pyrazinamide   Click here for help

GtoPdb Ligand ID: 7287

Synonyms: Zinamide®
Approved drug PDB Ligand
pyrazinamide is an approved drug (FDA (no history prior to 1971))
Compound class: Synthetic organic
Comment: This drug is often contained in fixed-mixture formulations with other antibacterial drugs beneficial in the treatment of TB (eg isoniazid and rifampicin).
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 CDK toolkit. 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 1
Topological polar surface area 69.86
Molecular weight 123.04
XLogP -0.37
No. Lipinski's rules broken 0
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.

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Canonical SMILES OC(=N)c1cnccn1
Isomeric SMILES OC(=N)c1cnccn1
InChI InChI=1S/C5H5N3O/c6-5(9)4-3-7-1-2-8-4/h1-3H,(H2,6,9)
InChI Key IPEHBUMCGVEMRF-UHFFFAOYSA-N
Classification Click here for help
Compound class Synthetic organic
Approved drug? Yes (FDA (no history prior to 1971))
WHO Essential Medicine WHO Model List of Essential Medicines (21st List, 2019). Access PDF version.
IUPAC Name Click here for help
pyrazine-2-carboximidic acid
International Nonproprietary Names Click here for help
INN number INN
786 pyrazinamide
Synonyms Click here for help
Zinamide®
Database Links Click here for help
CAS Registry No. 98-96-4
ChEMBL Ligand CHEMBL614
DrugBank Ligand DB00339
DrugCentral Ligand 2328
GtoPdb PubChem SID 178103861
PubChem CID 1046
RCSB PDB Ligand PZA
Search Google for chemical match using the InChIKey IPEHBUMCGVEMRF-UHFFFAOYSA-N
Search Google for chemicals with the same backbone IPEHBUMCGVEMRF
Search PubMed clinical trials pyrazinamide
Search PubMed titles pyrazinamide
Search PubMed titles/abstracts pyrazinamide
Search UniChem for chemical match using the InChIKey IPEHBUMCGVEMRF-UHFFFAOYSA-N
Search UniChem for chemicals with the same backbone IPEHBUMCGVEMRF
Wikipedia Pyrazinamide