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protionamide   Click here for help

GtoPdb Ligand ID: 14280

Synonyms: prothionamide
Approved drug
protionamide is an approved drug
Compound class: Synthetic organic
Comment: Protionamide is a thioamide compound with potent antibacterial activity against mycobacteria. It is an analogue of ethionamide and can be used as a therapeutic alternative in the treatment of multidrug-resistant tuberculosis. Protionamide requires intracellular activation, by the monooxygenase EthA, in Mycobacterium tuberculosis [1].

protionamide is commercially available from our sponsors

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 2
Hydrogen bond donors 1
Rotatable bonds 3
Topological polar surface area 70.47
Molecular weight 180.27
XLogP 0.34
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 CCCC1=CC(=CC=N1)C(=S)N
Isomeric SMILES CCCC1=NC=CC(=C1)C(=S)N
InChI InChI=1S/C9H12N2S/c1-2-3-8-6-7(9(10)12)4-5-11-8/h4-6H,2-3H2,1H3,(H2,10,12)
InChI Key VRDIULHPQTYCLN-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.
WHO Essential Medicine WHO Essential Medicines List (EML) (24th List, 2025). Download PDF version.
Click to view more information about the WHO Model Lists of Essential Medicines.
IUPAC Name Click here for help
2-propylpyridine-4-carbothioamide
International Nonproprietary Names Click here for help
INN number INN
2031 protionamide
Synonyms Click here for help
prothionamide
Database Links Click here for help
Specialist databases
Antibiotic DB Antibiotic DB Database logo Protionamide
Other databases
CAS Registry No. 14222-60-7 (source: Scifinder)
ChEBI CHEBI:32066
ChEMBL Ligand CHEMBL1378024
DrugBank Ligand DB12667
DrugCentral Ligand 2314
GtoPdb PubChem SID 521588920
PubChem CID 666418
Search Google for chemical match using the InChIKey VRDIULHPQTYCLN-UHFFFAOYSA-N
Search Google for chemicals with the same backbone VRDIULHPQTYCLN
Search PubMed clinical trials protionamide
Search PubMed titles protionamide
Search PubMed titles/abstracts protionamide
UniChem Compound Search for chemical match using the InChIKey VRDIULHPQTYCLN-UHFFFAOYSA-N
UniChem Connectivity Search for chemical match using the InChIKey VRDIULHPQTYCLN-UHFFFAOYSA-N

Product suppliers

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Product supplier links are provided as a service to assist in identifying commercial suppliers of reagents that are mentioned on the IUPHAR/BPS Guide to PHARMACOLOGY database website, and do not imply their endorsement by NC-IUPHAR.

Links are provided in return for sponsorship, used to fund improvements to this database. The sponsorship account is managed and audited by the University of Edinburgh, a charitable body registered in Scotland, SC005336. If you are interested in sponsoring the database, please contact us.

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MedChemExpress
Prothionamide (links to external site)
Cat. No. HY-B0306