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topiramate 🐶 Veterinary Use | Indications/Contra | FAERs-F | FAERs-M | Orange Bk | BioActivity |

Stem definition	Drug id	CAS RN
	2706	97240-79-4

Description:

Molecule	Description
Molfile Inchi Smiles Synonyms: topiramate beta-D-fructopyranose sulfamate epitoma epitomax topamac topamax topimax topomax topina	The precise mechanisms by which topiramate exerts its anticonvulsant and migraine prophylaxis effects are unknown; however, preclinical studies have revealed four properties that may contribute to topiramate's efficacy for epilepsy and migraine prophylaxis. Electrophysiological and biochemical evidence suggests that topiramate, at pharmacologically relevant concentrations, blocks voltage-dependent sodium channels, augments the activity of the neurotransmitter gamma-aminobutyrate at some subtypes of the GABA-A receptor, antagonizes the AMPA/kainate subtype of the glutamate receptor, and inhibits the carbonic anhydrase enzyme, particularly isozymes II and IV. Molecular weight: 339.36 Formula: C12H21NO8S CLOGP: 0.04 LIPINSKI: 0 HAC: 9 HDO: 1 TPSA: 115.54 ALOGS: -1.70 ROTB: 3 Status: OFP Legend: OFP - off patent OFM - off market ONP - on patent

Molecule

Description

Molfile Inchi Smiles

Synonyms:

topiramate
beta-D-fructopyranose sulfamate
epitoma
epitomax
topamac
topamax
topimax
topomax
topina

The precise mechanisms by which topiramate exerts its anticonvulsant and migraine prophylaxis effects are unknown; however, preclinical studies have revealed four properties that may contribute to topiramate's efficacy for epilepsy and migraine prophylaxis. Electrophysiological and biochemical evidence suggests that topiramate, at pharmacologically relevant concentrations, blocks voltage-dependent sodium channels, augments the activity of the neurotransmitter gamma-aminobutyrate at some subtypes of the GABA-A receptor, antagonizes the AMPA/kainate subtype of the glutamate receptor, and inhibits the carbonic anhydrase enzyme, particularly isozymes II and IV.

Molecular weight: 339.36
Formula: C12H21NO8S
CLOGP: 0.04
LIPINSKI: 0
HAC: 9
HDO: 1
TPSA: 115.54
ALOGS: -1.70
ROTB: 3

Status: OFP

Legend:
OFP - off patent
OFM - off market
ONP - on patent

Drug dosage:

Dose	Unit	Route
0.30	g	O

ADMET properties:

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Property	Value	Reference
S (Water solubility)	9.80 mg/mL	Benet LZ, Broccatelli F, Oprea TI
EoM (Fraction excreted unchanged in urine)	70 %	Benet LZ, Broccatelli F, Oprea TI
BA (Bioavailability)	70 %	Kim MT, Sedykh A, Chakravarti SK, Saiakhov RD, Zhu H
t_half (Half-life)	34.80 hours	Lombardo F, Berellini G, Obach RS
BDDCS (Biopharmaceutical Drug Disposition Classification System)	3	Benet LZ, Broccatelli F, Oprea TI
MRTD (Maximum Recommended Therapeutic Daily Dose)	19.65 µM/kg/day	Contrera JF, Matthews EJ, Kruhlak NL, Benz RD
Vd (Volume of distribution)	0.80 L/kg	Lombardo F, Berellini G, Obach RS
fu (Fraction unbound in plasma)	0.72 %	Lombardo F, Berellini G, Obach RS
CL (Clearance)	0.27 mL/min/kg	Lombardo F, Berellini G, Obach RS

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Approvals:

Date	Agency	Company	Orphan
Dec. 24, 1996	FDA	JANSSEN PHARMS
July 1, 2007	PMDA

FDA Adverse Event Reporting System (Female)

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MedDRA adverse event term	Likelihood ratio	Likelihood ratio threshold	Patients taking drug having adverse event	Patients taking drug not having adverse event	Patients not taking drug having adverse event	Patients not taking drug not having adverse event
Angle closure glaucoma	1193.04	10.27	340	108134	1879	63378669
Seizure	1171.40	10.27	1282	107192	131352	63249196
Migraine	639.36	10.27	834	107640	102512	63278036
Product substitution issue	472.99	10.27	311	108163	15685	63364863
Myopia	452.58	10.27	151	108323	1504	63379044
Drug ineffective for unapproved indication	424	10.27	397	108077	33666	63346882
Completed suicide	420.12	10.27	830	107644	144843	63235705
Choroidal effusion	396.53	10.27	103	108371	373	63380175
Multiple-drug resistance	353.57	10.27	174	108300	4996	63375552
Intentional self-injury	326.63	10.27	303	108171	25384	63355164

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FDA Adverse Event Reporting System (Male)

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MedDRA adverse event term	Likelihood ratio	Likelihood ratio threshold	Patients taking drug having adverse event	Patients taking drug not having adverse event	Patients not taking drug having adverse event	Patients not taking drug not having adverse event
Seizure	1001.68	13.17	824	33440	104033	34818634
Drug ineffective	374.64	13.17	1134	33130	455617	34467050
Status epilepticus	341.95	13.17	190	34074	12424	34910243
Angle closure glaucoma	285.63	13.17	82	34182	875	34921792
Multiple-drug resistance	279.37	13.17	125	34139	5114	34917553
Sedation	257.70	13.17	192	34072	20814	34901853
Aggression	254.80	13.17	248	34016	38716	34883951
Nephrolithiasis	254.60	13.17	222	34042	30111	34892556
Heat stroke	245.29	13.17	73	34191	892	34921775
Somnolence	177.84	13.17	358	33906	110758	34811909

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FDA Adverse Event Reporting System (Geriatric)

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MedDRA adverse event term	Likelihood ratio	Likelihood ratio threshold	Patients taking drug having adverse event	Patients taking drug not having adverse event	Patients not taking drug having adverse event	Patients not taking drug not having adverse event
Angle closure glaucoma	1348.37	10.77	381	110066	2595	79631346
Seizure	1299.72	10.77	1449	108998	187385	79446556
Migraine	684.05	10.77	719	109728	86774	79547167
Myopia	599.25	10.77	185	110262	1771	79632170
Choroidal effusion	522.04	10.77	132	110315	545	79633396
Completed suicide	502.92	10.77	1074	109373	244693	79389248
Multiple-drug resistance	457.86	10.77	230	110217	8578	79625363
Drug ineffective	438.39	10.77	2769	107678	1078144	78555797
Drug ineffective for unapproved indication	419.85	10.77	432	110015	50806	79583135
Status epilepticus	408.43	10.77	312	110135	24729	79609212

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FDA Adverse Event Reporting System (Pediatric)

None

Pharmacologic Action:

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Source	Code	Description
ATC	A08AA51	ALIMENTARY TRACT AND METABOLISM ANTIOBESITY PREPARATIONS, EXCL. DIET PRODUCTS ANTIOBESITY PREPARATIONS, EXCL. DIET PRODUCTS Centrally acting antiobesity products
ATC	N03AX11	NERVOUS SYSTEM ANTIEPILEPTICS ANTIEPILEPTICS Other antiepileptics
CHEBI has role	CHEBI:35623	anticonvulsants
CHEBI has role	CHEBI:38633	sodium channel blockers
FDA MoA	N0000182140	Cytochrome P450 2C19 Inhibitors
FDA MoA	N0000185506	Cytochrome P450 3A4 Inducers
FDA PE	N0000008486	Decreased Central Nervous System Disorganized Electrical Activity
MeSH PA	D000927	Anticonvulsants
MeSH PA	D002491	Central Nervous System Agents
MeSH PA	D007004	Hypoglycemic Agents

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Drug Use | Suggest Off label Use Form| |View source of the data|

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Disease	Relation	SNOMED_ID	DOID
Lennox-Gastaut syndrome	indication	230418006
Tonic-clonic epilepsy	indication	352818000	DOID:7725
Epilepsy characterized by intractable complex partial seizures	indication	442481002
Simple partial seizure	indication	117891000119100
Migraine Prevention	indication
Alcoholism	off-label use	7200002
Essential tremor	off-label use	609558009	DOID:4990
Ocular hypertension	contraindication	4210003	DOID:9282
Suicidal thoughts	contraindication	6471006
Reduced visual acuity	contraindication	13164000

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🐶 Veterinary Drug Use

None

🐶 Veterinary products

None

Acid dissociation constants calculated using MoKa v3.0.0

Dissociation level	Dissociation constant	Type (acidic/basic)
pKa1	8.6	acidic

Orange Book patent data (new drug applications)

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Formulation strength	Trade name	Applicant	Application number	Approval date	Type	Dose form	Route	Patent number	Patent expiration date	Patent use
100MG	TROKENDI XR	SUPERNUS PHARMS	N201635	Aug. 16, 2013	RX	CAPSULE, EXTENDED RELEASE	ORAL	10314790	Nov. 16, 2027	USE OF TROKENDI XR FOR PROPHYLACTIC TREATMENT OF MIGRAINE
100MG	TROKENDI XR	SUPERNUS PHARMS	N201635	Aug. 16, 2013	RX	CAPSULE, EXTENDED RELEASE	ORAL	10314790	Nov. 16, 2027	USE OF TROKENDI XR FOR THE TREATMENT OF EPILEPSY
100MG	TROKENDI XR	SUPERNUS PHARMS	N201635	Aug. 16, 2013	RX	CAPSULE, EXTENDED RELEASE	ORAL	8298580	Nov. 16, 2027	TREATMENT OF EPILEPSY
100MG	TROKENDI XR	SUPERNUS PHARMS	N201635	Aug. 16, 2013	RX	CAPSULE, EXTENDED RELEASE	ORAL	8298580	Nov. 16, 2027	USE OF TROKENDI XR FOR PROPHYLACTIC TREATMENT OF MIGRAINE
100MG	TROKENDI XR	SUPERNUS PHARMS	N201635	Aug. 16, 2013	RX	CAPSULE, EXTENDED RELEASE	ORAL	8663683	Nov. 16, 2027	TREATMENT OF EPILEPSY
100MG	TROKENDI XR	SUPERNUS PHARMS	N201635	Aug. 16, 2013	RX	CAPSULE, EXTENDED RELEASE	ORAL	8663683	Nov. 16, 2027	USE OF TROKENDI XR FOR PROPHYLACTIC TREATMENT OF MIGRAINE
100MG	TROKENDI XR	SUPERNUS PHARMS	N201635	Aug. 16, 2013	RX	CAPSULE, EXTENDED RELEASE	ORAL	8877248	Nov. 16, 2027	TREATMENT OF EPILEPSY
100MG	TROKENDI XR	SUPERNUS PHARMS	N201635	Aug. 16, 2013	RX	CAPSULE, EXTENDED RELEASE	ORAL	8877248	Nov. 16, 2027	USE OF TROKENDI XR FOR PROPHYLACTIC TREATMENT OF MIGRAINE
100MG	TROKENDI XR	SUPERNUS PHARMS	N201635	Aug. 16, 2013	RX	CAPSULE, EXTENDED RELEASE	ORAL	8889191	Nov. 16, 2027	TREATMENT OF EPILEPSY
100MG	TROKENDI XR	SUPERNUS PHARMS	N201635	Aug. 16, 2013	RX	CAPSULE, EXTENDED RELEASE	ORAL	8889191	Nov. 16, 2027	USE OF TROKENDI XR FOR PROPHYLACTIC TREATMENT OF MIGRAINE

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Orange Book exclusivity data (new drug applications)

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Formulation strength	Trade name	Applicant	Application number	Approval date	Type	Dose form	Route	Exclusivity date	Description
EQ 11.25MG BASE;69MG	QSYMIA	VIVUS	N022580	July 17, 2012	RX	CAPSULE, EXTENDED RELEASE	ORAL	June 24, 2025	NEW PATIENT POPULATION
EQ 15MG BASE;92MG	QSYMIA	VIVUS	N022580	July 17, 2012	RX	CAPSULE, EXTENDED RELEASE	ORAL	June 24, 2025	NEW PATIENT POPULATION
EQ 3.75MG BASE;23MG	QSYMIA	VIVUS	N022580	July 17, 2012	RX	CAPSULE, EXTENDED RELEASE	ORAL	June 24, 2025	NEW PATIENT POPULATION
EQ 7.5MG BASE;46MG	QSYMIA	VIVUS	N022580	July 17, 2012	RX	CAPSULE, EXTENDED RELEASE	ORAL	June 24, 2025	NEW PATIENT POPULATION

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Bioactivity Summary:

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Target	Class	Pharos	UniProt	Action	Type	Activity value (-log[M])	Bioact source	MoA source
Carbonic anhydrase 4	Enzyme	P22748	CAH4_HUMAN	INHIBITOR	Ki	5.31	CHEMBL	CHEMBL
GABA-A receptor alpha-1/beta-2/gamma-2	Ion channel	P14867 P18507 P47870	GBRA1_HUMAN GBRG2_HUMAN GBRB2_HUMAN	POSITIVE MODULATOR			WOMBAT-PK	CHEMBL
Carbonic anhydrase 2	Enzyme	P00918	CAH2_HUMAN	INHIBITOR	Ki	8.30	CHEMBL	CHEMBL
Glutamate receptor ionotropic kainate	Ion channel	P39086 Q13002 Q13003 Q16099 Q16478	GRIK1_HUMAN GRIK2_HUMAN GRIK3_HUMAN GRIK4_HUMAN GRIK5_HUMAN	ANTAGONIST			CHEMBL	CHEMBL
Glutamate receptor ionotropic AMPA	Ion channel	P42261 P42262 P42263 P48058	GRIA1_HUMAN GRIA2_HUMAN GRIA3_HUMAN GRIA4_HUMAN	ANTAGONIST			CHEMBL	CHEMBL
Sodium channel protein type 1 subunit alpha	Ion channel	P35498	SCN1A_HUMAN	BLOCKER			DRUGBANK	CHEMBL
Sodium channel protein type 5 subunit alpha	Ion channel	Q14524	SCN5A_HUMAN	BLOCKER			WOMBAT-PK	CHEMBL
Carbonic anhydrase 7	Enzyme	P43166	CAH7_HUMAN		Ki	9.06	CHEMBL
Carbonic anhydrase 6	Enzyme	P23280	CAH6_HUMAN		Ki	7.35	CHEMBL
Carbonic anhydrase 14	Enzyme	Q9ULX7	CAH14_HUMAN		Ki	5.84	CHEMBL

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External reference:

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ID	Source
TOR	PDB_CHEM_ID
005453	NDDF
0H73WJJ391	UNII
108400009	SNOMEDCT_US
162273	MMSL
220343	RXNORM
386844006	SNOMEDCT_US
4021026	VUID
4021026	VANDF
5284627	PUBCHEM_CID

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Pharmaceutical products:

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Product	Category	Ingredients	NDC	Form	Quantity	Route	Marketing	Label
QUDEXY XR	HUMAN PRESCRIPTION DRUG LABEL	1	0245-1071	CAPSULE, EXTENDED RELEASE	25 mg	ORAL	NDA	30 sections
QUDEXY XR	HUMAN PRESCRIPTION DRUG LABEL	1	0245-1071	CAPSULE, EXTENDED RELEASE	25 mg	ORAL	NDA	30 sections
QUDEXY XR	HUMAN PRESCRIPTION DRUG LABEL	1	0245-1072	CAPSULE, EXTENDED RELEASE	50 mg	ORAL	NDA	30 sections
QUDEXY XR	HUMAN PRESCRIPTION DRUG LABEL	1	0245-1072	CAPSULE, EXTENDED RELEASE	50 mg	ORAL	NDA	30 sections
QUDEXY XR	HUMAN PRESCRIPTION DRUG LABEL	1	0245-1073	CAPSULE, EXTENDED RELEASE	200 mg	ORAL	NDA	30 sections
QUDEXY XR	HUMAN PRESCRIPTION DRUG LABEL	1	0245-1073	CAPSULE, EXTENDED RELEASE	200 mg	ORAL	NDA	30 sections
QUDEXY XR	HUMAN PRESCRIPTION DRUG LABEL	1	0245-1074	CAPSULE, EXTENDED RELEASE	100 mg	ORAL	NDA	30 sections
QUDEXY XR	HUMAN PRESCRIPTION DRUG LABEL	1	0245-1074	CAPSULE, EXTENDED RELEASE	100 mg	ORAL	NDA	30 sections
QUDEXY XR	HUMAN PRESCRIPTION DRUG LABEL	1	0245-1075	CAPSULE, EXTENDED RELEASE	150 mg	ORAL	NDA	30 sections
QUDEXY XR	HUMAN PRESCRIPTION DRUG LABEL	1	0245-1075	CAPSULE, EXTENDED RELEASE	150 mg	ORAL	NDA	30 sections

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