thiethylperazine   Click here for help

GtoPdb Ligand ID: 7306

Synonyms: GS-95 | Torecan®
Approved drug
thiethylperazine is an approved drug (FDA (1961))
Compound class: Synthetic organic
Comment: Thiethylperazine is a phenothiazine class antiemetic. Experiments in a mouse model suggest it may have potential to clear amyloid-β (Aβ) load in Alzheimer's disease [1].
2D Structure
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2D Structure

An image of the ligand's 2D structure. For small molecules with SMILES these are drawn using the NCI/CADD Chemical Identifier Resolver. Click on the image to access the chemical structure search tool with the ligand pre-loaded in the structure editor. For other types of ligands, e.g. longer nucleotides and peptides, a manually drawn representation of the molecule may be provided.

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Physico-chemical Properties
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Physico-chemical Properties

Calculated molecular properties are available for small molecules and natural products (not peptides). Properties were generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/). All properties were selected to enable the prediction of the Lipinski Rule-of-Five profile or ‘druglikeness’ for each ligand. For more info on each category see the help pages.

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Hydrogen bond acceptors 3
Hydrogen bond donors 0
Rotatable bonds 6
Topological polar surface area 60.32
Molecular weight 399.18
XLogP 5.04
No. Lipinski's rules broken 1

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
SMILES / InChI / InChIKey
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SMILES / InChI / InChIKey

SMILES (Simplified Molecular Input Line Entry Specification) A specification for unambiguously describing the structure of chemical molecules using short ASCII strings. Canonical SMILES specify a unique representation of the 2D structure without chiral or isotopic specifications. Isomeric SMILES include chiral specification and isotopes.

Standard InChI (IUPAC International Chemical Identifier) and InChIKey InChI is a non-proprietary, standard, textual identifier for chemical substances designed to facilitate linking of information and database searching. An InChIKey is a simplified version of a full InChI, designed for easier web searching.

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)

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Canonical SMILES CCSc1ccc2c(c1)N(CCCN1CCN(CC1)C)c1c(S2)cccc1
Isomeric 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
InChI Key XCTYLCDETUVOIP-UHFFFAOYSA-N

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
Classification Click here for help
Compound class Synthetic organic
Approved drug? Yes (FDA (1961))
Withdrawn drug? Yes
IUPAC Name Click here for help
2-(ethylsulfanyl)-10-[3-(4-methylpiperazin-1-yl)propyl]-10H-phenothiazine
International Nonproprietary Names Click here for help
INN number INN
1034 thiethylperazine
Synonyms Click here for help
GS-95 | Torecan®
Database Links Click here for help
CAS Registry No. 1420-55-9
ChEMBL Ligand CHEMBL1378
DrugBank Ligand DB00372
DrugCentral Ligand 2630
GtoPdb PubChem SID 178103879
PubChem CID 5440
Search Google for chemical match using the InChIKey XCTYLCDETUVOIP-UHFFFAOYSA-N
Search Google for chemicals with the same backbone XCTYLCDETUVOIP
Search PubMed clinical trials thiethylperazine
Search PubMed titles thiethylperazine
Search PubMed titles/abstracts thiethylperazine
UniChem Compound Search for chemical match using the InChIKey XCTYLCDETUVOIP-UHFFFAOYSA-N
UniChem Connectivity Search for chemical match using the InChIKey XCTYLCDETUVOIP-UHFFFAOYSA-N
Wikipedia Thiethylperazine