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

Stem definitionDrug idCAS RN
2872 68291-97-4

Description:

MoleculeDescription

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:

DoseUnitRoute
0.20 g O

ADMET properties:

PropertyValueReference
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 ┬ÁM/kg/day Contrera JF, Matthews EJ, Kruhlak NL, Benz RD
BA (Bioavailability) 99 % Kim MT, Sedykh A, Chakravarti SK, Saiakhov RD, Zhu H

Approvals:

DateAgencyCompanyOrphan
March 27, 2000 FDA EISAI INC

FDA Adverse Event Reporting System (Female)

MedDRA adverse event termLikelihood ratioLikelihood ratio thresholdPatients taking drug having adverse eventPatients taking drug not having adverse eventPatients not taking drug having adverse eventPatients 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 termLikelihood ratioLikelihood ratio thresholdPatients taking drug having adverse eventPatients taking drug not having adverse eventPatients not taking drug having adverse eventPatients 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:

SourceCodeDescription
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)

DiseaseRelationSNOMED_IDDOID
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 levelDissociation constantType (acidic/basic)
pKa1 10.47 acidic

Orange Book patent data (new drug applications)

None

Orange Book exclusivity data (new drug applications)

None

Bioactivity Summary:

TargetClassPharosUniProtActionTypeActivity value
(-log[M])
Mechanism
action
Bioact sourceMoA source
Sodium channel protein type 1 subunit alpha Ion channel BLOCKER WOMBAT-PK CHEMBL
Carbonic anhydrase 5A, mitochondrial Enzyme Ki 7.70 CHEMBL
Carbonic anhydrase 14 Enzyme Ki 5.28 CHEMBL
Carbonic anhydrase 7 Enzyme Ki 6.93 CHEMBL
Carbonic anhydrase V Enzyme Ki 7.69 CHEMBL
Carbonic anhydrase 4 Enzyme Ki 5.07 CHEMBL
Carbonic anhydrase 5B, mitochondrial Enzyme Ki 5.22 CHEMBL
Amine oxidase [flavin-containing] B Enzyme Ki 5.51 CHEMBL
Carbonic anhydrase 13 Enzyme Ki 6.37 CHEMBL
Carbonic anhydrase 6 Enzyme Ki 7.05 CHEMBL
Carbonic anhydrase 9 Enzyme Ki 8.30 WOMBAT-PK
Carbonic anhydrase 1 Enzyme Ki 7.25 WOMBAT-PK
Voltage-dependent T-type calcium channel subunit alpha-1G Ion channel WOMBAT-PK
Carbonic anhydrase 2 Enzyme Ki 6.99 WOMBAT-PK
Carbonic anhydrase 12 Enzyme INHIBITOR Ki 4.96 IUPHAR
Carbonic anhydrase Unclassified Ki 6.19 CHEMBL
Delta carbonic anhydrase Unclassified Ki 6.39 CHEMBL
Carbonic anhydrase 2 Unclassified Ki 6.01 CHEMBL
Carbonic anhydrase Enzyme Ki 6.97 CHEMBL
Carbonic anhydrase Enzyme Ki 6.66 CHEMBL
Carbonic anhydrase 15 Enzyme Ki 6.20 CHEMBL
Alpha carbonic anhydrase Unclassified Ki 6.59 CHEMBL
Probable transmembrane carbonic anhydrase (Carbonate dehydratase) (Carbonic dehydratase); Transmembrane carbonic anhydrase Enzyme Ki 6.68 CHEMBL
Carbonic anhydrase 3 Enzyme Ki 5.07 CHEMBL
Astrosclerin-3 Unclassified Ki 6.78 CHEMBL
Amine oxidase [flavin-containing] B Enzyme Ki 5.54 CHEMBL
Amine oxidase [flavin-containing] Unclassified Ki 4.51 CHEMBL
Carbonic anhydrase Enzyme Ki 7.46 CHEMBL
Beta-carbonic anhydrase 1 Enzyme Ki 4.54 CHEMBL
Carbonic anhydrase 2 Enzyme Ki 6.06 CHEMBL
Carbonic anhydrase Unclassified Ki 6.58 CHEMBL
Carbonic anhydrase Enzyme Ki 6.94 CHEMBL

External reference:

IDSource
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:

ProductCategoryIngredientsNDCFormQuantityRouteMarketingLabel
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