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Topiramate

Base Information Edit
  • Chemical Name:Topiramate
  • CAS No.:97240-79-4
  • Molecular Formula:C12H21NO8S
  • Molecular Weight:339.367
  • Hs Code.:29350090
  • European Community (EC) Number:619-263-3
  • NSC Number:759251
  • UNII:0H73WJJ391
  • DSSTox Substance ID:DTXSID8023688
  • Nikkaji Number:J345.989F
  • Wikipedia:Topiramate
  • Wikidata:Q221174
  • NCI Thesaurus Code:C47764
  • RXCUI:38404
  • Pharos Ligand ID:6G275DDMHZ4N
  • Metabolomics Workbench ID:38716
  • ChEMBL ID:CHEMBL220492
  • Mol file:97240-79-4.mol
Topiramate

Synonyms:2,3-4,5-bis-O-(1-methylethylidene)-beta-D-fructopyranose sulfamate;Epitomax;McN 4853;McN-4853;McN4853;Topamax;topiramate;USL255

Suppliers and Price of Topiramate
Supply Marketing:Edit
Business phase:
The product has achieved commercial mass production*data from LookChem market partment
Manufacturers and distributors:
  • Manufacture/Brand
  • Chemicals and raw materials
  • Packaging
  • price
  • Usbiological
  • Topiramate
  • 100mg
  • $ 403.00
  • TRC
  • Topiramate
  • 100mg
  • $ 95.00
  • Tocris
  • Topiramate ≥99%(HPLC)
  • 10
  • $ 100.00
  • Tocris
  • Topiramate ≥99%(HPLC)
  • 50
  • $ 420.00
  • TCI Chemical
  • Topiramate >98.0%(HPLC)(T)
  • 5g
  • $ 303.00
  • TCI Chemical
  • Topiramate >98.0%(HPLC)(T)
  • 1g
  • $ 90.00
  • Sigma-Aldrich
  • Topiramate solution 1.0?mg/mL in methanol, ampule of 1?mL, certified reference material, Cerilliant?
  • 1 mL
  • $ 86.60
  • Sigma-Aldrich
  • Topiramate solution 1.0 mg/mL in methanol, ampule of 1 mL, certified reference material
  • 039-1ml
  • $ 83.90
  • Sigma-Aldrich
  • Topiramate European Pharmacopoeia (EP) Reference Standard
  • $ 130.00
  • Sigma-Aldrich
  • Topiramate ≥98% (HPLC), solid
  • 10mg
  • $ 128.00
Total 240 raw suppliers
Chemical Property of Topiramate Edit
Chemical Property:
  • Appearance/Colour:white to off-white crystalline powder 
  • Vapor Pressure:6.76E-08mmHg at 25°C 
  • Melting Point:125 °C 
  • Refractive Index:1.497 
  • Boiling Point:438.7 °C at 760 mmHg 
  • PKA:9.22±0.70(Predicted) 
  • Flash Point:219.1 °C 
  • PSA:123.92000 
  • Density:1.336 g/cm3 
  • LogP:1.38570 
  • Storage Temp.:2-8°C 
  • Solubility.:DMSO: ~44 mg/mL 
  • Water Solubility.:9.705g/L(temperature not stated) 
  • XLogP3:-0.8
  • Hydrogen Bond Donor Count:1
  • Hydrogen Bond Acceptor Count:9
  • Rotatable Bond Count:3
  • Exact Mass:339.09878780
  • Heavy Atom Count:22
  • Complexity:556
Purity/Quality:

99%, *data from raw suppliers

Topiramate *data from reagent suppliers

Safty Information:
  • Pictogram(s): IrritantXi 
  • Hazard Codes:Xi,T,F 
  • Statements: 36/37/38-39/23/24/25-23/24/25-11 
  • Safety Statements: 26-36-45-36/37-16-7 
MSDS Files:

SDS file from LookChem

Useful:
  • Drug Classes:Anticonvulsants
  • Canonical SMILES:CC1(OC2COC3(C(C2O1)OC(O3)(C)C)COS(=O)(=O)N)C
  • Isomeric SMILES:CC1(O[C@@H]2CO[C@@]3([C@H]([C@@H]2O1)OC(O3)(C)C)COS(=O)(=O)N)C
  • Recent ClinicalTrials:Study of Human Non-Shivering Thermogenesis and Basal Metabolic Rate
  • Recent EU Clinical Trials:A 12-month prospective, randomized, interventional, global, multi-center, active-controlled study comparing sustained benefit of two treatment paradigms (erenumab qm vs. oral prophylactics) in adult episodic migraine patients
  • Recent NIPH Clinical Trials:Effect of zonisamide on psychotropic drug induced weight gain
  • Indications Epilepsy: monotherapy and adjunctive therapy of focal and generalized seizures. Recommendations summarized from NICE (2012) Seizure types: first line (myoclonic seizures), adjunctive (generalized tonicclonic seizures, focal seizures, myoclonic seizures), on referral to tertiary care (tonic/ atonic seizures, absence seizures). Epilepsy types: first line (juvenile myoclonic epilepsy, idiopathic generalized epilepsy, Dravet), adjunctive (juvenile myoclonic epilepsy, epilepsy with generalized tonic- clonic seizures only, idiopathic generalized epilepsy, benign epilepsy with centrotemporal spikes, Panayiotopoulos syndrome, late- onset childhood occipital epilepsy), on referral to tertiary care (absence syndromes), contraindicated (Lennox– Gastaut syndrome). Neurology: migraine prophylaxis
  • Description Topiramate, a novel sulfamate-substituted D-fructose derivative, was launched in the United Kingdom as an adjunct therapy for use in partial seizures with or without secondary generalized seizures in adult patients inadequately controlled on conventional antiepileptics. Topiramate is structurally distinct from other available antiepileptics and functions through a unique combination of several mechanisms. It appears to act by blocking voltage-sensitive sodium channels to raise the action potential threshold and block the spread of seizure, enhancing GABA activity at postsynaptic GABA receptors and reducing glutamate activity at postsynaptic AMPAtype receptors, and is also a carbonic anhydrase inhibitor. Topiramate is orally active with rapid absorption, high bioavailability, and long duration of action. Excellent efficacy has been reported as an add-on therapy in epilepsy and it is also being evaluated as a monotherapy.
  • Uses Used as an anticonvulsant anticonvulsant, antimigraine, GABA-A agonist, AMP/kinate glutamate receptor antagonist, carbonic anhydrase inhibitor Used for the treatment and control of partial seizures and severe tonic-clonic (grand mal) seizures and also for the prevention of migraine headaches. In children it is also used for treatment of Lennox-Gastaut syndrome. Qsymia? is indicated for the treat Topiramate may be used as a pharmaceutical reference standard for the quantification of the analyte in pharmaceutical formulations using high-performance liquid chromatography technique and spectrophotometric technique.
  • Biological Functions Topiramate is most useful in patients with generalized tonic–clonic seizures and those with partial complex seizures. Topiramate causes a higher incidence of CNSrelated side effects (primarily cognitive slowing and confusion) than other AEDs. It does not appear to cause a significant incidence of rashes or other hypersensitivity reactions; however, a significantly higher incidence of kidney stones has been observed in persons receiving topiramate than in a similar untreated population.
  • Clinical Use Topiramate is a sulfamate-substituted monosaccharide derived from fructose with a broad spectrum of AED activity. It is approved for monotherapy or as an adjunct drug for partial or primary generalized tonic-clonic seizures in patients older than 10 years, as adjunct therapy in children aged from 2 to 10 years with partial-onset seizures, and in persons older than 2 years with Lennox-Gastaut syndrome. Topiramate also is approved for the prophylaxis of migraine headaches.
  • Drug interactions Potentially hazardous interactions with other drugs Antidepressants: antagonism of anticonvulsant effect; avoid with St John’s wort. Antiepileptics: concentration reduced by fosphenytoin, phenytoin, carbamazepine and possibly phenobarbital; increases fosphenytoin and phenytoin concentration; reduces concentration of perampanel; hyperammonaemia and CNS toxicity reported with valproate. Antimalarials: mefloquine antagonises anticonvulsant effect. Antipsychotics: anticonvulsant effect antagonised. Oestrogens and progestogens: reduced contraceptive effect. Orlistat: possibly increased risk of convulsions. Ulipristal: reduced contraceptive effect - avoid.
Technology Process of Topiramate

There total 16 articles about Topiramate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:
Guidance literature:
With ammonia; In tetrahydrofuran; hexane; at 20 ℃; for 3h; Solvent; Temperature;

Reference yield: 90.0%

Guidance literature:
With hydrazine hydrate; In ethanol; at 20 ℃; for 1h;
DOI:10.1080/00397911.2017.1361999
Guidance literature:
With pyridine; 2,2,2-trifluoro-1-(trifluoromethyl)ethyl sulfamate; In dichloromethane; at 30 ℃; for 8h;
DOI:10.1021/acs.orglett.1c00855
Refernces Edit
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