Structure of Enoxacin
CAS No.: 74011-58-8
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The BI-3802 was designed by Boehringer Ingelheim and could be obtained free of charge through the Boehringer Ingelheim open innovation portal opnMe.com, associated with its negative control.
Enoxacin is a broad-spectrum 6-fluoronaphthyridinone antibacterial agent.
Synonyms: CI 919; AT 2266; Sesquihydrate, Enoxacin
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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 |
GHS Pictogram: |
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Signal Word: | Warning |
Hazard Statements: | H302-H315-H320-H335 |
Precautionary Statements: | P261-P280-P301+P312-P302+P352-P305+P351+P338 |
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].
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Target |
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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 << |
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 |
Tags: Enoxacin | AT 2266 | CI 919 | AT2266 | AT-2266 | CI919 | CI 919 | CI-919 | Bacterial | DNA Synthesis | MicroRNA | Antibiotic | miRNA | DNA gyrase | topoisomerase | siRNA | mRNA | gram-positive | gram-negative | TAR-RNA | fluoroquinolone | DNA gyrase inhibitor | topoisomerase IV inhibitor | miRNA processing | siRNA | mRNA degradation | TAR RNA-binding protein 2 | TRBP | TRBP-mediated microRNA processing | 74011-58-8
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P265 | Wash skin thouroughly after handling. |
P270 | Do not eat, drink or smoke when using this product. |
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P272 | Contaminated work clothing should not be allowed out of the workplace. |
P273 | Avoid release to the environment. |
P280 | Wear protective gloves/protective clothing/eye protection/face protection. |
P281 | Use personal protective equipment as required. |
P282 | Wear cold insulating gloves/face shield/eye protection. |
P283 | Wear fire/flame resistant/retardant clothing. |
P284 | Wear respiratory protection. |
P285 | In case of inadequate ventilation wear respiratory protection. |
P231 + P232 | Handle under inert gas. Protect from moisture. |
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Code | Phrase |
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P304 | IF INHALED: |
P305 | IF IN EYES: |
P306 | IF ON CLOTHING: |
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P308 | IF exposed or concerned: |
P309 | IF exposed or if you feel unwell: |
P310 | Immediately call a POISON CENTER or doctor/physician. |
P311 | Call a POISON CENTER or doctor/physician. |
P312 | Call a POISON CENTER or doctor/physician if you feel unwell. |
P313 | Get medical advice/attention. |
P314 | Get medical advice/attention if you feel unwell. |
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P321 | |
P322 | |
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P341 | If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing. |
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P350 | Gently wash with plenty of soap and water. |
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P378 | |
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P304 + P340 | IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing. |
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P332 + P313 | IF SKIN irritation occurs: Get medical advice/attention. |
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P335 + P334 | Brush off loose particles from skin. Immerse in cool water/wrap in wet bandages. |
P337 + P313 | IF eye irritation persists: Get medical advice/attention. |
P342 + P311 | IF experiencing respiratory symptoms: call a POISON CENTER or doctor/physician. |
P370 + P376 | In case of fire: Stop leak if safe to Do so. |
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H231 | May react explosively even in the absence of air at elevated pressure and/or temperature |
H240 | Heating may cause an explosion |
H241 | Heating may cause a fire or explosion |
H242 | Heating may cause a fire |
H250 | Catches fire spontaneously if exposed to air |
H251 | Self-heating; may catch fire |
H252 | Self-heating in large quantities; may catch fire |
H260 | In contact with water releases flammable gases which may ignite spontaneously |
H261 | In contact with water releases flammable gas |
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H290 | May be corrosive to metals |
Health hazards | |
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H300 | Fatal if swallowed |
H301 | Toxic if swallowed |
H302 | Harmful if swallowed |
H303 | May be harmful if swallowed |
H304 | May be fatal if swallowed and enters airways |
H305 | May be harmful if swallowed and enters airways |
H310 | Fatal in contact with skin |
H311 | Toxic in contact with skin |
H312 | Harmful in contact with skin |
H313 | May be harmful in contact with skin |
H314 | Causes severe skin burns and eye damage |
H315 | Causes skin irritation |
H316 | Causes mild skin irritation |
H317 | May cause an allergic skin reaction |
H318 | Causes serious eye damage |
H319 | Causes serious eye irritation |
H320 | Causes eye irritation |
H330 | Fatal if inhaled |
H331 | Toxic if inhaled |
H332 | Harmful if inhaled |
H333 | May be harmful if inhaled |
H334 | May cause allergy or asthma symptoms or breathing difficulties if inhaled |
H335 | May cause respiratory irritation |
H336 | May cause drowsiness or dizziness |
H340 | May cause genetic defects |
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H350 | May cause cancer |
H351 | Suspected of causing cancer |
H360 | May damage fertility or the unborn child |
H361 | Suspected of damaging fertility or the unborn child |
H361d | Suspected of damaging the unborn child |
H362 | May cause harm to breast-fed children |
H370 | Causes damage to organs |
H371 | May cause damage to organs |
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H373 | May cause damage to organs through prolonged or repeated exposure |
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H402 | Harmful to aquatic life |
H410 | Very toxic to aquatic life with long-lasting effects |
H411 | Toxic to aquatic life with long-lasting effects |
H412 | Harmful to aquatic life with long-lasting effects |
H413 | May cause long-lasting harmful effects to aquatic life |
H420 | Harms public health and the environment by destroying ozone in the upper atmosphere |
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