Topiramate

A summary of the most common chemical descriptors (InChI Key and SMILES codes) for Topiramate are summarized together with 3D and 2D structures and relevant physico-chemical properties.

What is the Topiramate?

The molecule Topiramate presents a molecular formula of C12H21NO8S and its IUPAC name is [(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.

Topiramate (brand name Topamax) is an anti-epileptic medication used in the treatment of epilepsy and migraine headaches. It is a sulfamate-substituted monosaccharide with a molecular formula of C12H21NO8S. The drug was first synthesized in 1979 by Bruce E. Maryanoff and John W. Steedman while working for McNeil Pharmaceuticals. It was approved by the U.S. Food and Drug Administration (FDA) in 1996 for the treatment of epilepsy, and has since been approved for the treatment of migraine headaches and as an adjunct treatment for alcohol dependence..

Topiramate has a wide range of pharmacological effects, including anticonvulsant, antidepressant, anxiolytic, mood-stabilizing, and anorectic effects. The exact mechanism of action of topiramate is unknown, but it is thought to work by modulating neurotransmitter activity in the brain..

The most common side effects of topiramate include weight loss, fatigue, dizziness, and nausea. More serious side effects include kidney stones, an increase in suicidal thoughts and behavior, and birth defects..

Topiramate is a relatively new medication, and more research is needed to determine its long-term safety and efficacy. However, it has shown promise as a treatment for epilepsy and migraine headaches, and may also be helpful in treating other conditions such as alcohol dependence and obesity..

3D structure

Cartesian coordinates

Geometry of Topiramate in x, y and z coordinates (Å units) to copy/paste elsewhere. Generated with Open Babel software.

2D drawing

 

Topiramate KJADKKWYZYXHBB-XBWDGYHZSA-N chemical compound 2D structure molecule svg
Topiramate

 

Molecule descriptors

 
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
InChI codeInChI=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 KeyKJADKKWYZYXHBB-XBWDGYHZSA-N
SMILESCC1(C)O[C@@H]2CO[C@@]3(COS(N)(=O)=O)OC(C)(C)O[C@H]3[C@@H]2O1

Other names (synonyms)

IUPAC nomenclature provides a standardized method for naming chemical compounds. Although this system is widely used in chemistry, many chemical compounds have also other names commonly used in different contexts. These synonyms can come from a variety of sources and are used for a variety of purposes.

One common source of synonyms for chemical compounds is the common or trivial names, assigned on the basis of appearance, properties, or origin of the molecule.

Another source of synonyms are historical or obsolete names employed in the past, however replaced nowadays by more modern or standardized names.

In addition to common and historical names, chemical compounds may also have synonyms that are specific to a particular field or industry.

  • ((3aS,5aR,8aR,8bS)-2,2,7,7-tetramethyltetrahydro-3aH-bis([1,3]dioxolo)[4,5-b:4',5'-d]pyran-3a-yl)methyl sulfamate
  • ((3aS,5aR,8aR,8bS)-2,2,7,7-tetramethyltetrahydro-3aH-bis[1,3]dioxolo[4,5-b:4',5'-d]pyran-3a-yl)methyl sulfamate
  • (-)-topiramate
  • .beta.-D-Fructopyranose, 2,3:4,5-bis-O-(1-methylethylidene)-, 1-sulfamate
  • .beta.-D-Fructopyranose, 2,3:4,5-bis-O-(1-methylethylidene)-, sulfamate
  • 0H73WJJ391
  • 2,3:4,5-Bis-O-(1-methylethylidene)-?-D-fructopyranose sulfamate
  • 2,3:4,5-Bis-O-(1-methylethylidene)-beta-D-fructopyranose sulfamate
  • 2,3:4,5-DI-O-ISOPROPYLIDENE-.BETA.-D-FRUCTOPYRANOSE SULFAMATE
  • 2,3:4,5-Di-O-isopropylidene-beta-D-fructopyranose sulfamate
  • 2,3:4,5-bis-O-(1-methylethylidene)-beta-D-fructopyranose 1-sulfamate;2,3:4,5-di-O-isopropylidene-beta-D-fructopyranose sulfamate; Topamax; Tracrium; Toiramate:
  • 240T794
  • 3hku
  • 3lxe
  • 97240-79-4
  • A900173
  • AB00639961-06
  • AB00639961-08
  • AB00639961_09
  • AB00639961_10
  • ACT09031
  • BDBM10887
  • BIDD:GT0854
  • BIDD:PXR0127
  • BRN 5988957
  • BSPBio_002306
  • BT167048
  • C07502
  • C12H21NO8S
  • CBChromo1_000352
  • CCG-100940
  • CS-1885
  • D00537
  • DB00273
  • DSSTox_CID_3688
  • DSSTox_GSID_23688
  • DSSTox_RID_77148
  • EPRONTIA
  • Epitoma
  • Epitomax
  • F20536
  • GTPL6849
  • HMS1922H06
  • HMS2051L09
  • HMS2093D20
  • HMS2232H21
  • HMS3414C15
  • HMS3678C15
  • HMS3715I12
  • HMS3884C17
  • HSDB 7531
  • HY-B0122
  • KS-1122
  • MFCD00865320
  • MLS000759431
  • MLS001424070
  • McN 4853
  • McN-4853
  • NC00190
  • NCGC00095181-01
  • NCGC00178714-01
  • NCGC00178714-04
  • NCGC00178714-18
  • NCGC00255221-01
  • NSC 759251
  • NSC-759251
  • NSC759251
  • Pharmakon1600-01505801
  • Q-201845
  • Q221174
  • QSYMIA COMPONENT TOPIRAMATE
  • Qudexy
  • Qudexy XR
  • RWJ 17021
  • RWJ-17021
  • RWJ-17021-000
  • SBI-0206907.P001
  • SMR000466325
  • SPECTRUM1505801
  • SR-01000759409
  • SR-01000759409-4
  • SW197570-3
  • Sincronil
  • Sulfamate 7
  • TOPIRAMATE COMPONENT OF QSYMIA
  • TOR
  • TPM
  • Tipiramate
  • Tipiramato
  • Topamac
  • Topamax
  • Topamax Sprinkle
  • Topax
  • Topimax
  • Topina
  • Topiragen
  • Topiramate
  • Topiramate (JAN/USP/INN)
  • Topiramate (TPM)
  • Topiramate 1.0 mg/ml in Acetonitrile
  • Topiramate solution
  • Topiramate- Bio-X
  • Topiramato
  • Topiramatum
  • Topomax
  • Trokendi XR
  • USL 255
  • USL-255
  • USL255
  • W-60376
  • Z1522553470
  • [(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
  • [(1R,2S,6S,9R)-4,4,11,11-tetramethyl-3,5,7,10,12-pentaoxatricyclo[7.3.0.0^{2,6}]dodecan-6-yl]methyl sulfamate
  • [(3aS,5aR,8aR,8bS)-2,2,7,7-tetramethyl-5,5a,8a,8b-tetrahydrodi[1,3]dioxolo[4,5-a:5',3'-d]pyran-3a-yl]methyl sulfamate
  • [(3aS,5aR,8aR,8bS)-2,2,7,7-tetramethyl-5,5a,8a,8b-tetrahydrodi[1,3]dioxolo[5,4-b:5',3'-d]pyran-3a-yl]methyl sulfamate
  • [(3aS,5aR,8aR,8bS)-2,2,7,7-tetramethyltetrahydro-3aH-bis[1,3]dioxolo[4,5-b:4',5'-d]pyran-3a-yl]methyl sulfamate
  • [(3aS,5aR,8aR,8bS)-2,2,7,7-tetramethyltetrahydro-3aH-bis[1,3]dioxolo[4,5-b:4',5'-d]pyran-3a-yl]methyl sulfamate (non-preferred name)
  • beta-D-Fructopyranose, 2,3:4,5-bis-O-(1-methylethylidene)-, sulfamate
  • s1438
  • topiramate

Reference codes for other databases

There exist several different chemical codes commonly used in orded to identify molecules:
  • ZINC95616603
  • CAS-97240-79-4
  • UNII-0H73WJJ391
  • AKOS000424547
  • ALBB-022457
  • DTXSID8023688
  • CHEMBL220492
  • CHEBI:63631
  • Tox21_111472
  • Tox21_302401
  • Tox21_111472_1
  • SPBio_000995
  • SCHEMBL34631
  • Spectrum2_001128

Physico-Chemical properties

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
Molecular formulaC12H21NO8S
Molecular weight339.362
Melting point (ºC)
Boiling point (ºC)
Density (g/cm3)
Molar refractivity71.75
LogP1.4
Topological polar surface area123.9

LogP and topological polar surface area (TPSA) values were estimated using Open Babel software.

The n-octanol/water partition coeficient (Kow) data is applied in toxicology and drug research. Kow values are used, to guess the environmental fate of persistent organic pollutants. High partition coefficients values, tend to accumulate in the fatty tissue of organisms. Molecules with a log(Kow) (or LogP) greater than 5 are considered to bioaccumulate.

TPSA values are the sum of the surface area over all polar atoms or molecules, mainly oxygen and nitrogen, also including hydrogen atoms.

In medicinal chemistry, TPSA is used to assess the ability of a drug to permeabilise cells.

For molecules to penetrate the blood-brain barrier (and act on receptors in the central nervous system), TPSA values below 90 Å2 are required. Thus, molecules with a polar surface area greater than 140 Å2 tend to be poorly permeable to cell membranes.