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: 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

NAMES AND DATABASE IDS

Names

• 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

Database IDs

• 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

CALCULATED PROPERTIES

JChem

• H Acceptors: 3
• H Donor: 0
• LogD (pH = 5.5): 1.858934
• LogD (pH = 7.4): 3.623811
• Log P: 4.6593223
• Molar Refractivity: 122.5583 cm^3
• Polarizability: 47.19488 Å^3
• Polar Surface Area: 9.72 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 5.12
• LOG S: -4.91
• Solubility (Water): 4.87e-03 g/l

PROPERTIES

Physical Property

• Solubility: 0.0584 mg/L
• Hydrophobicity(logP): 5

Pharmacology Properties

• Protein Bound: 60%

DETAILS

DrugBank - DB00372

• 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

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