SYNTHESIS OF AZITHROMYCIN DIHYDRATE AS AN ACTIVE PHARMACEUTICAL INGREDIENT (API) ANTIBIOTICS FOR BACTERIAL INFECTIONS AND SYNTHESIS OF ITS DERIVATIVE COMPOUND FROM AZAERYTHROMYCIN PRECURSOR

• Main Author: Hansel Yonathan, Carel
• Format: Final Project
• Language: Indonesia
• Subjects: Kimia
• Online Access: https://digilib.itb.ac.id/gdl/view/64832
• Institution: Institut Teknologi Bandung

Azithromycin dihydrate is an active pharmaceutical ingredient (API) antibiotic for bacterial infection. Azithromycin dihydrate has high activity against several gram-negative bacteria such as Haemophilus influenzae, Neisseria gonorrheae, and Moxaxella catarrhalis. The aim of this research was to synthesized azithromycin dihydrate and its derivatives from azaerythromycin precursor. In this research, the synthesized azithromycin dihydrate will be used as a raw material for drugs or API. In synthesizing azithromycin dihydrates there are 2 stages where in the first stage crude azithromycin is synthesized from azaerythromycin as a precursor using Eschweiler-Clarke methylation reaction, then in the second stage, azithromycin dihydrate is synthesized from crude azithromycin using acetone-water mixture. In the first stage, two methods are used to synthesized crude azithromycin, namely the conventional heating method or reflux and the MAOS (Microwave Assisted Organic Synthesis) method. In addition, various solvents are used in the synthesis of crude azithromycin. Crude azithromycin that was synthesized by reflux methods resulted in a yield of up to 83.89% with isopropyl alcohol as a solvent and with the MAOS method resulted in a yield of up to 91.40% with acetone as a solvent. Then the synthesis of azithromycin dihydrate resulted in the yield of up to 91.85%. Azithromycin structure was identified using 1H and 13C NMR, MS (Mass Spectrometry), XRD (X-Ray Diffraction), and FTIR. Then in this study also carried out the synthesis of azithromycin derivates compounds namely azithromycin N-oxide and Cope elimination of azithromycin N-oxide. The synthesis of azithromycin N-oxide resulted in the yield of up to 82.09%. Azithromycin N-oxide structure was identified using 1H and 13C NMR, MS (Mass Spectrometry), and FTIR. Cope elimination of azithromycin N-oxide resulted in an anti-Zaitsev product 82,07% and Zaitsev of 17,93% obtained by HPLC (High Performance Liquid Chromatography)