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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 02:51:50 UTC

HMDB ID

HMDB0015026

Secondary Accession Numbers

HMDB15026

Metabolite Identification

Common Name

Granisetron

Description

Granisetron is only found in individuals that have used or taken this drug. It is a serotonin receptor (5HT-3 selective) antagonist that has been used as an antiemetic and antinauseant for cancer chemotherapy patients. [PubChem]Granisetron is a potent, selective antagonist of 5-HT₃ receptors. The antiemetic activity of the drug is brought about through the inhibition of 5-HT3 receptors present both centrally (medullary chemoreceptor zone) and peripherally (GI tract). This inhibition of 5-HT3 receptors in turn inhibits the visceral afferent stimulation of the vomiting center, likely indirectly at the level of the area postrema, as well as through direct inhibition of serotonin activity within the area postrema and the chemoreceptor trigger zone.

Structure

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

HMDB0015026
     RDKit          3D
Granisetron
 47 50  0  0  0  0  0  0  0  0999 V2000
   -2.5113   -1.1439    1.4505 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5224   -0.4231    0.3381 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6123   -0.8089   -0.9738 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1253   -0.6950   -1.2479 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9778   -0.4630   -0.0187 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4074    0.6249    0.9286 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1629    0.9114    0.3123 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0152    1.7265    0.4942 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1207    1.2756   -0.6963 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1215    0.7181   -0.2212 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.3252    1.3574   -0.5459 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2765    2.4515   -1.2608 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6752    0.9814   -0.1929 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7584    1.8231   -0.1632 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.8465    1.1747    0.1669 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.2036    1.6789    0.3162 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5292   -0.1141    0.3665 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2850   -1.2069    0.7128 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7083   -2.4507    0.8419 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3613   -2.5839    0.6182 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5936   -1.4993    0.2716 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1619   -0.2545    0.1427 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8487    0.3443   -1.6582 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2829   -1.9154    1.6743 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5176   -0.4823    2.3700 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5370   -1.7143    1.5789 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2110   -1.7851   -1.2175 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3496   -0.0234   -2.0876 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4221   -1.7228   -1.6036 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2915   -1.3552    0.5036 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9255    0.0009   -0.4265 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0678    1.4867    1.0172 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4107    0.1345    1.9463 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4873    1.2251   -0.7396 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1514    2.8134    0.4844 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4448    1.4795    1.4143 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9000    2.1829   -1.2810 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0881   -0.1198    0.3635 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5529    1.6040    1.3642 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8754    1.0389   -0.2911 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2966    2.7147   -0.0553 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3523   -1.0876    0.8871 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2820   -3.3411    1.1167 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8926   -3.5640    0.7165 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5483   -1.6692    0.0891 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0042   -0.1722   -2.2075 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4270    0.8472   -2.4258 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
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  2  0
 11 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  1  0
 15 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
  9 23  1  0
  7  2  1  0
 22 13  1  0
 23  3  1  0
 22 17  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  3 27  1  0
  4 28  1  0
  4 29  1  0
  5 30  1  0
  5 31  1  0
  6 32  1  0
  6 33  1  0
  7 34  1  0
  8 35  1  0
  8 36  1  0
  9 37  1  0
 10 38  1  0
 16 39  1  0
 16 40  1  0
 16 41  1  0
 18 42  1  0
 19 43  1  0
 20 44  1  0
 21 45  1  0
 23 46  1  0
 23 47  1  0
M  END

889
  Mrv0541 02231215052D          

 23 26  0  0  1  0            999 V2000
    3.5650   -0.0905    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8553    3.0458    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.9232   -0.5344    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.3411   -2.1527    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.8597   -2.8166    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.8490    2.8483    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2223    2.1125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6957    0.9181    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9646    0.5033    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1795    0.2497    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2407    3.6008    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8446    2.4104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9752    3.2250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0711    3.3021    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1159   -0.7046    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8597   -1.4887    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0790   -1.7402    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0790   -2.5652    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -1.3277    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -2.9777    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1159   -3.6008    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500   -1.7402    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500   -2.5652    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1 15  2  0  0  0  0
  2  6  1  0  0  0  0
  2  7  1  0  0  0  0
  2 14  1  0  0  0  0
  3 10  1  0  0  0  0
  3 15  1  0  0  0  0
  4  5  1  0  0  0  0
  4 16  2  0  0  0  0
  5 18  1  0  0  0  0
  5 21  1  0  0  0  0
  6  8  1  0  0  0  0
  6 11  1  0  0  0  0
  7  9  1  0  0  0  0
  7 12  1  0  0  0  0
  8 10  1  0  0  0  0
  9 10  1  0  0  0  0
 11 13  1  0  0  0  0
 12 13  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 17 19  2  0  0  0  0
 18 20  2  0  0  0  0
 19 22  1  0  0  0  0
 20 23  1  0  0  0  0
 22 23  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0015026

> <DATABASE_NAME>
hmdb

> <SMILES>
CN1N=C(C(=O)NC2CC3CCCC(C2)N3C)C2=CC=CC=C12

> <INCHI_IDENTIFIER>
InChI=1S/C18H24N4O/c1-21-13-6-5-7-14(21)11-12(10-13)19-18(23)17-15-8-3-4-9-16(15)22(2)20-17/h3-4,8-9,12-14H,5-7,10-11H2,1-2H3,(H,19,23)

> <INCHI_KEY>
MFWNKCLOYSRHCJ-UHFFFAOYSA-N

> <FORMULA>
C18H24N4O

> <MOLECULAR_WEIGHT>
312.4094

> <EXACT_MASS>
312.19501141

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
35.39211417032121

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
1-methyl-N-{9-methyl-9-azabicyclo[3.3.1]nonan-3-yl}-1H-indazole-3-carboxamide

> <ALOGPS_LOGP>
2.64

> <JCHEM_LOGP>
1.8768568383333333

> <ALOGPS_LOGS>
-2.86

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.750398416935884

> <JCHEM_PKA_STRONGEST_BASIC>
9.000258953534946

> <JCHEM_POLAR_SURFACE_AREA>
50.160000000000004

> <JCHEM_REFRACTIVITY>
101.82570000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.34e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
GRAN

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0015026
     RDKit          3D
Granisetron
 47 50  0  0  0  0  0  0  0  0999 V2000
   -2.5113   -1.1439    1.4505 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5224   -0.4231    0.3381 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6123   -0.8089   -0.9738 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1253   -0.6950   -1.2479 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9778   -0.4630   -0.0187 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4074    0.6249    0.9286 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1629    0.9114    0.3123 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0152    1.7265    0.4942 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1207    1.2756   -0.6963 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1215    0.7181   -0.2212 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.3252    1.3574   -0.5459 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2765    2.4515   -1.2608 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6752    0.9814   -0.1929 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7584    1.8231   -0.1632 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.8465    1.1747    0.1669 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.2036    1.6789    0.3162 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5292   -0.1141    0.3665 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2850   -1.2069    0.7128 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7083   -2.4507    0.8419 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3613   -2.5839    0.6182 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5936   -1.4993    0.2716 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1619   -0.2545    0.1427 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8487    0.3443   -1.6582 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2829   -1.9154    1.6743 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5176   -0.4823    2.3700 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5370   -1.7143    1.5789 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2110   -1.7851   -1.2175 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3496   -0.0234   -2.0876 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4221   -1.7228   -1.6036 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2915   -1.3552    0.5036 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9255    0.0009   -0.4265 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0678    1.4867    1.0172 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4107    0.1345    1.9463 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4873    1.2251   -0.7396 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1514    2.8134    0.4844 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4448    1.4795    1.4143 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9000    2.1829   -1.2810 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0881   -0.1198    0.3635 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5529    1.6040    1.3642 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8754    1.0389   -0.2911 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2966    2.7147   -0.0553 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3523   -1.0876    0.8871 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2820   -3.3411    1.1167 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8926   -3.5640    0.7165 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5483   -1.6692    0.0891 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0042   -0.1722   -2.2075 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4270    0.8472   -2.4258 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
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  2  0
 11 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  1  0
 15 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
  9 23  1  0
  7  2  1  0
 22 13  1  0
 23  3  1  0
 22 17  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  3 27  1  0
  4 28  1  0
  4 29  1  0
  5 30  1  0
  5 31  1  0
  6 32  1  0
  6 33  1  0
  7 34  1  0
  8 35  1  0
  8 36  1  0
  9 37  1  0
 10 38  1  0
 16 39  1  0
 16 40  1  0
 16 41  1  0
 18 42  1  0
 19 43  1  0
 20 44  1  0
 21 45  1  0
 23 46  1  0
 23 47  1  0
M  END

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 889                                               
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  O   UNK     0       6.655  -0.169   0.000  0.00  0.00           O+0
HETATM    2  N   UNK     0       9.063   5.685   0.000  0.00  0.00           N+0
HETATM    3  N   UNK     0       9.190  -0.998   0.000  0.00  0.00           N+0
HETATM    4  N   UNK     0       8.103  -4.018   0.000  0.00  0.00           N+0
HETATM    5  N   UNK     0       7.205  -5.258   0.000  0.00  0.00           N+0
HETATM    6  C   UNK     0      10.918   5.317   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      11.615   3.943   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       8.765   1.714   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      11.134   0.939   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       9.668   0.466   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      13.516   6.721   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      14.643   4.499   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      14.887   6.020   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       7.599   6.164   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       7.683  -1.315   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       7.205  -2.779   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       5.747  -3.248   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       5.747  -4.788   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       4.414  -2.478   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       4.414  -5.558   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       7.683  -6.721   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       3.080  -3.248   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       3.080  -4.788   0.000  0.00  0.00           C+0
CONECT    1   15                                                            
CONECT    2    6    7   14                                                  
CONECT    3   10   15                                                       
CONECT    4    5   16                                                       
CONECT    5    4   18   21                                                  
CONECT    6    2    8   11                                                  
CONECT    7    2    9   12                                                  
CONECT    8    6   10                                                       
CONECT    9    7   10                                                       
CONECT   10    3    8    9                                                  
CONECT   11    6   13                                                       
CONECT   12    7   13                                                       
CONECT   13   11   12                                                       
CONECT   14    2                                                            
CONECT   15    1    3   16                                                  
CONECT   16    4   15   17                                                  
CONECT   17   16   18   19                                                  
CONECT   18    5   17   20                                                  
CONECT   19   17   22                                                       
CONECT   20   18   23                                                       
CONECT   21    5                                                            
CONECT   22   19   23                                                       
CONECT   23   20   22                                                       
MASTER        0    0    0    0    0    0    0    0   23    0   52    0
END

COMPND    HMDB0015026
HETATM    1  C1  UNL     1      -2.511  -1.144   1.451  1.00  0.00           C  
HETATM    2  N1  UNL     1      -2.522  -0.423   0.338  1.00  0.00           N  
HETATM    3  C2  UNL     1      -2.612  -0.809  -0.974  1.00  0.00           C  
HETATM    4  C3  UNL     1      -4.125  -0.695  -1.248  1.00  0.00           C  
HETATM    5  C4  UNL     1      -4.978  -0.463  -0.019  1.00  0.00           C  
HETATM    6  C5  UNL     1      -4.407   0.625   0.929  1.00  0.00           C  
HETATM    7  C6  UNL     1      -3.163   0.911   0.312  1.00  0.00           C  
HETATM    8  C7  UNL     1      -2.015   1.727   0.494  1.00  0.00           C  
HETATM    9  C8  UNL     1      -1.121   1.276  -0.696  1.00  0.00           C  
HETATM   10  N2  UNL     1       0.122   0.718  -0.221  1.00  0.00           N  
HETATM   11  C9  UNL     1       1.325   1.357  -0.546  1.00  0.00           C  
HETATM   12  O1  UNL     1       1.276   2.452  -1.261  1.00  0.00           O  
HETATM   13  C10 UNL     1       2.675   0.981  -0.193  1.00  0.00           C  
HETATM   14  N3  UNL     1       3.758   1.823  -0.163  1.00  0.00           N  
HETATM   15  N4  UNL     1       4.847   1.175   0.167  1.00  0.00           N  
HETATM   16  C11 UNL     1       6.204   1.679   0.316  1.00  0.00           C  
HETATM   17  C12 UNL     1       4.529  -0.114   0.367  1.00  0.00           C  
HETATM   18  C13 UNL     1       5.285  -1.207   0.713  1.00  0.00           C  
HETATM   19  C14 UNL     1       4.708  -2.451   0.842  1.00  0.00           C  
HETATM   20  C15 UNL     1       3.361  -2.584   0.618  1.00  0.00           C  
HETATM   21  C16 UNL     1       2.594  -1.499   0.272  1.00  0.00           C  
HETATM   22  C17 UNL     1       3.162  -0.255   0.143  1.00  0.00           C  
HETATM   23  C18 UNL     1      -1.849   0.344  -1.658  1.00  0.00           C  
HETATM   24  H1  UNL     1      -3.283  -1.915   1.674  1.00  0.00           H  
HETATM   25  H2  UNL     1      -2.518  -0.482   2.370  1.00  0.00           H  
HETATM   26  H3  UNL     1      -1.537  -1.714   1.579  1.00  0.00           H  
HETATM   27  H4  UNL     1      -2.211  -1.785  -1.217  1.00  0.00           H  
HETATM   28  H5  UNL     1      -4.350  -0.023  -2.088  1.00  0.00           H  
HETATM   29  H6  UNL     1      -4.422  -1.723  -1.604  1.00  0.00           H  
HETATM   30  H7  UNL     1      -5.291  -1.355   0.504  1.00  0.00           H  
HETATM   31  H8  UNL     1      -5.925   0.001  -0.427  1.00  0.00           H  
HETATM   32  H9  UNL     1      -5.068   1.487   1.017  1.00  0.00           H  
HETATM   33  H10 UNL     1      -4.411   0.135   1.946  1.00  0.00           H  
HETATM   34  H11 UNL     1      -3.487   1.225  -0.740  1.00  0.00           H  
HETATM   35  H12 UNL     1      -2.151   2.813   0.484  1.00  0.00           H  
HETATM   36  H13 UNL     1      -1.445   1.480   1.414  1.00  0.00           H  
HETATM   37  H14 UNL     1      -0.900   2.183  -1.281  1.00  0.00           H  
HETATM   38  H15 UNL     1       0.088  -0.120   0.363  1.00  0.00           H  
HETATM   39  H16 UNL     1       6.553   1.604   1.364  1.00  0.00           H  
HETATM   40  H17 UNL     1       6.875   1.039  -0.291  1.00  0.00           H  
HETATM   41  H18 UNL     1       6.297   2.715  -0.055  1.00  0.00           H  
HETATM   42  H19 UNL     1       6.352  -1.088   0.887  1.00  0.00           H  
HETATM   43  H20 UNL     1       5.282  -3.341   1.117  1.00  0.00           H  
HETATM   44  H21 UNL     1       2.893  -3.564   0.717  1.00  0.00           H  
HETATM   45  H22 UNL     1       1.548  -1.669   0.089  1.00  0.00           H  
HETATM   46  H23 UNL     1      -1.004  -0.172  -2.208  1.00  0.00           H  
HETATM   47  H24 UNL     1      -2.427   0.847  -2.426  1.00  0.00           H  
CONECT    1    2   24   25   26
CONECT    2    3    7
CONECT    3    4   23   27
CONECT    4    5   28   29
CONECT    5    6   30   31
CONECT    6    7   32   33
CONECT    7    8   34
CONECT    8    9   35   36
CONECT    9   10   23   37
CONECT   10   11   38
CONECT   11   12   12   13
CONECT   13   14   14   22
CONECT   14   15
CONECT   15   16   17
CONECT   16   39   40   41
CONECT   17   18   18   22
CONECT   18   19   42
CONECT   19   20   20   43
CONECT   20   21   44
CONECT   21   22   22   45
CONECT   23   46   47
END

HMDB0015026
     RDKit          3D
Granisetron
 47 50  0  0  0  0  0  0  0  0999 V2000
   -2.5113   -1.1439    1.4505 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5224   -0.4231    0.3381 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6123   -0.8089   -0.9738 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1253   -0.6950   -1.2479 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9778   -0.4630   -0.0187 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4074    0.6249    0.9286 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1629    0.9114    0.3123 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0152    1.7265    0.4942 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1207    1.2756   -0.6963 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1215    0.7181   -0.2212 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.3252    1.3574   -0.5459 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2765    2.4515   -1.2608 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6752    0.9814   -0.1929 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7584    1.8231   -0.1632 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.8465    1.1747    0.1669 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.2036    1.6789    0.3162 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5292   -0.1141    0.3665 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2850   -1.2069    0.7128 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7083   -2.4507    0.8419 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3613   -2.5839    0.6182 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5936   -1.4993    0.2716 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1619   -0.2545    0.1427 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8487    0.3443   -1.6582 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2829   -1.9154    1.6743 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5176   -0.4823    2.3700 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5370   -1.7143    1.5789 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2110   -1.7851   -1.2175 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3496   -0.0234   -2.0876 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4221   -1.7228   -1.6036 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2915   -1.3552    0.5036 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9255    0.0009   -0.4265 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0678    1.4867    1.0172 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4107    0.1345    1.9463 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4873    1.2251   -0.7396 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1514    2.8134    0.4844 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4448    1.4795    1.4143 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9000    2.1829   -1.2810 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0881   -0.1198    0.3635 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5529    1.6040    1.3642 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8754    1.0389   -0.2911 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2966    2.7147   -0.0553 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3523   -1.0876    0.8871 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2820   -3.3411    1.1167 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8926   -3.5640    0.7165 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5483   -1.6692    0.0891 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0042   -0.1722   -2.2075 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4270    0.8472   -2.4258 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
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  2  0
 11 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  1  0
 15 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
  9 23  1  0
  7  2  1  0
 22 13  1  0
 23  3  1  0
 22 17  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  3 27  1  0
  4 28  1  0
  4 29  1  0
  5 30  1  0
  5 31  1  0
  6 32  1  0
  6 33  1  0
  7 34  1  0
  8 35  1  0
  8 36  1  0
  9 37  1  0
 10 38  1  0
 16 39  1  0
 16 40  1  0
 16 41  1  0
 18 42  1  0
 19 43  1  0
 20 44  1  0
 21 45  1  0
 23 46  1  0
 23 47  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Sancuso	HMDB
Kytril	HMDB
APF530	HMDB
Granisetron base	HMDB
1-Methyl-N-(endo-9-methyl-9-azabicyclo(3.3.1)non-3-yl)-1H-indazole-3-carboxamide	HMDB
Hydrochloride, granisetron	HMDB
Monohydrochloride, granisetron	HMDB
Granisetron hydrochloride	HMDB
Granisetron monohydrochloride	HMDB
Granisetron	MeSH

Chemical Formula

C₁₈H₂₄N₄O

Average Molecular Weight

312.4094

Monoisotopic Molecular Weight

312.19501141

IUPAC Name

1-methyl-N-{9-methyl-9-azabicyclo[3.3.1]nonan-3-yl}-1H-indazole-3-carboxamide

Traditional Name

GRAN

CAS Registry Number

109889-09-0

SMILES

CN1N=C(C(=O)NC2CC3CCCC(C2)N3C)C2=CC=CC=C12

InChI Identifier

InChI=1S/C18H24N4O/c1-21-13-6-5-7-14(21)11-12(10-13)19-18(23)17-15-8-3-4-9-16(15)22(2)20-17/h3-4,8-9,12-14H,5-7,10-11H2,1-2H3,(H,19,23)

InChI Key

MFWNKCLOYSRHCJ-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as indazole-3-carboxamides. These are aromatic compounds containing an indazole ring system that is substituted at the 3-position with a carboxamide group.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Benzopyrazoles

Sub Class

Indazoles

Direct Parent

Indazole-3-carboxamides

Alternative Parents

Substituents

Indazole-3-carboxamide
2-heteroaryl carboxamide
Pyrazole-5-carboxamide
Piperidine
Benzenoid
Azole
Heteroaromatic compound
Pyrazole
Amino acid or derivatives
Carboxamide group
Tertiary aliphatic amine
Tertiary amine
Secondary carboxylic acid amide
Carboxylic acid derivative
Azacycle
Amine
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Organic oxide
Organopnictogen compound
Organic oxygen compound
Organic nitrogen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Not Available

Urine (PMID: 21059682)

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 21059682)

Cellular substructure

Membrane (HMDB: HMDB0015026)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	219 °C (hydrochloride salt)	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	0.43 g/L	Not Available
LogP	2.6	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.43 g/L	ALOGPS
logP	2.64	ALOGPS
logP	1.88	ChemAxon
logS	-2.9	ALOGPS
pKa (Strongest Acidic)	14.75	ChemAxon
pKa (Strongest Basic)	9	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	50.16 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	101.83 m³·mol⁻¹	ChemAxon
Polarizability	35.39 Å³	ChemAxon
Number of Rings	4	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]+	174.241	31661259
DarkChem	[M-H]-	173.936	31661259
DeepCCS	[M-2H]-	203.304	30932474
DeepCCS	[M+Na]+	178.869	30932474
AllCCS	[M+H]+	178.9	32859911
AllCCS	[M+H-H2O]+	175.8	32859911
AllCCS	[M+NH4]+	181.8	32859911
AllCCS	[M+Na]+	182.6	32859911
AllCCS	[M-H]-	178.8	32859911
AllCCS	[M+Na-2H]-	178.7	32859911
AllCCS	[M+HCOO]-	178.7	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Granisetron	CN1N=C(C(=O)NC2CC3CCCC(C2)N3C)C2=CC=CC=C12	3246.1	Standard polar	33892256
Granisetron	CN1N=C(C(=O)NC2CC3CCCC(C2)N3C)C2=CC=CC=C12	2812.3	Standard non polar	33892256
Granisetron	CN1N=C(C(=O)NC2CC3CCCC(C2)N3C)C2=CC=CC=C12	3016.6	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Granisetron,1TMS,isomer #1	CN1C2CCCC1CC(N(C(=O)C1=NN(C)C3=CC=CC=C13)[Si](C)(C)C)C2	2789.3	Semi standard non polar	33892256
Granisetron,1TMS,isomer #1	CN1C2CCCC1CC(N(C(=O)C1=NN(C)C3=CC=CC=C13)[Si](C)(C)C)C2	2688.6	Standard non polar	33892256
Granisetron,1TMS,isomer #1	CN1C2CCCC1CC(N(C(=O)C1=NN(C)C3=CC=CC=C13)[Si](C)(C)C)C2	3686.8	Standard polar	33892256
Granisetron,1TBDMS,isomer #1	CN1C2CCCC1CC(N(C(=O)C1=NN(C)C3=CC=CC=C13)[Si](C)(C)C(C)(C)C)C2	3020.0	Semi standard non polar	33892256
Granisetron,1TBDMS,isomer #1	CN1C2CCCC1CC(N(C(=O)C1=NN(C)C3=CC=CC=C13)[Si](C)(C)C(C)(C)C)C2	2922.2	Standard non polar	33892256
Granisetron,1TBDMS,isomer #1	CN1C2CCCC1CC(N(C(=O)C1=NN(C)C3=CC=CC=C13)[Si](C)(C)C(C)(C)C)C2	3772.4	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Granisetron GC-MS (Non-derivatized) - 70eV, Positive	splash10-06r2-2940000000-146f2d5e07d055b758bf	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Granisetron GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Granisetron 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 - Granisetron 10V, Positive-QTOF	splash10-03di-0109000000-232e7ada728ba5e5eb79	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Granisetron 20V, Positive-QTOF	splash10-03dr-0917000000-f907d6c8c007ae63ac0b	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Granisetron 40V, Positive-QTOF	splash10-000l-3900000000-65402ff64bc089f9409d	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Granisetron 10V, Negative-QTOF	splash10-03di-0109000000-940597d64f870c91eba1	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Granisetron 20V, Negative-QTOF	splash10-03e9-0916000000-a4c50b145efacab49b7c	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Granisetron 40V, Negative-QTOF	splash10-0udi-1900000000-fd471a7d475cefc66041	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Granisetron 10V, Positive-QTOF	splash10-03di-0009000000-0101d8fc4b8c14abec93	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Granisetron 20V, Positive-QTOF	splash10-03di-0509000000-ba9334d40b5fbc530c60	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Granisetron 40V, Positive-QTOF	splash10-0pb9-1930000000-732dbcf74b657cbc6fd4	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Granisetron 10V, Negative-QTOF	splash10-03di-0009000000-e08aa460b7cc8027561a	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Granisetron 20V, Negative-QTOF	splash10-03di-1219000000-ec7a87708cc27df4400b	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Granisetron 40V, Negative-QTOF	splash10-001i-4911000000-ea14fc27c91eaf8eb0c2	2021-10-11	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

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 DB00889	21059682	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB00889	21059682	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

3390

KEGG Compound ID

C07023

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Granisetron

METLIN ID

Not Available

PubChem Compound

3510

PDB ID

Not Available

ChEBI ID

154547

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

Gan TJ: Selective serotonin 5-HT3 receptor antagonists for postoperative nausea and vomiting: are they all the same? CNS Drugs. 2005;19(3):225-38. [PubMed:15740177 ]
Tan M: Granisetron: new insights into its use for the treatment of chemotherapy-induced nausea and vomiting. Expert Opin Pharmacother. 2003 Sep;4(9):1563-71. [PubMed:12943486 ]
Feyer P, Seegenschmiedt MH, Steingraeber M: Granisetron in the control of radiotherapy-induced nausea and vomiting: a comparison with other antiemetic therapies. Support Care Cancer. 2005 Sep;13(9):671-8. Epub 2005 Jul 26. [PubMed:16044252 ]
MEDSAFE [Link]

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

Tan M: Granisetron: new insights into its use for the treatment of chemotherapy-induced nausea and vomiting. Expert Opin Pharmacother. 2003 Sep;4(9):1563-71. [PubMed:12943486 ]
Janicki PK: Cytochrome P450 2D6 metabolism and 5-hydroxytryptamine type 3 receptor antagonists for postoperative nausea and vomiting. Med Sci Monit. 2005 Oct;11(10):RA322-8. Epub 2005 Sep 26. [PubMed:16192915 ]
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 2D6

General function:: Involved in monooxygenase activity
Specific function:: Responsible for the metabolism of many drugs and environmental chemicals that it oxidizes. It is involved in the metabolism of drugs such as antiarrhythmics, adrenoceptor antagonists, and tricyclic antidepressants.
Gene Name:: CYP2D6
Uniprot ID:: P10635
Molecular weight:: 55768.94

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. Cytochrome P450 3A5

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.
Gene Name:: CYP3A5
Uniprot ID:: P20815
Molecular weight:: 57108.065

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

4. Cytochrome P450 1A1

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.
Gene Name:: CYP1A1
Uniprot ID:: P04798
Molecular weight:: 58164.815

References

Nakamura H, Ariyoshi N, Okada K, Nakasa H, Nakazawa K, Kitada M: CYP1A1 is a major enzyme responsible for the metabolism of granisetron in human liver microsomes. Curr Drug Metab. 2005 Oct;6(5):469-80. [PubMed:16248838 ]
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

5. 5-hydroxytryptamine receptor 3A

General function:: Involved in extracellular ligand-gated ion channel activity
Specific function:: This is one of the several different receptors for 5- hydroxytryptamine (serotonin), a biogenic hormone that functions as a neurotransmitter, a hormone, and a mitogen. This receptor is a ligand-gated ion channel, which when activated causes fast, depolarizing responses in neurons. It is a cation-specific, but otherwise relatively nonselective, ion channel
Gene Name:: HTR3A
Uniprot ID:: P46098
Molecular weight:: 55279.8

References

Hillsley K, Grundy D: Plasticity in the mesenteric afferent response to cisplatin following vagotomy in the rat. J Auton Nerv Syst. 1999 May 28;76(2-3):93-8. [PubMed:10412832 ]
Turvill JL, Connor P, Farthing MJ: The inhibition of cholera toxin-induced 5-HT release by the 5-HT(3) receptor antagonist, granisetron, in the rat. Br J Pharmacol. 2000 Jul;130(5):1031-6. [PubMed:10882387 ]
Cappelli A, Anzini M, Vomero S, Mennuni L, Makovec F, Doucet E, Hamon M, Menziani MC, De Benedetti PG, Giorgi G, Ghelardini C, Collina S: Novel potent 5-HT(3) receptor ligands based on the pyrrolidone structure: synthesis, biological evaluation, and computational rationalization of the ligand-receptor interaction modalities. Bioorg Med Chem. 2002 Mar;10(3):779-801. [PubMed:11814868 ]
Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]
Gan TJ: Selective serotonin 5-HT3 receptor antagonists for postoperative nausea and vomiting: are they all the same? CNS Drugs. 2005;19(3):225-38. [PubMed:15740177 ]
Tan M: Granisetron: new insights into its use for the treatment of chemotherapy-induced nausea and vomiting. Expert Opin Pharmacother. 2003 Sep;4(9):1563-71. [PubMed:12943486 ]
Ho KY, Gan TJ: Pharmacology, pharmacogenetics, and clinical efficacy of 5-hydroxytryptamine type 3 receptor antagonists for postoperative nausea and vomiting. Curr Opin Anaesthesiol. 2006 Dec;19(6):606-11. [PubMed:17093363 ]
Abdelsayed GG: Management of radiation-induced nausea and vomiting. Exp Hematol. 2007 Apr;35(4 Suppl 1):34-6. [PubMed:17379085 ]
Feyer P, Seegenschmiedt MH, Steingraeber M: Granisetron in the control of radiotherapy-induced nausea and vomiting: a comparison with other antiemetic therapies. Support Care Cancer. 2005 Sep;13(9):671-8. Epub 2005 Jul 26. [PubMed:16044252 ]

Showing metabocard for Granisetron (HMDB0015026)

MOL for HMDB0015026 (Granisetron)

3D MOL for HMDB0015026 (Granisetron)

3D SDF for HMDB0015026 (Granisetron)

3D-SDF for HMDB0015026 (Granisetron)

PDB for HMDB0015026 (Granisetron)

3D PDB for HMDB0015026 (Granisetron)

SMILES for HMDB0015026 (Granisetron)

INCHI for HMDB0015026 (Granisetron)

Structure for HMDB0015026 (Granisetron)

3D Structure for HMDB0015026 (Granisetron)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

Enzymes

References

References

References

References

References