General
Preferred name
ZIPRASIDONE
Synonyms
ZIPRASIDONE MESYLATE ()
Cp-88,059-01 ()
CP-880591 ()
Geodon ()
Zeldox ()
CP-8805927 ()
Ziprasidone D8 ()
Ziprasidone (hydrochloride) ()
CP-88059 D8 ()
CP-88059 hydrochloride ()
ZIPRASIDONE HYDROCHLORIDE ()
CP 88059 ()
Ziprasidone hydrochloride monohydrate ()
Ziprasidone Hydrochloride ()
Ziprasidone (hydrochloride monohydrate) ()
Ziprasidone HCl ()
CP-88059 ()
CP 88059 (hydrochloride monohydrate) ()
CP-88059-27 ()
CP-88059-1 ()
CP-88,059-1 ()
Ziprasidone hydrochloride hydrate ()
Zipradon ()
Ziprasidone mesilate ()
Ziprasidone mesylate anhydrous ()
CP-88,059-27 ()
Ziprasidone mesilate trihydrate ()
CP-88, 059-27 ()
NSC-760351 ()
Ziprasidone (hydrochloride hydrate) ()
Ziprasidone-d8 ()
P&D ID
PD010148
CAS
199191-69-0
138982-67-9
122883-93-6
146939-27-7
185021-64-1
1126745-58-1
Tags
natural product
drug
available
Approved by
FDA
First approval
2001
2002
Drug Status
approved
Drug indication
Antipsychotic
Schizophrenia
Max Phase
Phase 4
Structure
Probe scores
P&D probe-likeness score
[[ v.score ]]%
Structure formats
[[ format ]]
[[ compound[format === 'MOL' ? 'molblock' : format.toLowerCase()] ]]
Description
(extracted from source data)
ROE Ziprasidone is extensively metabolized after oral administration with only a small amount excreted in the urine (<1%) or feces (<4%) as unchanged drug.
TOXICITY The most common adverse reactions reported with ziprasidone include somnolence, respiratory tract infections, extrapyramidal symptoms, dizziness, akathisia, abnormal vision, asthenia, vomiting, headache and nausea. [FDA Label]
HALF-LIFE The half life of ziprasidone is 6-7 hours. [A174562]
MOA Ziprasidone is classified as a "second generation" or "atypical" antipsychotic and is a dopamine and 5HT2A receptor antagonist with a unique receptor binding profile. As previously mentioned, ziprasidone has a very high 5-HT2A/D2 affinity ratio, binds to multiple serotonin receptors in addition to 5-HT2A, and blocks monoamine transporters preventing 5HT and NE reuptake. On the other hand, ziprasidone has a low affinity for muscarinic cholinergic M1, histamine H1, and alpha1-adrenergic receptors. [A174562]
INDICATION In it's oral form, ziprasidone is approved for the treatment of Schizophrenia and Bipolar I disorder while the injectable formulation is approved for treatment of acute agitation in schizophrenia.
ROE Ziprasidone is extensively metabolized after oral administration with only a small amount excreted in the urine (<1%) or feces (<4%) as unchanged drug. ;
METABOLISM Ziprasidone is heavily metabolized in the liver with less than 5% of the drug excreted unchanged in the urine. There are 2 enzyme systems that are primarily responsible for it's metabolism: aldehyde oxidase catalyzes the primary reductive pathway while CYP3A4 catalyzes 2 other less prominent oxidation pathways. Since they CYP3A4 system is responsible for only 1/3 of ziprasidone metabolism, there is a lower risk of interactions with other CYP3A4 substrates and inhibitors.[A174277]
ABSORPTION In the absence of food, ziprasidone's oral bioavailability is 60%, while absorption may reach up to 100% if ziprasidone is taken with a meal equal or greater than 500 kcal. The difference in bioavailability has little to do with the fat content of the food and appears to be related to the bulk of the meal since more absorption occurs the longer ziprasidone remains in the stomach. [A174562]
PHARMACODYNAMICS The effects of ziprasidone are differentiated from other antispychotics based on it's preference and affinity for certain receptors. Ziprasidone binds to serotonin-2A (5-HT2A) and dopamine D2 receptors similar to other atypical antipsychotics; however, one key difference is that ziprasidone has a higher affinity ratio to these receptors when compared to other antipsychotics such as olanzapine, quetiapine, risperidone, and aripiprazole. Ziprasidone offers enhanced modulation of mood, notable negative symptom relief, overall cognitive improvement and reduced motor dysfunction which is linked to it's potent interaction with 5-HT2C, 5-HT1D, and 5-HT1A receptors in brain tissue. Ziprasidone can bind to norepinephrine reuptake sites with moderate affinity which may contribute to antidepressant and anxiolytic activity. Patient's taking ziprasidone will likely experience a lower incidence of orthostatic hypotension, cognitive disturbance, sedation, weight gain, and disruption in prolactin levels since ziprasidone has a lower affinity for histamine H1, muscarinic M1, and alpha1-adrenoceptors. [A363]
DESCRIPTION Ziprasidone is a monoaminergic antagonist with affinity for a range of receptors including dopamine receptors, alpha 1 and 2 adrenoceptors, the histamine H1 receptor, and serotonin 5-HT receptors. Marketed formulations may contain ziprasidone hydrochloride (PubChem CID 219099). (GtoPdb)
Compound Sets
29
AdooQ Bioactive Compound Library
A15286
Axon Medchem Screening Library
1446
Cayman Chemical Bioactives
15031
30737
ChEMBL Approved Drugs
CHEMBL1375743
CHEMBL708
CHEMBL3989833
ChEMBL Drugs
CHEMBL1375743
CHEMBL708
CHEMBL3989833
Concise Guide to Pharmacology 2017/18
59
Concise Guide to Pharmacology 2019/20
59
Concise Guide to Pharmacology 2021/22
59
Concise Guide to Pharmacology 2023/24
59
Drug Repurposing Hub
DrugBank
DB00246
DrugBank Approved Drugs
DB00246
DrugCentral
2865
DrugCentral Approved Drugs
2865
DrugMAP
DMM58JY
DrugMAP Approved Drugs
DMM58JY
DrugMatrix
EU-OPENSCREEN Bioactive Compound Library
EOS100693
Guide to Pharmacology
59
Ki Database
Ziprasidone
LSP-MoA library (Laboratory of Systems Pharmacology)
CHEMBL1712
CHEMBL708
MedChem Express Bioactive Compound Library
HY-17407
HY-14542
NCATS Inxight Approved Drugs
6UKA5VEJ6X
NPC Screening Collection
Other bioactive compounds
Prestwick Chemical Library
ReFrame library
Selleckchem Bioactive Compound Library
Ziprasidone-hydrochloride
TargetMol Bioactive Compound Library
T0031
External IDs
104
Properties
(calculated by RDKit )
Molecular Weight
412.11
Hydrogen Bond Acceptors
5
Hydrogen Bond Donors
1
Rotatable Bonds
4
Ring Count
5
Aromatic Ring Count
3
cLogP
3.81
TPSA
48.47
Fraction CSP3
0.33
Chiral centers
0.0
Largest ring
6.0
QED
0.71
Structural alerts
0
No structural alerts detected
Related compounds
Custom attributes
(extracted from source data)
Target
Dopamine Receptor
5-HT Receptor
5-HT transporter
5-HT1A
5-HT1B
5-HT1D
5-HT2A
5-HT2C
5-HT6
5-HT7
??1A-adrenergic receptor
??2A-adrenergic receptor
D1
D2
D3
H1 receptor
norepinephrine transporter (NET)
¦Á1A-adrenergic receptor
¦Á2A-adrenergic receptor
ADRA1A, ADRA1B, ADRA2A, ADRA2B, ADRA2C, CHRM1, CHRM2, CHRM3, CHRM4, CHRM5, DRD1, DRD2, DRD3, DRD4, DRD5, HRH1, HTR1A, HTR1B, HTR1D, HTR1E, HTR2A, HTR2C, HTR3A, HTR6, HTR7, SLC6A4
Atypical antipsychotic
5-HT Receptor,Dopamine Receptor
Pathway
GPCR/G protein
Neuronal Signaling
Neuroscience
Immunology/Inflammation
MOA
5-HT Receptor antagonist
Adrenergic Receptor antagonist
Dopamine Receptor antagonist
Histamine Receptor antagonist
Norepinephrine antagonist
dopamine receptor antagonist, serotonin receptor antagonist
Indication
schizophrenia, bipolar disorder
Therapeutic Class
Antipsychotic Agents
Source data