metronidazole   Click here for help

GtoPdb Ligand ID: 10914

Synonyms: BAY-5360 | BAYER 5360 | Flagyl® | Metrogel® | ROZEX®
Approved drug PDB Ligand
metronidazole is an approved drug (FDA (1963))
Compound class: Synthetic organic
Comment: Metronidazole is a synthetic nitroimidazole derivative that exhibits antiprotozoal and antibacterial (against anaerobic bacteria) activities. It also acts as a a radiosensitising agent in tumour cells.
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 81.19
Molecular weight 171.06
XLogP -0.14
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 OCCn1c(C)ncc1[N+](=O)[O-]
Isomeric SMILES OCCn1c(C)ncc1[N+](=O)[O-]
InChI InChI=1S/C6H9N3O3/c1-5-7-4-6(9(11)12)8(5)2-3-10/h4,10H,2-3H2,1H3
InChI Key VAOCPAMSLUNLGC-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 (1963))
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
2-(2-methyl-5-nitroimidazol-1-yl)ethanol
International Nonproprietary Names Click here for help
INN number INN
1032 metronidazole
Synonyms Click here for help
BAY-5360 | BAYER 5360 | Flagyl® | Metrogel® | ROZEX®
Database Links Click here for help
Specialist databases
Antibiotic DB Antibiotic DB Database logo Metronidazole (Flagyl)
Other databases
BindingDB Ligand 50375309
CAS Registry No. 443-48-1 (source: PubChem)
ChEMBL Ligand CHEMBL137
DrugBank Ligand DB00916
DrugCentral Ligand 1790
GtoPdb PubChem SID 405560355
PubChem CID 4173
RCSB PDB Ligand 2MN
Search Google for chemical match using the InChIKey VAOCPAMSLUNLGC-UHFFFAOYSA-N
Search Google for chemicals with the same backbone VAOCPAMSLUNLGC
Search PubMed clinical trials metronidazole
Search PubMed titles metronidazole
Search PubMed titles/abstracts metronidazole
UniChem Compound Search for chemical match using the InChIKey VAOCPAMSLUNLGC-UHFFFAOYSA-N
UniChem Connectivity Search for chemical match using the InChIKey VAOCPAMSLUNLGC-UHFFFAOYSA-N