Enoxacin | CAS#74011-58-8 | Topoisomerase Activators

MedKoo Cat#: 317772 | Name: Enoxacin

Featured

Description:

WARNING: This product is for research use only, not for human or veterinary use.

Enoxacin is an oral broad-spectrum fluoroquinolone antibacterial agent used in the treatment of urinary tract infections and gonorrhea. Enoxacin is a broad-spectrum antibacterial agent that is structurally related to nalidixic acid. It acts on DNA gyrase. Insomnia is a common adverse effect. Recently, enoxacin has been shown recently that it may have cancer inhibiting effect.

Chemical Structure

Enoxacin

CAS#74011-58-8

Theoretical Analysis

MedKoo Cat#: 317772

Name: Enoxacin

CAS#: 74011-58-8

Chemical Formula: C15H17FN4O3

Exact Mass: 320.1285

Molecular Weight: 320.32

Elemental Analysis: C, 56.24; H, 5.35; F, 5.93; N, 17.49; O, 14.98

Price and Availability

Size	Price	Availability
500mg	USD 250.00	2 Weeks
1g	USD 450.00	2 Weeks
5g	USD 950.00	2 Weeks

Bulk Inquiry

Buy Now

Add to Cart

Related CAS #

No Data

Synonym

Enoxacin; Penetrex; Enoxacine; Comprecin; Enoxacino; PD 107779; PD-107779; PD107779; NSC 629661; NSC629661; NSC-629661; CI-919; CI 919; CI919;

IUPAC/Chemical Name

1-ethyl-6-fluoro-4-oxo-7-piperazin-1-yl-1,8-naphthyridine-3-carboxylic acid

InChi Key

IDYZIJYBMGIQMJ-UHFFFAOYSA-N

InChi Code

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)

SMILES Code

CCN1C=C(C(=O)C2=CC(=C(N=C21)N3CCNCC3)F)C(=O)O

Appearance

Solid powder

Purity

>98% (or refer to the Certificate of Analysis)

Shipping Condition

Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition

Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility

Soluble in DMSO, not in water

Shelf Life

>2 years if stored properly

Drug Formulation

This drug may be formulated in DMSO

Stock Solution Storage

0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code

2934.99.9001

More Info

Product Data

Product Data

Instruction

View handling instruction

Biological target:

Enoxacin (AT 2266), interferes with DNA replication and inhibits bacterial DNA gyrase (IC50=126 µg/ml) and topoisomerase IV (IC50=26.5 µg/ml).

In vitro activity:

Enoxacin demonstrated potent anti-proliferative activities against PC-3 cells in a dose-dependent manner, evidenced by counting the cell number and MTT assay (Figure 1). Reference: Technol Cancer Res Treat. 2021; 20: 1533033821995284. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7923966/

In vivo activity:

Mice treated with enoxacin gained 31% less weight on HFD in comparison to vehicle-treated mice (Fig. 2A). This was accompanied by reduced WAT mass and no changes in BAT mass (Fig. 2B). Consistent with reduced adiposity, enoxacin treatment decreased fasting glucose levels (Fig. 2C), improved glucose tolerance (Fig. 2, D and E), and increased insulin sensitivity (Fig. 2, F and G), although no differences were observed in insulin levels (fig. S3A). Reference: Sci Adv. 2020 Dec; 6(49): eabc6250. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7710362/

	Solvent	mg/mL	mM
Solubility
	DMSO	23.5	73.36
	DMF	0.1	0.31
	PBS (pH 7.2)	10.0	31.22

Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 320.32 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Concentration / Solvent Volume / Mass	1 mg	5 mg	10 mg
1 mM	1.15 mL	5.76 mL	11.51 mL
5 mM	0.23 mL	1.15 mL	2.3 mL
10 mM	0.12 mL	0.58 mL	1.15 mL
50 mM	0.02 mL	0.12 mL	0.23 mL

Formulation protocol:

1. Xu H, Mao M, Zhao R, Zhao Q. Enoxacin Exerts Anti-Tumor Effects Against Prostate Cancer Through Inducing Apoptosis. Technol Cancer Res Treat. 2021 Jan-Dec;20:1533033821995284. doi: 10.1177/1533033821995284. PMID: 33641532; PMCID: PMC7923966. 2. Luo X, Liu X, Tao Q, Yao C, Wang F, Gu Z, Li F, Yu X, Zhang B, Fan H, Dai M, Nie T. Enoxacin inhibits proliferation and invasion of human osteosarcoma cells and reduces bone tumour volume in a murine xenograft model. Oncol Lett. 2020 Aug;20(2):1400-1408. doi: 10.3892/ol.2020.11656. Epub 2020 May 21. PMID: 32724382; PMCID: PMC7377056. 3. Itoh A, Adams D, Huang W, Wu Y, Kachapati K, Bednar KJ, Leung PSC, Zhang W, Flavell RA, Gershwin ME, Ridgway WM. Enoxacin upregulates microRNA biogenesis and downregulates cytotoxic CD8 T cell function in autoimmune cholangitis. Hepatology. 2021 Jan 19. doi: 10.1002/hep.31724. Epub ahead of print. PMID: 33462854. 4. Rocha AL, de Lima TI, de Souza GP, Corrêa RO, Ferrucci DL, Rodrigues B, Lopes-Ramos C, Nilsson D, Knittel TL, Castro PR, Fernandes MF, Dos Santos Martins F, Parmigiani RB, Silveira LR, Carvalho HF, Auwerx J, Vinolo MAR, Boucher J, Mori MA. Enoxacin induces oxidative metabolism and mitigates obesity by regulating adipose tissue miRNA expression. Sci Adv. 2020 Dec 2;6(49):eabc6250. doi: 10.1126/sciadv.abc6250. PMID: 33268375; PMCID: PMC7710362.

In vitro protocol:

In vivo protocol:

1. Itoh A, Adams D, Huang W, Wu Y, Kachapati K, Bednar KJ, Leung PSC, Zhang W, Flavell RA, Gershwin ME, Ridgway WM. Enoxacin upregulates microRNA biogenesis and downregulates cytotoxic CD8 T cell function in autoimmune cholangitis. Hepatology. 2021 Jan 19. doi: 10.1002/hep.31724. Epub ahead of print. PMID: 33462854. 2. Rocha AL, de Lima TI, de Souza GP, Corrêa RO, Ferrucci DL, Rodrigues B, Lopes-Ramos C, Nilsson D, Knittel TL, Castro PR, Fernandes MF, Dos Santos Martins F, Parmigiani RB, Silveira LR, Carvalho HF, Auwerx J, Vinolo MAR, Boucher J, Mori MA. Enoxacin induces oxidative metabolism and mitigates obesity by regulating adipose tissue miRNA expression. Sci Adv. 2020 Dec 2;6(49):eabc6250. doi: 10.1126/sciadv.abc6250. PMID: 33268375; PMCID: PMC7710362.

1: Chase SL, Sloskey GE. Encainide hydrochloride and flecainide acetate: two class 1c antiarrhythmic agents. Clin Pharm. 1987 Nov;6(11):839-50. Review. Erratum in: Clin Pharm 1988 Apr;7(4):269. PubMed PMID: 3119276. 2: Treatment of life-threatening ventricular tachycardia with encainide hydrochloride in patients with left ventricular dysfunction. The Encainide-Ventricular Tachycardia Study Group. Am J Cardiol. 1988 Sep 15;62(9):571-5. PubMed PMID: 3137797. 3: Myerburg RJ, Kessler KM, Cox MM, Huikuri H, Terracall E, Interian A Jr, Fernandez P, Castellanos A. Reversal of proarrhythmic effects of flecainide acetate and encainide hydrochloride by propranolol. Circulation. 1989 Dec;80(6):1571-9. PubMed PMID: 2480856. 4: Horowitz LN. Encainide in lethal ventricular arrhythmias evaluated by electrophysiologic testing and decrease in symptoms. Am J Cardiol. 1986 Aug 29;58(5):83C-86C. Review. PubMed PMID: 3092624. 5: Morganroth J, Somberg JC, Pool PE, Hsu PH, Lee IK, Durkee J, Salerno DM. Comparative study of encainide and quinidine in the treatment of ventricular arrhythmias. J Am Coll Cardiol. 1986 Jan;7(1):9-16. Erratum in: J Am Coll Cardiol 1986 Oct;8(4):992. PubMed PMID: 3079781. 6: Svensson CK, Knowlton PW. Effect of encainide on in vivo drug metabolism in the rat. Res Commun Chem Pathol Pharmacol. 1987 May;56(2):285-8. PubMed PMID: 3110886. 7: Bartek MJ, Mayol RF, Boarman MP, Gammans RE, Gallo DG. Analysis of encainide and metabolites in plasma and urine by high-performance liquid chromatography. Ther Drug Monit. 1988;10(4):446-52. PubMed PMID: 3144068. 8: Anderson JL, Platia EV, Hallstrom A, Henthorn RW, Buckingham TA, Carlson MD, Carson PE. Interaction of baseline characteristics with the hazard of encainide, flecainide, and moricizine therapy in patients with myocardial infarction. A possible explanation for increased mortality in the Cardiac Arrhythmia Suppression Trial (CAST). Circulation. 1994 Dec;90(6):2843-52. PubMed PMID: 7994829. 9: Case CL, Hewett KW, Gillette PC. Developmental electrophysiology of encainide and its major metabolites on the Purkinje fiber action potential. Biol Neonate. 1994;66(6):330-8. PubMed PMID: 7727615. 10: Wallace AA, Stupienski RF 3rd, Kothstein T, Gehret JR, Lynch JJ Jr. Demonstration of proarrhythmic activity with the class IC antiarrhythmic agent encainide in a canine model of previous myocardial infarction. J Cardiovasc Pharmacol. 1993 Mar;21(3):397-404. PubMed PMID: 7681500. 11: Funck-Brentano C, Thomas G, Jacqz-Aigrain E, Poirier JM, Simon T, Béréziat G, Jaillon P. Polymorphism of dextromethorphan metabolism: relationships between phenotype, genotype and response to the administration of encainide in humans. J Pharmacol Exp Ther. 1992 Nov;263(2):780-6. PubMed PMID: 1432700. 12: Winter WE, Funahashi M, Koons J. Encainide-induced diabetes: analysis of islet cell function. Res Commun Chem Pathol Pharmacol. 1992 Jun;76(3):259-68. PubMed PMID: 1636050. 13: Buchanan LV, Kabell G, Turcotte UM, Brunden MN, Gibson JK. Effects of ibutilide on spontaneous and induced ventricular arrhythmias in 24-hour canine myocardial infarction: a comparative study with sotalol and encainide. J Cardiovasc Pharmacol. 1992 Feb;19(2):256-63. PubMed PMID: 1376795. 14: Hilleman DE, Mohiuddin SM, Destache CJ, Stoysich AM, Nipper HC, Malesker MA. Impact of food on the bioavailability of encainide. J Clin Pharmacol. 1992 Sep;32(9):833-7. PubMed PMID: 1430302. 15: Akiyama T, Pawitan Y, Greenberg H, Kuo CS, Reynolds-Haertle RA. Increased risk of death and cardiac arrest from encainide and flecainide in patients after non-Q-wave acute myocardial infarction in the Cardiac Arrhythmia Suppression Trial. CAST Investigators. Am J Cardiol. 1991 Dec 15;68(17):1551-5. PubMed PMID: 1720917. 16: Lee JH, Rosen MR. Use-dependent actions and effects on transmembrane action potentials of flecainide, encainide, and ethmozine in canine Purkinje fibers. J Cardiovasc Pharmacol. 1991 Aug;18(2):285-92. PubMed PMID: 1717791. 17: Roden DM, Lee JT, Woosley RL, Echt DS. Antiarrhythmic efficacy, clinical electrophysiology, and pharmacokinetics of 3-methoxy-O-desmethyl encainide (MODE) in patients with inducible ventricular tachycardia or fibrillation. Circulation. 1989 Nov;80(5):1247-58. PubMed PMID: 2805262. 18: Dawson AK, Roden DM, Duff HJ, Woosley RL, Smith RF. Differential effects of O-demethyl encainide on induced and spontaneous arrhythmias in the conscious dog. Am J Cardiol. 1984 Sep 1;54(6):654-8. PubMed PMID: 6475789. 19: Duff HJ, Dawson AK, Roden DM, Oates JA, Smith RF, Woosley RL. Electrophysiologic actions of O-demethyl encainide: an active metabolite. Circulation. 1983 Aug;68(2):385-91. PubMed PMID: 6861313. 20: Ware DL, Lee JT, Murray KT, Hanyok JJ, Roden DM, Echt DS. Intravenous 3-methoxy-O-desmethyl-encainide in reentrant supraventricular tachycardia: a randomized double-blind placebo-controlled trial in patients undergoing EP study. Pacing Clin Electrophysiol. 1991 Sep;14(9):1343-50. PubMed PMID: 1720527.