enoxacin   Click here for help

GtoPdb Ligand ID: 8882

Synonyms: AT-2266 | CI-919 | Penetrex®
Approved drug
enoxacin is an approved drug (FDA (1991))
Compound class: Synthetic organic
Comment: Enoxacin was developed as a oral broad-spectrum fluoroquinolone antibacterial for the treatment of urinary tract infections and gonorrhea.
Enoxacin has been reported as an inhibitor of the interaction between the B2 subunit of vacuolar H+-ATPase (ATP6V1B2) and microfilaments [2], an interaction required for translocation of the ATPase to the plasma membrane. This process effects activation of osteoclasts and regulates bone resorption, making this interaction a novel target for pharmaceutical intervention to reduce the pathologies associated with bone-loss condtions [3].
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 6
Hydrogen bond donors 2
Rotatable bonds 3
Topological polar surface area 87.46
Molecular weight 320.13
XLogP 3.57
No. Lipinski's rules broken 0
SMILES / InChI / InChIKey
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Canonical SMILES CCn1cc(C(=O)O)c(=O)c2c1nc(N1CCNCC1)c(c2)F
Isomeric SMILES CCn1cc(C(=O)O)c(=O)c2c1nc(N1CCNCC1)c(c2)F
InChI InChI=1S/C15H17FN4O3/c1-2-19-8-10(15(22)23)12(21)9-7-11(16)14(18-13(9)19)20-5-3-17-4-6-20/h7-8,17H,2-6H2,1H3,(H,22,23)
InChI Key IDYZIJYBMGIQMJ-UHFFFAOYSA-N
References
1. Emde A, Eitan C, Liou LL, Libby RT, Rivkin N, Magen I, Reichenstein I, Oppenheim H, Eilam R, Silvestroni A et al.. (2015)
Dysregulated miRNA biogenesis downstream of cellular stress and ALS-causing mutations: a new mechanism for ALS.
EMBO J, 34 (21): 2633-51. [PMID:26330466]
2. Ostrov DA, Magis AT, Wronski TJ, Chan EK, Toro EJ, Donatelli RE, Sajek K, Haroun IN, Nagib MI, Piedrahita A et al.. (2009)
Identification of enoxacin as an inhibitor of osteoclast formation and bone resorption by structure-based virtual screening.
J Med Chem, 52 (16): 5144-51. [PMID:19630402]
3. Qin A, Cheng TS, Pavlos NJ, Lin Z, Dai KR, Zheng MH. (2012)
V-ATPases in osteoclasts: structure, function and potential inhibitors of bone resorption.
Int J Biochem Cell Biol, 44 (9): 1422-35. [PMID:22652318]
4. Valdez G, Heyer MP, Feng G, Sanes JR. (2014)
The role of muscle microRNAs in repairing the neuromuscular junction.
PLoS ONE, 9 (3): e93140. [PMID:24664281]