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thiopental   Click here for help

GtoPdb Ligand ID: 2579

Synonyms: Sodium Pentothal® | thiopental sodium | Trapanal®
Approved drug
thiopental is an approved drug (FDA (approval date not specified))
Compound class: Synthetic organic
Comment: Thiopential is a barbiturate general anesthetic.
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Ligand Activity Visualisation Charts

These are box plot that provide a unique visualisation, summarising all the activity data for a ligand taken from ChEMBL and GtoPdb across multiple targets and species. Click on a plot to see the median, interquartile range, low and high data points. A value of zero indicates that no data are available. A separate chart is created for each target, and where possible the algorithm tries to merge ChEMBL and GtoPdb targets by matching them on name and UniProt accession, for each available species. However, please note that inconsistency in naming of targets may lead to data for the same target being reported across multiple charts.

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View interactive charts of activity data across species

IUPHAR Pharmacology Education Project (PEP) logo

View more information in the IUPHAR Pharmacology Education Project: thiopental

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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Click here for structure editor
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 4
Hydrogen bond donors 2
Rotatable bonds 4
Topological polar surface area 90.29
Molecular weight 242.11
XLogP 2.33
No. Lipinski's rules broken 0

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 CCCC(C1(CC)C(=O)NC(=S)NC1=O)C
Isomeric SMILES CCCC(C1(CC)C(=O)NC(=S)NC1=O)C
InChI InChI=1S/C11H18N2O2S/c1-4-6-7(3)11(5-2)8(14)12-10(16)13-9(11)15/h7H,4-6H2,1-3H3,(H2,12,13,14,15,16)
InChI Key IUJDSEJGGMCXSG-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. US FDA (0)
WHO Essential Medicine WHO Essential Medicines List (EML) (23rd List, 2023). Access PDF version.
Click to view more information about the WHO Model Lists of Essential Medicines.
IUPAC Name Click here for help
5-ethyl-5-pentan-2-yl-2-sulfanylidene-1,3-diazinane-4,6-dione
International Nonproprietary Names Click here for help
INN number INN
433 thiopental sodium
Synonyms Click here for help
Sodium Pentothal® | thiopental sodium | Trapanal®
Database Links Click here for help
BindingDB Ligand 50058058
CAS Registry No. 76-75-5 (source: Scifinder)
ChEBI CHEBI:102166
ChEMBL Ligand CHEMBL441
DrugBank Ligand DB00599
DrugCentral Ligand 2633
GtoPdb PubChem SID 135651257
PubChem CID 3000715
Search Google for chemical match using the InChIKey IUJDSEJGGMCXSG-UHFFFAOYSA-N
Search Google for chemicals with the same backbone IUJDSEJGGMCXSG
Search PubMed clinical trials thiopental sodium
Search PubMed titles thiopental sodium
Search PubMed titles/abstracts thiopental sodium
UniChem Compound Search for chemical match using the InChIKey IUJDSEJGGMCXSG-UHFFFAOYSA-N
UniChem Connectivity Search for chemical match using the InChIKey IUJDSEJGGMCXSG-UHFFFAOYSA-N
Wikipedia Sodium_thiopental