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1420-55-9 molecular structure
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2-(ethylsulfanyl)-10-[3-(4-methylpiperazin-1-yl)propyl]-10H-phenothiazine

ChemBase ID: 256
Molecular Formular: C22H29N3S2
Molecular Mass: 399.61576
Monoisotopic Mass: 399.18028994
SMILES and InChIs

SMILES:
S1c2c(N(CCCN3CCN(CC3)C)c3c1cccc3)cc(SCC)cc2
Canonical SMILES:
CCSc1ccc2c(c1)N(CCCN1CCN(CC1)C)c1c(S2)cccc1
InChI:
InChI=1S/C22H29N3S2/c1-3-26-18-9-10-22-20(17-18)25(19-7-4-5-8-21(19)27-22)12-6-11-24-15-13-23(2)14-16-24/h4-5,7-10,17H,3,6,11-16H2,1-2H3
InChIKey:
XCTYLCDETUVOIP-UHFFFAOYSA-N

Cite this record

CBID:256 http://www.chembase.cn/molecule-256.html

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NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
IUPAC name
2-(ethylsulfanyl)-10-[3-(4-methylpiperazin-1-yl)propyl]-10H-phenothiazine
IUPAC Traditional name
thiethylperazine
Brand Name
Norzine
Torecan
Synonyms
Ethylthioperazine
Theithylperazine
Thiethylperazine
CAS Number
1420-55-9
PubChem SID
160963719
46506502
PubChem CID
5440
CHEBI ID
9544
ATC CODE
R06AD03
CHEMBL
1378
Chemspider ID
5245
DrugBank ID
DB00372
KEGG ID
D02354
Unique Ingredient Identifier
8ETK1WAF6R
Wikipedia Title
Thiethylperazine

DATA SOURCES

DATA SOURCES

All Sources Commercial Sources Non-commercial Sources
Data Source Data ID Price

CALCULATED PROPERTIES

CALCULATED PROPERTIES

JChem ALOGPS 2.1
H Acceptors H Donor
LogD (pH = 5.5) 1.858934  LogD (pH = 7.4) 3.623811 
Log P 4.6593223  Molar Refractivity 122.5583 cm3
Polarizability 47.19488 Å3 Polar Surface Area 9.72 Å2
Rotatable Bonds Lipinski's Rule of Five true 
Log P 5.12  LOG S -4.91 
Solubility (Water) 4.87e-03 g/l 

PROPERTIES

PROPERTIES

Physical Property Pharmacology Properties Bioassay(PubChem)
Solubility
0.0584 mg/L expand Show data source
Hydrophobicity(logP)
5 expand Show data source
Protein Bound
60% expand Show data source

DETAILS

DETAILS

DrugBank DrugBank Wikipedia Wikipedia
DrugBank - DB00372 external link
Item Information
Drug Groups approved
Description A dopamine antagonist that is particularly useful in treating the nausea and vomiting associated with anesthesia, mildly emetic cancer chemotherapy agents, radiation therapy, and toxins. This piperazine phenothiazine does not prevent vertigo or motion sickness. (From AMA Drug Evaluations Annual, 1994, p457)
Indication For the treatment or relief of nausea and vomiting.
Pharmacology Thiethylperazine, an atypical antipsychotic agent, is used to treat both negative and positive symptoms of schizophrenia, acute mania with bipolar disorder, agitation, and psychotic symptoms in dementia. Future uses may include the treatment of obsessive-compulsive disorder and severe behavioral disorders in autism. Structurally and pharmacologically similar to clozapine, Thiethylperazine binds to alpha(1), dopamine, histamine H1, muscarinic, and serotonin type 2 (5-HT2) receptors.
Toxicity Manifestations of acute overdosage of TORECAN (thiethylperazine) can be expected to reflect the CNS effects of the drug and include extrapyramidal symptoms (E.P.S), confusion and convulsions with reduced or absent reflexes, respiratory depression and hypotension.
Affected Organisms
Humans and other mammals
Protein Binding 60%
Elimination Thiethylperazine is eliminated in the urine.
References
Maurer H, Pfleger K: Identification of phenothiazine antihistamines and their metabolites in urine. Arch Toxicol. 1988;62(2-3):185-91. [Pubmed]
External Links
Wikipedia
RxList
Drugs.com

REFERENCES

REFERENCES

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  • • Maurer H, Pfleger K: Identification of phenothiazine antihistamines and their metabolites in urine. Arch Toxicol. 1988;62(2-3):185-91. Pubmed
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PATENTS

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