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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 02:51:51 UTC

HMDB ID

HMDB0015087

Secondary Accession Numbers

HMDB15087

Metabolite Identification

Common Name

Naratriptan

Description

Naratriptan, also known as naramig or amerge, belongs to the class of organic compounds known as 3-alkylindoles. 3-alkylindoles are compounds containing an indole moiety that carries an alkyl chain at the 3-position. It was covered by U.S. Patent no. 4997841; the FDA lists the patent as expiring on July 7, 2010. Naratriptan is a drug which is used for the acute treatment of migraine attacks with or without aura in adults. Side-effects which are unlikely and which should be promptly reported include: chest pain/pressure, throat pain/pressure, unusually fast/slow/irregular pulse, one-sided muscle weakness, vision problems, cold/bluish hands or feet, stomach pain, bloody diarrhea, mental/mood changes, and fainting. Because Teva and Sandoz are the only approved suppliers of generic Naratriptan in Canada, the quarantine resulted in Naratriptan being placed on the Canadian drug shortage list. Naratriptan is a very strong basic compound (based on its pKa). Naratriptan is a potentially toxic compound. Naratriptan is used for the treatment of the acute migraine attacks and the symptoms of migraine, including severe, throbbing headaches that sometimes are accompanied by nausea and sensitivity to sound or light. Symptoms of a serious allergic reaction include: rash, itching, swelling, severe dizziness, trouble breathing (swelling of the throat). In July 2010, in the wake of the patent expiration, several drug manufacturers, including Roxane Labs, Sandoz and Teva Pharmaceuticals, announced that they were launching generic Naratriptan medications. A meta-analysis of 53 clinical trials has shown that all triptans are effective for treating migraine at marketed doses and that naratriptan, although less effective than sumatriptan and rizatriptan was more effective than placebo in reducing migraine symptoms at two hours and efficacy was demonstrated in almost two thirds of subjects after four hours of treatment. Naratriptan (trade names include Amerge) is a triptan drug marketed by GlaxoSmithKline and is used for the treatment of migraine headaches. It had previously been covered by Canadian patent 1210968; but both Sandoz and Teva (formerly Novopharm) have offered generic equivalents in Canada since that patent's expiration December 1, 2009.

Structure

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

HMDB0015087
     RDKit          3D
Naratriptan
 48 50  0  0  0  0  0  0  0  0999 V2000
    4.4799   -1.0804    1.5314 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0792   -0.3719    0.3018 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.6012   -1.2118   -1.1046 S   0  0  0  0  0  6  0  0  0  0  0  0
    5.3308   -2.4646   -0.6258 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6294   -0.4178   -1.8679 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2368   -1.6712   -2.0886 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4518   -0.5496   -2.7015 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9228    0.4263   -1.7576 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7244    1.5263   -1.4863 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2604    2.4596   -0.5972 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0185    2.2944    0.0079 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4241    3.0821    0.8964 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7275    2.5232    1.1987 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8938    1.3128    0.4700 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1427    0.5452    0.5917 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8156    0.8519    1.9195 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8658   -0.1808    2.1847 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4747   -0.5919    0.9576 N   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8570   -0.8574    0.9717 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6268   -1.3965    0.1673 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1851   -0.8586    0.2054 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2299    1.2009   -0.2694 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6852    0.2587   -1.1594 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2950   -0.4305    1.9582 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8168   -2.0910    1.3247 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6600   -1.0344    2.2659 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0131   -0.4935    0.3220 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6266   -2.3761   -2.8709 H   0  0  0  0  0  0  0  0  0  0  0  0
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    1.6480   -1.0413   -3.3112 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0958   -0.0475   -3.4583 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7069    1.6423   -1.9721 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8704    3.3234   -0.3738 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7554    3.9785    1.3127 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4574    2.9019    1.8883 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8739    1.0668   -0.1484 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0850    0.8157    2.7574 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3079    1.8481    1.8614 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4206   -1.1196    2.6385 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6220    0.1508    2.9184 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2852   -1.2026    0.0283 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4000    0.1027    1.2388 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0919   -1.5230    1.8523 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0282   -1.4108   -0.8791 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6265   -2.4412    0.5483 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5587   -1.5710    0.7859 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8884   -0.9222   -0.8905 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1059   -0.6091   -1.3908 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  3  5  2  0
  3  6  1  0
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  7  8  1  0
  8  9  2  0
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 23 48  1  0
M  END

952
  Mrv0541 02231215072D          

 23 25  0  0  0  0            999 V2000
    3.0791   -0.5003    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    3.4916    0.2142    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6665   -1.2148    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.2010    1.6912    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.4321   -1.9892    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -0.0878    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.6884    0.1228    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4957    0.2930    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1374    0.7369    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7520    1.0771    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3937    1.5211    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4321   -0.6613    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6515   -0.9128    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9136   -1.3253    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6515   -1.7378    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4573    2.4754    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9370   -0.5003    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2224   -0.9128    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9370   -2.1503    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080   -0.5003    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2224   -1.7378    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935   -0.9128    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500   -0.5003    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  1  3  2  0  0  0  0
  1  6  1  0  0  0  0
  1 22  1  0  0  0  0
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  7  9  1  0  0  0  0
  7 12  1  0  0  0  0
  8 10  1  0  0  0  0
  9 11  1  0  0  0  0
 12 13  1  0  0  0  0
 12 14  2  0  0  0  0
 13 15  2  0  0  0  0
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 20 22  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0015087

> <DATABASE_NAME>
hmdb

> <SMILES>
CNS(=O)(=O)CCC1=CC2=C(NC=C2C2CCN(C)CC2)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C17H25N3O2S/c1-18-23(21,22)10-7-13-3-4-17-15(11-13)16(12-19-17)14-5-8-20(2)9-6-14/h3-4,11-12,14,18-19H,5-10H2,1-2H3

> <INCHI_KEY>
AMKVXSZCKVJAGH-UHFFFAOYSA-N

> <FORMULA>
C17H25N3O2S

> <MOLECULAR_WEIGHT>
335.464

> <EXACT_MASS>
335.166747749

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
38.00236193067244

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
N-methyl-2-[3-(1-methylpiperidin-4-yl)-1H-indol-5-yl]ethane-1-sulfonamide

> <ALOGPS_LOGP>
2.16

> <JCHEM_LOGP>
1.440624933

> <ALOGPS_LOGS>
-3.47

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
17.113643722273398

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.549356572949735

> <JCHEM_PKA_STRONGEST_BASIC>
9.182862337667046

> <JCHEM_POLAR_SURFACE_AREA>
65.2

> <JCHEM_REFRACTIVITY>
94.25720000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.14e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
naratriptan

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0015087
     RDKit          3D
Naratriptan
 48 50  0  0  0  0  0  0  0  0999 V2000
    4.4799   -1.0804    1.5314 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0792   -0.3719    0.3018 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.6012   -1.2118   -1.1046 S   0  0  0  0  0  6  0  0  0  0  0  0
    5.3308   -2.4646   -0.6258 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6294   -0.4178   -1.8679 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2368   -1.6712   -2.0886 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4518   -0.5496   -2.7015 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9228    0.4263   -1.7576 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7244    1.5263   -1.4863 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2604    2.4596   -0.5972 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0185    2.2944    0.0079 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4241    3.0821    0.8964 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7275    2.5232    1.1987 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8938    1.3128    0.4700 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1427    0.5452    0.5917 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8156    0.8519    1.9195 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8658   -0.1808    2.1847 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4747   -0.5919    0.9576 N   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8570   -0.8574    0.9717 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6268   -1.3965    0.1673 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1851   -0.8586    0.2054 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2299    1.2009   -0.2694 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6852    0.2587   -1.1594 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2950   -0.4305    1.9582 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -4.6220    0.1508    2.9184 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2852   -1.2026    0.0283 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4000    0.1027    1.2388 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -3.6265   -2.4412    0.5483 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5587   -1.5710    0.7859 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8884   -0.9222   -0.8905 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1059   -0.6091   -1.3908 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
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 17 40  1  0
 19 41  1  0
 19 42  1  0
 19 43  1  0
 20 44  1  0
 20 45  1  0
 21 46  1  0
 21 47  1  0
 23 48  1  0
M  END

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 952                                               
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  S   UNK     0       5.748  -0.934   0.000  0.00  0.00           S+0
HETATM    2  O   UNK     0       6.518   0.400   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0       4.977  -2.268   0.000  0.00  0.00           O+0
HETATM    4  N   UNK     0      15.309   3.157   0.000  0.00  0.00           N+0
HETATM    5  N   UNK     0      13.873  -3.713   0.000  0.00  0.00           N+0
HETATM    6  N   UNK     0       4.414  -0.164   0.000  0.00  0.00           N+0
HETATM    7  C   UNK     0      14.352   0.229   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      15.859   0.547   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      13.323   1.376   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      16.337   2.011   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      13.802   2.839   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      13.873  -1.234   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      12.416  -1.704   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      14.772  -2.474   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      12.416  -3.244   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      15.787   4.621   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      11.082  -0.934   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       9.748  -1.704   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      11.082  -4.014   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       8.415  -0.934   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       9.748  -3.244   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       7.081  -1.704   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       3.080  -0.934   0.000  0.00  0.00           C+0
CONECT    1    2    3    6   22                                             
CONECT    2    1                                                            
CONECT    3    1                                                            
CONECT    4   10   11   16                                                  
CONECT    5   14   15                                                       
CONECT    6    1   23                                                       
CONECT    7    8    9   12                                                  
CONECT    8    7   10                                                       
CONECT    9    7   11                                                       
CONECT   10    4    8                                                       
CONECT   11    4    9                                                       
CONECT   12    7   13   14                                                  
CONECT   13   12   15   17                                                  
CONECT   14    5   12                                                       
CONECT   15    5   13   19                                                  
CONECT   16    4                                                            
CONECT   17   13   18                                                       
CONECT   18   17   20   21                                                  
CONECT   19   15   21                                                       
CONECT   20   18   22                                                       
CONECT   21   18   19                                                       
CONECT   22    1   20                                                       
CONECT   23    6                                                            
MASTER        0    0    0    0    0    0    0    0   23    0   50    0
END

COMPND    HMDB0015087
HETATM    1  C1  UNL     1       4.480  -1.080   1.531  1.00  0.00           C  
HETATM    2  N1  UNL     1       4.079  -0.372   0.302  1.00  0.00           N  
HETATM    3  S1  UNL     1       4.601  -1.212  -1.105  1.00  0.00           S  
HETATM    4  O1  UNL     1       5.331  -2.465  -0.626  1.00  0.00           O  
HETATM    5  O2  UNL     1       5.629  -0.418  -1.868  1.00  0.00           O  
HETATM    6  C2  UNL     1       3.237  -1.671  -2.089  1.00  0.00           C  
HETATM    7  C3  UNL     1       2.452  -0.550  -2.702  1.00  0.00           C  
HETATM    8  C4  UNL     1       1.923   0.426  -1.758  1.00  0.00           C  
HETATM    9  C5  UNL     1       2.724   1.526  -1.486  1.00  0.00           C  
HETATM   10  C6  UNL     1       2.260   2.460  -0.597  1.00  0.00           C  
HETATM   11  C7  UNL     1       1.018   2.294   0.008  1.00  0.00           C  
HETATM   12  N2  UNL     1       0.424   3.082   0.896  1.00  0.00           N  
HETATM   13  C8  UNL     1      -0.727   2.523   1.199  1.00  0.00           C  
HETATM   14  C9  UNL     1      -0.894   1.313   0.470  1.00  0.00           C  
HETATM   15  C10 UNL     1      -2.143   0.545   0.592  1.00  0.00           C  
HETATM   16  C11 UNL     1      -2.816   0.852   1.919  1.00  0.00           C  
HETATM   17  C12 UNL     1      -3.866  -0.181   2.185  1.00  0.00           C  
HETATM   18  N3  UNL     1      -4.475  -0.592   0.958  1.00  0.00           N  
HETATM   19  C13 UNL     1      -5.857  -0.857   0.972  1.00  0.00           C  
HETATM   20  C14 UNL     1      -3.627  -1.397   0.167  1.00  0.00           C  
HETATM   21  C15 UNL     1      -2.185  -0.859   0.205  1.00  0.00           C  
HETATM   22  C16 UNL     1       0.230   1.201  -0.269  1.00  0.00           C  
HETATM   23  C17 UNL     1       0.685   0.259  -1.159  1.00  0.00           C  
HETATM   24  H1  UNL     1       5.295  -0.431   1.958  1.00  0.00           H  
HETATM   25  H2  UNL     1       4.817  -2.091   1.325  1.00  0.00           H  
HETATM   26  H3  UNL     1       3.660  -1.034   2.266  1.00  0.00           H  
HETATM   27  H4  UNL     1       3.013  -0.494   0.322  1.00  0.00           H  
HETATM   28  H5  UNL     1       3.627  -2.376  -2.871  1.00  0.00           H  
HETATM   29  H6  UNL     1       2.566  -2.345  -1.473  1.00  0.00           H  
HETATM   30  H7  UNL     1       1.648  -1.041  -3.311  1.00  0.00           H  
HETATM   31  H8  UNL     1       3.096  -0.048  -3.458  1.00  0.00           H  
HETATM   32  H9  UNL     1       3.707   1.642  -1.972  1.00  0.00           H  
HETATM   33  H10 UNL     1       2.870   3.323  -0.374  1.00  0.00           H  
HETATM   34  H11 UNL     1       0.755   3.979   1.313  1.00  0.00           H  
HETATM   35  H12 UNL     1      -1.457   2.902   1.888  1.00  0.00           H  
HETATM   36  H13 UNL     1      -2.874   1.067  -0.148  1.00  0.00           H  
HETATM   37  H14 UNL     1      -2.085   0.816   2.757  1.00  0.00           H  
HETATM   38  H15 UNL     1      -3.308   1.848   1.861  1.00  0.00           H  
HETATM   39  H16 UNL     1      -3.421  -1.120   2.639  1.00  0.00           H  
HETATM   40  H17 UNL     1      -4.622   0.151   2.918  1.00  0.00           H  
HETATM   41  H18 UNL     1      -6.285  -1.203   0.028  1.00  0.00           H  
HETATM   42  H19 UNL     1      -6.400   0.103   1.239  1.00  0.00           H  
HETATM   43  H20 UNL     1      -6.092  -1.523   1.852  1.00  0.00           H  
HETATM   44  H21 UNL     1      -4.028  -1.411  -0.879  1.00  0.00           H  
HETATM   45  H22 UNL     1      -3.627  -2.441   0.548  1.00  0.00           H  
HETATM   46  H23 UNL     1      -1.559  -1.571   0.786  1.00  0.00           H  
HETATM   47  H24 UNL     1      -1.888  -0.922  -0.891  1.00  0.00           H  
HETATM   48  H25 UNL     1       0.106  -0.609  -1.391  1.00  0.00           H  
CONECT    1    2   24   25   26
CONECT    2    3   27
CONECT    3    4    4    5    5
CONECT    3    6
CONECT    6    7   28   29
CONECT    7    8   30   31
CONECT    8    9    9   23
CONECT    9   10   32
CONECT   10   11   11   33
CONECT   11   12   22
CONECT   12   13   34
CONECT   13   14   14   35
CONECT   14   15   22
CONECT   15   16   21   36
CONECT   16   17   37   38
CONECT   17   18   39   40
CONECT   18   19   20
CONECT   19   41   42   43
CONECT   20   21   44   45
CONECT   21   46   47
CONECT   22   23   23
CONECT   23   48
END

HMDB0015087
     RDKit          3D
Naratriptan
 48 50  0  0  0  0  0  0  0  0999 V2000
    4.4799   -1.0804    1.5314 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0792   -0.3719    0.3018 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.6012   -1.2118   -1.1046 S   0  0  0  0  0  6  0  0  0  0  0  0
    5.3308   -2.4646   -0.6258 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6294   -0.4178   -1.8679 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2368   -1.6712   -2.0886 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4518   -0.5496   -2.7015 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9228    0.4263   -1.7576 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7244    1.5263   -1.4863 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2604    2.4596   -0.5972 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0185    2.2944    0.0079 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4241    3.0821    0.8964 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7275    2.5232    1.1987 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8938    1.3128    0.4700 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1427    0.5452    0.5917 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8156    0.8519    1.9195 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8658   -0.1808    2.1847 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4747   -0.5919    0.9576 N   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8570   -0.8574    0.9717 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6268   -1.3965    0.1673 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1851   -0.8586    0.2054 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2299    1.2009   -0.2694 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6852    0.2587   -1.1594 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2950   -0.4305    1.9582 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8168   -2.0910    1.3247 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6600   -1.0344    2.2659 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0131   -0.4935    0.3220 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6266   -2.3761   -2.8709 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5663   -2.3454   -1.4727 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6480   -1.0413   -3.3112 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0958   -0.0475   -3.4583 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7069    1.6423   -1.9721 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8704    3.3234   -0.3738 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7554    3.9785    1.3127 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4574    2.9019    1.8883 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8739    1.0668   -0.1484 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0850    0.8157    2.7574 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3079    1.8481    1.8614 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4206   -1.1196    2.6385 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6220    0.1508    2.9184 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2852   -1.2026    0.0283 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4000    0.1027    1.2388 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0919   -1.5230    1.8523 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0282   -1.4108   -0.8791 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6265   -2.4412    0.5483 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5587   -1.5710    0.7859 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8884   -0.9222   -0.8905 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1059   -0.6091   -1.3908 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  3  5  2  0
  3  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
 13 14  2  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 18 20  1  0
 20 21  1  0
 14 22  1  0
 22 23  2  0
 23  8  1  0
 22 11  1  0
 21 15  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  2 27  1  0
  6 28  1  0
  6 29  1  0
  7 30  1  0
  7 31  1  0
  9 32  1  0
 10 33  1  0
 12 34  1  0
 13 35  1  0
 15 36  1  0
 16 37  1  0
 16 38  1  0
 17 39  1  0
 17 40  1  0
 19 41  1  0
 19 42  1  0
 19 43  1  0
 20 44  1  0
 20 45  1  0
 21 46  1  0
 21 47  1  0
 23 48  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
N-Methyl-2-(3-(1-methylpiperiden-4-yl)indole-5-yl)ethanesulfonamide	ChEBI
N-Methyl-2-[3-(1-methyl-4-piperidyl)-1H-indol-5-yl]-ethanesulfonamide	ChEBI
Naratriptanum	ChEBI
Naramig	Kegg
N-Methyl-2-(3-(1-methylpiperiden-4-yl)indole-5-yl)ethanesulphonamide	Generator
N-Methyl-2-[3-(1-methyl-4-piperidyl)-1H-indol-5-yl]-ethanesulphonamide	Generator
Faes brand OF naratriptan hydrochloride	HMDB
Amerge	HMDB
Colatan	HMDB
Glaxo wellcome brand OF naratriptan hydrochloride	HMDB
GlaxoSmithKline brand OF naratriptan hydrochloride	HMDB
Schwarz brand OF naratriptan hydrochloride	HMDB
Naratriptan hydrochloride	HMDB
N-Methyl-3-(1-methyl-4-piperidinyl)-1H-indole-5-ethanesulfonamide	HMDB
N-Methyl-3-(1-methyl-4-piperidyl)indole-5-ethanesulfonamide monohydrochloride	HMDB
1H-Indole-5-ethanesulfonamide, N-methyl-3-(1-methyl-4-piperidinyl)-, monohydrochloride	HMDB

Chemical Formula

C₁₇H₂₅N₃O₂S

Average Molecular Weight

335.464

Monoisotopic Molecular Weight

335.166747749

IUPAC Name

N-methyl-2-[3-(1-methylpiperidin-4-yl)-1H-indol-5-yl]ethane-1-sulfonamide

Traditional Name

naratriptan

CAS Registry Number

121679-13-8

SMILES

CNS(=O)(=O)CCC1=CC2=C(NC=C2C2CCN(C)CC2)C=C1

InChI Identifier

InChI=1S/C17H25N3O2S/c1-18-23(21,22)10-7-13-3-4-17-15(11-13)16(12-19-17)14-5-8-20(2)9-6-14/h3-4,11-12,14,18-19H,5-10H2,1-2H3

InChI Key

AMKVXSZCKVJAGH-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 3-alkylindoles. 3-Alkylindoles are compounds containing an indole moiety that carries an alkyl chain at the 3-position.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Indoles and derivatives

Sub Class

Indoles

Direct Parent

3-alkylindoles

Alternative Parents

Substituents

3-alkylindole
Aralkylamine
Piperidine
Substituted pyrrole
Organic sulfonic acid amide
Benzenoid
Organosulfonic acid amide
Pyrrole
Organic sulfonic acid or derivatives
Heteroaromatic compound
Organosulfonic acid or derivatives
Aminosulfonyl compound
Sulfonyl
Tertiary aliphatic amine
Tertiary amine
Azacycle
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Organic oxygen compound
Organic nitrogen compound
Organosulfur compound
Organonitrogen compound
Amine
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

sulfonamide (CHEBI:7478 )
tryptamines (CHEBI:7478 )
heteroarylpiperidine (CHEBI:7478 )

Ontology

Not Available

Urine (PMID: 21059682)

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 21059682)

Cellular substructure

Process

Not Available

Role

Industrial application

Manufacturing industry

Material processing agent

Coloring agent

Fluorescent agent

vasoconstrictor agent (HMDB: HMDB0015087)
serotonergic agonist (HMDB: HMDB0015087)

Biological role

serotonergic agonist (HMDB: HMDB0015087)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	246 °C (hydrochloride salt)	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	0.11 g/L	Not Available
LogP	1.6	Not Available

Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct Type	Data Source	CCS Value (Å²)	Reference
[M+H]+	CBM	174.3	30932474

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.11 g/L	ALOGPS
logP	2.16	ALOGPS
logP	1.44	ChemAxon
logS	-3.5	ALOGPS
pKa (Strongest Acidic)	11.55	ChemAxon
pKa (Strongest Basic)	9.18	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	65.2 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	94.26 m³·mol⁻¹	ChemAxon
Polarizability	38 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]+	180.404	31661259
DarkChem	[M-H]-	179.634	31661259
DeepCCS	[M+H]+	172.695	30932474
DeepCCS	[M-H]-	170.337	30932474
DeepCCS	[M-2H]-	203.632	30932474
DeepCCS	[M+Na]+	178.858	30932474
AllCCS	[M+H]+	180.0	32859911
AllCCS	[M+H-H2O]+	177.0	32859911
AllCCS	[M+NH4]+	182.8	32859911
AllCCS	[M+Na]+	183.6	32859911
AllCCS	[M-H]-	181.6	32859911
AllCCS	[M+Na-2H]-	181.9	32859911
AllCCS	[M+HCOO]-	182.5	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Naratriptan	CNS(=O)(=O)CCC1=CC2=C(NC=C2C2CCN(C)CC2)C=C1	4530.2	Standard polar	33892256
Naratriptan	CNS(=O)(=O)CCC1=CC2=C(NC=C2C2CCN(C)CC2)C=C1	3193.2	Standard non polar	33892256
Naratriptan	CNS(=O)(=O)CCC1=CC2=C(NC=C2C2CCN(C)CC2)C=C1	3217.4	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Naratriptan,1TMS,isomer #1	CN1CCC(C2=C[NH]C3=CC=C(CCS(=O)(=O)N(C)[Si](C)(C)C)C=C23)CC1	3126.2	Semi standard non polar	33892256
Naratriptan,1TMS,isomer #1	CN1CCC(C2=C[NH]C3=CC=C(CCS(=O)(=O)N(C)[Si](C)(C)C)C=C23)CC1	2973.1	Standard non polar	33892256
Naratriptan,1TMS,isomer #1	CN1CCC(C2=C[NH]C3=CC=C(CCS(=O)(=O)N(C)[Si](C)(C)C)C=C23)CC1	3881.8	Standard polar	33892256
Naratriptan,1TMS,isomer #2	CNS(=O)(=O)CCC1=CC=C2C(=C1)C(C1CCN(C)CC1)=CN2[Si](C)(C)C	3027.5	Semi standard non polar	33892256
Naratriptan,1TMS,isomer #2	CNS(=O)(=O)CCC1=CC=C2C(=C1)C(C1CCN(C)CC1)=CN2[Si](C)(C)C	2926.4	Standard non polar	33892256
Naratriptan,1TMS,isomer #2	CNS(=O)(=O)CCC1=CC=C2C(=C1)C(C1CCN(C)CC1)=CN2[Si](C)(C)C	4002.1	Standard polar	33892256
Naratriptan,2TMS,isomer #1	CN1CCC(C2=CN([Si](C)(C)C)C3=CC=C(CCS(=O)(=O)N(C)[Si](C)(C)C)C=C23)CC1	3118.1	Semi standard non polar	33892256
Naratriptan,2TMS,isomer #1	CN1CCC(C2=CN([Si](C)(C)C)C3=CC=C(CCS(=O)(=O)N(C)[Si](C)(C)C)C=C23)CC1	3105.9	Standard non polar	33892256
Naratriptan,2TMS,isomer #1	CN1CCC(C2=CN([Si](C)(C)C)C3=CC=C(CCS(=O)(=O)N(C)[Si](C)(C)C)C=C23)CC1	3737.6	Standard polar	33892256
Naratriptan,1TBDMS,isomer #1	CN1CCC(C2=C[NH]C3=CC=C(CCS(=O)(=O)N(C)[Si](C)(C)C(C)(C)C)C=C23)CC1	3304.5	Semi standard non polar	33892256
Naratriptan,1TBDMS,isomer #1	CN1CCC(C2=C[NH]C3=CC=C(CCS(=O)(=O)N(C)[Si](C)(C)C(C)(C)C)C=C23)CC1	3251.9	Standard non polar	33892256
Naratriptan,1TBDMS,isomer #1	CN1CCC(C2=C[NH]C3=CC=C(CCS(=O)(=O)N(C)[Si](C)(C)C(C)(C)C)C=C23)CC1	3938.6	Standard polar	33892256
Naratriptan,1TBDMS,isomer #2	CNS(=O)(=O)CCC1=CC=C2C(=C1)C(C1CCN(C)CC1)=CN2[Si](C)(C)C(C)(C)C	3211.5	Semi standard non polar	33892256
Naratriptan,1TBDMS,isomer #2	CNS(=O)(=O)CCC1=CC=C2C(=C1)C(C1CCN(C)CC1)=CN2[Si](C)(C)C(C)(C)C	3167.4	Standard non polar	33892256
Naratriptan,1TBDMS,isomer #2	CNS(=O)(=O)CCC1=CC=C2C(=C1)C(C1CCN(C)CC1)=CN2[Si](C)(C)C(C)(C)C	4064.5	Standard polar	33892256
Naratriptan,2TBDMS,isomer #1	CN1CCC(C2=CN([Si](C)(C)C(C)(C)C)C3=CC=C(CCS(=O)(=O)N(C)[Si](C)(C)C(C)(C)C)C=C23)CC1	3476.7	Semi standard non polar	33892256
Naratriptan,2TBDMS,isomer #1	CN1CCC(C2=CN([Si](C)(C)C(C)(C)C)C3=CC=C(CCS(=O)(=O)N(C)[Si](C)(C)C(C)(C)C)C=C23)CC1	3609.4	Standard non polar	33892256
Naratriptan,2TBDMS,isomer #1	CN1CCC(C2=CN([Si](C)(C)C(C)(C)C)C3=CC=C(CCS(=O)(=O)N(C)[Si](C)(C)C(C)(C)C)C=C23)CC1	3814.3	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Naratriptan GC-MS (Non-derivatized) - 70eV, Positive	splash10-0563-6592000000-ddbcdc8fb1564ab67954	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Naratriptan GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Naratriptan 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 - Naratriptan 10V, Positive-QTOF	splash10-0079-0019000000-6a6e24b9a465404217cb	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Naratriptan 20V, Positive-QTOF	splash10-052f-5196000000-d65d77c315f42655bc94	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Naratriptan 40V, Positive-QTOF	splash10-00dj-9181000000-5426adb0583eefe0387d	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Naratriptan 10V, Negative-QTOF	splash10-001i-2009000000-94e23cf10a35640e1665	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Naratriptan 20V, Negative-QTOF	splash10-056r-9047000000-e204b450ea7d67367377	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Naratriptan 40V, Negative-QTOF	splash10-03fu-9010000000-4168e596b68161b1f564	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Naratriptan 10V, Positive-QTOF	splash10-000i-0009000000-eb77fa3eb994fd4f881e	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Naratriptan 20V, Positive-QTOF	splash10-03di-0091000000-3e0656c2932e26031087	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Naratriptan 40V, Positive-QTOF	splash10-001j-8974000000-f06f269baa785ea29ed4	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Naratriptan 10V, Negative-QTOF	splash10-001i-0009000000-0fe6fb135327a243d85b	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Naratriptan 20V, Negative-QTOF	splash10-001l-1096000000-9e82cb949d18ff9c097d	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Naratriptan 40V, Negative-QTOF	splash10-0200-2091000000-28483e9f079277138f81	2021-10-11	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 DB00952	21059682	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB00952	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

DB00952

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

4287

KEGG Compound ID

C07792

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Naratriptan

METLIN ID

Not Available

PubChem Compound

4440

PDB ID

Not Available

ChEBI ID

7478

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

Villalon CM, Centurion D, Valdivia LF, de Vries P, Saxena PR: Migraine: pathophysiology, pharmacology, treatment and future trends. Curr Vasc Pharmacol. 2003 Mar;1(1):71-84. [PubMed:15320857 ]
Massiou H: Naratriptan. Curr Med Res Opin. 2001;17 Suppl 1:s51-3. [PubMed:12463278 ]
Lambert GA: Preclinical neuropharmacology of naratriptan. CNS Drug Rev. 2005 Autumn;11(3):289-316. [PubMed:16389295 ]

Enzymes

Enzyme Details

1. Amine oxidase [flavin-containing] A

General function:: Involved in oxidoreductase activity
Specific function:: Catalyzes the oxidative deamination of biogenic and xenobiotic amines and has important functions in the metabolism of neuroactive and vasoactive amines in the central nervous system and peripheral tissues. MAOA preferentially oxidizes biogenic amines such as 5-hydroxytryptamine (5-HT), norepinephrine and epinephrine.
Gene Name:: MAOA
Uniprot ID:: P21397
Molecular weight:: 59681.27

References

Millson DS, Tepper SJ, Rapoport AM: Migraine pharmacotherapy with oral triptans: a rational approach to clinical management. Expert Opin Pharmacother. 2000 Mar;1(3):391-404. [PubMed:11249525 ]

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

Akin D, Onaran HO, Gurdal H: Agonist-directed trafficking explaining the difference between response pattern of naratriptan and sumatriptan in rabbit common carotid artery. Br J Pharmacol. 2002 May;136(2):171-6. [PubMed:12010764 ]
Hoskin KL, Lambert GA, Donaldson C, Zagami AS: The 5-hydroxytryptamine1B/1D/1F receptor agonists eletriptan and naratriptan inhibit trigeminovascular input to the nucleus tractus solitarius in the cat. Brain Res. 2004 Feb 13;998(1):91-9. [PubMed:14725972 ]
Boers PM, Donaldson C, Zagami AS, Lambert GA: Naratriptan has a selective inhibitory effect on trigeminovascular neurones at central 5-HT1A and 5-HT(1B/1D) receptors in the cat: implications for migraine therapy. Cephalalgia. 2004 Feb;24(2):99-109. [PubMed:14728705 ]
Pauwels PJ, Palmier C, Dupuis DS, Colpaert FC: Interaction of 5-HT1B/D ligands with recombinant h 5-HT1A receptors: intrinsic activity and modulation by G-protein activation state. Naunyn Schmiedebergs Arch Pharmacol. 1998 May;357(5):490-9. [PubMed:9650800 ]
Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]
Johnston MM, Rapoport AM: Triptans for the management of migraine. Drugs. 2010 Aug 20;70(12):1505-18. doi: 10.2165/11537990-000000000-00000. [PubMed:20687618 ]
Dulli DA: Naratriptan: an alternative for migraine. Ann Pharmacother. 1999 Jun;33(6):704-11. [PubMed:10410185 ]
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 ]
Massiou H: Naratriptan. Curr Med Res Opin. 2001;17 Suppl 1:s51-3. [PubMed:12463278 ]
Lambert GA: Preclinical neuropharmacology of naratriptan. CNS Drug Rev. 2005 Autumn;11(3):289-316. [PubMed:16389295 ]

Enzyme Details

3. 5-hydroxytryptamine receptor 1F

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:: HTR1F
Uniprot ID:: P30939
Molecular weight:: 41708.5

References

Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]
Hoskin KL, Lambert GA, Donaldson C, Zagami AS: The 5-hydroxytryptamine1B/1D/1F receptor agonists eletriptan and naratriptan inhibit trigeminovascular input to the nucleus tractus solitarius in the cat. Brain Res. 2004 Feb 13;998(1):91-9. [PubMed:14725972 ]
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 ]
Massiou H: Naratriptan. Curr Med Res Opin. 2001;17 Suppl 1:s51-3. [PubMed:12463278 ]
Villalon CM, Centurion D, Valdivia LF, de Vries P, Saxena PR: Migraine: pathophysiology, pharmacology, treatment and future trends. Curr Vasc Pharmacol. 2003 Mar;1(1):71-84. [PubMed:15320857 ]
Goadsby PJ, Classey JD: Evidence for serotonin (5-HT)1B, 5-HT1D and 5-HT1F receptor inhibitory effects on trigeminal neurons with craniovascular input. Neuroscience. 2003;122(2):491-8. [PubMed:14614913 ]
Villalon CM, Centurion D, Valdivia LF, De Vries P, Saxena PR: An introduction to migraine: from ancient treatment to functional pharmacology and antimigraine therapy. Proc West Pharmacol Soc. 2002;45:199-210. [PubMed:12434581 ]

Enzyme Details

4. 5-hydroxytryptamine receptor 1A

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:: HTR1A
Uniprot ID:: P08908
Molecular weight:: 46106.3

References

Boers PM, Donaldson C, Zagami AS, Lambert GA: Naratriptan has a selective inhibitory effect on trigeminovascular neurones at central 5-HT1A and 5-HT(1B/1D) receptors in the cat: implications for migraine therapy. Cephalalgia. 2004 Feb;24(2):99-109. [PubMed:14728705 ]
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 ]

Enzyme Details

5. 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

Hargreaves RJ, Shepheard SL: Pathophysiology of migraine--new insights. Can J Neurol Sci. 1999 Nov;26 Suppl 3:S12-9. [PubMed:10563228 ]
Donaldson C, Boers PM, Hoskin KL, Zagami AS, Lambert GA: The role of 5-HT1B and 5-HT1D receptors in the selective inhibitory effect of naratriptan on trigeminovascular neurons. Neuropharmacology. 2002 Mar;42(3):374-85. [PubMed:11897116 ]
Pauwels PJ, Colpaert FC: Selective antagonism of human 5-HT1D and 5-HT1B receptor-mediated responses in stably transfected C6-glial cells by ketanserin and GR 127,935. Eur J Pharmacol. 1996 Apr 4;300(1-2):141-5. [PubMed:8741180 ]
Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]
Akin D, Onaran HO, Gurdal H: Agonist-directed trafficking explaining the difference between response pattern of naratriptan and sumatriptan in rabbit common carotid artery. Br J Pharmacol. 2002 May;136(2):171-6. [PubMed:12010764 ]
Hoskin KL, Lambert GA, Donaldson C, Zagami AS: The 5-hydroxytryptamine1B/1D/1F receptor agonists eletriptan and naratriptan inhibit trigeminovascular input to the nucleus tractus solitarius in the cat. Brain Res. 2004 Feb 13;998(1):91-9. [PubMed:14725972 ]
Boers PM, Donaldson C, Zagami AS, Lambert GA: Naratriptan has a selective inhibitory effect on trigeminovascular neurones at central 5-HT1A and 5-HT(1B/1D) receptors in the cat: implications for migraine therapy. Cephalalgia. 2004 Feb;24(2):99-109. [PubMed:14728705 ]
Johnston MM, Rapoport AM: Triptans for the management of migraine. Drugs. 2010 Aug 20;70(12):1505-18. doi: 10.2165/11537990-000000000-00000. [PubMed:20687618 ]
Dulli DA: Naratriptan: an alternative for migraine. Ann Pharmacother. 1999 Jun;33(6):704-11. [PubMed:10410185 ]
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 ]
Massiou H: Naratriptan. Curr Med Res Opin. 2001;17 Suppl 1:s51-3. [PubMed:12463278 ]
Lambert GA: Preclinical neuropharmacology of naratriptan. CNS Drug Rev. 2005 Autumn;11(3):289-316. [PubMed:16389295 ]

Showing metabocard for Naratriptan (HMDB0015087)

MOL for HMDB0015087 (Naratriptan)

3D MOL for HMDB0015087 (Naratriptan)

3D SDF for HMDB0015087 (Naratriptan)

3D-SDF for HMDB0015087 (Naratriptan)

PDB for HMDB0015087 (Naratriptan)

3D PDB for HMDB0015087 (Naratriptan)

SMILES for HMDB0015087 (Naratriptan)

INCHI for HMDB0015087 (Naratriptan)

Structure for HMDB0015087 (Naratriptan)

3D Structure for HMDB0015087 (Naratriptan)

Experimental Collision Cross Sections

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

Enzymes

References

References

References

References

References