499 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1680    2.0174   -1.0625 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9856    1.0940    1.6250 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3257   -0.9348    1.1386 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6187   -0.5311   -0.9258 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1071   -0.2754   -1.8117 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0868   -2.5265   -2.0349 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0096   -3.1167    0.2648 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5642   -4.0377   -1.2273 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4707   -2.5296   -1.4321 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1603    1.2889   -0.5907 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0369    0.1053   -1.0156 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2377    1.8159    0.6621 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  1  0
  5  6  1  0
  6  7  1  0
  6  8  1  0
  8  9  2  0
  8 10  2  0
  8 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 14 16  2  0
 14 17  2  0
 13 18  2  0
 18 19  1  0
 19  4  1  0
 19 11  2  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
  2 23  1  0
  2 24  1  0
  3 25  1  0
  4 26  1  1
  5 27  1  0
  5 28  1  0
  6 29  1  6
  7 30  1  0
  7 31  1  0
  7 32  1  0
 15 33  1  0
 15 34  1  0
 18 35  1  0
M  END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
(4S,6S)-4-Ethylamino-6-methyl-7,7-dioxo-4,5,6,7-tetrahydro-7lambda6-thieno[2,3-b]thiopyran-2-sulfonic acid amide	ChEBI
(4S,trans)-4-(Ethylamino)-6-methyl-5,6-dihydro-4H-thieno[2,3-b]thiopyran-2-sulfonamide 7,7-dioxide	ChEBI
(4S-trans)-4-(ETHYLAMINO)-5,6-dihydro-6-methyl-4H-thieno(2,3-b)thiopyran-2-sulfonamide-7,7-dioxide	ChEBI
4-Ethylamino-6-methyl-7,7-dioxo-4,5,6,7-tetrahydro-7lambda6-thieno[2,3-b]thiopyran-2-sulfonic acid amide	ChEBI
4-Ethylamino-6-methyl-7,7-dioxo-4,5,6,7-tetrahydro-7lambda6-thieno[2,3-b]thiopyran-2-sulfonic acid amide	ChEBI
4S,6S-Dorzolamide	ChEBI
Trusopt	Kegg
(4S,6S)-4-Ethylamino-6-methyl-7,7-dioxo-4,5,6,7-tetrahydro-7lambda6-thieno[2,3-b]thiopyran-2-sulfonate amide	Generator
(4S,6S)-4-Ethylamino-6-methyl-7,7-dioxo-4,5,6,7-tetrahydro-7lambda6-thieno[2,3-b]thiopyran-2-sulphonate amide	Generator
(4S,6S)-4-Ethylamino-6-methyl-7,7-dioxo-4,5,6,7-tetrahydro-7lambda6-thieno[2,3-b]thiopyran-2-sulphonic acid amide	Generator
(4S,trans)-4-(Ethylamino)-6-methyl-5,6-dihydro-4H-thieno[2,3-b]thiopyran-2-sulphonamide 7,7-dioxide	Generator
(4S-trans)-4-(ETHYLAMINO)-5,6-dihydro-6-methyl-4H-thieno(2,3-b)thiopyran-2-sulphonamide-7,7-dioxide	Generator
4-Ethylamino-6-methyl-7,7-dioxo-4,5,6,7-tetrahydro-7lambda6-thieno[2,3-b]thiopyran-2-sulfonate amide	Generator
4-Ethylamino-6-methyl-7,7-dioxo-4,5,6,7-tetrahydro-7lambda6-thieno[2,3-b]thiopyran-2-sulphonate amide	Generator
4-Ethylamino-6-methyl-7,7-dioxo-4,5,6,7-tetrahydro-7lambda6-thieno[2,3-b]thiopyran-2-sulphonic acid amide	Generator
4-Ethylamino-6-methyl-7,7-dioxo-4,5,6,7-tetrahydro-7lambda6-thieno[2,3-b]thiopyran-2-sulfonate amide	Generator
4-Ethylamino-6-methyl-7,7-dioxo-4,5,6,7-tetrahydro-7lambda6-thieno[2,3-b]thiopyran-2-sulphonate amide	Generator
4-Ethylamino-6-methyl-7,7-dioxo-4,5,6,7-tetrahydro-7lambda6-thieno[2,3-b]thiopyran-2-sulphonic acid amide	Generator
5,6-Dihydro-4-ethylamino-6-methyl-4H-thieno(2,3-b)thiopyran-2-sulfonamide-7,7-dioxide	HMDB
Dorzolamide hydrochloride	HMDB
Dorzolamide chibret	HMDB
Dorzolamide, (trans)-isomer	HMDB
4-Ethylamino-5,6-dihydro-6-methyl-7,7-dioxide-4H-thieno(2,3-b)thiopyran-2-sulfonamide	HMDB

Chemical Formula

C₁₀H₁₆N₂O₄S₃

Average Molecular Weight

324.44

Monoisotopic Molecular Weight

324.02721908

IUPAC Name

(2S,4S)-4-(ethylamino)-2-methyl-1,1-dioxo-2H,3H,4H-1λ⁶-thieno[2,3-b]thiopyran-6-sulfonamide

Traditional Name

dorzolamide

CAS Registry Number

120279-96-1

SMILES

CCN[C@H]1C[C@H](C)S(=O)(=O)C2=C1C=C(S2)S(N)(=O)=O

InChI Identifier

InChI=1S/C10H16N2O4S3/c1-3-12-8-4-6(2)18(13,14)10-7(8)5-9(17-10)19(11,15)16/h5-6,8,12H,3-4H2,1-2H3,(H2,11,15,16)/t6-,8-/m0/s1

InChI Key

IAVUPMFITXYVAF-XPUUQOCRSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 2,3,5-trisubstituted thiophenes. These are organic compounds containing a thiophene that is trisubstituted at the C-2, C3- and C5-positions.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Thiophenes

Sub Class

2,3,5-trisubstituted thiophenes

Direct Parent

2,3,5-trisubstituted thiophenes

Alternative Parents

Substituents

2,3,5-trisubstituted thiophene
Aralkylamine
Organosulfonic acid amide
Thiopyran
Sulfone
Organic sulfonic acid or derivatives
Organosulfonic acid or derivatives
Sulfonyl
Aminosulfonyl compound
Heteroaromatic compound
Secondary aliphatic amine
Secondary amine
Organonitrogen compound
Organic nitrogen compound
Amine
Organic oxygen compound
Organosulfur compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

sulfonamide (CHEBI:4702 )
thiophenes (CHEBI:4702 )

Ontology

Not Available

Urine (PMID: 21059682)

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 21059682)

Cellular substructure

Cytoplasm (HMDB: HMDB0015007)
Membrane (HMDB: HMDB0015007)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	283 - 285 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	0.7 g/L	Not Available
LogP	-1	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.7 g/L	ALOGPS
logP	-0.5	ALOGPS
logP	-0.15	ChemAxon
logS	-2.7	ALOGPS
pKa (Strongest Acidic)	8.18	ChemAxon
pKa (Strongest Basic)	7.14	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	106.33 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	72.46 m³·mol⁻¹	ChemAxon
Polarizability	31.55 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]+	173.107	31661259
DarkChem	[M-H]-	168.721	31661259
DeepCCS	[M+H]+	172.105	30932474
DeepCCS	[M-H]-	169.747	30932474
DeepCCS	[M-2H]-	203.275	30932474
DeepCCS	[M+Na]+	178.503	30932474
AllCCS	[M+H]+	168.9	32859911
AllCCS	[M+H-H2O]+	165.8	32859911
AllCCS	[M+NH4]+	171.8	32859911
AllCCS	[M+Na]+	172.6	32859911
AllCCS	[M-H]-	166.2	32859911
AllCCS	[M+Na-2H]-	166.5	32859911
AllCCS	[M+HCOO]-	166.9	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Dorzolamide	CCN[C@H]1C[C@H](C)S(=O)(=O)C2=C1C=C(S2)S(N)(=O)=O	4238.3	Standard polar	33892256
Dorzolamide	CCN[C@H]1C[C@H](C)S(=O)(=O)C2=C1C=C(S2)S(N)(=O)=O	3204.1	Standard non polar	33892256
Dorzolamide	CCN[C@H]1C[C@H](C)S(=O)(=O)C2=C1C=C(S2)S(N)(=O)=O	2920.5	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Dorzolamide,1TMS,isomer #1	CCN[C@H]1C[C@H](C)S(=O)(=O)C2=C1C=C(S(=O)(=O)N[Si](C)(C)C)S2	2800.1	Semi standard non polar	33892256
Dorzolamide,1TMS,isomer #1	CCN[C@H]1C[C@H](C)S(=O)(=O)C2=C1C=C(S(=O)(=O)N[Si](C)(C)C)S2	2788.2	Standard non polar	33892256
Dorzolamide,1TMS,isomer #1	CCN[C@H]1C[C@H](C)S(=O)(=O)C2=C1C=C(S(=O)(=O)N[Si](C)(C)C)S2	3771.2	Standard polar	33892256
Dorzolamide,1TMS,isomer #2	CCN([C@H]1C[C@H](C)S(=O)(=O)C2=C1C=C(S(N)(=O)=O)S2)[Si](C)(C)C	2839.5	Semi standard non polar	33892256
Dorzolamide,1TMS,isomer #2	CCN([C@H]1C[C@H](C)S(=O)(=O)C2=C1C=C(S(N)(=O)=O)S2)[Si](C)(C)C	2882.7	Standard non polar	33892256
Dorzolamide,1TMS,isomer #2	CCN([C@H]1C[C@H](C)S(=O)(=O)C2=C1C=C(S(N)(=O)=O)S2)[Si](C)(C)C	4592.2	Standard polar	33892256
Dorzolamide,2TMS,isomer #1	CCN([C@H]1C[C@H](C)S(=O)(=O)C2=C1C=C(S(=O)(=O)N[Si](C)(C)C)S2)[Si](C)(C)C	2802.5	Semi standard non polar	33892256
Dorzolamide,2TMS,isomer #1	CCN([C@H]1C[C@H](C)S(=O)(=O)C2=C1C=C(S(=O)(=O)N[Si](C)(C)C)S2)[Si](C)(C)C	3011.7	Standard non polar	33892256
Dorzolamide,2TMS,isomer #1	CCN([C@H]1C[C@H](C)S(=O)(=O)C2=C1C=C(S(=O)(=O)N[Si](C)(C)C)S2)[Si](C)(C)C	3650.3	Standard polar	33892256
Dorzolamide,2TMS,isomer #2	CCN[C@H]1C[C@H](C)S(=O)(=O)C2=C1C=C(S(=O)(=O)N([Si](C)(C)C)[Si](C)(C)C)S2	2819.1	Semi standard non polar	33892256
Dorzolamide,2TMS,isomer #2	CCN[C@H]1C[C@H](C)S(=O)(=O)C2=C1C=C(S(=O)(=O)N([Si](C)(C)C)[Si](C)(C)C)S2	2982.7	Standard non polar	33892256
Dorzolamide,2TMS,isomer #2	CCN[C@H]1C[C@H](C)S(=O)(=O)C2=C1C=C(S(=O)(=O)N([Si](C)(C)C)[Si](C)(C)C)S2	3670.7	Standard polar	33892256
Dorzolamide,3TMS,isomer #1	CCN([C@H]1C[C@H](C)S(=O)(=O)C2=C1C=C(S(=O)(=O)N([Si](C)(C)C)[Si](C)(C)C)S2)[Si](C)(C)C	2860.2	Semi standard non polar	33892256
Dorzolamide,3TMS,isomer #1	CCN([C@H]1C[C@H](C)S(=O)(=O)C2=C1C=C(S(=O)(=O)N([Si](C)(C)C)[Si](C)(C)C)S2)[Si](C)(C)C	3209.7	Standard non polar	33892256
Dorzolamide,3TMS,isomer #1	CCN([C@H]1C[C@H](C)S(=O)(=O)C2=C1C=C(S(=O)(=O)N([Si](C)(C)C)[Si](C)(C)C)S2)[Si](C)(C)C	3543.7	Standard polar	33892256
Dorzolamide,1TBDMS,isomer #1	CCN[C@H]1C[C@H](C)S(=O)(=O)C2=C1C=C(S(=O)(=O)N[Si](C)(C)C(C)(C)C)S2	3032.7	Semi standard non polar	33892256
Dorzolamide,1TBDMS,isomer #1	CCN[C@H]1C[C@H](C)S(=O)(=O)C2=C1C=C(S(=O)(=O)N[Si](C)(C)C(C)(C)C)S2	3049.4	Standard non polar	33892256
Dorzolamide,1TBDMS,isomer #1	CCN[C@H]1C[C@H](C)S(=O)(=O)C2=C1C=C(S(=O)(=O)N[Si](C)(C)C(C)(C)C)S2	3819.2	Standard polar	33892256
Dorzolamide,1TBDMS,isomer #2	CCN([C@H]1C[C@H](C)S(=O)(=O)C2=C1C=C(S(N)(=O)=O)S2)[Si](C)(C)C(C)(C)C	3064.2	Semi standard non polar	33892256
Dorzolamide,1TBDMS,isomer #2	CCN([C@H]1C[C@H](C)S(=O)(=O)C2=C1C=C(S(N)(=O)=O)S2)[Si](C)(C)C(C)(C)C	3126.0	Standard non polar	33892256
Dorzolamide,1TBDMS,isomer #2	CCN([C@H]1C[C@H](C)S(=O)(=O)C2=C1C=C(S(N)(=O)=O)S2)[Si](C)(C)C(C)(C)C	4640.5	Standard polar	33892256
Dorzolamide,2TBDMS,isomer #1	CCN([C@H]1C[C@H](C)S(=O)(=O)C2=C1C=C(S(=O)(=O)N[Si](C)(C)C(C)(C)C)S2)[Si](C)(C)C(C)(C)C	3218.1	Semi standard non polar	33892256
Dorzolamide,2TBDMS,isomer #1	CCN([C@H]1C[C@H](C)S(=O)(=O)C2=C1C=C(S(=O)(=O)N[Si](C)(C)C(C)(C)C)S2)[Si](C)(C)C(C)(C)C	3529.1	Standard non polar	33892256
Dorzolamide,2TBDMS,isomer #1	CCN([C@H]1C[C@H](C)S(=O)(=O)C2=C1C=C(S(=O)(=O)N[Si](C)(C)C(C)(C)C)S2)[Si](C)(C)C(C)(C)C	3708.8	Standard polar	33892256
Dorzolamide,2TBDMS,isomer #2	CCN[C@H]1C[C@H](C)S(=O)(=O)C2=C1C=C(S(=O)(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)S2	3272.6	Semi standard non polar	33892256
Dorzolamide,2TBDMS,isomer #2	CCN[C@H]1C[C@H](C)S(=O)(=O)C2=C1C=C(S(=O)(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)S2	3496.4	Standard non polar	33892256
Dorzolamide,2TBDMS,isomer #2	CCN[C@H]1C[C@H](C)S(=O)(=O)C2=C1C=C(S(=O)(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)S2	3711.3	Standard polar	33892256
Dorzolamide,3TBDMS,isomer #1	CCN([C@H]1C[C@H](C)S(=O)(=O)C2=C1C=C(S(=O)(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)S2)[Si](C)(C)C(C)(C)C	3456.7	Semi standard non polar	33892256
Dorzolamide,3TBDMS,isomer #1	CCN([C@H]1C[C@H](C)S(=O)(=O)C2=C1C=C(S(=O)(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)S2)[Si](C)(C)C(C)(C)C	3981.5	Standard non polar	33892256
Dorzolamide,3TBDMS,isomer #1	CCN([C@H]1C[C@H](C)S(=O)(=O)C2=C1C=C(S(=O)(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)S2)[Si](C)(C)C(C)(C)C	3656.8	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Dorzolamide GC-MS (Non-derivatized) - 70eV, Positive	splash10-0ar3-2393000000-5fee748c257c96fe4cc6	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Dorzolamide GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Dorzolamide 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
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dorzolamide 10V, Positive-QTOF	splash10-004i-1039000000-bc26f50a987e66b2d85f	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dorzolamide 20V, Positive-QTOF	splash10-0udi-1940000000-b593686cdeed391e6252	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dorzolamide 40V, Positive-QTOF	splash10-0006-9200000000-37bcca2a8a93f29e705e	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dorzolamide 10V, Negative-QTOF	splash10-00b9-7495000000-d579bf9a53d7355310be	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dorzolamide 20V, Negative-QTOF	splash10-0fa9-5960000000-4180bf8ab95c96f57f15	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dorzolamide 40V, Negative-QTOF	splash10-004i-9010000000-0ef2ea7db65e541aecef	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dorzolamide 10V, Positive-QTOF	splash10-004i-0009000000-2467b7c2962f7a83efdc	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dorzolamide 20V, Positive-QTOF	splash10-004i-0097000000-a04c8c4869eb06d72260	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dorzolamide 40V, Positive-QTOF	splash10-016r-0390000000-5e9ea339d753845f7c98	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dorzolamide 10V, Negative-QTOF	splash10-00di-0009000000-77ced8018945af0b8737	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dorzolamide 20V, Negative-QTOF	splash10-00dr-4439000000-3349264d7067d02efbca	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dorzolamide 40V, Negative-QTOF	splash10-004i-9740000000-a0afe72c11e381401a2f	2021-10-11	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Membrane

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 DB00869	21059682	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB00869	21059682	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB00869

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

4447604

KEGG Compound ID

C06969

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Dorzolamide

METLIN ID

Not Available

PubChem Compound

5284549

PDB ID

Not Available

ChEBI ID

4702

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

Balfour JA, Wilde MI: Dorzolamide. A review of its pharmacology and therapeutic potential in the management of glaucoma and ocular hypertension. Drugs Aging. 1997 May;10(5):384-403. [PubMed:9143858 ]
Ponticello GS, Sugrue MF, Plazonnet B, Durand-Cavagna G: Dorzolamide, a 40-year wait. From an oral to a topical carbonic anhydrase inhibitor for the treatment of glaucoma. Pharm Biotechnol. 1998;11:555-74. [PubMed:9760696 ]
Martens-Lobenhoffer J, Banditt P: Clinical pharmacokinetics of dorzolamide. Clin Pharmacokinet. 2002;41(3):197-205. [PubMed:11929320 ]
Almeida GC Jr, Faria e Souza SJ: Effect of topical dorzolamide on rabbit central corneal thickness. Braz J Med Biol Res. 2006 Feb;39(2):277-81. Epub 2006 Feb 2. [PubMed:16470316 ]
Grover S, Apushkin MA, Fishman GA: Topical dorzolamide for the treatment of cystoid macular edema in patients with retinitis pigmentosa. Am J Ophthalmol. 2006 May;141(5):850-8. Epub 2006 Mar 20. [PubMed:16546110 ]
Plummer CE, MacKay EO, Gelatt KN: Comparison of the effects of topical administration of a fixed combination of dorzolamide-timolol to monotherapy with timolol or dorzolamide on IOP, pupil size, and heart rate in glaucomatous dogs. Vet Ophthalmol. 2006 Jul-Aug;9(4):245-9. [PubMed:16771760 ]

Enzymes

Enzyme Details

1. Cytochrome P450 3A4

General function:: Involved in monooxygenase activity
Specific function:: Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation reactions (e.g. caffeine 8-oxidation, omeprazole sulphoxidation, midazolam 1'-hydroxylation and midazolam 4-hydroxylation) of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Acts as a 1,8-cineole 2-exo-monooxygenase. The enzyme also hydroxylates etoposide.
Gene Name:: CYP3A4
Uniprot ID:: P08684
Molecular weight:: 57255.585

References

Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]

Enzyme Details

2. Cytochrome P450 2C9

General function:: Involved in monooxygenase activity
Specific function:: Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. This enzyme contributes to the wide pharmacokinetics variability of the metabolism of drugs such as S-warfarin, diclofenac, phenytoin, tolbutamide and losartan.
Gene Name:: CYP2C9
Uniprot ID:: P11712
Molecular weight:: 55627.365

References

Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]

Enzyme Details

3. Carbonic anhydrase 1

General function:: Involved in carbonate dehydratase activity
Specific function:: Reversible hydration of carbon dioxide. Can hydrates cyanamide to urea.
Gene Name:: CA1
Uniprot ID:: P00915
Molecular weight:: 28870.0

References

Hasegawa T, Hara K, Hata S: Binding of dorzolamide and its metabolite, N-deethylated dorzolamide, to human erythrocytes in vitro. Drug Metab Dispos. 1994 May-Jun;22(3):377-82. [PubMed:8070313 ]
Maren TH, Conroy CW, Wynns GC, Levy NS: Ocular absorption, blood levels, and excretion of dorzolamide, a topically active carbonic anhydrase inhibitor. J Ocul Pharmacol Ther. 1997 Feb;13(1):23-30. [PubMed:9029437 ]
Sugrue MF: The preclinical pharmacology of dorzolamide hydrochloride, a topical carbonic anhydrase inhibitor. J Ocul Pharmacol Ther. 1996 Fall;12(3):363-76. [PubMed:8875343 ]

Enzyme Details

4. Carbonic anhydrase 2

General function:: Involved in carbonate dehydratase activity
Specific function:: Essential for bone resorption and osteoclast differentiation (By similarity). Reversible hydration of carbon dioxide. Can hydrate cyanamide to urea. Involved in the regulation of fluid secretion into the anterior chamber of the eye.
Gene Name:: CA2
Uniprot ID:: P00918
Molecular weight:: 29245.895

References

Lachmann C, Jorg KM, Trinkmann R: [Postoperative behavior of intraocular pressure after posterior Nd:YAG laser capsulotomy--critical evaluation in preventive administration of local carbonic anhydrase II inhibitor dorzolamide hydrochloride (Trusopt)]. Klin Monbl Augenheilkd. 1998 Dec;213(6):326-30. [PubMed:10048009 ]
Wong BK, Bruhin PJ, Barrish A, Lin JH: Nonlinear dorzolamide pharmacokinetics in rats: concentration-dependent erythrocyte distribution and drug-metabolite displacement interaction. Drug Metab Dispos. 1996 Jun;24(6):659-63. [PubMed:8781782 ]
Berg JT, Ramanathan S, Gabrielli MG, Swenson ER: Carbonic anhydrase in mammalian vascular smooth muscle. J Histochem Cytochem. 2004 Aug;52(8):1101-6. [PubMed:15258186 ]
Hasegawa T, Hara K, Hata S: Binding of dorzolamide and its metabolite, N-deethylated dorzolamide, to human erythrocytes in vitro. Drug Metab Dispos. 1994 May-Jun;22(3):377-82. [PubMed:8070313 ]
Maren TH, Conroy CW, Wynns GC, Levy NS: Ocular absorption, blood levels, and excretion of dorzolamide, a topically active carbonic anhydrase inhibitor. J Ocul Pharmacol Ther. 1997 Feb;13(1):23-30. [PubMed:9029437 ]
Sugrue MF: Pharmacological and ocular hypotensive properties of topical carbonic anhydrase inhibitors. Prog Retin Eye Res. 2000 Jan;19(1):87-112. [PubMed:10614682 ]
Sugrue MF: The preclinical pharmacology of dorzolamide hydrochloride, a topical carbonic anhydrase inhibitor. J Ocul Pharmacol Ther. 1996 Fall;12(3):363-76. [PubMed:8875343 ]
Srinivas SP, Ong A, Zhai CB, Bonanno JA: Inhibition of carbonic anhydrase activity in cultured bovine corneal endothelial cells by dorzolamide. Invest Ophthalmol Vis Sci. 2002 Oct;43(10):3273-8. [PubMed:12356834 ]
Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]

Enzyme Details

5. Carbonic anhydrase 4

General function:: Involved in carbonate dehydratase activity
Specific function:: Reversible hydration of carbon dioxide. May stimulate the sodium/bicarbonate transporter activity of SLC4A4 that acts in pH homeostasis. It is essential for acid overload removal from the retina and retina epithelium, and acid release in the choriocapillaris in the choroid.
Gene Name:: CA4
Uniprot ID:: P22748
Molecular weight:: 35032.075

References

Sugrue MF: The preclinical pharmacology of dorzolamide hydrochloride, a topical carbonic anhydrase inhibitor. J Ocul Pharmacol Ther. 1996 Fall;12(3):363-76. [PubMed:8875343 ]

Showing metabocard for Dorzolamide (HMDB0015007)

MOL for HMDB0015007 (Dorzolamide)

3D MOL for HMDB0015007 (Dorzolamide)

3D SDF for HMDB0015007 (Dorzolamide)

3D-SDF for HMDB0015007 (Dorzolamide)

PDB for HMDB0015007 (Dorzolamide)

3D PDB for HMDB0015007 (Dorzolamide)

SMILES for HMDB0015007 (Dorzolamide)

INCHI for HMDB0015007 (Dorzolamide)

Structure for HMDB0015007 (Dorzolamide)

3D Structure for HMDB0015007 (Dorzolamide)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

Enzymes

References

References

References

References

References