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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-06 15:16:51 UTC

Update Date

2022-03-07 02:51:52 UTC

HMDB ID

HMDB0015133

Secondary Accession Numbers

HMDB15133

Metabolite Identification

Common Name

Frovatriptan

Description

Frovatriptan, also known as Frova (trade name), belongs to a class of medications known as 5-hydroxytryptamine agonists (triptan) (PMID: 18001261 ). It is widely indicated for the treatment of migraine headaches with or without aura in adults (PMID: 22900951 , 27103792 ). It works in the brain to relieve migraine symptoms including headache, pain, nausea, vomiting, sensitivity to light/sound. However, it is not used to treat patients with hemiplegic, ophthalmoplegic or basilar migraine. Frovatriptan binds with high affinity for serotonin 5-HT1B and 5-HT1D receptors, thereby relieving pain by narrowing blood vessels (PMID: 11735616 , 12517245 ). Patient’s may experience some side effects, especially who have heart or blood vessel disease. Frovatriptan is only found in individuals who have consumed or used this drug.

Structure

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

HMDB0015133
     RDKit          3D
Frovatriptan
 35 37  0  0  0  0  0  0  0  0999 V2000
   -3.3976    2.3111    0.0934 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3891    1.4644   -1.0729 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5027    0.3291   -0.9362 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.9199   -0.5932    0.1812 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2738   -1.9487   -0.1486 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8012   -1.6772    0.0259 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1558   -2.5128    0.4253 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.3386   -1.8389    0.4404 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6317   -2.2107    0.7688 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6437   -1.2973    0.6880 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4029    0.0036    0.2812 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5078    0.9483    0.2084 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3793    2.2584   -0.3108 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.6324    0.5799    0.6284 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1111    0.3602   -0.0426 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0704   -0.5487    0.0321 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2949   -0.4252   -0.2379 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0796    0.7375   -0.6967 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9314    1.8608    0.9703 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9172    3.2718   -0.2152 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4515    2.5540    0.3318 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3310    1.1798   -1.3852 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5372   -0.2176   -1.9035 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4232   -0.2549    1.1185 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0002   -0.6807    0.3008 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6355   -2.7493    0.4879 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4299   -2.0939   -1.2354 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1133   -3.5226    0.7015 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8342   -3.2292    1.0896 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6512   -1.5994    0.9473 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4613    2.6210   -0.6129 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1969    2.8977   -0.4065 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8849    1.3768   -0.3671 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0313    1.5564    0.0686 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6684    1.0894   -1.6716 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  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  1  0
 12 14  2  0
 11 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  1  0
 18  3  1  0
 17  6  2  0
 16  8  1  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
  2 22  1  0
  3 23  1  6
  4 24  1  0
  4 25  1  0
  5 26  1  0
  5 27  1  0
  7 28  1  0
  9 29  1  0
 10 30  1  0
 13 31  1  0
 13 32  1  0
 15 33  1  0
 18 34  1  0
 18 35  1  0
M  END

998
  Mrv0541 02231215102D          

 18 20  0  0  1  0            999 V2000
    6.6612   -1.7546    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6342    1.2635    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.3595   -1.0023    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.6843   -0.8406    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.8873   -0.4116    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.6956   -0.5770    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6323    0.3731    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2382    0.0447    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1892    0.9819    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9934    0.7979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0303    0.0447    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2750    0.7979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5729   -0.5770    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0793    0.9819    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3812   -0.4116    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5842   -0.8406    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6361    0.3731    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9089   -1.0023    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1 18  2  0  0  0  0
  2 10  1  0  0  0  0
  2 12  1  0  0  0  0
  5  3  1  6  0  0  0
  3 16  1  0  0  0  0
  4 18  1  0  0  0  0
  5  6  1  0  0  0  0
  5  7  1  0  0  0  0
  6  8  1  0  0  0  0
  7  9  1  0  0  0  0
  8 10  2  0  0  0  0
  8 11  1  0  0  0  0
  9 10  1  0  0  0  0
 11 12  2  0  0  0  0
 11 13  1  0  0  0  0
 12 14  1  0  0  0  0
 13 15  2  0  0  0  0
 14 17  2  0  0  0  0
 15 17  1  0  0  0  0
 15 18  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0015133

> <DATABASE_NAME>
hmdb

> <SMILES>
CN[C@@H]1CCC2=C(C1)C1=C(N2)C=CC(=C1)C(N)=O

> <INCHI_IDENTIFIER>
InChI=1S/C14H17N3O/c1-16-9-3-5-13-11(7-9)10-6-8(14(15)18)2-4-12(10)17-13/h2,4,6,9,16-17H,3,5,7H2,1H3,(H2,15,18)/t9-/m1/s1

> <INCHI_KEY>
XPSQPHWEGNHMSK-SECBINFHSA-N

> <FORMULA>
C14H17N3O

> <MOLECULAR_WEIGHT>
243.3043

> <EXACT_MASS>
243.137162181

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
27.552154348371012

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(3R)-3-(methylamino)-2,3,4,9-tetrahydro-1H-carbazole-6-carboxamide

> <ALOGPS_LOGP>
1.20

> <JCHEM_LOGP>
1.0779760430000005

> <ALOGPS_LOGS>
-3.30

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
17.269376698433437

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.5361936626193

> <JCHEM_PKA_STRONGEST_BASIC>
10.421212164263157

> <JCHEM_POLAR_SURFACE_AREA>
70.91

> <JCHEM_REFRACTIVITY>
71.8382

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.23e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
frovatriptan

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0015133
     RDKit          3D
Frovatriptan
 35 37  0  0  0  0  0  0  0  0999 V2000
   -3.3976    2.3111    0.0934 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3891    1.4644   -1.0729 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5027    0.3291   -0.9362 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.9199   -0.5932    0.1812 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2738   -1.9487   -0.1486 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8012   -1.6772    0.0259 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1558   -2.5128    0.4253 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.3386   -1.8389    0.4404 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6317   -2.2107    0.7688 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6437   -1.2973    0.6880 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4029    0.0036    0.2812 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5078    0.9483    0.2084 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3793    2.2584   -0.3108 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.6324    0.5799    0.6284 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1111    0.3602   -0.0426 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0704   -0.5487    0.0321 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2949   -0.4252   -0.2379 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0796    0.7375   -0.6967 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9314    1.8608    0.9703 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9172    3.2718   -0.2152 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4515    2.5540    0.3318 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3310    1.1798   -1.3852 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5372   -0.2176   -1.9035 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4232   -0.2549    1.1185 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0002   -0.6807    0.3008 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6355   -2.7493    0.4879 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4299   -2.0939   -1.2354 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1133   -3.5226    0.7015 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8342   -3.2292    1.0896 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6512   -1.5994    0.9473 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4613    2.6210   -0.6129 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1969    2.8977   -0.4065 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8849    1.3768   -0.3671 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0313    1.5564    0.0686 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6684    1.0894   -1.6716 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  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  1  0
 12 14  2  0
 11 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  1  0
 18  3  1  0
 17  6  2  0
 16  8  1  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
  2 22  1  0
  3 23  1  6
  4 24  1  0
  4 25  1  0
  5 26  1  0
  5 27  1  0
  7 28  1  0
  9 29  1  0
 10 30  1  0
 13 31  1  0
 13 32  1  0
 15 33  1  0
 18 34  1  0
 18 35  1  0
M  END

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 998                                               
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  O   UNK     0      12.434  -3.275   0.000  0.00  0.00           O+0
HETATM    2  N   UNK     0       8.651   2.359   0.000  0.00  0.00           N+0
HETATM    3  N   UNK     0       4.404  -1.871   0.000  0.00  0.00           N+0
HETATM    4  N   UNK     0      14.344  -1.569   0.000  0.00  0.00           N+0
HETATM    5  C   UNK     0       5.390  -0.768   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       6.898  -1.077   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.914   0.696   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       7.911   0.083   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.953   1.833   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       7.454   1.489   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       9.390   0.083   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       9.847   1.489   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      10.403  -1.077   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      11.348   1.833   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      11.912  -0.768   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       2.957  -1.569   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      12.387   0.696   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      12.897  -1.871   0.000  0.00  0.00           C+0
CONECT    1   18                                                            
CONECT    2   10   12                                                       
CONECT    3    5   16                                                       
CONECT    4   18                                                            
CONECT    5    3    6    7                                                  
CONECT    6    5    8                                                       
CONECT    7    5    9                                                       
CONECT    8    6   10   11                                                  
CONECT    9    7   10                                                       
CONECT   10    2    8    9                                                  
CONECT   11    8   12   13                                                  
CONECT   12    2   11   14                                                  
CONECT   13   11   15                                                       
CONECT   14   12   17                                                       
CONECT   15   13   17   18                                                  
CONECT   16    3                                                            
CONECT   17   14   15                                                       
CONECT   18    1    4   15                                                  
MASTER        0    0    0    0    0    0    0    0   18    0   40    0
END

COMPND    HMDB0015133
HETATM    1  C1  UNL     1      -3.398   2.311   0.093  1.00  0.00           C  
HETATM    2  N1  UNL     1      -3.389   1.464  -1.073  1.00  0.00           N  
HETATM    3  C2  UNL     1      -2.503   0.329  -0.936  1.00  0.00           C  
HETATM    4  C3  UNL     1      -2.920  -0.593   0.181  1.00  0.00           C  
HETATM    5  C4  UNL     1      -2.274  -1.949  -0.149  1.00  0.00           C  
HETATM    6  C5  UNL     1      -0.801  -1.677   0.026  1.00  0.00           C  
HETATM    7  N2  UNL     1       0.156  -2.513   0.425  1.00  0.00           N  
HETATM    8  C6  UNL     1       1.339  -1.839   0.440  1.00  0.00           C  
HETATM    9  C7  UNL     1       2.632  -2.211   0.769  1.00  0.00           C  
HETATM   10  C8  UNL     1       3.644  -1.297   0.688  1.00  0.00           C  
HETATM   11  C9  UNL     1       3.403   0.004   0.281  1.00  0.00           C  
HETATM   12  C10 UNL     1       4.508   0.948   0.208  1.00  0.00           C  
HETATM   13  N3  UNL     1       4.379   2.258  -0.311  1.00  0.00           N  
HETATM   14  O1  UNL     1       5.632   0.580   0.628  1.00  0.00           O  
HETATM   15  C11 UNL     1       2.111   0.360  -0.043  1.00  0.00           C  
HETATM   16  C12 UNL     1       1.070  -0.549   0.032  1.00  0.00           C  
HETATM   17  C13 UNL     1      -0.295  -0.425  -0.238  1.00  0.00           C  
HETATM   18  C14 UNL     1      -1.080   0.738  -0.697  1.00  0.00           C  
HETATM   19  H1  UNL     1      -2.931   1.861   0.970  1.00  0.00           H  
HETATM   20  H2  UNL     1      -2.917   3.272  -0.215  1.00  0.00           H  
HETATM   21  H3  UNL     1      -4.452   2.554   0.332  1.00  0.00           H  
HETATM   22  H4  UNL     1      -4.331   1.180  -1.385  1.00  0.00           H  
HETATM   23  H5  UNL     1      -2.537  -0.218  -1.903  1.00  0.00           H  
HETATM   24  H6  UNL     1      -2.423  -0.255   1.118  1.00  0.00           H  
HETATM   25  H7  UNL     1      -4.000  -0.681   0.301  1.00  0.00           H  
HETATM   26  H8  UNL     1      -2.636  -2.749   0.488  1.00  0.00           H  
HETATM   27  H9  UNL     1      -2.430  -2.094  -1.235  1.00  0.00           H  
HETATM   28  H10 UNL     1       0.113  -3.523   0.702  1.00  0.00           H  
HETATM   29  H11 UNL     1       2.834  -3.229   1.090  1.00  0.00           H  
HETATM   30  H12 UNL     1       4.651  -1.599   0.947  1.00  0.00           H  
HETATM   31  H13 UNL     1       3.461   2.621  -0.613  1.00  0.00           H  
HETATM   32  H14 UNL     1       5.197   2.898  -0.406  1.00  0.00           H  
HETATM   33  H15 UNL     1       1.885   1.377  -0.367  1.00  0.00           H  
HETATM   34  H16 UNL     1      -1.031   1.556   0.069  1.00  0.00           H  
HETATM   35  H17 UNL     1      -0.668   1.089  -1.672  1.00  0.00           H  
CONECT    1    2   19   20   21
CONECT    2    3   22
CONECT    3    4   18   23
CONECT    4    5   24   25
CONECT    5    6   26   27
CONECT    6    7   17   17
CONECT    7    8   28
CONECT    8    9    9   16
CONECT    9   10   29
CONECT   10   11   11   30
CONECT   11   12   15
CONECT   12   13   14   14
CONECT   13   31   32
CONECT   15   16   16   33
CONECT   16   17
CONECT   17   18
CONECT   18   34   35
END

HMDB0015133
     RDKit          3D
Frovatriptan
 35 37  0  0  0  0  0  0  0  0999 V2000
   -3.3976    2.3111    0.0934 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3891    1.4644   -1.0729 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5027    0.3291   -0.9362 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.9199   -0.5932    0.1812 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2738   -1.9487   -0.1486 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8012   -1.6772    0.0259 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1558   -2.5128    0.4253 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.3386   -1.8389    0.4404 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6317   -2.2107    0.7688 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6437   -1.2973    0.6880 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4029    0.0036    0.2812 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5078    0.9483    0.2084 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3793    2.2584   -0.3108 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.6324    0.5799    0.6284 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1111    0.3602   -0.0426 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0704   -0.5487    0.0321 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2949   -0.4252   -0.2379 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0796    0.7375   -0.6967 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9314    1.8608    0.9703 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9172    3.2718   -0.2152 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4515    2.5540    0.3318 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3310    1.1798   -1.3852 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5372   -0.2176   -1.9035 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4232   -0.2549    1.1185 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0002   -0.6807    0.3008 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6355   -2.7493    0.4879 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4299   -2.0939   -1.2354 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1133   -3.5226    0.7015 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8342   -3.2292    1.0896 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6512   -1.5994    0.9473 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4613    2.6210   -0.6129 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1969    2.8977   -0.4065 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8849    1.3768   -0.3671 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0313    1.5564    0.0686 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6684    1.0894   -1.6716 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  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  1  0
 12 14  2  0
 11 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  1  0
 18  3  1  0
 17  6  2  0
 16  8  1  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
  2 22  1  0
  3 23  1  6
  4 24  1  0
  4 25  1  0
  5 26  1  0
  5 27  1  0
  7 28  1  0
  9 29  1  0
 10 30  1  0
 13 31  1  0
 13 32  1  0
 15 33  1  0
 18 34  1  0
 18 35  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Allergo filmtabletten	Kegg
Frovatriptan succinate	HMDB
3-Methylamino-6-carboxamido-1,2,3,4-tetrahydrocarbazole	HMDB
Frovelan	HMDB
VML-251	HMDB
Allegro	HMDB
Frova	HMDB
(+)-(R)-5,6,7,8-Tetrahydro-6-(methylamino)carbazole-3-carboxamide succinate (1:1), monohydrate	HMDB

Chemical Formula

C₁₄H₁₇N₃O

Average Molecular Weight

243.3043

Monoisotopic Molecular Weight

243.137162181

IUPAC Name

(3R)-3-(methylamino)-2,3,4,9-tetrahydro-1H-carbazole-6-carboxamide

Traditional Name

frovatriptan

CAS Registry Number

158747-02-5

SMILES

CN[C@@H]1CCC2=C(C1)C1=C(N2)C=CC(=C1)C(N)=O

InChI Identifier

InChI=1S/C14H17N3O/c1-16-9-3-5-13-11(7-9)10-6-8(14(15)18)2-4-12(10)17-13/h2,4,6,9,16-17H,3,5,7H2,1H3,(H2,15,18)/t9-/m1/s1

InChI Key

XPSQPHWEGNHMSK-SECBINFHSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as carbazoles. Carbazoles are compounds containing a three ring system containing a pyrrole ring fused on either side to a benzene ring.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Indoles and derivatives

Sub Class

Carbazoles

Direct Parent

Carbazoles

Alternative Parents

Substituents

Carbazole
Indolecarboxamide derivative
Indolecarboxylic acid derivative
3-alkylindole
Indole
Aralkylamine
Benzenoid
Heteroaromatic compound
Pyrrole
Amino acid or derivatives
Carboxamide group
Primary carboxylic acid amide
Carboxylic acid derivative
Secondary aliphatic amine
Azacycle
Secondary amine
Hydrocarbon derivative
Organic oxide
Organic nitrogen compound
Amine
Organopnictogen compound
Organonitrogen compound
Organooxygen compound
Organic oxygen 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

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	0.12 g/L	Not Available
LogP	0.9	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.12 g/L	ALOGPS
logP	1.2	ALOGPS
logP	1.08	ChemAxon
logS	-3.3	ALOGPS
pKa (Strongest Acidic)	14.54	ChemAxon
pKa (Strongest Basic)	10.42	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	70.91 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	71.84 m³·mol⁻¹	ChemAxon
Polarizability	27.55 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]+	158.953	31661259
DarkChem	[M-H]-	158.84	31661259
DeepCCS	[M+H]+	157.518	30932474
DeepCCS	[M-H]-	155.16	30932474
DeepCCS	[M-2H]-	188.935	30932474
DeepCCS	[M+Na]+	163.981	30932474
AllCCS	[M+H]+	157.9	32859911
AllCCS	[M+H-H2O]+	154.1	32859911
AllCCS	[M+NH4]+	161.4	32859911
AllCCS	[M+Na]+	162.4	32859911
AllCCS	[M-H]-	162.2	32859911
AllCCS	[M+Na-2H]-	162.0	32859911
AllCCS	[M+HCOO]-	162.0	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Frovatriptan	CN[C@@H]1CCC2=C(C1)C1=C(N2)C=CC(=C1)C(N)=O	4022.3	Standard polar	33892256
Frovatriptan	CN[C@@H]1CCC2=C(C1)C1=C(N2)C=CC(=C1)C(N)=O	2691.1	Standard non polar	33892256
Frovatriptan	CN[C@@H]1CCC2=C(C1)C1=C(N2)C=CC(=C1)C(N)=O	2991.4	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Frovatriptan,1TMS,isomer #1	CN[C@@H]1CCC2=C(C1)C1=CC(C(=O)N[Si](C)(C)C)=CC=C1[NH]2	2791.0	Semi standard non polar	33892256
Frovatriptan,1TMS,isomer #1	CN[C@@H]1CCC2=C(C1)C1=CC(C(=O)N[Si](C)(C)C)=CC=C1[NH]2	2653.5	Standard non polar	33892256
Frovatriptan,1TMS,isomer #1	CN[C@@H]1CCC2=C(C1)C1=CC(C(=O)N[Si](C)(C)C)=CC=C1[NH]2	3298.0	Standard polar	33892256
Frovatriptan,1TMS,isomer #2	CN([C@@H]1CCC2=C(C1)C1=CC(C(N)=O)=CC=C1[NH]2)[Si](C)(C)C	2813.7	Semi standard non polar	33892256
Frovatriptan,1TMS,isomer #2	CN([C@@H]1CCC2=C(C1)C1=CC(C(N)=O)=CC=C1[NH]2)[Si](C)(C)C	2591.6	Standard non polar	33892256
Frovatriptan,1TMS,isomer #2	CN([C@@H]1CCC2=C(C1)C1=CC(C(N)=O)=CC=C1[NH]2)[Si](C)(C)C	3559.1	Standard polar	33892256
Frovatriptan,1TMS,isomer #3	CN[C@@H]1CCC2=C(C1)C1=CC(C(N)=O)=CC=C1N2[Si](C)(C)C	2741.0	Semi standard non polar	33892256
Frovatriptan,1TMS,isomer #3	CN[C@@H]1CCC2=C(C1)C1=CC(C(N)=O)=CC=C1N2[Si](C)(C)C	2505.1	Standard non polar	33892256
Frovatriptan,1TMS,isomer #3	CN[C@@H]1CCC2=C(C1)C1=CC(C(N)=O)=CC=C1N2[Si](C)(C)C	3371.6	Standard polar	33892256
Frovatriptan,2TMS,isomer #1	CN([C@@H]1CCC2=C(C1)C1=CC(C(=O)N[Si](C)(C)C)=CC=C1[NH]2)[Si](C)(C)C	2821.1	Semi standard non polar	33892256
Frovatriptan,2TMS,isomer #1	CN([C@@H]1CCC2=C(C1)C1=CC(C(=O)N[Si](C)(C)C)=CC=C1[NH]2)[Si](C)(C)C	2736.1	Standard non polar	33892256
Frovatriptan,2TMS,isomer #1	CN([C@@H]1CCC2=C(C1)C1=CC(C(=O)N[Si](C)(C)C)=CC=C1[NH]2)[Si](C)(C)C	3234.5	Standard polar	33892256
Frovatriptan,2TMS,isomer #2	CN[C@@H]1CCC2=C(C1)C1=CC(C(=O)N[Si](C)(C)C)=CC=C1N2[Si](C)(C)C	2742.8	Semi standard non polar	33892256
Frovatriptan,2TMS,isomer #2	CN[C@@H]1CCC2=C(C1)C1=CC(C(=O)N[Si](C)(C)C)=CC=C1N2[Si](C)(C)C	2587.7	Standard non polar	33892256
Frovatriptan,2TMS,isomer #2	CN[C@@H]1CCC2=C(C1)C1=CC(C(=O)N[Si](C)(C)C)=CC=C1N2[Si](C)(C)C	3023.3	Standard polar	33892256
Frovatriptan,2TMS,isomer #3	CN[C@@H]1CCC2=C(C1)C1=CC(C(=O)N([Si](C)(C)C)[Si](C)(C)C)=CC=C1[NH]2	2720.8	Semi standard non polar	33892256
Frovatriptan,2TMS,isomer #3	CN[C@@H]1CCC2=C(C1)C1=CC(C(=O)N([Si](C)(C)C)[Si](C)(C)C)=CC=C1[NH]2	2762.7	Standard non polar	33892256
Frovatriptan,2TMS,isomer #3	CN[C@@H]1CCC2=C(C1)C1=CC(C(=O)N([Si](C)(C)C)[Si](C)(C)C)=CC=C1[NH]2	3195.9	Standard polar	33892256
Frovatriptan,2TMS,isomer #4	CN([C@@H]1CCC2=C(C1)C1=CC(C(N)=O)=CC=C1N2[Si](C)(C)C)[Si](C)(C)C	2792.9	Semi standard non polar	33892256
Frovatriptan,2TMS,isomer #4	CN([C@@H]1CCC2=C(C1)C1=CC(C(N)=O)=CC=C1N2[Si](C)(C)C)[Si](C)(C)C	2620.9	Standard non polar	33892256
Frovatriptan,2TMS,isomer #4	CN([C@@H]1CCC2=C(C1)C1=CC(C(N)=O)=CC=C1N2[Si](C)(C)C)[Si](C)(C)C	3306.3	Standard polar	33892256
Frovatriptan,3TMS,isomer #1	CN([C@@H]1CCC2=C(C1)C1=CC(C(=O)N[Si](C)(C)C)=CC=C1N2[Si](C)(C)C)[Si](C)(C)C	2802.8	Semi standard non polar	33892256
Frovatriptan,3TMS,isomer #1	CN([C@@H]1CCC2=C(C1)C1=CC(C(=O)N[Si](C)(C)C)=CC=C1N2[Si](C)(C)C)[Si](C)(C)C	2726.0	Standard non polar	33892256
Frovatriptan,3TMS,isomer #1	CN([C@@H]1CCC2=C(C1)C1=CC(C(=O)N[Si](C)(C)C)=CC=C1N2[Si](C)(C)C)[Si](C)(C)C	2963.4	Standard polar	33892256
Frovatriptan,3TMS,isomer #2	CN([C@@H]1CCC2=C(C1)C1=CC(C(=O)N([Si](C)(C)C)[Si](C)(C)C)=CC=C1[NH]2)[Si](C)(C)C	2790.3	Semi standard non polar	33892256
Frovatriptan,3TMS,isomer #2	CN([C@@H]1CCC2=C(C1)C1=CC(C(=O)N([Si](C)(C)C)[Si](C)(C)C)=CC=C1[NH]2)[Si](C)(C)C	2838.4	Standard non polar	33892256
Frovatriptan,3TMS,isomer #2	CN([C@@H]1CCC2=C(C1)C1=CC(C(=O)N([Si](C)(C)C)[Si](C)(C)C)=CC=C1[NH]2)[Si](C)(C)C	3091.8	Standard polar	33892256
Frovatriptan,3TMS,isomer #3	CN[C@@H]1CCC2=C(C1)C1=CC(C(=O)N([Si](C)(C)C)[Si](C)(C)C)=CC=C1N2[Si](C)(C)C	2709.2	Semi standard non polar	33892256
Frovatriptan,3TMS,isomer #3	CN[C@@H]1CCC2=C(C1)C1=CC(C(=O)N([Si](C)(C)C)[Si](C)(C)C)=CC=C1N2[Si](C)(C)C	2717.7	Standard non polar	33892256
Frovatriptan,3TMS,isomer #3	CN[C@@H]1CCC2=C(C1)C1=CC(C(=O)N([Si](C)(C)C)[Si](C)(C)C)=CC=C1N2[Si](C)(C)C	2896.0	Standard polar	33892256
Frovatriptan,4TMS,isomer #1	CN([C@@H]1CCC2=C(C1)C1=CC(C(=O)N([Si](C)(C)C)[Si](C)(C)C)=CC=C1N2[Si](C)(C)C)[Si](C)(C)C	2817.9	Semi standard non polar	33892256
Frovatriptan,4TMS,isomer #1	CN([C@@H]1CCC2=C(C1)C1=CC(C(=O)N([Si](C)(C)C)[Si](C)(C)C)=CC=C1N2[Si](C)(C)C)[Si](C)(C)C	2831.1	Standard non polar	33892256
Frovatriptan,4TMS,isomer #1	CN([C@@H]1CCC2=C(C1)C1=CC(C(=O)N([Si](C)(C)C)[Si](C)(C)C)=CC=C1N2[Si](C)(C)C)[Si](C)(C)C	2834.1	Standard polar	33892256
Frovatriptan,1TBDMS,isomer #1	CN[C@@H]1CCC2=C(C1)C1=CC(C(=O)N[Si](C)(C)C(C)(C)C)=CC=C1[NH]2	3016.1	Semi standard non polar	33892256
Frovatriptan,1TBDMS,isomer #1	CN[C@@H]1CCC2=C(C1)C1=CC(C(=O)N[Si](C)(C)C(C)(C)C)=CC=C1[NH]2	2900.1	Standard non polar	33892256
Frovatriptan,1TBDMS,isomer #1	CN[C@@H]1CCC2=C(C1)C1=CC(C(=O)N[Si](C)(C)C(C)(C)C)=CC=C1[NH]2	3381.4	Standard polar	33892256
Frovatriptan,1TBDMS,isomer #2	CN([C@@H]1CCC2=C(C1)C1=CC(C(N)=O)=CC=C1[NH]2)[Si](C)(C)C(C)(C)C	3068.1	Semi standard non polar	33892256
Frovatriptan,1TBDMS,isomer #2	CN([C@@H]1CCC2=C(C1)C1=CC(C(N)=O)=CC=C1[NH]2)[Si](C)(C)C(C)(C)C	2845.9	Standard non polar	33892256
Frovatriptan,1TBDMS,isomer #2	CN([C@@H]1CCC2=C(C1)C1=CC(C(N)=O)=CC=C1[NH]2)[Si](C)(C)C(C)(C)C	3639.4	Standard polar	33892256
Frovatriptan,1TBDMS,isomer #3	CN[C@@H]1CCC2=C(C1)C1=CC(C(N)=O)=CC=C1N2[Si](C)(C)C(C)(C)C	2972.3	Semi standard non polar	33892256
Frovatriptan,1TBDMS,isomer #3	CN[C@@H]1CCC2=C(C1)C1=CC(C(N)=O)=CC=C1N2[Si](C)(C)C(C)(C)C	2745.9	Standard non polar	33892256
Frovatriptan,1TBDMS,isomer #3	CN[C@@H]1CCC2=C(C1)C1=CC(C(N)=O)=CC=C1N2[Si](C)(C)C(C)(C)C	3444.1	Standard polar	33892256
Frovatriptan,2TBDMS,isomer #1	CN([C@@H]1CCC2=C(C1)C1=CC(C(=O)N[Si](C)(C)C(C)(C)C)=CC=C1[NH]2)[Si](C)(C)C(C)(C)C	3281.9	Semi standard non polar	33892256
Frovatriptan,2TBDMS,isomer #1	CN([C@@H]1CCC2=C(C1)C1=CC(C(=O)N[Si](C)(C)C(C)(C)C)=CC=C1[NH]2)[Si](C)(C)C(C)(C)C	3232.2	Standard non polar	33892256
Frovatriptan,2TBDMS,isomer #1	CN([C@@H]1CCC2=C(C1)C1=CC(C(=O)N[Si](C)(C)C(C)(C)C)=CC=C1[NH]2)[Si](C)(C)C(C)(C)C	3378.1	Standard polar	33892256
Frovatriptan,2TBDMS,isomer #2	CN[C@@H]1CCC2=C(C1)C1=CC(C(=O)N[Si](C)(C)C(C)(C)C)=CC=C1N2[Si](C)(C)C(C)(C)C	3188.2	Semi standard non polar	33892256
Frovatriptan,2TBDMS,isomer #2	CN[C@@H]1CCC2=C(C1)C1=CC(C(=O)N[Si](C)(C)C(C)(C)C)=CC=C1N2[Si](C)(C)C(C)(C)C	3082.4	Standard non polar	33892256
Frovatriptan,2TBDMS,isomer #2	CN[C@@H]1CCC2=C(C1)C1=CC(C(=O)N[Si](C)(C)C(C)(C)C)=CC=C1N2[Si](C)(C)C(C)(C)C	3176.1	Standard polar	33892256
Frovatriptan,2TBDMS,isomer #3	CN[C@@H]1CCC2=C(C1)C1=CC(C(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=CC=C1[NH]2	3192.1	Semi standard non polar	33892256
Frovatriptan,2TBDMS,isomer #3	CN[C@@H]1CCC2=C(C1)C1=CC(C(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=CC=C1[NH]2	3223.6	Standard non polar	33892256
Frovatriptan,2TBDMS,isomer #3	CN[C@@H]1CCC2=C(C1)C1=CC(C(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=CC=C1[NH]2	3311.3	Standard polar	33892256
Frovatriptan,2TBDMS,isomer #4	CN([C@@H]1CCC2=C(C1)C1=CC(C(N)=O)=CC=C1N2[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3236.7	Semi standard non polar	33892256
Frovatriptan,2TBDMS,isomer #4	CN([C@@H]1CCC2=C(C1)C1=CC(C(N)=O)=CC=C1N2[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3101.8	Standard non polar	33892256
Frovatriptan,2TBDMS,isomer #4	CN([C@@H]1CCC2=C(C1)C1=CC(C(N)=O)=CC=C1N2[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3382.2	Standard polar	33892256
Frovatriptan,3TBDMS,isomer #1	CN([C@@H]1CCC2=C(C1)C1=CC(C(=O)N[Si](C)(C)C(C)(C)C)=CC=C1N2[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3444.8	Semi standard non polar	33892256
Frovatriptan,3TBDMS,isomer #1	CN([C@@H]1CCC2=C(C1)C1=CC(C(=O)N[Si](C)(C)C(C)(C)C)=CC=C1N2[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3401.7	Standard non polar	33892256
Frovatriptan,3TBDMS,isomer #1	CN([C@@H]1CCC2=C(C1)C1=CC(C(=O)N[Si](C)(C)C(C)(C)C)=CC=C1N2[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3231.6	Standard polar	33892256
Frovatriptan,3TBDMS,isomer #2	CN([C@@H]1CCC2=C(C1)C1=CC(C(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=CC=C1[NH]2)[Si](C)(C)C(C)(C)C	3507.4	Semi standard non polar	33892256
Frovatriptan,3TBDMS,isomer #2	CN([C@@H]1CCC2=C(C1)C1=CC(C(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=CC=C1[NH]2)[Si](C)(C)C(C)(C)C	3519.0	Standard non polar	33892256
Frovatriptan,3TBDMS,isomer #2	CN([C@@H]1CCC2=C(C1)C1=CC(C(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=CC=C1[NH]2)[Si](C)(C)C(C)(C)C	3315.2	Standard polar	33892256
Frovatriptan,3TBDMS,isomer #3	CN[C@@H]1CCC2=C(C1)C1=CC(C(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=CC=C1N2[Si](C)(C)C(C)(C)C	3339.9	Semi standard non polar	33892256
Frovatriptan,3TBDMS,isomer #3	CN[C@@H]1CCC2=C(C1)C1=CC(C(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=CC=C1N2[Si](C)(C)C(C)(C)C	3367.7	Standard non polar	33892256
Frovatriptan,3TBDMS,isomer #3	CN[C@@H]1CCC2=C(C1)C1=CC(C(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=CC=C1N2[Si](C)(C)C(C)(C)C	3148.1	Standard polar	33892256
Frovatriptan,4TBDMS,isomer #1	CN([C@@H]1CCC2=C(C1)C1=CC(C(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=CC=C1N2[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3658.3	Semi standard non polar	33892256
Frovatriptan,4TBDMS,isomer #1	CN([C@@H]1CCC2=C(C1)C1=CC(C(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=CC=C1N2[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3634.0	Standard non polar	33892256
Frovatriptan,4TBDMS,isomer #1	CN([C@@H]1CCC2=C(C1)C1=CC(C(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=CC=C1N2[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3169.0	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Frovatriptan GC-MS (Non-derivatized) - 70eV, Positive	splash10-004i-3690000000-20d2133e95fbc6b1f414	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Frovatriptan 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 - Frovatriptan 10V, Positive-QTOF	splash10-0006-0190000000-fc527e672048d9bf866c	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Frovatriptan 20V, Positive-QTOF	splash10-004i-0490000000-09182e67659519af87e7	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Frovatriptan 40V, Positive-QTOF	splash10-0l1i-0910000000-81f4aa818323e96b5464	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Frovatriptan 10V, Negative-QTOF	splash10-0006-0090000000-bd79ad698f8bd9fbb84b	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Frovatriptan 20V, Negative-QTOF	splash10-0006-2490000000-4632cbf11a6dc353d2cf	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Frovatriptan 40V, Negative-QTOF	splash10-0006-9200000000-948170ac23122892a5ad	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Frovatriptan 10V, Positive-QTOF	splash10-0006-0090000000-168fda82142bf345541b	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Frovatriptan 20V, Positive-QTOF	splash10-002f-0090000000-3dac4efa84856ab16486	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Frovatriptan 40V, Positive-QTOF	splash10-000i-0910000000-bdfabb283d321aa1d9e3	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Frovatriptan 10V, Negative-QTOF	splash10-0006-0090000000-932ee60351365d51e611	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Frovatriptan 20V, Negative-QTOF	splash10-0006-1190000000-c3fd5753f8f9a8a098eb	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Frovatriptan 40V, Negative-QTOF	splash10-0006-4910000000-8fac1192455fd2253b72	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 DB00998	21059682	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB00998	21059682	details

Abnormal Concentrations

Not Available

Predicted Concentrations

Biospecimen	Value	Original age	Original sex	Original condition	Comments
Blood	0.000 uM	Adult (>18 years old)	Both	Normal	Predicted based on drug qualities
Blood	0.000 umol/mmol creatinine	Adult (>18 years old)	Both	Normal	Predicted based on drug qualities

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB00998

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

70378

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Frovatriptan

METLIN ID

Not Available

PubChem Compound

77992

PDB ID

Not Available

ChEBI ID

350328

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

Easthope SE, Goa KL: Frovatriptan. CNS Drugs. 2001;15(12):969-76; discussion 977-8. [PubMed:11735616 ]
Balbisi EA: Frovatriptan succinate, a 5-HT1B/1D receptor agonist for migraine. Int J Clin Pract. 2004 Jul;58(7):695-705. [PubMed:15311727 ]
Balbisi EA: Frovatriptan: a review of pharmacology, pharmacokinetics and clinical potential in the treatment of menstrual migraine. Ther Clin Risk Manag. 2006 Sep;2(3):303-8. [PubMed:18360605 ]
Elkind AH, Wade A, Ishkanian G: Pharmacokinetics of frovatriptan in adolescent migraineurs. J Clin Pharmacol. 2004 Oct;44(10):1158-65. [PubMed:15342617 ]
Markus F, Mikko K: Frovatriptan review. Expert Opin Pharmacother. 2007 Dec;8(17):3029-33. [PubMed:18001261 ]
Jhee SS, Shiovitz T, Crawford AW, Cutler NR: Pharmacokinetics and pharmacodynamics of the triptan antimigraine agents: a comparative review. Clin Pharmacokinet. 2001;40(3):189-205. [PubMed:11327198 ]
Sanford M: Frovatriptan: a review of its use in the acute treatment of migraine. CNS Drugs. 2012 Sep 1;26(9):791-811. doi: 10.2165/11209380-000000000-00000. [PubMed:22900951 ]
Cady RK, Farmer K: Managing migraine by patient profile: role of frovatriptan. Patient Prefer Adherence. 2016 Apr 5;10:501-10. doi: 10.2147/PPA.S85795. eCollection 2016. [PubMed:27103792 ]
Goldstein J: Frovatriptan: a review. Expert Opin Pharmacother. 2003 Jan;4(1):83-93. doi: 10.1517/14656566.4.1.83. [PubMed:12517245 ]

Enzymes

Enzyme Details

1. Cytochrome P450 1A2

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. Most active in catalyzing 2-hydroxylation. Caffeine is metabolized primarily by cytochrome CYP1A2 in the liver through an initial N3-demethylation. Also acts in the metabolism of aflatoxin B1 and acetaminophen. Participates in the bioactivation of carcinogenic aromatic and heterocyclic amines. Catalizes the N-hydroxylation of heterocyclic amines and the O-deethylation of phenacetin.
Gene Name:: CYP1A2
Uniprot ID:: P05177
Molecular weight:: 58406.915

References

Easthope SE, Goa KL: Frovatriptan. CNS Drugs. 2001;15(12):969-76; discussion 977-8. [PubMed:11735616 ]
Buchan P, Keywood C, Wade A, Ward C: Clinical pharmacokinetics of frovatriptan. Headache. 2002 Apr;42 Suppl 2:S54-62. [PubMed:12028321 ]
Buchan P, Wade A, Ward C, Oliver SD, Stewart AJ, Freestone S: Frovatriptan: a review of drug-drug interactions. Headache. 2002 Apr;42 Suppl 2:S63-73. [PubMed:12028322 ]
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. 5-hydroxytryptamine receptor 1B

General function:: Involved in G-protein coupled receptor protein signaling pathway
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. The activity of this receptor is mediated by G proteins that inhibit adenylate cyclase activity
Gene Name:: HTR1B
Uniprot ID:: P28222
Molecular weight:: 43567.5

References

Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]
Balbisi EA: Frovatriptan succinate, a 5-HT1B/1D receptor agonist for migraine. Int J Clin Pract. 2004 Jul;58(7):695-705. [PubMed:15311727 ]
Comer MB: Pharmacology of the selective 5-HT(1B/1D) agonist frovatriptan. Headache. 2002 Apr;42 Suppl 2:S47-53. [PubMed:12028320 ]
Parsons AA, Raval P, Smith S, Tilford N, King FD, Kaumann AJ, Hunter J: Effects of the novel high-affinity 5-HT(1B/1D)-receptor ligand frovatriptan in human isolated basilar and coronary arteries. J Cardiovasc Pharmacol. 1998 Aug;32(2):220-4. [PubMed:9700983 ]
Easthope SE, Goa KL: Frovatriptan. CNS Drugs. 2001;15(12):969-76; discussion 977-8. [PubMed:11735616 ]
Dodick DW, Sandrini G, Williams P: Use of the sustained pain-free plus no adverse events endpoint in clinical trials of triptans in acute migraine. CNS Drugs. 2007;21(1):73-82. [PubMed:17190530 ]
Tfelt-Hansen P, De Vries P, Saxena PR: Triptans in migraine: a comparative review of pharmacology, pharmacokinetics and efficacy. Drugs. 2000 Dec;60(6):1259-87. [PubMed:11152011 ]
Deleu D, Hanssens Y: Current and emerging second-generation triptans in acute migraine therapy: a comparative review. J Clin Pharmacol. 2000 Jul;40(7):687-700. [PubMed:10883409 ]
Markus F, Mikko K: Frovatriptan review. Expert Opin Pharmacother. 2007 Dec;8(17):3029-33. [PubMed:18001261 ]
Balbisi EA: Frovatriptan: a review of pharmacology, pharmacokinetics and clinical potential in the treatment of menstrual migraine. Ther Clin Risk Manag. 2006 Sep;2(3):303-8. [PubMed:18360605 ]
Elkind AH, Wade A, Ishkanian G: Pharmacokinetics of frovatriptan in adolescent migraineurs. J Clin Pharmacol. 2004 Oct;44(10):1158-65. [PubMed:15342617 ]
Buchan P, Wade A, Ward C, Oliver SD, Stewart AJ, Freestone S: Frovatriptan: a review of drug-drug interactions. Headache. 2002 Apr;42 Suppl 2:S63-73. [PubMed:12028322 ]

Enzyme Details

3. 5-hydroxytryptamine receptor 1D

General function:: Involved in G-protein coupled receptor protein signaling pathway
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. The activity of this receptor is mediated by G proteins that inhibit adenylate cyclase activity
Gene Name:: HTR1D
Uniprot ID:: P28221
Molecular weight:: 41906.4

References

Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]
Easthope SE, Goa KL: Frovatriptan. CNS Drugs. 2001;15(12):969-76; discussion 977-8. [PubMed:11735616 ]
Comer MB: Pharmacology of the selective 5-HT(1B/1D) agonist frovatriptan. Headache. 2002 Apr;42 Suppl 2:S47-53. [PubMed:12028320 ]
Tfelt-Hansen P, De Vries P, Saxena PR: Triptans in migraine: a comparative review of pharmacology, pharmacokinetics and efficacy. Drugs. 2000 Dec;60(6):1259-87. [PubMed:11152011 ]
Deleu D, Hanssens Y: Current and emerging second-generation triptans in acute migraine therapy: a comparative review. J Clin Pharmacol. 2000 Jul;40(7):687-700. [PubMed:10883409 ]
Jahnichen S, Radtke OA, Pertz HH: Involvement of 5-HT1B receptors in triptan-induced contractile responses in guinea-pig isolated iliac artery. Naunyn Schmiedebergs Arch Pharmacol. 2004 Jul;370(1):54-63. Epub 2004 Jun 8. [PubMed:15185063 ]
Balbisi EA: Frovatriptan succinate, a 5-HT1B/1D receptor agonist for migraine. Int J Clin Pract. 2004 Jul;58(7):695-705. [PubMed:15311727 ]
Parsons AA, Raval P, Smith S, Tilford N, King FD, Kaumann AJ, Hunter J: Effects of the novel high-affinity 5-HT(1B/1D)-receptor ligand frovatriptan in human isolated basilar and coronary arteries. J Cardiovasc Pharmacol. 1998 Aug;32(2):220-4. [PubMed:9700983 ]
Balbisi EA: Frovatriptan: a review of pharmacology, pharmacokinetics and clinical potential in the treatment of menstrual migraine. Ther Clin Risk Manag. 2006 Sep;2(3):303-8. [PubMed:18360605 ]
Elkind AH, Wade A, Ishkanian G: Pharmacokinetics of frovatriptan in adolescent migraineurs. J Clin Pharmacol. 2004 Oct;44(10):1158-65. [PubMed:15342617 ]
Buchan P, Wade A, Ward C, Oliver SD, Stewart AJ, Freestone S: Frovatriptan: a review of drug-drug interactions. Headache. 2002 Apr;42 Suppl 2:S63-73. [PubMed:12028322 ]

Showing metabocard for Frovatriptan (HMDB0015133)

MOL for HMDB0015133 (Frovatriptan)

3D MOL for HMDB0015133 (Frovatriptan)

3D SDF for HMDB0015133 (Frovatriptan)

3D-SDF for HMDB0015133 (Frovatriptan)

PDB for HMDB0015133 (Frovatriptan)

3D PDB for HMDB0015133 (Frovatriptan)

SMILES for HMDB0015133 (Frovatriptan)

INCHI for HMDB0015133 (Frovatriptan)

Structure for HMDB0015133 (Frovatriptan)

3D Structure for HMDB0015133 (Frovatriptan)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

Enzymes

References

References

References