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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (6) Show 6 proteins XML

Record Information

Version

5.0

Status

Detected and Quantified

Creation Date

2006-05-18 08:50:34 UTC

Update Date

2022-03-07 02:49:25 UTC

HMDB ID

HMDB0005034

Secondary Accession Numbers

HMDB05034

Metabolite Identification

Common Name

Topiramate

Description

Topiramate is an anticonvulsant drug used to treat epilepsy in both children and adults. In children it is also indicated for treatment of Lennox-Gastaut syndrome (a disorder that causes seizures and developmental delays). It is also Food and Drug Administration (FDA) approved, and now most frequently prescribed for, the prevention of migraines. It has been used by psychiatrists to treat bipolar disorder, although it is not FDA approved for this purpose and such use is somewhat controversial. This drug has been investigated for use in treatment of obesity, especially to aid in the reduction of binge eating, and also as a possible treatment for alcoholism. However, these uses are not actively promoted by the manufacturer, and like its use for bipolar disorder, are 'off-label' uses. The drug is also used in clinical trials to treat Post Traumatic Stress Disorder. A pilot study suggests that Topiramate is possibly effective against infantile spasm; Chemically, topiramate is a sulfamate-substituted monosaccharide, related to fructose, a rather unusual chemical structure for an anticonvulsant. Topiramate is quickly absorbed after oral use. Most of the drug (70%) is excreted in the urine as unchanged drug. The remainder is extensively metabolized by hydroxylation, hydrolysis, and glucuronidation. Six metabolites have been identified in humans, none of which constitutes more than 5% of an administered dose. Topiramate enhances GABA-activated chloride channels. In addition, topiramate inhibits excitatory neurotransmission, through actions on kainate and AMPA receptors. There is evidence that topiramate has a specific effect on GluR5 kainate receptors. It is also an inhibitor of carbonic anhydrase, particularly subtypes II and IV, but this action is weak and unlikely to be related to its anticonvulsant actions, but may account for the bad taste and the development of renal stones seen during treatment. Its possible effect as a mood stabilizer seems to occur before anticonvulsant qualities at lower dosages. Topiramate inhibits maximal electroshock and pentylenetetrazol-induced seizures as well as partial and secondarily generalized tonic-clonic seizures in the kindling model, findings predictive of a broad spectrum of antiseizure activities clinically; Johnson. It is used to treat epilepsy in both children and adults. In children it is also indicated for treatment of Lennox-Gastaut syndrome (a disorder that causes seizures and developmental delays). It is also Food and Drug Administration (FDA) approved for, and now most frequently prescribed for, the prevention of migraines. It has been used by psychiatrists to treat bipolar disorder, although it is not FDA approved for this purpose and such use is somewhat controversial. This drug has been investigated for use in treatment of obesity, especially to aid in the reduction of binge eating, and also as a possible treatment for alcoholism. However, these uses are not actively promoted by the manufacturer, and like its use for bipolar disorder, are 'off-label' uses. The drug is also used in clinical trials to treat Post Traumatic Stress Disorder. A pilot study suggests that Topiramate is possibly effective against infantile spasm. In May 2006 the U.S. National Institutes of Health web site clinicaltrials.gov listed several studies sponsored by Ortho-McNeil which propose to examine the use of topiramate on migraine, cluster, and severe headaches within various demographics; Topiramate (brand name: Topamax) is an anticonvulsant drug produced by Ortho-McNeil, a division of Johnson & Topiramate (brand name: Topamax) is an anticonvulsant drug produced by Ortho-McNeil, a division of Johnson & Johnson. It is used to treat epilepsy in both children and adults. In children it is also indicated for treatment of Lennox-Gastaut syndrome (a disorder that causes seizures and developmental delays). It is also Food and Drug Administration (FDA) approved for, and now most frequently prescribed for, the prevention of migraines. It has been used by psychiatrists to treat bipolar disorder, although it is not FDA approved for this purpose and such use is somewhat controversial. This drug has been investigated for use in treatment of obesity, especially to aid in the reduction of binge eating, and also as a possible treatment for alcoholism. However, these uses are not actively promoted by the manufacturer, and like its use for bipolar disorder, are 'off-label' uses. The drug is also used in clinical trials to treat Post Traumatic Stress Disorder. A pilot study suggests that Topiramate is possibly effective against infantile spasm. In May 2006 the U.S. National Institutes of Health web site clinicaltrials.gov listed several studies sponsored by Ortho-McNeil which propose to examine the use of topiramate on migraine, cluster, and severe headaches within various demographics.

Structure

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

HMDB0005034
     RDKit          3D
Topiramate
 43 45  0  0  0  0  0  0  0  0999 V2000
    3.0623    2.5653    0.3703 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8930    1.0727    0.3940 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1152    0.3974    1.0033 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6738    0.6624   -0.9176 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3886    0.1440   -0.9601 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.4336    1.3090   -0.9326 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8851    0.9464   -0.7750 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0950   -0.3090   -0.2724 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.4507   -0.2776    0.4266 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4971    0.9595    1.0906 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6355    1.9860    0.4307 S   0  0  0  0  0  6  0  0  0  0  0  0
   -3.1809    3.6073    0.8224 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6092    1.8175   -1.0668 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0051    1.7135    0.9823 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0218   -1.3117   -1.2276 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7276   -2.4835   -0.5561 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9914   -3.3291   -0.5769 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3263   -3.3031   -1.2918 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3195   -2.1615    0.7226 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1075   -0.7734    0.7501 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.3174   -0.4584    0.4392 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.8060    0.6521    1.1507 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5139    3.0918    1.1653 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1634    2.7618    0.4130 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7394    3.0084   -0.6060 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8357   -0.6342    1.3302 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3444    0.9584    1.9441 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9831    0.4056    0.3309 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2088   -0.5810   -1.7531 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5603    1.9162   -1.8495 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7038    1.8954   -0.0165 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5000   -1.0404    1.2459 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2891   -0.3658   -0.2764 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5446    3.8214    1.7870 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6316    4.3107    0.1925 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5894   -3.0589   -1.4841 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7573   -4.4156   -0.7100 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5688   -3.2588    0.3532 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2430   -2.7235   -1.4889 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1257   -3.6062   -2.2651 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5862   -4.1666   -0.6608 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3830   -0.4489    1.7747 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0174   -1.2958    0.5678 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  1
  9 10  1  0
 10 11  1  0
 11 12  1  0
 11 13  2  0
 11 14  2  0
  8 15  1  0
 15 16  1  0
 16 17  1  0
 16 18  1  0
 16 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22  2  1  0
 21  5  1  0
 20  8  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  3 26  1  0
  3 27  1  0
  3 28  1  0
  5 29  1  6
  6 30  1  0
  6 31  1  0
  9 32  1  0
  9 33  1  0
 12 34  1  0
 12 35  1  0
 17 36  1  0
 17 37  1  0
 17 38  1  0
 18 39  1  0
 18 40  1  0
 18 41  1  0
 20 42  1  1
 21 43  1  6
M  END

273
  Mrv0541 02231214342D          

 25 27  0  0  1  0            999 V2000
    7.1521    0.8041    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    4.4667   -0.8226    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0086    1.2167    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6167   -0.1587    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7990    0.1403    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7990    1.4680    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4376    0.3916    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.5646    0.0897    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.7396    1.5186    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.8666    1.2167    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.2941   -0.0209    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.5796    0.3916    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.0086    0.3916    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.5796    1.2167    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.2941    1.6292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2824   -0.9077    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3175    0.8041    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7231    0.8041    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0361   -1.2432    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1962   -1.7282    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500    0.3192    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500    1.2891    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7607   -0.4095    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5098   -0.2647    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5098    1.8730    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  7  1  0  0  0  0
  1  8  2  0  0  0  0
  1  9  2  0  0  0  0
  1 10  1  0  0  0  0
  2 11  1  0  0  0  0
  2 16  1  0  0  0  0
  3 13  1  0  0  0  0
  3 15  1  0  0  0  0
  4 13  1  0  0  0  0
  4 16  1  0  0  0  0
  5 12  1  0  0  0  0
  5 17  1  0  0  0  0
  6 14  1  0  0  0  0
  6 17  1  0  0  0  0
  7 18  1  0  0  0  0
 11 12  1  0  0  0  0
 11 13  1  0  0  0  0
 11 23  1  6  0  0  0
 12 14  1  0  0  0  0
 12 24  1  1  0  0  0
 13 18  1  6  0  0  0
 14 15  1  0  0  0  0
 14 25  1  1  0  0  0
 16 19  1  0  0  0  0
 16 20  1  0  0  0  0
 17 21  1  0  0  0  0
 17 22  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0005034

> <DATABASE_NAME>
hmdb

> <SMILES>
[H][C@@]12CO[C@@]3(COS(N)(=O)=O)OC(C)(C)O[C@@]3([H])[C@]1([H])OC(C)(C)O2

> <INCHI_IDENTIFIER>
InChI=1S/C12H21NO8S/c1-10(2)18-7-5-16-12(6-17-22(13,14)15)9(8(7)19-10)20-11(3,4)21-12/h7-9H,5-6H2,1-4H3,(H2,13,14,15)/t7-,8-,9+,12+/m1/s1

> <INCHI_KEY>
KJADKKWYZYXHBB-XBWDGYHZSA-N

> <FORMULA>
C12H21NO8S

> <MOLECULAR_WEIGHT>
339.362

> <EXACT_MASS>
339.098787343

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_AVERAGE_POLARIZABILITY>
32.42098488706586

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
[(1R,2S,6S,9R)-4,4,11,11-tetramethyl-3,5,7,10,12-pentaoxatricyclo[7.3.0.0²,⁶]dodecan-6-yl]methyl sulfamate

> <ALOGPS_LOGP>
1.29

> <JCHEM_LOGP>
0.12695973433333307

> <ALOGPS_LOGS>
-1.70

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.087057933607165

> <JCHEM_PKA_STRONGEST_BASIC>
-3.723039569510656

> <JCHEM_POLAR_SURFACE_AREA>
115.54

> <JCHEM_REFRACTIVITY>
72.30200000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.80e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
topiramate

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0005034
     RDKit          3D
Topiramate
 43 45  0  0  0  0  0  0  0  0999 V2000
    3.0623    2.5653    0.3703 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8930    1.0727    0.3940 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1152    0.3974    1.0033 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6738    0.6624   -0.9176 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3886    0.1440   -0.9601 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.4336    1.3090   -0.9326 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8851    0.9464   -0.7750 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0950   -0.3090   -0.2724 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.4507   -0.2776    0.4266 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4971    0.9595    1.0906 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6355    1.9860    0.4307 S   0  0  0  0  0  6  0  0  0  0  0  0
   -3.1809    3.6073    0.8224 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6092    1.8175   -1.0668 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0051    1.7135    0.9823 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0218   -1.3117   -1.2276 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7276   -2.4835   -0.5561 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9914   -3.3291   -0.5769 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3263   -3.3031   -1.2918 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3195   -2.1615    0.7226 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1075   -0.7734    0.7501 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.3174   -0.4584    0.4392 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.8060    0.6521    1.1507 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5139    3.0918    1.1653 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1634    2.7618    0.4130 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7394    3.0084   -0.6060 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8357   -0.6342    1.3302 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3444    0.9584    1.9441 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9831    0.4056    0.3309 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2088   -0.5810   -1.7531 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5603    1.9162   -1.8495 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7038    1.8954   -0.0165 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5000   -1.0404    1.2459 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2891   -0.3658   -0.2764 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5446    3.8214    1.7870 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6316    4.3107    0.1925 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5894   -3.0589   -1.4841 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7573   -4.4156   -0.7100 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5688   -3.2588    0.3532 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2430   -2.7235   -1.4889 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1257   -3.6062   -2.2651 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5862   -4.1666   -0.6608 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3830   -0.4489    1.7747 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0174   -1.2958    0.5678 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  1
  9 10  1  0
 10 11  1  0
 11 12  1  0
 11 13  2  0
 11 14  2  0
  8 15  1  0
 15 16  1  0
 16 17  1  0
 16 18  1  0
 16 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22  2  1  0
 21  5  1  0
 20  8  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  3 26  1  0
  3 27  1  0
  3 28  1  0
  5 29  1  6
  6 30  1  0
  6 31  1  0
  9 32  1  0
  9 33  1  0
 12 34  1  0
 12 35  1  0
 17 36  1  0
 17 37  1  0
 17 38  1  0
 18 39  1  0
 18 40  1  0
 18 41  1  0
 20 42  1  1
 21 43  1  6
M  END

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 273                                               
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  S   UNK     0      13.351   1.501   0.000  0.00  0.00           S+0
HETATM    2  O   UNK     0       8.338  -1.536   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0       9.349   2.271   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0      10.485  -0.296   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0       5.225   0.262   0.000  0.00  0.00           O+0
HETATM    6  O   UNK     0       5.225   2.740   0.000  0.00  0.00           O+0
HETATM    7  O   UNK     0      12.017   0.731   0.000  0.00  0.00           O+0
HETATM    8  O   UNK     0      14.121   0.167   0.000  0.00  0.00           O+0
HETATM    9  O   UNK     0      12.581   2.835   0.000  0.00  0.00           O+0
HETATM   10  N   UNK     0      14.684   2.271   0.000  0.00  0.00           N+0
HETATM   11  C   UNK     0       8.016  -0.039   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       6.682   0.731   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       9.349   0.731   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       6.682   2.271   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       8.016   3.041   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       9.860  -1.694   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       4.326   1.501   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      10.683   1.501   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      11.267  -2.321   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       9.700  -3.226   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       3.080   0.596   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       3.080   2.406   0.000  0.00  0.00           C+0
HETATM   23  H   UNK     0       7.020  -0.764   0.000  0.00  0.00           H+0
HETATM   24  H   UNK     0       6.552  -0.494   0.000  0.00  0.00           H+0
HETATM   25  H   UNK     0       6.552   3.496   0.000  0.00  0.00           H+0
CONECT    1    7    8    9   10                                             
CONECT    2   11   16                                                       
CONECT    3   13   15                                                       
CONECT    4   13   16                                                       
CONECT    5   12   17                                                       
CONECT    6   14   17                                                       
CONECT    7    1   18                                                       
CONECT    8    1                                                            
CONECT    9    1                                                            
CONECT   10    1                                                            
CONECT   11    2   12   13   23                                             
CONECT   12    5   11   14   24                                             
CONECT   13    3    4   11   18                                             
CONECT   14    6   12   15   25                                             
CONECT   15    3   14                                                       
CONECT   16    2    4   19   20                                             
CONECT   17    5    6   21   22                                             
CONECT   18    7   13                                                       
CONECT   19   16                                                            
CONECT   20   16                                                            
CONECT   21   17                                                            
CONECT   22   17                                                            
CONECT   23   11                                                            
CONECT   24   12                                                            
CONECT   25   14                                                            
MASTER        0    0    0    0    0    0    0    0   25    0   54    0
END

COMPND    HMDB0005034
HETATM    1  C1  UNL     1       3.062   2.565   0.370  1.00  0.00           C  
HETATM    2  C2  UNL     1       2.893   1.073   0.394  1.00  0.00           C  
HETATM    3  C3  UNL     1       4.115   0.397   1.003  1.00  0.00           C  
HETATM    4  O1  UNL     1       2.674   0.662  -0.918  1.00  0.00           O  
HETATM    5  C4  UNL     1       1.389   0.144  -0.960  1.00  0.00           C  
HETATM    6  C5  UNL     1       0.434   1.309  -0.933  1.00  0.00           C  
HETATM    7  O2  UNL     1      -0.885   0.946  -0.775  1.00  0.00           O  
HETATM    8  C6  UNL     1      -1.095  -0.309  -0.272  1.00  0.00           C  
HETATM    9  C7  UNL     1      -2.451  -0.278   0.427  1.00  0.00           C  
HETATM   10  O3  UNL     1      -2.497   0.960   1.091  1.00  0.00           O  
HETATM   11  S1  UNL     1      -3.636   1.986   0.431  1.00  0.00           S  
HETATM   12  N1  UNL     1      -3.181   3.607   0.822  1.00  0.00           N  
HETATM   13  O4  UNL     1      -3.609   1.818  -1.067  1.00  0.00           O  
HETATM   14  O5  UNL     1      -5.005   1.714   0.982  1.00  0.00           O  
HETATM   15  O6  UNL     1      -1.022  -1.312  -1.228  1.00  0.00           O  
HETATM   16  C8  UNL     1      -0.728  -2.483  -0.556  1.00  0.00           C  
HETATM   17  C9  UNL     1      -1.991  -3.329  -0.577  1.00  0.00           C  
HETATM   18  C10 UNL     1       0.326  -3.303  -1.292  1.00  0.00           C  
HETATM   19  O7  UNL     1      -0.319  -2.161   0.723  1.00  0.00           O  
HETATM   20  C11 UNL     1      -0.107  -0.773   0.750  1.00  0.00           C  
HETATM   21  C12 UNL     1       1.317  -0.458   0.439  1.00  0.00           C  
HETATM   22  O8  UNL     1       1.806   0.652   1.151  1.00  0.00           O  
HETATM   23  H1  UNL     1       2.514   3.092   1.165  1.00  0.00           H  
HETATM   24  H2  UNL     1       4.163   2.762   0.413  1.00  0.00           H  
HETATM   25  H3  UNL     1       2.739   3.008  -0.606  1.00  0.00           H  
HETATM   26  H4  UNL     1       3.836  -0.634   1.330  1.00  0.00           H  
HETATM   27  H5  UNL     1       4.344   0.958   1.944  1.00  0.00           H  
HETATM   28  H6  UNL     1       4.983   0.406   0.331  1.00  0.00           H  
HETATM   29  H7  UNL     1       1.209  -0.581  -1.753  1.00  0.00           H  
HETATM   30  H8  UNL     1       0.560   1.916  -1.850  1.00  0.00           H  
HETATM   31  H9  UNL     1       0.704   1.895  -0.016  1.00  0.00           H  
HETATM   32  H10 UNL     1      -2.500  -1.040   1.246  1.00  0.00           H  
HETATM   33  H11 UNL     1      -3.289  -0.366  -0.276  1.00  0.00           H  
HETATM   34  H12 UNL     1      -3.545   3.821   1.787  1.00  0.00           H  
HETATM   35  H13 UNL     1      -3.632   4.311   0.193  1.00  0.00           H  
HETATM   36  H14 UNL     1      -2.589  -3.059  -1.484  1.00  0.00           H  
HETATM   37  H15 UNL     1      -1.757  -4.416  -0.710  1.00  0.00           H  
HETATM   38  H16 UNL     1      -2.569  -3.259   0.353  1.00  0.00           H  
HETATM   39  H17 UNL     1       1.243  -2.724  -1.489  1.00  0.00           H  
HETATM   40  H18 UNL     1      -0.126  -3.606  -2.265  1.00  0.00           H  
HETATM   41  H19 UNL     1       0.586  -4.167  -0.661  1.00  0.00           H  
HETATM   42  H20 UNL     1      -0.383  -0.449   1.775  1.00  0.00           H  
HETATM   43  H21 UNL     1       2.017  -1.296   0.568  1.00  0.00           H  
CONECT    1    2   23   24   25
CONECT    2    3    4   22
CONECT    3   26   27   28
CONECT    4    5
CONECT    5    6   21   29
CONECT    6    7   30   31
CONECT    7    8
CONECT    8    9   15   20
CONECT    9   10   32   33
CONECT   10   11
CONECT   11   12   13   13   14
CONECT   11   14
CONECT   12   34   35
CONECT   15   16
CONECT   16   17   18   19
CONECT   17   36   37   38
CONECT   18   39   40   41
CONECT   19   20
CONECT   20   21   42
CONECT   21   22   43
END

HMDB0005034
     RDKit          3D
Topiramate
 43 45  0  0  0  0  0  0  0  0999 V2000
    3.0623    2.5653    0.3703 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8930    1.0727    0.3940 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1152    0.3974    1.0033 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6738    0.6624   -0.9176 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3886    0.1440   -0.9601 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.4336    1.3090   -0.9326 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8851    0.9464   -0.7750 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0950   -0.3090   -0.2724 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.4507   -0.2776    0.4266 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4971    0.9595    1.0906 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6355    1.9860    0.4307 S   0  0  0  0  0  6  0  0  0  0  0  0
   -3.1809    3.6073    0.8224 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6092    1.8175   -1.0668 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0051    1.7135    0.9823 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0218   -1.3117   -1.2276 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7276   -2.4835   -0.5561 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9914   -3.3291   -0.5769 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3263   -3.3031   -1.2918 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3195   -2.1615    0.7226 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1075   -0.7734    0.7501 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.3174   -0.4584    0.4392 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.8060    0.6521    1.1507 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5139    3.0918    1.1653 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1634    2.7618    0.4130 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7394    3.0084   -0.6060 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8357   -0.6342    1.3302 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3444    0.9584    1.9441 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9831    0.4056    0.3309 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2088   -0.5810   -1.7531 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5603    1.9162   -1.8495 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7038    1.8954   -0.0165 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5000   -1.0404    1.2459 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2891   -0.3658   -0.2764 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5446    3.8214    1.7870 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6316    4.3107    0.1925 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5894   -3.0589   -1.4841 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7573   -4.4156   -0.7100 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5688   -3.2588    0.3532 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2430   -2.7235   -1.4889 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1257   -3.6062   -2.2651 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5862   -4.1666   -0.6608 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3830   -0.4489    1.7747 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0174   -1.2958    0.5678 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  1
  9 10  1  0
 10 11  1  0
 11 12  1  0
 11 13  2  0
 11 14  2  0
  8 15  1  0
 15 16  1  0
 16 17  1  0
 16 18  1  0
 16 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22  2  1  0
 21  5  1  0
 20  8  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  3 26  1  0
  3 27  1  0
  3 28  1  0
  5 29  1  6
  6 30  1  0
  6 31  1  0
  9 32  1  0
  9 33  1  0
 12 34  1  0
 12 35  1  0
 17 36  1  0
 17 37  1  0
 17 38  1  0
 18 39  1  0
 18 40  1  0
 18 41  1  0
 20 42  1  1
 21 43  1  6
M  END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
2,3:4,5-Bis-O-(1-methylethylidene)-beta-D-fructopyranose sulfamate	ChEBI
2,3:4,5-Di-O-isopropylidene-beta-D-fructopyranose sulfamate	ChEBI
MCN-4853	ChEBI
RWJ-17021	ChEBI
Tipiramate	ChEBI
Tipiramato	ChEBI
Topamax	ChEBI
Topiramato	ChEBI
Topiramatum	ChEBI
TPM	ChEBI
Trokendi XR	Kegg
2,3:4,5-Bis-O-(1-methylethylidene)-b-D-fructopyranose sulfamate	Generator
2,3:4,5-Bis-O-(1-methylethylidene)-b-D-fructopyranose sulfamic acid	Generator
2,3:4,5-Bis-O-(1-methylethylidene)-b-D-fructopyranose sulphamate	Generator
2,3:4,5-Bis-O-(1-methylethylidene)-b-D-fructopyranose sulphamic acid	Generator
2,3:4,5-Bis-O-(1-methylethylidene)-beta-D-fructopyranose sulfamic acid	Generator
2,3:4,5-Bis-O-(1-methylethylidene)-beta-D-fructopyranose sulphamate	Generator
2,3:4,5-Bis-O-(1-methylethylidene)-beta-D-fructopyranose sulphamic acid	Generator
2,3:4,5-Bis-O-(1-methylethylidene)-β-D-fructopyranose sulfamate	Generator
2,3:4,5-Bis-O-(1-methylethylidene)-β-D-fructopyranose sulfamic acid	Generator
2,3:4,5-Bis-O-(1-methylethylidene)-β-D-fructopyranose sulphamate	Generator
2,3:4,5-Bis-O-(1-methylethylidene)-β-D-fructopyranose sulphamic acid	Generator
2,3:4,5-Di-O-isopropylidene-b-D-fructopyranose sulfamate	Generator
2,3:4,5-Di-O-isopropylidene-b-D-fructopyranose sulfamic acid	Generator
2,3:4,5-Di-O-isopropylidene-b-D-fructopyranose sulphamate	Generator
2,3:4,5-Di-O-isopropylidene-b-D-fructopyranose sulphamic acid	Generator
2,3:4,5-Di-O-isopropylidene-beta-D-fructopyranose sulfamic acid	Generator
2,3:4,5-Di-O-isopropylidene-beta-D-fructopyranose sulphamate	Generator
2,3:4,5-Di-O-isopropylidene-beta-D-fructopyranose sulphamic acid	Generator
2,3:4,5-Di-O-isopropylidene-β-D-fructopyranose sulfamate	Generator
2,3:4,5-Di-O-isopropylidene-β-D-fructopyranose sulfamic acid	Generator
2,3:4,5-Di-O-isopropylidene-β-D-fructopyranose sulphamate	Generator
2,3:4,5-Di-O-isopropylidene-β-D-fructopyranose sulphamic acid	Generator
Tipiramic acid	Generator
Topiramic acid	Generator
Epitomax	HMDB
Topamax sprinkle	HMDB
Topomax	HMDB
2,3-4,5-Bis-O-(1-methylethylidene)-beta-D-fructopyranose sulfamate	HMDB

Chemical Formula

C₁₂H₂₁NO₈S

Average Molecular Weight

339.362

Monoisotopic Molecular Weight

339.098787343

IUPAC Name

[(1R,2S,6S,9R)-4,4,11,11-tetramethyl-3,5,7,10,12-pentaoxatricyclo[7.3.0.0²,⁶]dodecan-6-yl]methyl sulfamate

Traditional Name

topiramate

CAS Registry Number

97240-79-4

SMILES

[H][C@@]12CO[C@@]3(COS(N)(=O)=O)OC(C)(C)O[C@@]3([H])[C@]1([H])OC(C)(C)O2

InChI Identifier

InChI=1S/C12H21NO8S/c1-10(2)18-7-5-16-12(6-17-22(13,14)15)9(8(7)19-10)20-11(3,4)21-12/h7-9H,5-6H2,1-4H3,(H2,13,14,15)/t7-,8-,9+,12+/m1/s1

InChI Key

KJADKKWYZYXHBB-XBWDGYHZSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as dioxolopyrans. Dioxolopyrans are compounds containing a dioxolopyran moiety, which consists of a dioxole ring fused to a pyran ring.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Dioxolopyrans

Sub Class

Not Available

Direct Parent

Dioxolopyrans

Alternative Parents

Substituents

Dioxolopyran
Ketal
Oxane
Monosaccharide
Organic sulfuric acid or derivatives
Meta-dioxolane
Oxacycle
Acetal
Organic nitrogen compound
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

cyclic ketal (CHEBI:63631 )
sulfamate ester (CHEBI:63631 )
ketohexose derivative (CHEBI:63631 )

Ontology

Physiological effect

Health effect

Observation

Nervous system disorder

Central nervous system disorder

Psychiatric disorder

Mood disorder

Major depressive disorder (HMDB: HMDB0005034)

Organoleptic effect

Taste

Bitter

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 10704102)

Cellular substructure

Organ

Brain (HMDB: HMDB0005034)
Prostate (HMDB: HMDB0005034)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0005034)

Source

Exogenous

Exogenous (HMDB: HMDB0005034)

Process

Not Available

Role

Industrial application

Pharmaceutical industry

Pharmaceutical (HMDB: HMDB0005034)

Manufacturing industry

Material processing agent

Coloring agent

Fluorescent agent

Anticonvulsant (HMDB: HMDB0005034)
Anticonvulsant (HMDB: HMDB0005034)

Biological role

Sodium channel blocker (HMDB: HMDB0005034)
Sodium channel blocker (HMDB: HMDB0005034)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	125 - 126 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	6.8 g/L	ALOGPS
logP	1.29	ALOGPS
logP	0.13	ChemAxon
logS	-1.7	ALOGPS
pKa (Strongest Acidic)	11.09	ChemAxon
pKa (Strongest Basic)	-3.7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	115.54 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	72.3 m³·mol⁻¹	ChemAxon
Polarizability	32.42 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]+	176.967	31661259
DarkChem	[M-H]-	173.059	31661259
DeepCCS	[M-2H]-	214.689	30932474
DeepCCS	[M+Na]+	191.192	30932474
AllCCS	[M+H]+	175.2	32859911
AllCCS	[M+H-H2O]+	172.3	32859911
AllCCS	[M+NH4]+	177.8	32859911
AllCCS	[M+Na]+	178.6	32859911
AllCCS	[M-H]-	175.4	32859911
AllCCS	[M+Na-2H]-	175.5	32859911
AllCCS	[M+HCOO]-	175.7	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	3.26 minutes	32390414
Predicted by Siyang on May 30, 2022	13.1876 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.66 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	25.0 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	2283.6 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	303.6 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	146.2 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	165.6 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	92.0 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	642.9 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	381.8 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	70.6 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1022.9 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	418.8 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	1628.0 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	394.8 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	339.8 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	252.7 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	216.9 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	8.7 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Topiramate	[H][C@@]12CO[C@@]3(COS(N)(=O)=O)OC(C)(C)O[C@@]3([H])[C@]1([H])OC(C)(C)O2	3039.0	Standard polar	33892256
Topiramate	[H][C@@]12CO[C@@]3(COS(N)(=O)=O)OC(C)(C)O[C@@]3([H])[C@]1([H])OC(C)(C)O2	2252.4	Standard non polar	33892256
Topiramate	[H][C@@]12CO[C@@]3(COS(N)(=O)=O)OC(C)(C)O[C@@]3([H])[C@]1([H])OC(C)(C)O2	2240.7	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Topiramate,1TMS,isomer #1	CC1(C)O[C@@H]2CO[C@@]3(COS(=O)(=O)N[Si](C)(C)C)OC(C)(C)O[C@H]3[C@@H]2O1	2305.4	Semi standard non polar	33892256
Topiramate,1TMS,isomer #1	CC1(C)O[C@@H]2CO[C@@]3(COS(=O)(=O)N[Si](C)(C)C)OC(C)(C)O[C@H]3[C@@H]2O1	2477.2	Standard non polar	33892256
Topiramate,1TMS,isomer #1	CC1(C)O[C@@H]2CO[C@@]3(COS(=O)(=O)N[Si](C)(C)C)OC(C)(C)O[C@H]3[C@@H]2O1	3219.1	Standard polar	33892256
Topiramate,2TMS,isomer #1	CC1(C)O[C@@H]2CO[C@@]3(COS(=O)(=O)N([Si](C)(C)C)[Si](C)(C)C)OC(C)(C)O[C@H]3[C@@H]2O1	2370.4	Semi standard non polar	33892256
Topiramate,2TMS,isomer #1	CC1(C)O[C@@H]2CO[C@@]3(COS(=O)(=O)N([Si](C)(C)C)[Si](C)(C)C)OC(C)(C)O[C@H]3[C@@H]2O1	2685.7	Standard non polar	33892256
Topiramate,2TMS,isomer #1	CC1(C)O[C@@H]2CO[C@@]3(COS(=O)(=O)N([Si](C)(C)C)[Si](C)(C)C)OC(C)(C)O[C@H]3[C@@H]2O1	3161.8	Standard polar	33892256
Topiramate,1TBDMS,isomer #1	CC1(C)O[C@@H]2CO[C@@]3(COS(=O)(=O)N[Si](C)(C)C(C)(C)C)OC(C)(C)O[C@H]3[C@@H]2O1	2539.6	Semi standard non polar	33892256
Topiramate,1TBDMS,isomer #1	CC1(C)O[C@@H]2CO[C@@]3(COS(=O)(=O)N[Si](C)(C)C(C)(C)C)OC(C)(C)O[C@H]3[C@@H]2O1	2791.0	Standard non polar	33892256
Topiramate,1TBDMS,isomer #1	CC1(C)O[C@@H]2CO[C@@]3(COS(=O)(=O)N[Si](C)(C)C(C)(C)C)OC(C)(C)O[C@H]3[C@@H]2O1	3268.3	Standard polar	33892256
Topiramate,2TBDMS,isomer #1	CC1(C)O[C@@H]2CO[C@@]3(COS(=O)(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)OC(C)(C)O[C@H]3[C@@H]2O1	2771.3	Semi standard non polar	33892256
Topiramate,2TBDMS,isomer #1	CC1(C)O[C@@H]2CO[C@@]3(COS(=O)(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)OC(C)(C)O[C@H]3[C@@H]2O1	3223.3	Standard non polar	33892256
Topiramate,2TBDMS,isomer #1	CC1(C)O[C@@H]2CO[C@@]3(COS(=O)(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)OC(C)(C)O[C@H]3[C@@H]2O1	3257.0	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Topiramate GC-MS (Non-derivatized) - 70eV, Positive	splash10-003r-5893000000-57939ef42b569234ad29	2017-08-28	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Topiramate GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental LC-MS/MS	LC-MS/MS Spectrum - Topiramate LC-ESI-qTof , Positive-QTOF	splash10-03di-0239000000-994a7b97e101c455a792	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Topiramate LC-ESI-qTof , Positive-QTOF	splash10-01x0-1970000000-f0e80f5cc5d6fc2b6d38	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Topiramate Linear Ion Trap , negative-QTOF	splash10-01q9-2960000000-a11a150bcada5055d2e9	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Topiramate Linear Ion Trap , positive-QTOF	splash10-014i-0090000000-c1fa3d6ff15890fc1418	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Topiramate Linear Ion Trap , positive-QTOF	splash10-00di-0059000000-a6337903cab01edce60e	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Topiramate , positive-QTOF	splash10-03di-0239000000-994a7b97e101c455a792	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Topiramate , positive-QTOF	splash10-01x0-1970000000-f0e80f5cc5d6fc2b6d38	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Topiramate 60V, Negative-QTOF	splash10-004i-9000000000-a8df5a6ea132d69b9489	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Topiramate 45V, Negative-QTOF	splash10-004i-9000000000-f76d8f2283f18dfa20be	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Topiramate 75V, Negative-QTOF	splash10-004i-9000000000-316320612e65b9d317cb	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Topiramate 90V, Negative-QTOF	splash10-004i-9000000000-63d6b2cbde40b2bcd639	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Topiramate 30V, Negative-QTOF	splash10-004i-9003000000-0b8ee634478a6f2f0eee	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Topiramate 15V, Negative-QTOF	splash10-000i-0009000000-086098dbff51e692c04f	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Topiramate 35V, Positive-QTOF	splash10-0c0r-9850000000-ae199550ba647589f088	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Topiramate 35V, Negative-QTOF	splash10-004i-9000000000-eab734dd0ed786cbba6d	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Topiramate 10V, Positive-QTOF	splash10-0006-1029000000-37869fd8dcd3ec0f4cc1	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Topiramate 20V, Positive-QTOF	splash10-01po-4295000000-7cdbdca2d1d67b21879d	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Topiramate 40V, Positive-QTOF	splash10-03fr-9810000000-9b5c3fb12c27e09cf450	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Topiramate 10V, Negative-QTOF	splash10-002r-4239000000-e56f7b1fecd3064e8783	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Topiramate 20V, Negative-QTOF	splash10-004j-9164000000-892445ea4dcd3bf9420d	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Topiramate 40V, Negative-QTOF	splash10-004i-9100000000-7c64b90d0daae2c6e5b8	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Topiramate 10V, Positive-QTOF	splash10-0006-0009000000-9a74f9cc10019d27995c	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Topiramate 20V, Positive-QTOF	splash10-0006-0149000000-093e852afab8097cfa0f	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Topiramate 40V, Positive-QTOF	splash10-03dm-8790000000-0a33128bbe614c27cdf7	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Topiramate 10V, Negative-QTOF	splash10-000i-0019000000-345311bd602424b95a49	2021-09-24	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Membrane (predicted from logP)

Biospecimen Locations

Blood

Tissue Locations

Brain
Prostate

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected and Quantified	1.47 +/- 0.03 uM	Adult (>18 years old)	Both	Normal	10704102	details

Abnormal Concentrations

Not Available

Predicted Concentrations

Biospecimen	Value	Original age	Original sex	Original condition	Comments
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

DB00273

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB023601

KNApSAcK ID

Not Available

Chemspider ID

4447672

KEGG Compound ID

C07502

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Topiramate

METLIN ID

Not Available

PubChem Compound

5284627

PDB ID

TOR

ChEBI ID

63631

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Maryanoff, Bruce E.; Gardocki, Joseph F. Anticonvulsant sulfamate derivatives. U.S. (1985), CODEN: USXXAM US 4513006 A 19850423 CAN 103:37701 AN 1985:437701

Material Safety Data Sheet (MSDS)

Download (PDF)

General References

Sreekumar A, Poisson LM, Rajendiran TM, Khan AP, Cao Q, Yu J, Laxman B, Mehra R, Lonigro RJ, Li Y, Nyati MK, Ahsan A, Kalyana-Sundaram S, Han B, Cao X, Byun J, Omenn GS, Ghosh D, Pennathur S, Alexander DC, Berger A, Shuster JR, Wei JT, Varambally S, Beecher C, Chinnaiyan AM: Metabolomic profiles delineate potential role for sarcosine in prostate cancer progression. Nature. 2009 Feb 12;457(7231):910-4. doi: 10.1038/nature07762. [PubMed:19212411 ]
Petroff OA, Hyder F, Mattson RH, Rothman DL: Topiramate increases brain GABA, homocarnosine, and pyrrolidinone in patients with epilepsy. Neurology. 1999 Feb;52(3):473-8. [PubMed:10025774 ]

Enzymes

Enzyme Details

1. Cytochrome P450 2C19

General function:: Involved in monooxygenase activity
Specific function:: Responsible for the metabolism of a number of therapeutic agents such as the anticonvulsant drug S-mephenytoin, omeprazole, proguanil, certain barbiturates, diazepam, propranolol, citalopram and imipramine.
Gene Name:: CYP2C19
Uniprot ID:: P33261
Molecular weight:: 55944.565

Enzyme Details

2. Glutamate receptor, ionotropic kainate 1

General function:: Involved in ionotropic glutamate receptor activity
Specific function:: Ionotropic glutamate receptor. L-glutamate acts as an excitatory neurotransmitter at many synapses in the central nervous system. Binding of the excitatory neurotransmitter L- glutamate induces a conformation change, leading to the opening of the cation channel, and thereby converts the chemical signal to an electrical impulse. The receptor then desensitizes rapidly and enters a transient inactive state, characterized by the presence of bound agonist. May be involved in the transmission of light information from the retina to the hypothalamus
Gene Name:: GRIK1
Uniprot ID:: P39086
Molecular weight:: 103979.7

Enzyme Details

3. Carbonic anhydrase 2

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

Enzyme Details

4. Carbonic anhydrase 4

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

Enzyme Details

5. Gamma-aminobutyric acid receptor subunit alpha-1

General function:: Involved in ion transport
Specific function:: GABA, the major inhibitory neurotransmitter in the vertebrate brain, mediates neuronal inhibition by binding to the GABA/benzodiazepine receptor and opening an integral chloride channel
Gene Name:: GABRA1
Uniprot ID:: P14867
Molecular weight:: 51801.4

Enzyme Details

6. Sodium channel protein type 1 subunit alpha

General function:: Involved in ion channel activity
Specific function:: Mediates the voltage-dependent sodium ion permeability of excitable membranes. Assuming opened or closed conformations in response to the voltage difference across the membrane, the protein forms a sodium-selective channel through which Na(+) ions may pass in accordance with their electrochemical gradient
Gene Name:: SCN1A
Uniprot ID:: P35498
Molecular weight:: 228969.5

Showing metabocard for Topiramate (HMDB0005034)

MOL for HMDB0005034 (Topiramate)

3D MOL for HMDB0005034 (Topiramate)

3D SDF for HMDB0005034 (Topiramate)

3D-SDF for HMDB0005034 (Topiramate)

PDB for HMDB0005034 (Topiramate)

3D PDB for HMDB0005034 (Topiramate)

SMILES for HMDB0005034 (Topiramate)

INCHI for HMDB0005034 (Topiramate)

Structure for HMDB0005034 (Topiramate)

3D Structure for HMDB0005034 (Topiramate)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

Enzymes