Levofloxacin Hemihydrate
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| Category | Antibiotics |
| Catalog number | BBF-04635 |
| CAS | 138199-71-0 |
| Molecular Weight | 370.38 |
| Molecular Formula | C18H20FN3O4.1/2H2O |
| Purity | 98% |
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Description
The hydrate form of Levofloxacin, an Ofloxacin derivative, could be commonly used as an antibacterial agent through influencing DNA replication. It is an antibiotic with activity against gram-negative bacteria.
Specification
| Related CAS | 100986-85-4 (free base) |
| Synonyms | RWJ 25213; RWJ-25213; RWJ25213; (-)-(S)-9-Fluoro-2,3-dihydro-3-methyl-10-(4-methyl-1-piperazinyl)-7-oxo-7H-pyrido[1,2,3-de]-1,4-benzoxazine-6-carboxylic Acid Hemihydrate; Dynaquin; Levofloxacin Hydrate |
| Shelf Life | As supplied, 2 years from the QC date provided on the Certificate of Analysis, when stored properly |
| Storage | Preserve in tight containers, protected from light. |
| IUPAC Name | (2S)-7-fluoro-2-methyl-6-(4-methylpiperazin-1-yl)-10-oxo-4-oxa-1-azatricyclo[7.3.1.05,13]trideca-5(13),6,8,11-tetraene-11-carboxylic acid;hemihydrate |
| Canonical SMILES | CC1COC2=C3N1C=C(C(=O)C3=CC(=C2N4CCN(CC4)C)F)C(=O)O.CC1COC2=C3N1C=C(C(=O)C3=CC(=C2N4CCN(CC4)C)F)C(=O)O.O |
| InChI | InChI=1S/2C18H20FN3O4.H2O/c2*1-10-9-26-17-14-11(16(23)12(18(24)25)8-22(10)14)7-13(19)15(17)21-5-3-20(2)4-6-21;/h2*7-8,10H,3-6,9H2,1-2H3,(H,24,25);1H2/t2*10-;/m00./s1 |
| InChI Key | SUIQUYDRLGGZOL-RCWTXCDDSA-N |
| Source | Synthetic |
Properties
| Appearance | Pale Yellow Solid |
| Application | Anti-Bacterial Agents |
| Antibiotic Activity Spectrum | Gram-negative bacteria |
| Boiling Point | 571.5°C at 760 mmHg |
| Melting Point | 218-227°C |
| Density | 1.48 g/cm3 |
| Solubility | Slightly soluble in Basic Aqueous Solution, DMSO, Methanol |
Reference Reading
1.Micellar liquid chromatographic method for the simultaneous determination of Levofloxacin and Ambroxol in combined tablets: Application to biological fluids.
Belal FF1, Sharaf El-Din MK, El-Enany NM, Saad S. Chem Cent J. 2013 Oct 1;7(1):162. doi: 10.1186/1752-153X-7-162.
BACKGROUND: Levofloxacin hemihydrate (LEV) and ambroxol HCl (AMB) are available for the treatment of upper and lower respiratory tract infections. A survey of the literature reveals that two reversed phase HPLC methods were e reported for the simultaneous determination of LEV and AMB in pharmaceutical preparations. However the reported methods suffers from the low sensitivity, no application of the method in the combined tablets and no application to biological fluids. Also the toxic effects of the used solvents which are harmful to human beings. For this reason, our target was to develop a simple sensitive, less hazardous micellar HPLC method for the simultaneous determination of LEV and AMB in their combined dosage forms and plasma.
2.Understanding the dehydration of levofloxacin hemihydrate.
Gorman EM1, Samas B, Munson EJ. J Pharm Sci. 2012 Sep;101(9):3319-30. doi: 10.1002/jps.23200. Epub 2012 May 18.
Levofloxacin is a broad-spectrum antibiotic that exists as a hemihydrate under ambient conditions. In addition to the hemihydrate, there are three known crystalline anhydrate forms, denoted as α, β, and γ. In this study, differential scanning calorimetry (DSC), thermogravimetric analysis, Raman spectroscopy, single-crystal and powder X-ray diffraction, and solid-state NMR spectroscopy were used to investigate the transitions that occurred upon dehydration to the anhydrate as well as additional transitions that occurred to the anhydrous material upon heating/cooling. An enantiotropic conversion was observed in the DSC around 54°C corresponding to the conversion of the γ form to a new form, denoted as the δ form. Raman spectroscopy, powder X-ray diffraction, and solid-state NMR spectroscopy confirmed that a new crystalline form was being produced.
3.Formulation and in vitro evaluation of size expanding gastro-retentive systems of levofloxacin hemihydrate.
El-Zahaby SA1, Kassem AA2, El-Kamel AH3. Int J Pharm. 2014 Apr 10;464(1-2):10-8. doi: 10.1016/j.ijpharm.2014.01.024. Epub 2014 Jan 26.
Size increasing (plug-type) levofloxacin hemihydrate (LVF) tablets for eradication of Helicobacter pylori (H. pylori) were prepared using in situ gel forming polymers including: gellan gum, sodium alginate, pectin and xanthan gum. Effect of cross-linkers: calcium and aluminum chloride, on the drug release was also studied. The prepared tablets were evaluated for their physicochemical parameters: weight variation, thickness, friability, hardness, drug content, water uptake and in vitro drug release. The optimized formula was subjected to further studies such as radial swelling test, FT-IR and DSC. Results revealed that LVF release depends not only on the nature of the matrix but also on the type of cross linker used to form this polymeric matrix. The addition of either calcium chloride or aluminum chloride, as cross-linkers, to gellan gum formulations significantly decreased drug release. Other polymers' formulations resulted in increased drug release upon addition of the same cross-linkers.
4.Quantitative determination of levofloxacin hemihydrate in bulk and tablets by UV-spectrophotometry and first order derivative methods.
Shirkhedkar AA1, Surana SJ. Pak J Pharm Sci. 2009 Jul;22(3):301-2.
Two simple, rapid, accurate and economical 'UV Spectrophotometry' and 'First Order Derivative' methods have been developed for determination of levofloxacin hemihydrate in bulk and tablets. In (10% v/v) acetonitrile, the lambdamax of the drug was found to be 288 nm. The same spectrum was derivatised into first order derivative, using UV probe software of instrument (Shimadzu-2450), at Deltalambda=4. The amplitude of the trough was recorded at 297 nm. In both the proposed methods, levofloxacin hemihydrate follows linearity in the concentration range 2-12 microg/ml with a correlation coefficient of 0.9999. Assay results were in good agreement with label claim. The methods were validated statistically and by recovery studies. The relative standard deviation were found to be less than 2% with excellent precision and accuracy.
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Bio Calculators
* Our calculator is based on the following equation:
Concentration (start) x Volume (start) = Concentration (final) x Volume (final)
It is commonly abbreviated as: C1V1 = C2V2
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