Topiramate

Topiramate
Clinical data
Trade names	Topamax, Trokendi XR, Qudexy XR, others
Other names	Topiramic acid
AHFS/Drugs.com	Monograph
MedlinePlus	a697012
License data	US DailyMed: Topiramate;
Pregnancy; category	AU: D; ;
Routes of; administration	Oral
ATC code	N03AX11 (WHO) A08AA51 (WHO);
Legal status
Legal status	AU: S4 (Prescription only); BR: Class C1 (Other controlled substances); CA: ℞-only; UK: POM (Prescription only); US: ℞-only; EU: Rx-only;
Pharmacokinetic data
Bioavailability	80%
Protein binding	13–17%; 15–41%
Metabolism	Liver (20–30%)
Elimination half-life	21 hours
Excretion	Urine (70–80%)
Identifiers
	IUPAC name 2,3:4,5-Bis-O-(1-methylethylidene)-β-D-fructopyranose sulfamate;
CAS Number	97240-79-4 ;
PubChem CID	5284627;
IUPHAR/BPS	6849;
DrugBank	DB00273 ;
ChemSpider	4447672 ;
UNII	0H73WJJ391;
KEGG	D00537 ;
ChEMBL	ChEMBL220492 ;
PDB ligand	TOR (PDBe, RCSB PDB);
CompTox Dashboard (EPA)	DTXSID8023688 ;
ECHA InfoCard	100.129.713
Chemical and physical data
Formula	C12H21NO8S
Molar mass	339.36 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES O=S(=O)(OC[C@@]21OC(O[C@H]1[C@@H]3OC(O[C@@H]3CO2)(C)C)(C)C)N;
	InChI 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 ; Key:KJADKKWYZYXHBB-XBWDGYHZSA-N ;
	(what is this?) (verify)

Topiramate, marketed as Topamax and other brand names, is an oral medication primarily prescribed for the treatment of epilepsy and the prophylaxis of migraines. For epilepsy, this includes treatment for generalized or focal seizures. It has also been used off-label for alcohol dependence and essential tremor.

Common side effects include tingling, feeling tired, loss of appetite, abdominal pain, weight loss, and decreased cognitive function such as trouble concentrating. Serious side effects may include suicidal ideation, increased ammonia levels resulting in encephalopathy, and kidney stones. Topiramate can cause birth defects, including cleft lip and palate. Risks/benefits should be carefully discussed with the full treatment team. Topiramate is considered "probably compatible" with lactation and is not contraindicated for breastfeeding, though monitoring of the infant for diarrhea or poor weight gain may be considered. Its mechanism of action is unclear.

Topiramate was first synthesized with the intent of being an oral hypoglycemic agent; however, it received its initial approval as an anticonvulsant in 1996. It is available as a generic medication. In 2023, it was the 71st most commonly prescribed medication in the United States, with more than 9 million prescriptions.