Compound ID | 1977

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Pretomanid (Dovprela)

Synonym(s): PA-824

Class: Nitroimidazole

Agent Type: Synthetic; Small molecule; Direct acting;
Spectrum of activity: Gram-positive & Antimycobacterial
Mechanism of action: Inhibits the synthesis of protein and cell wall lipid; reported to inhibit mycolic acid synthesis
Combined with other compounds: Yes
Description: Nitroimidazopyran derivative. Developed for the treatment of multidrug-resistant Mycobacterium tuberculosis in combination with bedaquiline and linezolid.
Institute where first reported: Mylan Ireland Limited
Year first mentioned: 2000
Highest development stage: Approved by FDA in 2019
Development status: Approved
Chemical structure(s):
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Molecular weight: 359.26
Iso. SMILES: C1[C@@H](COC2=NC(=CN21)[N+](=O)[O-])OCC3=CC=C(C=C3)OC(F)(F)F
InChI Key: ZLHZLMOSPGACSZ-NSHDSACASA-N
Can. SMILES: C1=C(C=CC(=C1)OC(F)(F)F)CO[C@H]2CN3C=C(N=C3OC2)[N+](=O)[O-]
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
External links:
PubChem link: https://pubchem.ncbi.nlm.nih.gov/compound/456199
Guide to Pharmacology: pretomanid
Citations:
  • https://linkinghub.elsevier.com/retrieve/pii/S1198-743X(21)00464-X
  • https://www.nature.com/articles/35016103
  • https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2717523/
  • https://pubmed.ncbi.nlm.nih.gov/36053513/

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