ziprasidone indications/contra

Stem definitionDrug idCAS RN
2865 146939-27-7

Description:

MoleculeDescription

Molfile Inchi Smiles

Synonyms:

  • ziprasidone
  • zaprasidone
  • ziprasidone hydrochloride
  • ziprasidone mesylate
  • geodon
  • ziprasidone HCl
  • ziprasidone mesilate
a benzisothiazoylpiperazine derivative; has combined dopamine and serotonin receptor antagonist activity; structurally related to tiospirone
  • Molecular weight: 412.94
  • Formula: C21H21ClN4OS
  • CLOGP: 4.21
  • LIPINSKI: 0
  • HAC: 5
  • HDO: 1
  • TPSA: 48.47
  • ALOGS: -4.76
  • ROTB: 4

Drug dosage:

DoseUnitRoute
80 mg O
40 mg P

Approvals:

DateAgencyCompanyOrphan
Feb. 5, 2001 FDA PFIZER

FDA Adverse Event Reporting System

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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
Tardive dyskinesia 1603.66 36.58 305 5145 2206 3378203
Dystonia 1151.12 36.58 248 5202 3519 3376890
Neuroleptic malignant syndrome 1001.38 36.58 228 5222 4213 3376196
Extrapyramidal disorder 902.20 36.58 203 5247 3540 3376869
Completed suicide 764.14 36.58 284 5166 30830 3349579
Electrocardiogram QT prolonged 733.05 36.58 213 5237 10582 3369827
Akathisia 611.63 36.58 139 5311 2524 3377885
Sedation 529.44 36.58 146 5304 5955 3374454
Agitation 504.90 36.58 186 5264 19520 3360889
Dyskinesia 486.07 36.58 142 5308 7143 3373266
Somnolence 429.34 36.58 190 5260 32014 3348395
Tremor 413.95 36.58 178 5272 27966 3352443
Anxiety 406.86 36.58 195 5255 39434 3340975
Weight increased 392.77 36.58 169 5281 26571 3353838
Psychotic disorder 389.61 36.58 125 5325 8609 3371800
Drug ineffective 311.24 36.58 241 5209 115849 3264560
Mania 300.63 36.58 86 5364 3992 3376417
Insomnia 286.26 36.58 149 5301 35749 3344660
Drug hypersensitivity 269.94 36.58 143 5307 35537 3344872
Suicidal ideation 266.45 36.58 114 5336 17591 3362818
Depression 249.93 36.58 141 5309 39629 3340780
Aggression 238.60 36.58 93 5357 11292 3369117
Cardiac arrest 233.75 36.58 119 5331 27200 3353209
Priapism 227.94 36.58 54 5396 1175 3379234
Swollen tongue 213.80 36.58 75 5375 6768 3373641
Paranoia 212.67 36.58 65 5385 3794 3376615
Hallucination 200.90 36.58 86 5364 13254 3367155
Oculogyric crisis 196.23 36.58 42 5408 565 3379844
Catatonia 190.75 36.58 48 5402 1352 3379057
Dysphagia 189.79 36.58 93 5357 19558 3360851

Pharmacologic Action:

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SourceCodeDescription
ATC N05AE04 NERVOUS SYSTEM
PSYCHOLEPTICS
ANTIPSYCHOTICS
Indole derivatives
FDA EPC N0000175430 Atypical Antipsychotic
MeSH PA D014150 Antipsychotic Agents
MeSH PA D002491 Central Nervous System Agents
MeSH PA D002492 Central Nervous System Depressants
MeSH PA D015259 Dopamine Agents
MeSH PA D018492 Dopamine Antagonists
MeSH PA D018377 Neurotransmitter Agents
MeSH PA D011619 Psychotropic Drugs
MeSH PA D018490 Serotonin Agents
MeSH PA D012702 Serotonin Antagonists
MeSH PA D014149 Tranquilizing Agents
CHEBI has role CHEBI:35471 psychotropic drug
CHEBI has role CHEBI:37956 histamine antagonist
CHEBI has role CHEBI:48876 muscarinic antagonist
CHEBI has role CHEBI:48279 serotonergic antagonist
CHEBI has role CHEBI:48561 dopaminergic antagonist
CHEBI has role CHEBI:35476 antipsychotic agent

Drug Use (View source of the data)

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DiseaseRelationSNOMED_IDDOID
Mixed bipolar I disorder indication 16506000 DOID:3312
Schizophrenia indication 58214004
Bipolar disorder in remission indication 85248005
Bipolar affective disorder, current episode manic indication 191618007
Agitation associated with Schizophrenia indication
Tachyarrhythmia contraindication 6285003
Suicidal thoughts contraindication 6471006
Neuroleptic malignant syndrome contraindication 15244003 DOID:14464
Senile dementia contraindication 15662003
Agranulocytosis contraindication 17182001 DOID:12987
Myocardial infarction contraindication 22298006 DOID:5844
Hypovolemia contraindication 28560003
Orthostatic hypotension contraindication 28651003
Torsades de pointes contraindication 31722008
Dehydration contraindication 34095006
Dysphagia contraindication 40739000
Hypokalemia contraindication 43339004
Conduction disorder of the heart contraindication 44808001
Bradycardia contraindication 48867003
Hyperlipidemia contraindication 55822004 DOID:1168
Hepatic failure contraindication 59927004
Cerebrovascular disease contraindication 62914000 DOID:6713
Diabetes mellitus contraindication 73211009 DOID:9351
Extrapyramidal disease contraindication 76349003
Hyperglycemia contraindication 80394007 DOID:4195
Heart failure contraindication 84114007 DOID:6000
Epilepsy contraindication 84757009 DOID:1826
Leukopenia contraindication 84828003 DOID:615
Kidney disease contraindication 90708001 DOID:2527
Tardive dyskinesia contraindication 102449007
Prolonged QT interval contraindication 111975006
Hypomagnesemia contraindication 190855004
Decompensated cardiac failure contraindication 195111005
Metabolic syndrome X contraindication 237602007 DOID:14221
Neutropenic disorder contraindication 303011007 DOID:1227
Severe diarrhea contraindication 409587002
Breastfeeding (mother) contraindication 413712001
Myocardial ischemia contraindication 414795007 DOID:3393
Obesity contraindication 414916001 DOID:9970
Acquired torsion dystonia contraindication 433493000
Congenital long QT syndrome contraindication 442917000
Carcinoma of female breast contraindication 447782002
Bipolar affective disorder, current episode depression off-label use 191627008 DOID:3312
Depression Treatment Adjunct off-label use

Acid dissociation constants calculated using MoKa v3.0.0

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Dissociation levelDissociation constantType (acidic/basic)
pKa1 11.26 acidic
pKa2 7.35 Basic
pKa3 0.27 Basic

Orange Book patent data (new drug applications)

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Formulation strengthTrade nameApplicantApplication numberApproval dateTypeDose formRoutePatent numberPatent expiration datePatent use
EQ 20MG BASE GEODON PFIZER N020825 Feb. 5, 2001 RX CAPSULE ORAL 6245766 Dec. 18, 2018 TREATMENT OF BIPOLAR DISORDER
EQ 40MG BASE GEODON PFIZER N020825 Feb. 5, 2001 RX CAPSULE ORAL 6245766 Dec. 18, 2018 TREATMENT OF BIPOLAR DISORDER
EQ 60MG BASE GEODON PFIZER N020825 Feb. 5, 2001 RX CAPSULE ORAL 6245766 Dec. 18, 2018 TREATMENT OF BIPOLAR DISORDER
EQ 80MG BASE GEODON PFIZER N020825 Feb. 5, 2001 RX CAPSULE ORAL 6245766 Dec. 18, 2018 TREATMENT OF BIPOLAR DISORDER
EQ 10MG BASE/ML GEODON PFIZER INC N021483 March 29, 2006 DISCN SUSPENSION ORAL 6245766 Dec. 18, 2018 TREATMENT OF BIPOLAR DISORDER
EQ 10MG BASE/ML GEODON PFIZER INC N021483 March 29, 2006 DISCN SUSPENSION ORAL 6150366 May 27, 2019 TREATENT OF PSYCHOSIS

Orange Book exclusivity data (new drug applications)

None

Bioactivity Summary:

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TargetClassPharosUniProtActionTypeActivity value
(-log[M])
Mechanism
action
Bioact sourceMoA source
5-hydroxytryptamine receptor 2A GPCR ANTAGONIST Ki 9.40 WOMBAT-PK CHEMBL
D(2) dopamine receptor GPCR ANTAGONIST Ki 8.32 WOMBAT-PK CHEMBL
5-hydroxytryptamine receptor 5A GPCR Ki 6.54 PDSP
5-hydroxytryptamine receptor 2B GPCR Ki 7.56 PDSP
Alpha-1B adrenergic receptor GPCR Ki 8.05 PDSP
Histamine H2 receptor GPCR Ki 5.46 PDSP
D(1B) dopamine receptor GPCR Ki 6.82 PDSP
Muscarinic acetylcholine receptor M3 GPCR Ki 5 PDSP
Alpha-2C adrenergic receptor GPCR Ki 7.11 PDSP
Alpha-2B adrenergic receptor GPCR Ki 7.32 PDSP
Beta-1 adrenergic receptor GPCR Ki 5.59 PDSP
5-hydroxytryptamine receptor 1B GPCR AGONIST Ki 8.30 IUPHAR
5-hydroxytryptamine receptor 2C GPCR ANTAGONIST Ki 8.89 WOMBAT-PK
5-hydroxytryptamine receptor 1E GPCR Ki 6.44 WOMBAT-PK
5-hydroxytryptamine receptor 3A Ion channel Ki 6.40 WOMBAT-PK
5-hydroxytryptamine receptor 1D GPCR Ki 8.70 WOMBAT-PK
Muscarinic acetylcholine receptor M1 GPCR Ki 6.55 WOMBAT-PK
Histamine H1 receptor GPCR Ki 7.33 WOMBAT-PK
Alpha-1A adrenergic receptor GPCR Ki 8 WOMBAT-PK
5-hydroxytryptamine receptor 7 GPCR Ki 8.30 WOMBAT-PK
5-hydroxytryptamine receptor 6 GPCR Ki 7.22 WOMBAT-PK
5-hydroxytryptamine receptor 1A GPCR EC50 8.47 WOMBAT-PK
Sodium-dependent serotonin transporter Transporter IC50 7 WOMBAT-PK
Potassium voltage-gated channel subfamily H member 2 Ion channel IC50 6.92 WOMBAT-PK
Alpha-2A adrenergic receptor GPCR Ki 6.30 WOMBAT-PK
Sodium-dependent noradrenaline transporter Transporter Ki 7.36 PDSP
Muscarinic acetylcholine receptor M5 GPCR Ki 5.80 PDSP
Muscarinic acetylcholine receptor M4 GPCR Ki 5.80 PDSP
Muscarinic acetylcholine receptor M2 GPCR Ki 5.52 PDSP
Beta-2 adrenergic receptor GPCR Ki 5.30 PDSP
D(1A) dopamine receptor GPCR Ki 8.02 CHEMBL
Sodium-dependent dopamine transporter Transporter WOMBAT-PK
D(4) dopamine receptor GPCR ANTAGONIST Ki 7.30 WOMBAT-PK
D(3) dopamine receptor GPCR ANTAGONIST Ki 8.14 WOMBAT-PK
Transporter Transporter Ki 7.32 CHEMBL
Histamine H1 receptor GPCR IC50 6.82 CHEMBL
Adrenergic receptor alpha-1 GPCR Ki 7.96 CHEMBL
Alpha-1A adrenergic receptor GPCR Ki 9.30 CHEMBL
D(2) dopamine receptor GPCR Ki 8.32 CHEMBL
5-hydroxytryptamine receptor 2A GPCR Ki 9.38 CHEMBL
Histamine H1 receptor GPCR Ki 7.80 CHEMBL

External reference:

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IDSource
DB00246 DRUGBANK_ID
59 IUPHAR_LIGAND_ID
4021249 VUID
N0000148690 NUI
C0380393 UMLSCUI
D02100 KEGG_DRUG
216X081ORU UNII
138982-67-9 SECONDARY_CAS_RN
7155 INN_ID
CHEMBL708 ChEMBL_ID
4021249 VANDF
N0000005843 NDFRT
N0000148690 NDFRT
009104 NDDF
d04747 MMSL
115698 RXNORM
373389002 SNOMEDCT_US
409356003 SNOMEDCT_US
60854 PUBCHEM_CID
CHEMBL1712 ChEMBL_ID
CHEMBL1200997 ChEMBL_ID
C092292 MESH_SUPPLEMENTAL_RECORD_UI
CHEBI:10119 CHEBI

Pharmaceutical products:

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ProductCategoryIngredientsNDCFormQuantityRoute MarketingLabel
Geodon HUMAN PRESCRIPTION DRUG LABEL 1 0049-0052 CAPSULE 20 mg ORAL NDA 21 sections
Geodon HUMAN PRESCRIPTION DRUG LABEL 1 0049-0054 CAPSULE 40 mg ORAL NDA 21 sections
Geodon HUMAN PRESCRIPTION DRUG LABEL 1 0049-0056 CAPSULE 60 mg ORAL NDA 21 sections
Geodon HUMAN PRESCRIPTION DRUG LABEL 1 0049-0058 CAPSULE 80 mg ORAL NDA 21 sections
Geodon HUMAN PRESCRIPTION DRUG LABEL 1 0049-1203 INJECTION, POWDER, LYOPHILIZED, FOR SOLUTION 20 mg INTRAMUSCULAR NDA 19 sections
Geodon HUMAN PRESCRIPTION DRUG LABEL 1 0049-3920 INJECTION, POWDER, LYOPHILIZED, FOR SOLUTION 20 mg INTRAMUSCULAR NDA 21 sections
Geodon HUMAN PRESCRIPTION DRUG LABEL 1 0049-3960 CAPSULE 20 mg ORAL NDA 21 sections
Geodon HUMAN PRESCRIPTION DRUG LABEL 1 0049-3970 CAPSULE 40 mg ORAL NDA 21 sections
Geodon HUMAN PRESCRIPTION DRUG LABEL 1 0049-3980 CAPSULE 60 mg ORAL NDA 21 sections
Geodon HUMAN PRESCRIPTION DRUG LABEL 1 0049-3990 CAPSULE 80 mg ORAL NDA 21 sections
Ziprasidone Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 0378-7350 CAPSULE 20 mg ORAL ANDA 20 sections
Ziprasidone Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 0378-7351 CAPSULE 40 mg ORAL ANDA 20 sections
Ziprasidone Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 0378-7352 CAPSULE 60 mg ORAL ANDA 20 sections
Ziprasidone Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 0378-7353 CAPSULE 80 mg ORAL ANDA 20 sections
ziprasidone hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 0615-7703 CAPSULE 80 mg ORAL ANDA 20 sections
ziprasidone hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 0781-2164 CAPSULE 20 mg ORAL ANDA 19 sections
ziprasidone hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 0781-2166 CAPSULE 40 mg ORAL ANDA 19 sections
ziprasidone hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 0781-2167 CAPSULE 60 mg ORAL ANDA 19 sections
ziprasidone hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 0781-2168 CAPSULE 80 mg ORAL ANDA 19 sections
Ziprasidone Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 0904-6269 CAPSULE 20 mg ORAL ANDA 19 sections
Ziprasidone Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 0904-6270 CAPSULE 40 mg ORAL ANDA 19 sections
Ziprasidone Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 0904-6271 CAPSULE 60 mg ORAL ANDA 19 sections
Ziprasidone Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 0904-6272 CAPSULE 80 mg ORAL ANDA 19 sections
GEODON HUMAN PRESCRIPTION DRUG LABEL 1 16590-895 CAPSULE 20 mg ORAL NDA 20 sections
Geodon HUMAN PRESCRIPTION DRUG LABEL 1 21695-060 CAPSULE 20 mg ORAL NDA 20 sections
Geodon HUMAN PRESCRIPTION DRUG LABEL 1 21695-061 CAPSULE 40 mg ORAL NDA 20 sections
Geodon HUMAN PRESCRIPTION DRUG LABEL 1 21695-062 CAPSULE 60 mg ORAL NDA 20 sections
Geodon HUMAN PRESCRIPTION DRUG LABEL 1 21695-063 CAPSULE 80 mg ORAL NDA 20 sections
GEODON HUMAN PRESCRIPTION DRUG LABEL 1 24236-262 CAPSULE 20 mg ORAL NDA 18 sections
Ziprasidone Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 33342-144 CAPSULE 20 mg ORAL ANDA 20 sections