Scroll

zonisamide Indications/Contra | FAERs-F | FAERs-M | Orange Bk | BioActivity |

Stem definition	Drug id	CAS RN
	2872	68291-97-4

Description:

Molecule	Description
Molfile Inchi Smiles Synonyms: zonisamide exceglan excegram excegran zonegran	an antiseizure drug chemically classified as a sulfonamide and unrelated to other antiseizure agents, blocks sodium channels and reduces voltage-dependent, transient inward currents (T-type Ca2+ currents), consequently stabilizing neuronal membranes and suppressing neuronal hypersynchronization Molecular weight: 212.22 Formula: C8H8N2O3S CLOGP: -0.36 LIPINSKI: 0 HAC: 5 HDO: 1 TPSA: 86.19 ALOGS: -2.01 ROTB: 2 Status: OFP Legend: OFP - off patent OFM - off market ONP - on patent

Molecule

Description

Molfile Inchi Smiles

Synonyms:

zonisamide
exceglan
excegram
excegran
zonegran

an antiseizure drug chemically classified as a sulfonamide and unrelated to other antiseizure agents, blocks sodium channels and reduces voltage-dependent, transient inward currents (T-type Ca2+ currents), consequently stabilizing neuronal membranes and suppressing neuronal hypersynchronization

Molecular weight: 212.22
Formula: C8H8N2O3S
CLOGP: -0.36
LIPINSKI: 0
HAC: 5
HDO: 1
TPSA: 86.19
ALOGS: -2.01
ROTB: 2

Status: OFP

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

Drug dosage:

Dose	Unit	Route
0.20	g	O

ADMET properties:

Property	Value	Reference
BDDCS (Biopharmaceutical Drug Disposition Classification System)	1	Benet LZ, Broccatelli F, Oprea TI
S (Water solubility)	0.80 mg/mL	Benet LZ, Broccatelli F, Oprea TI
EoM (Fraction excreted unchanged in urine)	22 %	Benet LZ, Broccatelli F, Oprea TI
MRTD (Maximum Recommended Therapeutic Daily Dose)	40.39 µM/kg/day	Contrera JF, Matthews EJ, Kruhlak NL, Benz RD
BA (Bioavailability)	99 %	Kim MT, Sedykh A, Chakravarti SK, Saiakhov RD, Zhu H

Approvals:

Date	Agency	Company	Orphan
March 27, 2000	FDA	EISAI INC

FDA Adverse Event Reporting System (Female)

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	603.64	41.25	168	1117	24298	2332502
Drug reaction with eosinophilia and systemic symptoms	458.51	41.25	101	1184	5417	2351383
Stevens-Johnson syndrome	214.09	41.25	52	1233	4207	2352593
Drug ineffective	184.37	41.25	106	1179	101518	2255282
Epilepsy	131.80	41.25	36	1249	4603	2352197
Cognitive disorder	122.01	41.25	35	1250	5346	2351454
Toxic epidermal necrolysis	120.79	41.25	31	1254	3113	2353687
Multiple-drug resistance	120.32	41.25	20	1265	221	2356579
Drug eruption	119.69	41.25	31	1254	3228	2353572
Therapeutic response unexpected	109.81	41.25	30	1255	3829	2352971
Exposure during pregnancy	103.38	41.25	46	1239	25173	2331627
Product substitution issue	88.71	41.25	27	1258	5042	2351758
Rash	88.47	41.25	55	1230	59503	2297297
Condition aggravated	78.30	41.25	41	1244	31938	2324862
Psychotic disorder	77.93	41.25	24	1261	4655	2352145
Somnolence	77.84	41.25	37	1248	23448	2333352
Hyperammonaemic encephalopathy	74.85	41.25	14	1271	315	2356485
Suicidal behaviour	74.35	41.25	15	1270	506	2356294
Status epilepticus	73.87	41.25	20	1265	2458	2354342
Hepatic function abnormal	71.70	41.25	24	1261	6068	2350732
Generalised tonic-clonic seizure	70.59	41.25	23	1262	5349	2351451
Drug hypersensitivity	68.93	41.25	43	1242	46600	2310200
Depression	68.63	41.25	36	1249	28096	2328704
Pyrexia	68.22	41.25	45	1240	53663	2303137
Vomiting	67.63	41.25	50	1235	71552	2285248
Intentional overdose	67.47	41.25	27	1258	11294	2345506
Oculomucocutaneous syndrome	67.41	41.25	11	1274	107	2356693
Diplopia	67.24	41.25	20	1265	3445	2353355
Coma	66.01	41.25	25	1260	9031	2347769
Irritability	62.68	41.25	22	1263	6405	2350395
Lichen planus	58.39	41.25	12	1273	444	2356356
Drug interaction	56.34	41.25	32	1253	29131	2327669
Dizziness	50.91	41.25	39	1246	58626	2298174
Ureterolithiasis	50.62	41.25	10	1275	302	2356498
Abortion spontaneous	50.08	41.25	23	1262	13422	2343378
Calculus urinary	48.25	41.25	9	1276	199	2356601
Depressed mood	47.65	41.25	17	1268	5181	2351619
Lymphocyte stimulation test positive	46.71	41.25	9	1276	238	2356562
Ataxia	46.66	41.25	14	1271	2478	2354322
Weight decreased	46.50	41.25	28	1257	28343	2328457
Agranulocytosis	46.08	41.25	15	1270	3467	2353333
Decreased appetite	46.03	41.25	28	1257	28863	2327937
Nephrolithiasis	46.00	41.25	16	1269	4527	2352273
Brown tumour	45.11	41.25	6	1279	10	2356790
Erythema multiforme	44.12	41.25	13	1272	2162	2354638
Ovarian granulosa-theca cell tumour	43.20	41.25	6	1279	16	2356784
Migraine	42.10	41.25	19	1266	10634	2346166

FDA Adverse Event Reporting System (Male)

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	312.38	45.86	105	964	20336	1725376
Drug reaction with eosinophilia and systemic symptoms	245.98	45.86	64	1005	5006	1740706
Stevens-Johnson syndrome	215.20	45.86	53	1016	3304	1742408
Status epilepticus	186.62	45.86	43	1026	2003	1743709
Drug ineffective	118.70	45.86	76	993	63725	1681987
Aggression	116.16	45.86	40	1029	8075	1737637
Toxic epidermal necrolysis	110.07	45.86	29	1040	2342	1743370
Nephrolithiasis	108.12	45.86	32	1037	3960	1741752
Condition aggravated	97.24	45.86	46	1023	21104	1724608
Calculus urinary	84.58	45.86	16	1053	275	1745437
Drug eruption	81.54	45.86	24	1045	2902	1742810
Drug interaction	79.51	45.86	44	1025	27914	1717798
Pyrexia	72.99	45.86	50	1019	46350	1699362
Somnolence	72.51	45.86	35	1034	16704	1729008
Rash	71.20	45.86	46	1023	38647	1707065
Epilepsy	70.32	45.86	23	1046	3936	1741776
Neonatal pneumonia	67.47	45.86	10	1059	32	1745680
Foetal exposure during pregnancy	63.26	45.86	24	1045	6335	1739377
Neonatal hypotension	62.96	45.86	10	1059	56	1745656
Product substitution issue	62.04	45.86	20	1049	3266	1742446
Hepatic function abnormal	60.78	45.86	24	1045	7050	1738662
Oculomucocutaneous syndrome	60.67	45.86	10	1059	73	1745639
Agranulocytosis	56.39	45.86	19	1050	3557	1742155
Liver disorder	51.48	45.86	20	1049	5616	1740096
Aspartate aminotransferase increased	51.09	45.86	24	1045	10732	1734980
Neuroleptic malignant syndrome	50.71	45.86	17	1052	3131	1742581
Respiratory disorder neonatal	48.42	45.86	10	1059	273	1745439
Small for dates baby	46.06	45.86	11	1058	590	1745122

Pharmacologic Action:

Source	Code	Description
ATC	N03AX15	NERVOUS SYSTEM ANTIEPILEPTICS ANTIEPILEPTICS Other antiepileptics
FDA EPC	N0000175753	Anti-epileptic Agent
FDA PE	N0000008486	Decreased Central Nervous System Disorganized Electrical Activity
FDA CS	M0020790	Sulfonamides
FDA MoA	N0000000235	Carbonic Anhydrase Inhibitors
FDA MoA	N0000185503	P-Glycoprotein Inhibitors
CHEBI has role	CHEBI:35623	anticonvulsant
CHEBI has role	CHEBI:35470	central nervous system drug
CHEBI has role	CHEBI:50267	protective agent
MeSH PA	D000927	Anticonvulsants
MeSH PA	D002121	Calcium Channel Blockers
MeSH PA	D000077264	Calcium-Regulating Hormones and Agents
MeSH PA	D002317	Cardiovascular Agents
MeSH PA	D002491	Central Nervous System Agents
MeSH PA	D049990	Membrane Transport Modulators

Drug Use (View source of the data)

Disease	Relation	SNOMED_ID	DOID
Partial Epilepsy Treatment Adjunct	indication
Suicidal thoughts	contraindication	6471006
Agranulocytosis	contraindication	17182001	DOID:12987
Mood swings	contraindication	18963009
Depressive disorder	contraindication	35489007
Metabolic acidosis	contraindication	59455009
Diarrhea	contraindication	62315008
Psychotic disorder	contraindication	69322001
Kidney disease	contraindication	90708001	DOID:557
Kidney stone	contraindication	95570007
Diminished sweating	contraindication	111980002
Disease of liver	contraindication	235856003	DOID:409
Aplastic anemia	contraindication	306058006	DOID:12449
Severe chronic obstructive pulmonary disease	contraindication	313299006
Fever	contraindication	386661006
Surgical procedure	contraindication	387713003

Acid dissociation constants calculated using MoKa v3.0.0

Dissociation level	Dissociation constant	Type (acidic/basic)
pKa1	10.47	acidic

Orange Book patent data (new drug applications)

None

Orange Book exclusivity data (new drug applications)

None

Bioactivity Summary:

Target	Class	Pharos	UniProt	Action	Type	Activity value (-log[M])	Bioact source	MoA source
Sodium channel protein type 1 subunit alpha	Ion channel	P35498	SCN1A_HUMAN	BLOCKER			WOMBAT-PK	CHEMBL
Carbonic anhydrase 5A, mitochondrial	Enzyme	P35218	CAH5A_HUMAN		Ki	7.70	CHEMBL
Carbonic anhydrase 14	Enzyme	Q9ULX7	CAH14_HUMAN		Ki	5.28	CHEMBL
Carbonic anhydrase 7	Enzyme	P43166	CAH7_HUMAN		Ki	6.93	CHEMBL
Carbonic anhydrase V	Enzyme	P35218 Q9Y2D0	CAH5A_HUMAN CAH5B_HUMAN		Ki	7.69	CHEMBL
Carbonic anhydrase 4	Enzyme	P22748	CAH4_HUMAN		Ki	5.07	CHEMBL
Carbonic anhydrase 5B, mitochondrial	Enzyme	Q9Y2D0	CAH5B_HUMAN		Ki	5.22	CHEMBL
Amine oxidase [flavin-containing] B	Enzyme	P27338	AOFB_HUMAN		Ki	5.51	CHEMBL
Carbonic anhydrase 13	Enzyme	Q8N1Q1	CAH13_HUMAN		Ki	6.37	CHEMBL
Carbonic anhydrase 6	Enzyme	P23280	CAH6_HUMAN		Ki	7.05	CHEMBL
Carbonic anhydrase 9	Enzyme	Q16790	CAH9_HUMAN		Ki	8.30	WOMBAT-PK
Carbonic anhydrase 1	Enzyme	P00915	CAH1_HUMAN		Ki	7.25	WOMBAT-PK
Voltage-dependent T-type calcium channel subunit alpha-1G	Ion channel	O43497	CAC1G_HUMAN				WOMBAT-PK
Carbonic anhydrase 2	Enzyme	P00918	CAH2_HUMAN		Ki	6.99	WOMBAT-PK
Carbonic anhydrase 12	Enzyme	O43570	CAH12_HUMAN	INHIBITOR	Ki	4.96	IUPHAR
Carbonic anhydrase	Unclassified		C0IX24_9CNID		Ki	6.19	CHEMBL
Delta carbonic anhydrase	Unclassified		Q5U9J1_THAWE		Ki	6.39	CHEMBL
Carbonic anhydrase 2	Unclassified		Q3I4V7_CRYNV		Ki	6.01	CHEMBL
Carbonic anhydrase	Enzyme		CAN_YEAST		Ki	6.97	CHEMBL
Carbonic anhydrase	Enzyme		CYNT_HELPY		Ki	6.66	CHEMBL
Carbonic anhydrase 15	Enzyme		CAH15_MOUSE		Ki	6.20	CHEMBL
Alpha carbonic anhydrase	Unclassified		B5SU02_9CNID		Ki	6.59	CHEMBL
Probable transmembrane carbonic anhydrase (Carbonate dehydratase) (Carbonic dehydratase); Transmembrane carbonic anhydrase	Enzyme		P96878_MYCTU		Ki	6.68	CHEMBL
Carbonic anhydrase 3	Enzyme		CAH3_BOVIN		Ki	5.07	CHEMBL
Astrosclerin-3	Unclassified		A6YCJ1_9METZ		Ki	6.78	CHEMBL
Amine oxidase [flavin-containing] B	Enzyme		AOFB_RAT		Ki	5.54	CHEMBL
Amine oxidase [flavin-containing]	Unclassified		AOF_DANRE		Ki	4.51	CHEMBL
Carbonic anhydrase	Enzyme		CAN_CANAL		Ki	7.46	CHEMBL
Beta-carbonic anhydrase 1	Enzyme		MTCA1_MYCTU		Ki	4.54	CHEMBL
Carbonic anhydrase 2	Enzyme		MTCA2_MYCTU		Ki	6.06	CHEMBL
Carbonic anhydrase	Unclassified		Q5TU56_ANOGA		Ki	6.58	CHEMBL
Carbonic anhydrase	Enzyme		Q6FTL6_CANGA		Ki	6.94	CHEMBL

External reference:

ID	Source
D000078305	MESH_DESCRIPTOR_UI
4021224	VUID
N0000148668	NUI
C0078844	UMLSCUI
D00538	KEGG_DRUG
459384H98V	UNII
5575	INN_ID
398762003	SNOMEDCT_US
4021224	VANDF
73622	MMSL
008137	NDDF
d04527	MMSL
8781	MMSL
39998	RXNORM
125693002	SNOMEDCT_US
5734	PUBCHEM_CID
CHEBI:10127	CHEBI
CHEMBL750	ChEMBL_ID
DB00909	DRUGBANK_ID
ZON	PDB_CHEM_ID
7047	IUPHAR_LIGAND_ID

Pharmaceutical products:

Product	Category	Ingredients	NDC	Form	Quantity	Route	Marketing	Label
Zonisamide	HUMAN PRESCRIPTION DRUG LABEL	1	0185-0193	CAPSULE	25 mg	ORAL	ANDA	14 sections
Zonisamide	HUMAN PRESCRIPTION DRUG LABEL	1	0185-0199	CAPSULE	50 mg	ORAL	ANDA	14 sections
Zonisamide	HUMAN PRESCRIPTION DRUG LABEL	1	0185-0200	CAPSULE	100 mg	ORAL	ANDA	14 sections
zonisamide	HUMAN PRESCRIPTION DRUG LABEL	1	0615-8266	CAPSULE	100 mg	ORAL	ANDA	13 sections
ZONISAMIDE	HUMAN PRESCRIPTION DRUG LABEL	1	16590-539	CAPSULE	100 mg	ORAL	ANDA	15 sections
ZONISAMIDE	HUMAN PRESCRIPTION DRUG LABEL	1	16590-724	CAPSULE	25 mg	ORAL	ANDA	13 sections
ZONISAMIDE	HUMAN PRESCRIPTION DRUG LABEL	1	21695-155	CAPSULE	100 mg	ORAL	ANDA	14 sections
ZONISAMIDE	HUMAN PRESCRIPTION DRUG LABEL	1	21695-654	CAPSULE	50 mg	ORAL	ANDA	14 sections
Zonisamide	HUMAN PRESCRIPTION DRUG LABEL	1	31722-228	CAPSULE	100 mg	ORAL	ANDA	13 sections
ZONISAMIDE	HUMAN PRESCRIPTION DRUG LABEL	1	33261-843	CAPSULE	100 mg	ORAL	ANDA	12 sections
ZONISAMIDE	HUMAN PRESCRIPTION DRUG LABEL	1	35356-143	CAPSULE	100 mg	ORAL	ANDA	14 sections
Zonisamide	HUMAN PRESCRIPTION DRUG LABEL	1	43063-932	CAPSULE	25 mg	ORAL	ANDA	13 sections
Zonisamide	HUMAN PRESCRIPTION DRUG LABEL	1	50268-816	CAPSULE	100 mg	ORAL	ANDA	13 sections
Zonisamide	HUMAN PRESCRIPTION DRUG LABEL	1	51407-137	CAPSULE	25 mg	ORAL	ANDA	13 sections
Zonisamide	HUMAN PRESCRIPTION DRUG LABEL	1	51407-138	CAPSULE	50 mg	ORAL	ANDA	13 sections
Zonisamide	HUMAN PRESCRIPTION DRUG LABEL	1	51407-139	CAPSULE	100 mg	ORAL	ANDA	13 sections
zonisamide	HUMAN PRESCRIPTION DRUG LABEL	1	53217-301	CAPSULE	100 mg	ORAL	ANDA	13 sections
Zonisamide	HUMAN PRESCRIPTION DRUG LABEL	1	54868-5789	CAPSULE	100 mg	ORAL	ANDA	13 sections
Zonisamide	HUMAN PRESCRIPTION DRUG LABEL	1	54868-6221	CAPSULE	50 mg	ORAL	ANDA	13 sections
ZONISAMIDE	HUMAN PRESCRIPTION DRUG LABEL	1	55648-945	CAPSULE	25 mg	ORAL	ANDA	12 sections
ZONISAMIDE	HUMAN PRESCRIPTION DRUG LABEL	1	55648-946	CAPSULE	50 mg	ORAL	ANDA	12 sections
ZONISAMIDE	HUMAN PRESCRIPTION DRUG LABEL	1	55648-990	CAPSULE	100 mg	ORAL	ANDA	12 sections
Zonegran	HUMAN PRESCRIPTION DRUG LABEL	1	59212-680	CAPSULE	100 mg	ORAL	NDA	14 sections
Zonegran	HUMAN PRESCRIPTION DRUG LABEL	1	59212-681	CAPSULE	25 mg	ORAL	NDA	14 sections
Zonisamide	HUMAN PRESCRIPTION DRUG LABEL	1	60687-230	CAPSULE	100 mg	ORAL	ANDA	13 sections
ZONISAMIDE	HUMAN PRESCRIPTION DRUG LABEL	1	61919-275	CAPSULE	50 mg	ORAL	ANDA	11 sections
Zonisamide	HUMAN PRESCRIPTION DRUG LABEL	1	61919-591	CAPSULE	50 mg	ORAL	ANDA	14 sections
ZONISAMIDE	HUMAN PRESCRIPTION DRUG LABEL	1	61919-749	CAPSULE	50 mg	ORAL	ANDA	13 sections
ZONISAMIDE	HUMAN PRESCRIPTION DRUG LABEL	1	61919-775	CAPSULE	100 mg	ORAL	ANDA	13 sections
ZONISAMIDE	HUMAN PRESCRIPTION DRUG LABEL	1	61919-917	CAPSULE	100 mg	ORAL	ANDA	12 sections