isoniazid   Click here for help

GtoPdb Ligand ID: 12761

Synonyms: isonicotinic acid hydrazide | Nydrazid® | Rimifon®
Approved drug PDB Ligand
isoniazid is an approved drug (FDA (1952), UK)
Compound class: Synthetic organic
Comment: Isoniazid is an antimycobacterial drug used in the treatment of tuberculosis (TB) [1]. Functionally, it inhibits the synthesis of mycolic acid, an essential component of the mycobacterial cell wall [3].

isoniazid 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 4
Hydrogen bond donors 2
Rotatable bonds 2
Topological polar surface area 67.48
Molecular weight 137.14
XLogP -1.72
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 C1=C(C=CN=C1)C(=O)NN
Isomeric SMILES C1=CN=CC=C1C(=O)NN
InChI InChI=1S/C6H7N3O/c7-9-6(10)5-1-3-8-4-2-5/h1-4H,7H2,(H,9,10)
InChI Key QRXWMOHMRWLFEY-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 (1952)  |  UK (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
pyridine-4-carbohydrazide
International Nonproprietary Names Click here for help
INN number INN
4188 isoniazid
Synonyms Click here for help
isonicotinic acid hydrazide | Nydrazid® | Rimifon®
Database Links Click here for help
Specialist databases
Antibiotic DB Antibiotic DB Database logo Isoniazid
Other databases
BindingDB Ligand 50336507
CAS Registry No. 54-85-3 (source: Scifinder)
ChEBI CHEBI:6030
ChEMBL Ligand CHEMBL64
DrugBank Ligand DB00951
DrugCentral Ligand 1497
GtoPdb PubChem SID 483123309
PubChem CID 3767
RCSB PDB Ligand NIZ
Search Google for chemical match using the InChIKey QRXWMOHMRWLFEY-UHFFFAOYSA-N
Search Google for chemicals with the same backbone QRXWMOHMRWLFEY
Search PubMed clinical trials isoniazid
Search PubMed titles isoniazid
Search PubMed titles/abstracts isoniazid
UniChem Compound Search for chemical match using the InChIKey QRXWMOHMRWLFEY-UHFFFAOYSA-N
UniChem Connectivity Search for chemical match using the InChIKey QRXWMOHMRWLFEY-UHFFFAOYSA-N
Wikipedia Isoniazid

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MedChemExpress
Isoniazid (links to external site)
Cat. No. HY-B0329