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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Physico-chemical Properties
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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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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/)

References
1. Aher RB, Sarkar D. (2021)
Pharmacophore modeling of pretomanid (PA-824) derivatives for antitubercular potency against replicating and non-replicating Mycobacterium tuberculosis.
J Biomol Struct Dyn, 39 (3): 889-900. [PMID:31983295]
2. Conradie F, Diacon AH, Ngubane N, Howell P, Everitt D, Crook AM, Mendel CM, Egizi E, Moreira J, Timm J et al.. (2020)
Treatment of Highly Drug-Resistant Pulmonary Tuberculosis.
N Engl J Med, 382 (10): 893-902. [PMID:32130813]
3. Stover CK, Warrener P, VanDevanter DR, Sherman DR, Arain TM, Langhorne MH, Anderson SW, Towell JA, Yuan Y, McMurray DN et al.. (2000)
A small-molecule nitroimidazopyran drug candidate for the treatment of tuberculosis.
Nature, 405 (6789): 962-6. [PMID:10879539]
4. (2012)
Pretomanid.
LiverTox: Clinical and Research Information on Drug-Induced Liver Injury,. [PMID:31869193]