Ofloxacin
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MedKoo CAT#: 318382

CAS#: 82419-36-1 (free base)

Description: Ofloxacin is a synthetic antibiotic of the fluoroquinolone drug class considered to be a second-generation fluoroquinolone.


Chemical Structure

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Ofloxacin
CAS# 82419-36-1 (free base)

Theoretical Analysis

MedKoo Cat#: 318382
Name: Ofloxacin
CAS#: 82419-36-1 (free base)
Chemical Formula: C18H20FN3O4
Exact Mass: 361.14
Molecular Weight: 361.368
Elemental Analysis: C, 59.83; H, 5.58; F, 5.26; N, 11.63; O, 17.71

Price and Availability

Size Price Availability Quantity
5g USD 300 2 weeks
10g USD 550 2 weeks
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Related CAS #: 118120-51-7 (HCl)   82419-36-1 (free base),  

Synonym: Ofloxacin, DL-8280, DR-3355, Hoe-280, ORF-28489, Ru-43280,DL8280, DR3355, Hoe280, ORF28489, Ru43280, DL 8280, DR 3355, Hoe 280, ORF 28489, Ru 43280

IUPAC/Chemical Name: 9-fluoro-3-methyl-10-(4-methylpiperazin-1-yl)-7-oxo-3,7-dihydro-2H-[1,4]oxazino[2,3,4-ij]quinoline-6-carboxylic acid

InChi Key: GSDSWSVVBLHKDQ-UHFFFAOYSA-N

InChi Code: InChI=1S/C18H20FN3O4/c1-10-9-26-17-14-11(16(23)12(18(24)25)8-22(10)14)7-13(19)15(17)21-5-3-20(2)4-6-21/h7-8,10H,3-6,9H2,1-2H3,(H,24,25)

SMILES Code: CC1COC2=C3N1C=C(C(=O)C3=CC(=C2N4CCN(CC4)C)F)C(=O)O

Appearance: Off-white to light yellow crystalline powder.

Purity: >95% (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:
Biological target: Ofloxacin (Hoe-280) is a fluoroquinolone whose primary mechanism of action is inhibition of bacterial DNA gyrase.
In vitro activity: Chondrocytes from juvenile rabbit joints were incubated with ofloxacin at concentrations of 0, 5, 10, 20, 40 and 80 microg/ml, respectively. It was observed that ofloxacin induced a concentration-dependent increase in intracellular reactive oxygen species production, which may be an early mediator of ofloxacin cytotoxicity. Similarly, ofloxacin resulted in a significant lipid peroxidation, revealed by a concentration-dependent increase in the level of thiobarbituric acid reactive substances. Reference: Eur J Pharmacol. 2010 Jan 25;626(2-3):146-53. https://pubmed.ncbi.nlm.nih.gov/19818344/
In vivo activity: The antiviral activity of ofloxacin, a new quinolone derivative, against vaccinia virus (VV), herpes simplex virus (HSV) and influenza virus (InfV) was evaluated in both in vitro and in vivo experiments. As a result, ofloxacin showed inhibitory activity against VV in cultured mammalian cells, and prevented formation of pox tail lesions in VV-infected mice. The antiviral activity of ofloxacin assessed by VV tail-lesion test was strongest when administered to mice through the oral route daily for five consecutive days post-infection. Reference: Antiviral Res. 1987 Oct;8(3):103-13. https://pubmed.ncbi.nlm.nih.gov/2827566/

Solubility Data

Solvent Max Conc. mg/mL Max Conc. mM
Solubility
DMF 2.0 5.53
DMSO 2.1 5.90
DMSO:PBS (pH 7.2) (1:9) 0.1 0.28

Preparing Stock Solutions

The following data is based on the product molecular weight 361.37 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.

Recalculate based on batch purity %
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. Resch MD, Resch BE, Csizmazia E, Imre L, Németh J, Révész P, Csányi E. Permeability of human amniotic membrane to ofloxacin in vitro. Invest Ophthalmol Vis Sci. 2010 Feb;51(2):1024-7. doi: 10.1167/iovs.09-4254. Epub 2009 Sep 24. PMID: 19797205. 2. Li Q, Peng S, Sheng Z, Wang Y. Ofloxacin induces oxidative damage to joint chondrocytes of juvenile rabbits: excessive production of reactive oxygen species, lipid peroxidation and DNA damage. Eur J Pharmacol. 2010 Jan 25;626(2-3):146-53. doi: 10.1016/j.ejphar.2009.09.044. Epub 2009 Oct 7. PMID: 19818344. 3. Grosset JH, Guelpa-Lauras CC, Perani EG, Beoletto C. Activity of ofloxacin against Mycobacterium leprae in the mouse. Int J Lepr Other Mycobact Dis. 1988 Jun;56(2):259-64. PMID: 3045223. 4. Ikeda S, Yazawa M, Nishimura C. Antiviral activity and inhibition of topoisomerase by ofloxacin, a new quinolone derivative. Antiviral Res. 1987 Oct;8(3):103-13. doi: 10.1016/0166-3542(87)90064-7. PMID: 2827566.
In vitro protocol: 1. Resch MD, Resch BE, Csizmazia E, Imre L, Németh J, Révész P, Csányi E. Permeability of human amniotic membrane to ofloxacin in vitro. Invest Ophthalmol Vis Sci. 2010 Feb;51(2):1024-7. doi: 10.1167/iovs.09-4254. Epub 2009 Sep 24. PMID: 19797205. 2. Li Q, Peng S, Sheng Z, Wang Y. Ofloxacin induces oxidative damage to joint chondrocytes of juvenile rabbits: excessive production of reactive oxygen species, lipid peroxidation and DNA damage. Eur J Pharmacol. 2010 Jan 25;626(2-3):146-53. doi: 10.1016/j.ejphar.2009.09.044. Epub 2009 Oct 7. PMID: 19818344.
In vivo protocol: 1. Grosset JH, Guelpa-Lauras CC, Perani EG, Beoletto C. Activity of ofloxacin against Mycobacterium leprae in the mouse. Int J Lepr Other Mycobact Dis. 1988 Jun;56(2):259-64. PMID: 3045223. 2. Ikeda S, Yazawa M, Nishimura C. Antiviral activity and inhibition of topoisomerase by ofloxacin, a new quinolone derivative. Antiviral Res. 1987 Oct;8(3):103-13. doi: 10.1016/0166-3542(87)90064-7. PMID: 2827566.

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1: Lahouidak S, Soriano ML, Salghi R, Zougagh M, Ríos Á. Graphene quantum dots for enhancement of fluorimetric detection coupled to capillary electrophoresis for detection of ofloxacin. Electrophoresis. 2019 May 22. doi: 10.1002/elps.201900037. [Epub ahead of print] PubMed PMID: 31116440.

2: Li J, Zhao L, Wei C, Sun Z, Zhao S, Cai T, Gong B. Preparation of restricted access media-molecularly imprinted polymers for efficient separation and enrichment ofloxacin in bovine serum samples. J Sep Sci. 2019 May 20. doi: 10.1002/jssc.201900103. [Epub ahead of print] PubMed PMID: 31106511.

3: Yang X, Xu X, Wei X, Wan J, Zhang Y. Biomarker Effects in Carassius auratus Exposure to Ofloxacin, Sulfamethoxazole and Ibuprofen. Int J Environ Res Public Health. 2019 May 9;16(9). pii: E1628. doi: 10.3390/ijerph16091628. PubMed PMID: 31075982.

4: Eid HM, Elkomy MH, El Menshawe SF, Salem HF. Development, Optimization, and In Vitro/In Vivo Characterization of Enhanced Lipid Nanoparticles for Ocular Delivery of Ofloxacin: the Influence of Pegylation and Chitosan Coating. AAPS PharmSciTech. 2019 May 3;20(5):183. doi: 10.1208/s12249-019-1371-6. PubMed PMID: 31054011.

5: Singh V, Pandey B, Suthar S. Phytotoxicity and degradation of antibiotic ofloxacin in duckweed (Spirodela polyrhiza) system. Ecotoxicol Environ Saf. 2019 Sep 15;179:88-95. doi: 10.1016/j.ecoenv.2019.04.018. Epub 2019 Apr 23. PubMed PMID: 31026754.

6: Wang H, Han M, Zhou Y, Li J, Xiao X, Zhang W. Effects of Thermal Treatment on Porous Cerium Titanate Photocatalyst for Ofloxacin Degradation. J Nanosci Nanotechnol. 2019 Aug 1;19(8):5264-5270. doi: 10.1166/jnn.2019.16812. PubMed PMID: 30913843.

7: Wang C, Dong D, Zhang L, Song Z, Hua X, Guo Z. Response of Freshwater Biofilms to Antibiotic Florfenicol and Ofloxacin Stress: Role of Extracellular Polymeric Substances. Int J Environ Res Public Health. 2019 Feb 27;16(5). pii: E715. doi: 10.3390/ijerph16050715. PubMed PMID: 30818877; PubMed Central PMCID: PMC6427337.

8: Santos AM, Wong A, Vicentini FC, Fatibello-Filho O. Simultaneous voltammetric sensing of levodopa, piroxicam, ofloxacin and methocarbamol using a carbon paste electrode modified with graphite oxide and β-cyclodextrin. Mikrochim Acta. 2019 Feb 15;186(3):174. doi: 10.1007/s00604-019-3296-x. PubMed PMID: 30771008.

9: Marslin G, Revina AM, Kumar Megraj Khandelwal V, Balakumar K, Sheeba CJ, Franklin G. Corrigendum to "PEGylated ofloxacin nanoparticles render strong antibacterial activity against many clinically important human pathogens" [Colloids Surf. B: Biointerfaces 132 (2015) 62-70]. Colloids Surf B Biointerfaces. 2019 May 1;177:282-283. doi: 10.1016/j.colsurfb.2019.01.063. Epub 2019 Feb 12. PubMed PMID: 30769229.

10: Vakh C, Alaboud M, Lebedinets S, Bulatov A. A rotating cotton-based disk packed with a cation-exchange resin: Separation of ofloxacin from biological fluids followed by chemiluminescence determination. Talanta. 2019 May 1;196:117-123. doi: 10.1016/j.talanta.2018.12.024. Epub 2018 Dec 13. PubMed PMID: 30683340.

11: Gao B, Li P, Yang R, Li A, Yang H. Investigation of multiple adsorption mechanisms for efficient removal of ofloxacin from water using lignin-based adsorbents. Sci Rep. 2019 Jan 24;9(1):637. doi: 10.1038/s41598-018-37206-1. PubMed PMID: 30679691; PubMed Central PMCID: PMC6346052.

12: Chen P, Blaney L, Cagnetta G, Huang J, Wang B, Wang Y, Deng S, Yu G. Degradation of Ofloxacin by Perylene Diimide Supramolecular Nanofiber Sunlight-Driven Photocatalysis. Environ Sci Technol. 2019 Feb 5;53(3):1564-1575. doi: 10.1021/acs.est.8b05827. Epub 2019 Jan 11. PubMed PMID: 30604606.

13: Polachek H, Debotton N, Feinshtein V, Rubin M, Ben-Zvi Z, Holcberg G, Agbaria R, Dahan A. The role of various transporters in the placental uptake of ofloxacin in an in vitro model of human villous trophoblasts. Drug Des Devel Ther. 2018 Dec 4;12:4129-4138. doi: 10.2147/DDDT.S181493. eCollection 2018. PubMed PMID: 30584277; PubMed Central PMCID: PMC6284538.

14: Nuti S, Fernández-Lodeiro J, Del Secco B, Rampazzo E, Rodríguez-González B, Capelo JL, Silva V, Igrejas G, Poeta P, Torres C, Zaccheroni N, Prodi L, Oliveira E, Lodeiro C. Engineered Nanostructured Materials for Ofloxacin Delivery. Front Chem. 2018 Nov 27;6:554. doi: 10.3389/fchem.2018.00554. eCollection 2018. PubMed PMID: 30538980; PubMed Central PMCID: PMC6277636.

15: Tong X, Wang X, He X, Xu K, Mao F. Effects of ofloxacin on nitrogen removal and microbial community structure in constructed wetland. Sci Total Environ. 2019 Mar 15;656:503-511. doi: 10.1016/j.scitotenv.2018.11.358. Epub 2018 Nov 27. PubMed PMID: 30522033.

16: Xiao X, Wu J, Li Z, Jia L. Enantioseparation and sensitive analysis of ofloxacin by poly(3,4-dihydroxyphenylalanine) functionalized magnetic nanoparticles-based solid phase extraction in combination with on-line concentration capillary electrophoresis. J Chromatogr A. 2019 Feb 22;1587:14-23. doi: 10.1016/j.chroma.2018.11.026. Epub 2018 Nov 16. PubMed PMID: 30473108.

17: Yu Y, Huang F, He Y, Liu X, Song C, Xu Y, Zhang Y. Heterogeneous fenton-like degradation of ofloxacin over sludge derived carbon as catalysts: Mechanism and performance. Sci Total Environ. 2019 Mar 1;654:942-947. doi: 10.1016/j.scitotenv.2018.11.156. Epub 2018 Nov 12. PubMed PMID: 30453264.

18: Sirous M, Khosravi AD, Tabandeh MR, Salmanzadeh S, Ahmadkhosravi N, Amini S. Molecular detection of rifampin, isoniazid, and ofloxacin resistance in Iranian isolates of Mycobacterium tuberculosis by high-resolution melting analysis. Infect Drug Resist. 2018 Oct 18;11:1819-1829. doi: 10.2147/IDR.S178831. eCollection 2018. PubMed PMID: 30425535; PubMed Central PMCID: PMC6202043.

19: Ouni B, Fathallah N, Slim R, Brahim A, Ben Salem C. Anaphylactic shock secondary to oral ofloxacin administration with cross-reactivity to levofloxacin and ciprofloxacin. Therapie. 2018 Dec;73(6):555-556. doi: 10.1016/j.therap.2018.05.001. Epub 2018 Jun 20. PubMed PMID: 30401472.

20: Zhong X, Qin X, Du P, Chen J, Zhang Y, He Y, Liu F. [Simultaneous determination of ofloxacin enantiomers in water by high performance liquid chromatography]. Se Pu. 2018 Nov 1;36(11):1167-1172. doi: 10.3724/SP.J.1123.2018.07018. Chinese. PubMed PMID: 30378380.