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146939-27-7 molecular structure
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5-{2-[4-(1,2-benzothiazol-3-yl)piperazin-1-yl]ethyl}-6-chloro-2,3-dihydro-1H-indol-2-one

ChemBase ID: 131
Molecular Formular: C21H21ClN4OS
Molecular Mass: 412.93564
Monoisotopic Mass: 412.11245999
SMILES and InChIs

SMILES:
Clc1c(CCN2CCN(CC2)c2nsc3c2cccc3)cc2c(NC(=O)C2)c1
Canonical SMILES:
O=C1Nc2c(C1)cc(c(c2)Cl)CCN1CCN(CC1)c1nsc2c1cccc2
InChI:
InChI=1S/C21H21ClN4OS/c22-17-13-18-15(12-20(27)23-18)11-14(17)5-6-25-7-9-26(10-8-25)21-16-3-1-2-4-19(16)28-24-21/h1-4,11,13H,5-10,12H2,(H,23,27)
InChIKey:
MVWVFYHBGMAFLY-UHFFFAOYSA-N

Cite this record

CBID:131 http://www.chembase.cn/molecule-131.html

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NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
IUPAC name
5-{2-[4-(1,2-benzothiazol-3-yl)piperazin-1-yl]ethyl}-6-chloro-2,3-dihydro-1H-indol-2-one
IUPAC Traditional name
ziprasidone
Brand Name
Geodon
Zeldox
Geodon Oral
Synonyms
Ziprasidone hydrochloride
Ziprasidone mesylate trihydrate
Ziprasidone
CAS Number
146939-27-7
PubChem SID
46507627
160963594
PubChem CID
60854

DATA SOURCES

DATA SOURCES

All Sources Commercial Sources Non-commercial Sources
Data Source Data ID
PubChem 60854 external link
DrugBank DB00246 external link
Data Source Data ID Price

CALCULATED PROPERTIES

CALCULATED PROPERTIES

JChem ALOGPS 2.1
Acid pKa 13.181678  H Acceptors
H Donor LogD (pH = 5.5) 2.7102394 
LogD (pH = 7.4) 4.1316934  Log P 4.3040466 
Molar Refractivity 116.7248 cm3 Polarizability 44.12495 Å3
Polar Surface Area 48.47 Å2 Rotatable Bonds
Lipinski's Rule of Five true 
Log P 4.64  LOG S -4.76 
Solubility (Water) 7.18e-03 g/l 

PROPERTIES

PROPERTIES

Physical Property Bioassay(PubChem)
Hydrophobicity(logP)
3.8 expand Show data source

DETAILS

DETAILS

DrugBank DrugBank
DrugBank - DB00246 external link
Item Information
Drug Groups approved
Description Ziprasidone (marketed as Geodon, Zeldox) was the fifth atypical antipsychotic to gain FDA approval (February 2001). Ziprasidone is Food and Drug Administration (FDA) approved for the treatment of schizophrenia, and the intramuscular injection form of ziprasidone is approved for acute agitation in schizophrenic patients. Ziprasidone has also received approval for acute treatment of mania associated with bipolar disorder. [Wikipedia]
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 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.
Affected Organisms
Humans and other mammals
Biotransformation Hepatic
Absorption ~60%
Half Life 7 hours
Protein Binding 99%
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.
Distribution * 1.5 L/kg
Clearance * 7.5 mL/min/kg
References
Stahl SM, Shayegan DK: The psychopharmacology of ziprasidone: receptor-binding properties and real-world psychiatric practice. J Clin Psychiatry. 2003;64 Suppl 19:6-12. [Pubmed]
External Links
Wikipedia
RxList
Drugs.com

REFERENCES

REFERENCES

From Suppliers Google Scholar IconGoogle Scholar PubMed iconPubMed Google Books IconGoogle Books
  • • Stahl SM, Shayegan DK: The psychopharmacology of ziprasidone: receptor-binding properties and real-world psychiatric practice. J Clin Psychiatry. 2003;64 Suppl 19:6-12. Pubmed
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PATENTS

PATENTS

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