Compound ID | 2846

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HC2210

Synonym(s): 1-[(5-nitro-2-furyl)methyl]-4-(4-nitrophenyl)piperazine oxalate

Class: Nitroimidazole

Details of activity: Active against Mycobacterium tuberculosis, Mycobacterium smegmatis, and Mycobacterium abscessus
Propensity to select resistant mutants: Yes, at ~1.6x10^-6 mutation frequency at 2x or 6xMIC
Description: Synthetic small molecule identified from whole-cell screening of ~340,000 compounds of Molecular Libraries Small Molecular Repository; prodrug that requires deazaflavin-dependent reductase (Ddn) and possibly another F420-dependent reductase to be activated; orally bioavailable; reduces bacterial burden by 1.1 and 1.2 log CFU in chronic murine Mycobacterium tuberculosis infection model; analogues (i.e. HC2209 and HC2211) with similar antimicrobial profile reported
Institute where first reported: Department of Microbiology and Molecular Genetics, Michigan State University, East Lansing, Michigan, USA
Year first mentioned: 2023
Development status: Experimental
Chemical structure(s):
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Molecular weight: 422.35
Iso. SMILES: C1CN(CCN1CC2=CC=C(O2)[N+](=O)[O-])C3=CC=C(C=C3)[N+](=O)[O-].C(=O)(C(=O)O)O
InChI Key: KJBZNSKQKSWMBO-UHFFFAOYSA-N
Can. SMILES: C1=C(C=CC(=C1)[N+](=O)[O-])N2CCN(CC2)CC3=CC=C([N+](=O)[O-])O3.C(=O)(C(=O)O)O
InChI: InChI=1S/C15H16N4O5.C2H2O4/c20-18(21)13-3-1-12(2-4-13)17-9-7-16(8-10-17)11-14-5-6-15(24-14)19(22)23;3-1(4)2(5)6/h1-6H,7-11H2;(H,3,4)(H,5,6)
External links:
PubChem link: https://pubchem.ncbi.nlm.nih.gov/compound/6456149
Citation: https://journals.asm.org/doi/10.1128/aac.00474-23

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