Gatifloxacin sesquihydrate

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Gatifloxacin sesquihydrate
Category Antibiotics
Catalog number BBF-03999
CAS 180200-66-2
Molecular Weight 402.41
Molecular Formula C19H22FN3O4.3/2(H2O)
Purity ≥98%

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Description

Gatifloxacin is a fourth generation fluoroquinolone antibiotic. Gatifloxacin sesquihydrate is a bacterial DNA gyrase inhibitor used to treat tuberculosis and pneumonia.

Specification

Related CAS 112811-59-3 (anhydrous)
Storage Store at 2-8°C
IUPAC Name 1-cyclopropyl-6-fluoro-8-methoxy-7-(3-methylpiperazin-1-yl)-4-oxoquinoline-3-carboxylic acid;trihydrate
Canonical SMILES CC1CN(CCN1)C2=C(C=C3C(=C2OC)N(C=C(C3=O)C(=O)O)C4CC4)F.CC1CN(CCN1)C2=C(C=C3C(=C2OC)N(C=C(C3=O)C(=O)O)C4CC4)F.O.O.O
InChI InChI=1S/2C19H22FN3O4.3H2O/c2*1-10-8-22(6-5-21-10)16-14(20)7-12-15(18(16)27-2)23(11-3-4-11)9-13(17(12)24)19(25)26;;;/h2*7,9-11,21H,3-6,8H2,1-2H3,(H,25,26);3*1H2
InChI Key RMJMZKDEVNTXHE-UHFFFAOYSA-N
Source Synthetic

Properties

Appearance White to Light Yellow Crystal Powder
Boiling Point 607.8°C at 760 mmHg
Melting Point 182-185°C
Density 1.386 g/cm3
Solubility Soluble in Water

Reference Reading

1.Alginate-chitosan film for ocular drug delivery: effect of surface cross-linking on film properties and characterization.
Gilhotra RM1, Mishra DN. Pharmazie. 2008 Aug;63(8):576-9.
The characteristics of alginate-chitosan films intended for ocular drug delivery of gatifloxacin sesquihydrate were compared with the ionically surface cross-linked films of similar compositions. The effect of polymer ratios and cross-linking was studied relatively to various parameters of formulations including physicochemical, mechanical strength, swelling and bioadhesion. The drug release profiles and drug release mechanisms were compared. The folding endurance, tensile strength, bioadhesive strength considerably increased whereas swelling index, elongation at break decreased with surface cross-linking of the films. Surface cross-linked formulation F3 (2% w/v sodium alginate and 1% w/v chitosan) showed most prolonged drug release of 24 h indicating the potential of surface cross linking of the film to sustain drug release. As per the kinetic models both type of films showed a constant drug release, however the drug release mechanism transformed from erosion to diffusion after cross linking.
2.Ocular insert for sustained delivery of gatifloxacin sesquihydrate: Preparation and evaluations.
Khurana G1, Arora S, Pawar PK. Int J Pharm Investig. 2012 Apr;2(2):70-7. doi: 10.4103/2230-973X.100040.
BACKGROUND: Many polymeric systems have been used to fabricate ocular inserts for improve ocular bioavailability and retention to drug of which matrix systems have shown advantages of reduce dosing frequency and increased corneal residence time. The objective of the present investigation was to prepare and evaluate ocular inserts of gatifloxacin.
3.Cerebral vacuolation induced in rats by the administration of LUP-3FDC, an anti-tuberculosis cocktail.
Wells MY1, Krinke GJ. Exp Toxicol Pathol. 2008 Apr;59(6):365-72. doi: 10.1016/j.etp.2007.11.006. Epub 2008 Jan 25.
A study was conducted to determine the subacute oral toxicity of LUP-3FDC (a cocktail composed of rifampicin, isoniazid and pyrazinamide) and LUP-Q1 (gatifloxicin sesquihydrate) as well as the potential effects of their combination when administered as repeated sublethal oral (gavage) doses for a period of 90 days in seven (7) groups of Wistar rats. Three (3) additional groups were allowed to live for 28 days after the end of treatment to evaluate the potential reversibility of any toxic effects observed. Mortality was observed at all dose levels. General body weakness and hind limb paralysis (attributable to peripheral neuropathy) were observed in animals administered 1400mg/kg/day LUP-3FDC, 800mg/kg/day LUP 3-FDC+300mg/kg/day LUP Q1 and 1400mg/kg/day LUP-3FDC+300mg/kg/day LUP-Q1. The administration of LUP-3FDC at doses of 1100 or 1400mg/kg/day or a combination of 1400mg/kg/day LUP-3FDC and 300mg/kg/day LUP-Q1 induced an increased incidence of vacuolation in the brain compared to control animals.

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