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QuickView for Ziprasidone (compound)
PubChem
| Name: | ziprasidone |
|---|---|
| PubChem Compound ID: | 154068 |
| Molecular formula: | C22H25ClN4O4S2 |
| Molecular weight: | 509.043 g/mol |
| Synonyms: |
Ziprasidone mesylate; 199191-69-0; 185021-64-1; Ziprasidone mesylate [USAN]; 2H-Indol-2-one, 5-(2-(4-(1,2-benzisothiazol-3-yl)-1-piperazinyl)ethyl)-6-chloro-1,3-dihydro-, monomethanesulfonate
|
DrugBank
Identification
| Name: | ziprasidone |
|---|---|
| Name (isomeric): | DB00246 |
| Drug Type: | small molecule |
| Synonyms: |
Ziprasidone mesylate trihydrate; Ziprasidone hydrochloride
|
| Brand: | Geodon Oral, Geodon, Zeldox |
| Category: | Serotonin Antagonists, Dopamine Antagonists, Antipsychotic Agents, Antipsychotics |
| CAS number: | 146939-27-7 |
Pharmacology
| Indication: | For the treatment of schizophrenia and related psychotic disorders. |
|---|---|
| Pharmacology: |
Ziprasidone is a psychotropic agent belonging to the chemical class of benzisoxazole derivatives and is indicated for the treatment of schizophrenia. Ziprasidone is a selective monoaminergic antagonist with high affinity for the serotonin Type 2 (5HT2), dopamine Type 2 (D2), 1 and 2 adrenergic, and H1 histaminergic receptors. Ziprasidone acts as an...
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Ziprasidone is a psychotropic agent belonging to the chemical class of benzisoxazole derivatives and is indicated for the treatment of schizophrenia. Ziprasidone is a selective monoaminergic antagonist with high affinity for the serotonin Type 2 (5HT2), dopamine Type 2 (D2), 1 and 2 adrenergic, and H1 histaminergic receptors. Ziprasidone acts as an antagonist at other receptors, but with lower potency. Antagonism at receptors other than dopamine and 5HT2 with similar receptor affinities may explain some of the other therapeutic and side effects of Ziprasidone. Ziprasidone's antagonism of muscarinic M1-5 receptors may explain its anticholinergic effects. Ziprasidone's antagonism of histamine H1 receptors may explain the somnolence observed with this drug. Ziprasidone's antagonism of adrenergic a1 receptors may explain the orthostatic hypotension observed with this drug. Ziprasidone functions as an antagonist at the Dopamine D2 , 5HT-2A , and 5HT-1D receptors, and as an agonist at the 5HT-1A receptor. Ziprasidone also inhibits synaptic reuptake of serotonin and norepinephrine.
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| Mechanism of Action: | Ziprasidone's antipsychotic activity is likely due to a combination of its antagonistic function at D2 receptors in the mesolimbic pathways and at 5HT2A receptors in the frontal cortex. Alleviation of positive symptoms is due to antagonism at D2 receptors while relief of negative symptoms are due to 5HT2A antagonism. |
| Absorption: | ~60% |
| Protein binding: | 99% |
| Biotransformation: | Hepatic |
| Route of elimination: | Ziprasidone is extensively metabolized after oral administration with only a small amount excreted in the urine (<1%) or feces (<4%) as unchanged drug. Approximately 20% of the dose is excreted in the urine, with approximately 66% being eliminated in the feces. |
| Half Life: | 7 hours |
| Clearance: | 7.5 mL/min/kg |
| Affected organisms: | Humans and other mammals |
Interactions
| Food interaction: |
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| Drug interaction: |
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Targets
This is one of the five types (D1 to D5) of receptors for dopamine. The activity of this receptor is mediated by G proteins which inhibit adenylyl cyclase
| UniProt ID: | P14416 | ||||||
|---|---|---|---|---|---|---|---|
| Gene: | DRD2 | ||||||
| Actions: | antagonist | ||||||
| References: |
|
This is one of the several different receptors for 5- hydroxytryptamine (serotonin), a biogenic hormone that functions as a neurotransmitter, a hormone, and a mitogen. This receptor mediates its action by association with G proteins that activate a phosphatidylinositol-calcium second messenger system. This receptor is involved in tracheal smooth muscle contraction, bronchoconstriction, and control of aldosterone production
| UniProt ID: | P28223 | |||||||
|---|---|---|---|---|---|---|---|---|
| Gene: | HTR2A | |||||||
| Actions: | antagonist | |||||||
| References: |
|
This is one of the five types (D1 to D5) of receptors for dopamine. The activity of this receptor is mediated by G proteins which activate adenylyl cyclase
| UniProt ID: | P21728 | |
|---|---|---|
| Gene: | DRD1 | |
| Actions: | antagonist | |
| References: |
|
This is one of the five types (D1 to D5) of receptors for dopamine. The activity of this receptor is mediated by G proteins which activate adenylyl cyclase
| UniProt ID: | P21918 | |
|---|---|---|
| Gene: | DRD5 | |
| Actions: | antagonist | |
| References: |
|
This is one of the five types (D1 to D5) of receptors for dopamine. The activity of this receptor is mediated by G proteins which inhibit adenylyl cyclase
| UniProt ID: | P35462 | ||
|---|---|---|---|
| Gene: | DRD3 | ||
| Actions: | antagonist | ||
| References: |
|
This is one of the five types (D1 to D5) of receptors for dopamine. The activity of this receptor is mediated by G proteins which inhibit adenylyl cyclase
| UniProt ID: | P21917 | ||
|---|---|---|---|
| Gene: | DRD4 | ||
| Actions: | antagonist | ||
| References: |
|
This is one of the several different receptors for 5- hydroxytryptamine (serotonin), a biogenic hormone that functions as a neurotransmitter, a hormone, and a mitogen. The activity of this receptor is mediated by G proteins that inhibit adenylate cyclase activity
| UniProt ID: | P08908 | ||||||
|---|---|---|---|---|---|---|---|
| Gene: | HTR1A | ||||||
| Actions: | antagonist | ||||||
| References: |
|
This is one of the several different receptors for 5- hydroxytryptamine (serotonin), a biogenic hormone that functions as a neurotransmitter, a hormone, and a mitogen. The activity of this receptor is mediated by G proteins that inhibit adenylate cyclase activity
| UniProt ID: | P28222 | |
|---|---|---|
| Gene: | HTR1B | |
| Actions: | antagonist | |
| References: |
|
This is one of the several different receptors for 5- hydroxytryptamine (serotonin), a biogenic hormone that functions as a neurotransmitter, a hormone, and a mitogen. The activity of this receptor is mediated by G proteins that inhibit adenylate cyclase activity
| UniProt ID: | P28221 | |||||
|---|---|---|---|---|---|---|
| Gene: | HTR1D | |||||
| Actions: | antagonist | |||||
| References: |
|
This is one of the several different receptors for 5- hydroxytryptamine (serotonin), a biogenic hormone that functions as a neurotransmitter, a hormone, and a mitogen. The activity of this receptor is mediated by G proteins that inhibit adenylate cyclase activity
| UniProt ID: | P28566 | |
|---|---|---|
| Gene: | HTR1E | |
| Actions: | antagonist | |
| References: |
|
This is one of the several different receptors for 5- hydroxytryptamine (serotonin), a biogenic hormone that functions as a neurotransmitter, a hormone, and a mitogen. This receptor mediates its action by association with G proteins that activate a phosphatidylinositol-calcium second messenger system
| UniProt ID: | P28335 | |||||
|---|---|---|---|---|---|---|
| Gene: | HTR2C | |||||
| Actions: | antagonist | |||||
| References: |
|
This is one of the several different receptors for 5- hydroxytryptamine (serotonin), a biogenic hormone that functions as a neurotransmitter, a hormone, and a mitogen. This receptor is a ligand-gated ion channel, which when activated causes fast, depolarizing responses in neurons. It is a cation-specific, but otherwise relatively nonselective, ion channel
| UniProt ID: | P46098 | |
|---|---|---|
| Gene: | HTR3A | |
| Actions: | antagonist | |
| References: |
|
This is one of the several different receptors for 5- hydroxytryptamine (serotonin), a biogenic hormone that functions as a neurotransmitter, a hormone, and a mitogen. The activity of this receptor is mediated by G proteins that stimulate adenylate cyclase. It has a high affinity for tricyclic psychotropic drugs
| UniProt ID: | P50406 | |
|---|---|---|
| Gene: | HTR6 | |
| Actions: | antagonist | |
| References: |
|
This is one of the several different receptors for 5- hydroxytryptamine (serotonin), a biogenic hormone that functions as a neurotransmitter, a hormone, and a mitogen. The activity of this receptor is mediated by G proteins that stimulate adenylate cyclase
| UniProt ID: | P34969 | |||
|---|---|---|---|---|
| Gene: | HTR7 | |||
| Actions: | antagonist | |||
| References: |
|
In peripheral tissues, the H1 subclass of histamine receptors mediates the contraction of smooth muscles, increase in capillary permeability due to contraction of terminal venules, and catecholamine release from adrenal medulla, as well as mediating neurotransmission in the central nervous system
| UniProt ID: | P35367 | ||
|---|---|---|---|
| Gene: | HRH1 | ||
| Actions: | antagonist | ||
| References: |
|
This alpha-adrenergic receptor mediates its action by association with G proteins that activate a phosphatidylinositol- calcium second messenger system. Its effect is mediated by G(q) and G(11) proteins
| UniProt ID: | P35348 | ||
|---|---|---|---|
| Gene: | ADRA1A | ||
| Actions: | antagonist | ||
| References: |
|
This alpha-adrenergic receptor mediates its action by association with G proteins that activate a phosphatidylinositol- calcium second messenger system
| UniProt ID: | P35368 | |
|---|---|---|
| Gene: | ADRA1B | |
| Actions: | antagonist | |
| References: |
|
Alpha-2 adrenergic receptors mediate the catecholamine- induced inhibition of adenylate cyclase through the action of G proteins. The rank order of potency for agonists of this receptor is oxymetazoline > clonidine > epinephrine > norepinephrine > phenylephrine > dopamine > p-synephrine > p-tyramine > serotonin = p-octopamine. For antagonists, the rank order is yohimbine > phentolamine = mianserine > chlorpromazine = spiperone = prazosin > propanolol > alprenolol = pindolol
| UniProt ID: | P08913 | |
|---|---|---|
| Gene: | ADRA2A | |
| Actions: | antagonist | |
| References: |
|
Alpha-2 adrenergic receptors mediate the catecholamine- induced inhibition of adenylate cyclase through the action of G proteins. The rank order of potency for agonists of this receptor is clonidine > norepinephrine > epinephrine = oxymetazoline > dopamine > p-tyramine = phenylephrine > serotonin > p-synephrine / p-octopamine. For antagonists, the rank order is yohimbine > chlorpromazine > phentolamine > mianserine > spiperone > prazosin > alprenolol > propanolol > pindolol
| UniProt ID: | P18089 | |
|---|---|---|
| Gene: | ADRA2B | |
| Actions: | antagonist | |
| References: |
|
Alpha-2 adrenergic receptors mediate the catecholamine- induced inhibition of adenylate cyclase through the action of G proteins
| UniProt ID: | P18825 | |
|---|---|---|
| Gene: | ADRA2C | |
| Actions: | antagonist | |
| References: |
|
The muscarinic acetylcholine receptor mediates various cellular responses, including inhibition of adenylate cyclase, breakdown of phosphoinositides and modulation of potassium channels through the action of G proteins. Primary transducing effect is Pi turnover
| UniProt ID: | P11229 | |
|---|---|---|
| Gene: | CHRM1 | |
| Actions: | antagonist | |
| References: |
|
The muscarinic acetylcholine receptor mediates various cellular responses, including inhibition of adenylate cyclase, breakdown of phosphoinositides and modulation of potassium channels through the action of G proteins. Primary transducing effect is adenylate cyclase inhibition
| UniProt ID: | P08172 | |
|---|---|---|
| Gene: | CHRM2 | |
| Actions: | antagonist | |
| References: |
|
The muscarinic acetylcholine receptor mediates various cellular responses, including inhibition of adenylate cyclase, breakdown of phosphoinositides and modulation of potassium channels through the action of G proteins. Primary transducing effect is Pi turnover
| UniProt ID: | P20309 | |
|---|---|---|
| Gene: | CHRM3 | |
| Actions: | antagonist | |
| References: |
|
The muscarinic acetylcholine receptor mediates various cellular responses, including inhibition of adenylate cyclase, breakdown of phosphoinositides and modulation of potassium channels through the action of G proteins. Primary transducing effect is inhibition of adenylate cyclase
| UniProt ID: | P08173 | |
|---|---|---|
| Gene: | CHRM4 | |
| Actions: | antagonist | |
| References: |
|
The muscarinic acetylcholine receptor mediates various cellular responses, including inhibition of adenylate cyclase, breakdown of phosphoinositides and modulation of potassium channels through the action of G proteins. Primary transducing effect is Pi turnover
| UniProt ID: | P08912 | |
|---|---|---|
| Gene: | CHRM5 | |
| Actions: | antagonist | |
| References: |
|
Enzymes
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation reactions (e.g. caffeine 8-oxidation, omeprazole sulphoxidation, midazolam 1'-hydroxylation and midazolam 4- hydroxylation) of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. The enzyme also hydroxylates etoposide
| UniProt ID: | P08684 | ||||
|---|---|---|---|---|---|
| Gene: | CYP3A4 | ||||
| Actions: | substrate, inhibitor | ||||
| References: |
|
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics
| UniProt ID: | P20815 | |
|---|---|---|
| Gene: | CYP3A5 | |
| Actions: | substrate | |
| References: |
|
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics
| UniProt ID: | P24462 | |
|---|---|---|
| Gene: | CYP3A7 | |
| Actions: | substrate | |
| References: |
|
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Most active in catalyzing 2-hydroxylation. Caffeine is metabolized primarily by cytochrome CYP1A2 in the liver through an initial N3-demethylation. Also acts in the metabolism of aflatoxin B1 and acetaminophen
| UniProt ID: | P05177 | |
|---|---|---|
| Gene: | CYP1A2 | |
| Actions: | substrate | |
| References: |
|
Responsible for the metabolism of many drugs and environmental chemicals that it oxidizes. It is involved in the metabolism of drugs such as antiarrhythmics, adrenoceptor antagonists, and tricyclic antidepressants
| UniProt ID: | P10635 | |
|---|---|---|
| Gene: | CYP2D6 | |
| Actions: | inhibitor | |
| References: |
|
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