pretomanid   Click here for help

GtoPdb Ligand ID: 11172

Synonyms: PA-824 | PA824
Approved drug
pretomanid is an approved drug (FDA (2019), EMA (2020))
Compound class: Synthetic organic
Comment: Pretomanid is a nitroimidazole-based antibacterial used for the treatment of multi-drug-resistant pulmonary tuberculosis [3]. It is active against replicating and non-replicating Mycobacterium tuberculosis [1]. Pretomanid was developed by the non-profit organisation TB Alliance (www.tballiance.org.za).
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 2
Hydrogen bond donors 0
Rotatable bonds 6
Topological polar surface area 88.65
Molecular weight 359.07
XLogP 4.88
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 [O-][N+](=O)c1cn2c(n1)OC[C@H](C2)OCc1ccc(cc1)OC(F)(F)F
Isomeric SMILES [O-][N+](=O)c1cn2c(n1)OC[C@H](C2)OCc1ccc(cc1)OC(F)(F)F
InChI InChI=1S/C14H12F3N3O5/c15-14(16,17)25-10-3-1-9(2-4-10)7-23-11-5-19-6-12(20(21)22)18-13(19)24-8-11/h1-4,6,11H,5,7-8H2/t11-/m0/s1
InChI Key ZLHZLMOSPGACSZ-NSHDSACASA-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 (2019), EMA (2020))
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.
International Nonproprietary Names Click here for help
INN number INN
9871 pretomanid
Synonyms Click here for help
PA-824 | PA824
Database Links Click here for help
Specialist databases
Antibiotic DB Antibiotic DB Database logo Pretomanid (Dovprela)
Other databases
BindingDB Ligand 50363237
CAS Registry No. 187235-37-6 (source: WHO INN record)
ChEMBL Ligand CHEMBL227875
DrugBank Ligand DB05154
DrugCentral Ligand 5344
GtoPdb PubChem SID 434122232
PubChem CID 456199
Search Google for chemical match using the InChIKey ZLHZLMOSPGACSZ-NSHDSACASA-N
Search Google for chemicals with the same backbone ZLHZLMOSPGACSZ
Search PubMed clinical trials pretomanid
Search PubMed titles pretomanid
Search PubMed titles/abstracts pretomanid
UniChem Compound Search for chemical match using the InChIKey ZLHZLMOSPGACSZ-NSHDSACASA-N
UniChem Connectivity Search for chemical match using the InChIKey ZLHZLMOSPGACSZ-NSHDSACASA-N