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Chemical Structure| 74011-58-8 Chemical Structure| 74011-58-8

Structure of Enoxacin
CAS No.: 74011-58-8

Chemical Structure| 74011-58-8

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Enoxacin is a broad-spectrum 6-fluoronaphthyridinone antibacterial agent.

Synonyms: CI 919; AT 2266; Sesquihydrate, Enoxacin

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Product Details of Enoxacin

CAS No. :74011-58-8
Formula : C15H17FN4O3
M.W : 320.31
SMILES Code : O=C(C1=CN(CC)C2=C(C=C(F)C(N3CCNCC3)=N2)C1=O)O
Synonyms :
CI 919; AT 2266; Sesquihydrate, Enoxacin
MDL No. :MFCD00133308

Safety of Enoxacin

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302-H315-H320-H335
Precautionary Statements:P261-P280-P301+P312-P302+P352-P305+P351+P338

Related Pathways of Enoxacin

DNA

Isoform Comparison

Biological Activity

Description
Enoxacin (AT 2266) is a fluoroquinolone antibiotic, which disrupts bacterial DNA by inhibiting DNA gyrase and topoisomerase IV, with IC50 values of 126 µg/ml and 26.5 µg/ml, respectively. It also functions as a miRNA processing activator, enhancing siRNA-mediated mRNA degradation and promoting the biogenesis of endogenous miRNAs. Enoxacin exhibits potent antibacterial activity against both gram-positive and gram-negative bacteria and acts as a cancer-specific growth inhibitor by boosting TAR RNA-binding protein 2 (TRBP)-mediated microRNA processing[1].[2].[3].[4].
Target
  • Topo II

In Vitro:

Cell Line
Concentration Treated Time Description References
HeLa cells 50 µM 48 hours Enhances siRNA-mediated gene silencing PMC2831467
NIH3T3 cells 50 µM 48 hours Enhances siRNA-mediated gene silencing PMC2831467
HEK293 cells 50 µM 48 hours Enhances siRNA-mediated mRNA degradation and promotes the biogenesis of endogenous miRNAs PMC2831467
C2C12 myotubes 100 µM During differentiation for 4 days Enoxacin upregulated Ppargc1a and multiple PPAR target genes related to oxidative metabolism, increasing maximal mitochondrial respiration, proton leak, and spare capacity. PMC7710362
Human adipose-derived stem cells (hASC) 50 µM 10 days post-differentiation Enoxacin treatment increased UCP1 and PPARGC1A mRNA levels by 1.9- and 2.5-fold, respectively, with no changes in FABP4 expression. PMC7710362
Mouse subcutaneous preadipocytes (9W) 50 µM During differentiation (days 2 to 8) or for 24 hours post-differentiation Enoxacin treatment upregulated brown/beige fat markers (Ucp1, Dio2, Prdm16, Ppargc1a) without affecting overall adipogenesis (Fasn, Pparg, Fabp4). PMC7710362
HEK-293T cells 50 μM 48 hours Enoxacin enhanced amiRNA-mediated sgRNA repression by promoting the loading of amiRNAs onto miRISCs, thereby inhibiting the function of the CRISPR-Cas9 system PMC7295050
NSC-34 cells 100 μM 72 hours To test whether enoxacin could reverse the negative effect of ALS-causing mutant proteins on miRNA processing. Results showed that enoxacin partially ameliorated the impairments in pre-miRNA processing caused by FUS R495X, TDP-43 A315T, or SOD1 G93A mutations. PMC4641530
SW1736 cells 40 µg/mL 5 days Enhanced miRNA expression, reduced cell aggressiveness PMC6755984
TPC1 cells 40 µg/mL 5 days Enhanced miRNA expression, reduced cell aggressiveness PMC6755984
Cal62 cells 40 µg/mL 5 days Enhanced miRNA expression, reduced cell aggressiveness PMC6755984
Nthy-ori 3-1 cells 40 µg/mL 5 days Enhanced miRNA expression, reduced cell aggressiveness PMC6755984
Normal fibroblast cells (Wi-38 and MRC-5) 40 μg/mL 5 days To evaluate the effect of enoxacin on normal cells, results showed that enoxacin had no significant effect on the growth of normal fibroblast cells PMC3060242
Colorectal cancer cells (HCT-116) 40 μg/mL 5 days To evaluate the effect of enoxacin on cancer cell growth, results showed that enoxacin significantly inhibited the growth of HCT-116 cells PMC3060242
MC3T3-E1 cells 1, 10, 50, 100 μM Enoxacin at concentrations up to 50 μM had no effect on the growth and alkaline phosphatase activity of MC3T3-E1 cells, while 100 μM caused reduced growth and morphological changes PMC2889180
HEK293 cells 10 µM 48 hours Iron chelators enhance shRNA-EGFP-mediated gene silencing. PMC3613991
Mouse marrow cells 1, 10, 100 μM 7 days Enoxacin dose-dependently reduced the number of TRAP+ cells, inhibiting osteoclast differentiation PMC2889180

In Vivo:

Species
Animal Model
Administration Dosage Frequency Description References
Mice GFP transgenic mice Ear injection 100 µM Once daily for 3 consecutive days Enhances siRNA-mediated mRNA degradation PMC2831467
C57BL/6 mice High-fat diet-induced obesity model Intraperitoneal injection 10 mg/kg body weight/day 5 intraperitoneal injections/week for 10 weeks Enoxacin mitigated high-fat diet-induced obesity, increased energy expenditure, improved glucose tolerance and insulin sensitivity, with no effects on food intake or gut microbiota composition. PMC7710362
Mice SOD1 G93A ALS mouse model Oral 800 mg/kg body weight/day Once daily, starting from day 42 To evaluate the effect of enoxacin on neuromuscular function in ALS mice. Results showed that enoxacin treatment delayed the onset of neurological symptoms and improved neuromuscular function, but did not significantly extend lifespan. PMC4641530
Mice Human thyroid cancer xenograft model Intraperitoneal injection 15 mg/kg Daily for 28 days Inhibited tumor growth, upregulated key miRNA expression PMC6755984
Nude mice Xenograft model of colorectal cancer cells (HCT-116 and RKO) Intraperitoneal injection 10 mg/kg Once daily for 4 weeks To evaluate the inhibitory effect of enoxacin on tumor growth in vivo, results showed that enoxacin significantly inhibited the tumor growth of HCT-116 and RKO cells PMC3060242
Mice Marrow culture model Culture medium addition 10, 25, 100 μM 5 days Enoxacin dose-dependently reduced bone resorption area and pit numbers, with complete inhibition at 100 μM PMC2889180
Gnotobiotic mice ZIKV infection model Intraperitoneal injection 10 mg/kg Daily from E1.5 to E18.5 To evaluate the effect of enoxacin on ZIKV-associated fetal growth restriction and placental viral persistence, showing that enoxacin treatment abolished placental ZIKV persistence and rescued fetal growth restriction PMC10840961

Clinical Trial:

NCT Number Conditions Phases Recruitment Completion Date Locations
NCT02099240 Osteomyelitis Early Phase 1 Recruiting September 2019 United States, Kentucky ... More >> University of Louisville Recruiting Louisville, Kentucky, United States, 40202 Contact: Julio A Ramirez, MD    502-852-1148    jarami01@louisville.edu    Contact: David Seligson, MD    502-852-0923    d0seli01@louisville.edu    Sub-Investigator: Forest Arnold, DO          Sub-Investigator: Timothy Wiemkwn, PhD          Sub-Investigator: Robert Kelley, PhD          Sub-Investigator: James Summersgill, PhD          Sub-Investigator: Ruth Carrico, PhD          Sub-Investigator: Julie Harting, PharmD          Sub-Investigator: Paula Peyrani, MD          Principal Investigator: David Seligson, MD          Sub-Investigator: Craig Roberts, MD          Principal Investigator: Julio Ramirez, MD Less <<
NCT02305342 - Completed - Pakistan ... More >> Research facility ID ORG-001126 Karachi, Pakistan, 75190 Less <<

Protocol

Bio Calculators
Preparing Stock Solutions 1mg 5mg 10mg

1 mM

5 mM

10 mM

3.12mL

0.62mL

0.31mL

15.61mL

3.12mL

1.56mL

31.22mL

6.24mL

3.12mL

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