J. Serb. Chem. Soc. 71 (12) (2006) UDC *ofloxacin: :
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1 J. Serb. Chem. Soc. 71 (12) (2006) UDC *ofloxacin: : JSCS 3519 Short communication SHORT COMMUNICATION Design of targeted dosage form of ofloxacin + M. SHAHAR YAR *, A. AHAMED SIDDIQUI, M. ASHRAF ALI and E. MANOGRAN Faculty of Pharmacy, Jamia Hamdard University, Department of Pharmaceutical Chemistry, Hamdard Nagar, New Delhi, , India ( yarmsy@rediffmail.com) (Received 19 October 2005, revised 27 January 2006) Abstract: The targeted pro-drug is a classical pro-drug design often representing a non-specific chemical approach to mask undesirable drug properties, such as limited bioavailability, lack of site specificity, and chemical instability. On the other hand, targeted pro-drug design represents a new strategy for directed and efficient drug delivery. Quinolone antibiotics exert their pharmacological effect by inhibiting the cell wall synthesis of the pathogen. However, development of resistance exists, which instigates for a new higher congener to remain in clinical practice. To overcome this phenomenon and also to produce site-specific activity of the cell walls of the pathogen, ofloxacin is conjugated with a hydroxypropyl methacrylamide polymer backbone moiety. The results of in vitro release studies indicate the possibilities for the development of a new drug for site-specific therapy with an improved t 1/2 of the drug. This novel pro-drug may have opened a new vista in antibiotic chemotherapy. Keywords: ofloxacin, hydroxypropyl methacrylamide, bioavailability, pro-drug. INTRODUCTION 1-4 Ofloxacin is generally effective in the management of various systemic infections caused by a variety of pathogens. Ofloxacin is a quinolone series antibiotic, indicated in enteric infections. However, the drug has its own disadvantages and is associated with the development of several unwanted side effects. The polymeric pro-drug in which the drug is covalently bound to a hydroxypropyl methacrylamide polymeric backbone was conceived to overcome unwanted side effects, to improve site specificity, improve the half-life of the drug and improve complete absorption along with a reduction of the dosage form. In recent years, polymeric drug derivatives, in which drug molecules are linked to a polymeric backbone through covalent bonding with limited stability in physiological media are receiving considerable attention This is believed to be one of the most promising ways to modify the pharmacokinetics of drugs and to achieve preferential localization to target sites. + Partially presented at the 54 th Indian Pharmaceutical Congress. * Corresponding author. doi: /JSC S 1269
2 1270 YAR et al. The objective of this research was to develop a new vista in antibiotic chemotherapy. Ofloxacin was covalently attached to hydroxypropyl methacrylamide (a biocompatible polymer backbone) through an ester linkage. Such a system was expected to preferentially release the drug in the alkaline medium of the lower GI tract in a site-specific manner, rather than in the acidic medium of the upper GI tract. EXPERIMENTAL Preparation of the chloro derivative of hydroxypropyl methacrylamide Hydroxypropyl methacrylamide (26.09 g) and thionyl chloride (23.6 g) were heated in a 250 ml round-bottomed flask in an oil bath for 3 h. The excess thionyl chloride was distilled off to yield the chloro derivative of hydroxypropyl methacrylamide (Scheme 1). Scheme 1. Formation of the sodium salt of ofloxacin Ofloxacin (5 g) was treated with 1M sodium hydroxide to obtain the sodium salt of ofloxacin. Preparation of the monomer drug derivative The chloro derivative of hydroxypropyl methacrylamide was stirred with the sodium salt of the drug (2 g) in the dimethyl sulphoxide solvent at 120 C in an oil bath for 8 h. The solid compound was filtered and washed with water and acetone.
3 DESIGN OF DOSAGE FORM OF OFLOXACIN 1271 Polymerization of the drug derivative The monomer derivative of hydroxypropyl methacrylamide (2 g) was dissolved in 50 ml of dimethyl sulphoxide in a 250 ml round-bottomed flask. The reaction mixture was heated at 170 C in the presence of 0.1 g of benzoyl peroxide to obtain the polymeric pro-drug. The IR (KBr) spectrum of the monomeric drug derivative exhibits intense bands at: 1734 cm -1 (C=O, C F); 1114 cm -1 (C N); 1344 cm -1 (aromatic ether); 1270 cm -1 (N CH 3 ); 1440 cm -1 and 1653 cm -1 (C=C) and an absence of a band at 769 cm -1 (C Cl); 1 H-NMR (CDCl 3 ): 2.34 (3H, s,ch 3 ); 3.7 (s, cyclic CH 2 ); 9.4 (1H, s, NH); 4.01 (2H, m, CH 2 =C); 7.64 (2H, m, aromatic). In vitro studies The in vitro release was carried out using a USP type II dissolution apparatus at various ph values, i.e., 1.2 to 7.5 which mimic the ph in the upper and lower GI tract, respectively, over a period of 24 h. Samples were withdrawn at different time intervals and analyzed spectrophotometrically. Bioavailability study The bioavailability study was carried out in rats. Free drug and pro-drug containing an equivalent quantity of ofloxacin were administered orally as a suspension in 0.55 % w/v carboxymethyl cellulose (CMC). Blood samples were withdrawn at different time intervals over a period of 24 h and a spectrophotometric method was adopted to quantify the drug plasma levels. RESULTS AND DISCUSSION A macromolecule conjugate of hydroxypropyl methacrylamide ofloxacin was synthesized, the structure of which was confirmed by melting point, TLC, IR and NMR, etc.thein vitro release and bioavailability study showed that the drug release takes place in a sustained manner. The release was slower at ph 1.2 but was almost completely released at ph 7.5 (Fig. 1) when compared to the free drug. The bioavailability study showed a detectable concentration of the drug for more than 12 h in the case of the pro-drug but only for 10 h for the free drug. The peakplasmaconcentrationforthefreedrugwas640mg/mlwithin1h(t max ), Fig. 1. In vitro drug release profile of the pro-drug at ph 1.2 ( ) and ph 7.5 ( ).
4 1272 YAR et al. Fig. 2. Blood plasma levels of ofloxacin et various times alter oral administration of the pro-drug ( )and drug ( ) torats. whereas for the pro-drug it was 210 mg/ml after a period of 6 h. The delay was thus due to the slower rate of drug release from the pro-drug and its consequent absorption. There was no significant change in the extent of drug absorption between the free drug and pro-drug, as the areas under the plasma concentration were almost the same, namely 2076 and 2373 ng/ml, respectively. This confirms the complete release of drug from the polymeric pro-drug and its potential in sustaining drug release under in vivo conditions (Fig. 2). Conclusively, the results indicate that the covalent linkage of ofloxacin to a biocompatible polymer, poly(hydroxypropyl methacrylamide), through the ester group leads to a delivery system which is capable of releasing the drug in a sustained manner over the GIT. IZVOD DIZAJN DOZIRANIH OBLIKA OFLOKSACINA M. SHAHAR YAR, A. AHAMED SIDDIQUI, M. ASHRAF ALI i E. MANOGARAN Faculty of Pharmacy, Jamia Hamdard University, Department of Pharmaceutical Chemistry, Hamdard Nagar, New Delhi , India Ciqani dizajn proleka je klasi~an dizajn proleka koji predstavqa nespecifi- ~an hemijski pristup u ciqu maskirawa ne`eqenih osobina leka kao {to su ograni- ~ena bioraspolo`ivost, nedostatak specifi~nosti i hemijska nestabilnost. S druge strane, ciqani dizajn proleka daje novu strategiju za direktno i efikasno osloba awe leka. Hinolinski antibiotici pokazuju farmakolo{ki efekat inhibirawem sinteze }elijskog zida patogenih mikroorganizama. Ipak, zbog rezistencije koja nastaje istra`uju se srodna jediwewa koja bi se zadr`ala u klini~koj praksi. Radi prevazila`ewa ovog fenomena i ostvarivawa specifi~nog delovawa na }elijski zid patogenih }elija ofloksacin je konjugovan sa polimerom hidroksipropil-metakrilamida kao nosa~em. Rezultati in vitro studije ukazuju na mogu}nost razvoja novih
5 DESIGN OF DOSAGE FORM OF OFLOXACIN 1273 lekova specifi~nog delovawa i poboq{awa biolo{kog poluvremena eliminacije leka. Time se otvaraju nove mogu}nosti u savremenoj antibiotskoj hemoterapiji. (Primqeno 19. oktobra 2005, revidirano 27. januara 2006) REFERENCES 1. T. Ouchi, A. Fujino, Makromol. Chem. 190 (1989) A. Albert, Nature 182 (1958) C. J. Hawkey, Gastroenterology 109 (1995) E. Gershonov, I. Goldwaser, M. Fridkin, Y. Shelter, J. Med. Chem. 43 (2000) G. Battaghia, M. La Russa, M. Burno, Aranare, Ippolito, Brain Res. 860 (2000) J. Ranito, T. Nevalanian, H. Taipale, J. Med. Chem. 43 (2000) S. Gac, J. Condane, M. Boustta, J. Drug Targeting 7 (2000) M. Hashida, K. Akarnaslu, M. Nishikawa, Pharmazie 55 (2000) M. Saffran, G. S. Kumar, C. Savariar, J. S. Burnhan, Science 233 (1986) C. Cartlidge, R. Duncan, J. B. Lylod, P. J. Kopeckova, Controlled Release 4 (1987) N.R.Vyavahare,M.G.Kulkarni,R.A.Mashelkar,Polymer 33 (1992) 593.
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