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 750.44 14.44 433 11221 122621 46551787
Epilepsy 200.31 14.44 104 11550 23634 46650774
Drug reaction with eosinophilia and systemic symptoms 192.37 14.44 109 11545 29439 46644969
Multiple-drug resistance 134.42 14.44 42 11612 2523 46671885
Status epilepticus 131.69 14.44 66 11588 13913 46660495
Atonic seizures 117.73 14.44 28 11626 592 46673816
Generalised tonic-clonic seizure 117.19 14.44 77 11577 27045 46647363
Stevens-Johnson syndrome 105.19 14.44 68 11586 23229 46651179
Drug eruption 83.57 14.44 57 11597 21272 46653136
Irritability 72.24 14.44 59 11595 28887 46645521
Focal dyscognitive seizures 64.91 14.44 25 11629 2803 46671605
Cognitive disorder 63.67 14.44 61 11593 36822 46637586
Oculomucocutaneous syndrome 63.01 14.44 13 11641 138 46674270
Aggression 62.37 14.44 49 11605 22695 46651713
Product substitution issue 60.85 14.44 41 11613 14990 46659418
Ataxia 56.40 14.44 38 11616 13892 46660516
Choroidal effusion 54.18 14.44 14 11640 420 46673988
Partial seizures 54.17 14.44 26 11628 4984 46669424
Drug withdrawal convulsions 54.07 14.44 18 11636 1323 46673085
Suicidal behaviour 53.91 14.44 21 11633 2427 46671981
Petit mal epilepsy 51.63 14.44 22 11632 3198 46671210
Therapeutic response unexpected 50.21 14.44 37 11617 15579 46658829
Somnolence 48.47 14.44 115 11539 156406 46518002
Dyskinesia 46.47 14.44 46 11608 28879 46645529
Psychotic disorder 45.98 14.44 41 11613 22580 46651828
Hyperammonaemic encephalopathy 43.63 14.44 17 11637 1965 46672443
Drug ineffective 43.52 14.44 303 11351 677535 45996873
Hepatic function abnormal 41.52 14.44 47 11607 34374 46640034
Tonic convulsion 41.25 14.44 14 11640 1092 46673316
Infantile spasms 40.33 14.44 10 11644 253 46674155
Rheumatoid arthritis 40.28 14.44 6 11648 240209 46434199
Ovarian granulosa-theca cell tumour 39.81 14.44 7 11647 28 46674380
Vestibular migraine 37.65 14.44 8 11646 99 46674309
Epileptic psychosis 33.20 14.44 6 11648 29 46674379
Dyspnoea 32.65 14.44 49 11605 515499 46158909
Calculus urinary 32.19 14.44 11 11643 876 46673532
Drug interaction 31.73 14.44 117 11537 202977 46471431
Diplopia 31.42 14.44 31 11623 19374 46655034
Brown tumour 31.07 14.44 6 11648 44 46674364
Intentional overdose 29.70 14.44 56 11598 64888 46609520
Depressed level of consciousness 29.59 14.44 47 11607 47522 46626886
Mood altered 29.30 14.44 25 11629 12982 46661426
Placental infarction 29.04 14.44 8 11646 308 46674100
Diarrhoea 28.42 14.44 61 11593 559541 46114867
Therapeutic product effective for unapproved indication 28.41 14.44 6 11648 72 46674336
Myoclonic epilepsy 27.94 14.44 10 11644 913 46673495
Toxic epidermal necrolysis 27.85 14.44 31 11623 22247 46652161
Lichen planus 27.66 14.44 12 11642 1821 46672587
Suicidal ideation 27.51 14.44 50 11604 56332 46618076
Delusion 26.22 14.44 22 11632 11166 46663242
Depressed mood 25.10 14.44 36 11618 33283 46641125
Depression 24.90 14.44 96 11558 170008 46504400
Hallucination, visual 24.31 14.44 26 11628 17847 46656561
Encapsulating peritoneal sclerosis 22.99 14.44 7 11647 385 46674023
Hallucination, auditory 22.86 14.44 20 11634 10736 46663672
Upper respiratory tract inflammation 22.84 14.44 12 11642 2783 46671625
Arthralgia 22.70 14.44 35 11619 364568 46309840
Therapeutic product ineffective for unapproved indication 22.55 14.44 6 11648 202 46674206
Migraine 22.22 14.44 52 11602 69974 46604434
Anticonvulsant drug level decreased 21.61 14.44 9 11645 1235 46673173
Hallucination 21.51 14.44 42 11612 49909 46624499
Erythema multiforme 20.53 14.44 18 11636 9686 46664722
Anticonvulsant drug level increased 20.47 14.44 9 11645 1411 46672997
Neuroleptic malignant syndrome 20.33 14.44 19 11635 11103 46663305
Drug level increased 20.25 14.44 24 11630 18417 46655991
Dysmetria 19.85 14.44 6 11648 322 46674086
Myoclonus 19.73 14.44 21 11633 14331 46660077
Drug resistance 19.73 14.44 23 11631 17345 46657063
Lymphocyte stimulation test positive 19.73 14.44 7 11647 623 46673785
Nystagmus 19.44 14.44 14 11640 5685 46668723
Exposure during pregnancy 19.15 14.44 65 11589 108147 46566261
Suicide attempt 18.71 14.44 42 11612 54994 46619414
Developmental delay 18.70 14.44 8 11646 1174 46673234
Ureterolithiasis 18.61 14.44 9 11645 1753 46672655
Disturbance in attention 18.01 14.44 30 11624 31530 46642878
Insomnia 17.87 14.44 85 11569 164839 46509569
Abnormal behaviour 17.72 14.44 24 11630 21034 46653374
Sinus arrhythmia 17.62 14.44 8 11646 1352 46673056
Myopia 17.47 14.44 8 11646 1379 46673029
Placental disorder 17.35 14.44 8 11646 1401 46673007
Altered state of consciousness 17.25 14.44 25 11629 23323 46651085
Product complaint 17.16 14.44 18 11636 12083 46662325
Pregnancy 17.13 14.44 27 11627 27110 46647298
Coma 17.08 14.44 42 11612 58307 46616101
Bipolar disorder 16.58 14.44 14 11640 7163 46667245
Agitation 16.34 14.44 40 11614 55375 46619033
Sudden unexplained death in epilepsy 16.27 14.44 5 11649 284 46674124
Joint swelling 15.90 14.44 11 11643 166062 46508346
Human herpes virus 6 serology positive 15.81 14.44 4 11650 110 46674298
Electrocardiogram PR prolongation 15.75 14.44 6 11648 653 46673755
Abortion spontaneous 15.61 14.44 34 11620 43612 46630796
Hypothermia 15.31 14.44 17 11637 12166 46662242
Therapeutic response changed 15.05 14.44 6 11648 736 46673672
Retinogram abnormal 15.05 14.44 4 11650 134 46674274
Encephalocele 14.72 14.44 4 11650 146 46674262
Congenital tracheomalacia 14.70 14.44 3 11651 30 46674378
Renal hypoplasia 14.44 14.44 3 11651 33 46674375

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 508.20 17.66 318 7631 98157 29846372
Status epilepticus 245.69 17.66 97 7852 10975 29933554
Epilepsy 133.98 17.66 77 7872 20092 29924437
Generalised tonic-clonic seizure 117.60 17.66 70 7879 19481 29925048
Drug reaction with eosinophilia and systemic symptoms 107.25 17.66 76 7873 28412 29916117
Stevens-Johnson syndrome 100.75 17.66 61 7888 17495 29927034
Aggression 93.93 17.66 78 7871 36829 29907700
Somnolence 80.59 17.66 113 7836 96650 29847879
Partial seizures 76.52 17.66 31 7918 3736 29940793
Choroidal effusion 60.91 17.66 13 7936 154 29944375
Calculus urinary 57.95 17.66 19 7930 1252 29943277
Focal dyscognitive seizures 57.35 17.66 19 7930 1294 29943235
Multiple-drug resistance 55.63 17.66 23 7926 2918 29941611
Oculomucocutaneous syndrome 54.51 17.66 12 7937 166 29944363
Toxic epidermal necrolysis 52.12 17.66 41 7908 17899 29926630
Drug eruption 48.66 17.66 39 7910 17487 29927042
Drug ineffective 48.46 17.66 198 7751 340189 29604340
Dyspnoea 47.18 17.66 15 7934 333280 29611249
Nystagmus 47.06 17.66 23 7926 4315 29940214
Nephrolithiasis 44.36 17.66 43 7906 24767 29919762
Hepatic function abnormal 42.52 17.66 54 7895 41891 29902638
Myoclonus 42.10 17.66 32 7917 13280 29931249
Delusion 40.54 17.66 30 7919 11959 29932570
Irritability 39.43 17.66 39 7910 23011 29921518
Pneumonia aspiration 38.87 17.66 49 7900 37731 29906798
Product substitution issue 38.24 17.66 27 7922 10008 29934521
Abnormal behaviour 35.98 17.66 39 7910 25584 29918945
Ataxia 35.03 17.66 27 7922 11435 29933094
Hyperammonaemic encephalopathy 33.45 17.66 14 7935 1830 29942699
Psychotic disorder 32.42 17.66 34 7915 21481 29923048
Drug withdrawal convulsions 32.28 17.66 12 7937 1147 29943382
Neonatal pneumonia 32.13 17.66 7 7942 92 29944437
Altered state of consciousness 30.95 17.66 32 7917 19887 29924642
Neonatal hypotension 30.56 17.66 7 7942 117 29944412
Salivary hypersecretion 30.33 17.66 21 7928 7545 29936984
Sudden unexplained death in epilepsy 30.03 17.66 9 7940 441 29944088
Anticonvulsant drug level increased 29.16 17.66 12 7937 1503 29943026
Infantile spasms 28.99 17.66 8 7941 291 29944238
Condition aggravated 28.69 17.66 91 7858 137775 29806754
Hallucination 25.15 17.66 46 7903 49013 29895516
Congenital inguinal hernia 24.99 17.66 6 7943 124 29944405
Aminoaciduria 24.94 17.66 6 7943 125 29944404
Lymphocyte stimulation test positive 24.07 17.66 9 7940 874 29943655
Dyskinesia 23.53 17.66 29 7920 21805 29922724
Hypotension 23.46 17.66 12 7937 200553 29743976
Atonic seizures 23.32 17.66 6 7943 166 29944363
Arthralgia 23.31 17.66 4 7945 135787 29808742
Cytotoxic oedema 22.60 17.66 6 7943 188 29944341
Parkinsonism 21.94 17.66 17 7932 7252 29937277
Angle closure glaucoma 21.92 17.66 8 7941 726 29943803
Depressive symptom 21.76 17.66 10 7939 1635 29942894
Drug interaction 21.40 17.66 107 7842 199461 29745068
Death 21.37 17.66 39 7910 357244 29587285
Liver disorder 20.74 17.66 32 7917 29690 29914839
Foetal exposure during pregnancy 20.72 17.66 36 7913 36835 29907694
Product lot number issue 20.27 17.66 4 7945 31 29944498
Implant site pruritus 19.63 17.66 3 7946 3 29944526
Disseminated intravascular coagulation 18.54 17.66 26 7923 22145 29922384
Implant site rash 18.41 17.66 3 7946 6 29944523
Assisted delivery 18.41 17.66 3 7946 6 29944523
Electroencephalogram abnormal 18.28 17.66 10 7939 2364 29942165

Pharmacologic Action:

SourceCodeDescription
ATC N03AX15 NERVOUS SYSTEM
ANTIEPILEPTICS
ANTIEPILEPTICS
Other antiepileptics
FDA CS M0020790 Sulfonamides
FDA MoA N0000000235 Carbonic Anhydrase Inhibitors
FDA PE N0000008486 Decreased Central Nervous System Disorganized Electrical Activity
FDA EPC N0000175753 Anti-epileptic 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
CHEBI has role CHEBI:22586 antioxidants
CHEBI has role CHEBI:35470 cns agent
CHEBI has role CHEBI:35623 antiepileptic
CHEBI has role CHEBI:50267 protective agents
FDA MoA N0000185503 P-Glycoprotein Inhibitors

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
4021224 VUID
N0000148668 NUI
D00538 KEGG_DRUG
4021224 VANDF
C1710707 UMLSCUI
CHEBI:10127 CHEBI
ZON PDB_CHEM_ID
CHEMBL750 ChEMBL_ID
D000078305 MESH_DESCRIPTOR_UI
5734 PUBCHEM_CID
5575 INN_ID
459384H98V UNII
7047 IUPHAR_LIGAND_ID
DB00909 DRUGBANK_ID
261708 RXNORM
31898 MMSL
73622 MMSL
8781 MMSL
d04527 MMSL
008137 NDDF
125693002 SNOMEDCT_US
398762003 SNOMEDCT_US

Pharmaceutical products:

ProductCategoryIngredientsNDCFormQuantityRouteMarketingLabel
zonisamide HUMAN PRESCRIPTION DRUG LABEL 1 0615-8266 CAPSULE 100 mg ORAL ANDA 23 sections
ZONISAMIDE HUMAN PRESCRIPTION DRUG LABEL 1 16590-539 CAPSULE 100 mg ORAL ANDA 16 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 28 sections
ZONISAMIDE HUMAN PRESCRIPTION DRUG LABEL 1 21695-654 CAPSULE 50 mg ORAL ANDA 28 sections
Zonisamide HUMAN PRESCRIPTION DRUG LABEL 1 29300-428 CAPSULE 25 mg ORAL ANDA 12 sections
Zonisamide HUMAN PRESCRIPTION DRUG LABEL 1 29300-429 CAPSULE 50 mg ORAL ANDA 12 sections
Zonisamide HUMAN PRESCRIPTION DRUG LABEL 1 29300-430 CAPSULE 100 mg ORAL ANDA 12 sections
Zonisamide HUMAN PRESCRIPTION DRUG LABEL 1 31722-228 CAPSULE 100 mg ORAL ANDA 25 sections
ZONISAMIDE HUMAN PRESCRIPTION DRUG LABEL 1 33261-843 CAPSULE 100 mg ORAL ANDA 13 sections
ZONISAMIDE HUMAN PRESCRIPTION DRUG LABEL 1 35356-143 CAPSULE 100 mg ORAL ANDA 16 sections
Zonisamide HUMAN PRESCRIPTION DRUG LABEL 1 43063-932 CAPSULE 25 mg ORAL ANDA 22 sections
Zonisamide HUMAN PRESCRIPTION DRUG LABEL 1 50268-816 CAPSULE 100 mg ORAL ANDA 26 sections
Zonisamide HUMAN PRESCRIPTION DRUG LABEL 1 51407-137 CAPSULE 25 mg ORAL ANDA 22 sections
Zonisamide HUMAN PRESCRIPTION DRUG LABEL 1 51407-138 CAPSULE 50 mg ORAL ANDA 22 sections
Zonisamide HUMAN PRESCRIPTION DRUG LABEL 1 51407-139 CAPSULE 100 mg ORAL ANDA 22 sections
zonisamide HUMAN PRESCRIPTION DRUG LABEL 1 53217-301 CAPSULE 100 mg ORAL ANDA 24 sections
Zonisamide HUMAN PRESCRIPTION DRUG LABEL 1 54868-5789 CAPSULE 100 mg ORAL ANDA 14 sections
Zonisamide HUMAN PRESCRIPTION DRUG LABEL 1 54868-6221 CAPSULE 50 mg ORAL ANDA 14 sections
ZONISAMIDE HUMAN PRESCRIPTION DRUG LABEL 1 55648-945 CAPSULE 25 mg ORAL ANDA 13 sections
ZONISAMIDE HUMAN PRESCRIPTION DRUG LABEL 1 55648-946 CAPSULE 50 mg ORAL ANDA 13 sections
ZONISAMIDE HUMAN PRESCRIPTION DRUG LABEL 1 55648-990 CAPSULE 100 mg ORAL ANDA 13 sections
Zonegran Human Prescription Drug Label 1 59212-680 CAPSULE 100 mg ORAL NDA 26 sections
Zonegran Human Prescription Drug Label 1 59212-681 CAPSULE 25 mg ORAL NDA 26 sections
Zonisamide Human Prescription Drug Label 1 59651-378 CAPSULE 25 mg ORAL ANDA 23 sections
Zonisamide Human Prescription Drug Label 1 59651-379 CAPSULE 50 mg ORAL ANDA 23 sections
Zonisamide Human Prescription Drug Label 1 59651-380 CAPSULE 100 mg ORAL ANDA 23 sections
Zonisamide HUMAN PRESCRIPTION DRUG LABEL 1 60687-230 CAPSULE 100 mg ORAL ANDA 24 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