In-vitro Physicochemical Evaluation of Different Marketed Brands of Azithromycin Available in Aden-Yemen

In-vitro Physicochemical Evaluation of Different Marketed Brands of Azithromycin

Available in Aden-Yemen

Adel A.M. Saeed, Fadhl Al-Hariri, Amani K. Muthanna, Mayada Molhi, Ahmed Hassan,
Fadhel Mahmoud, Hadeel Adnan, Musab Muhammed, Ibrahim Mukhtar
Department of Chemistry, Faculty of Science. University of Aden, Yemen
The Supreme Board of Drug & Medical Appliances, Aden, Yemen

Abstract
The recent investigation is undertaken with an aim to compare quality evaluation and provide
concise information on three different brands of film-coated Azithromycin tablets (500 mg). The
evaluation of the physical characteristics of pharmaceutical products can ensure their identity as well
as quality. These include criteria for FTIR spectra, weight variation, uniformity of diameter, thickness,
hardness, and disintegration tests. The results showed the similarity among the studied brands.
Keywords: (Azithromycin drug, FTIR spectra, physical characteristics).

‫الملخص‬
‫تم إجراء الدراسة الحالية بهدف مقارنة وتقييم الجودة وتقديم معلومات موجزة عن ثالث منتجات دوائية مختلفة‬
‫ يمكن أن يضمن تقييم الخصائص الفيزيائية للمنتجات‬.)‫ مجم‬500( ‫من أقراص أزيثروميسين المغلفة بالفيلم‬
‫ وتوحيد‬،‫ واختالف الوزن‬،)FTIR( ‫ وتشمل هذه معايير أطياف تحت الحمراء‬.‫الصيدالنية هويتها وكذلك جودتها‬
.‫ أظهرت النتائج تشابه بين العالمات التجارية المدروسة‬.‫ واختبارات التفكك‬،‫ والصالبة‬،‫ والسمك‬،‫القطر‬
.)‫ والخصائص الفيزيائية‬،‫ وأطياف تحت الحمراء‬،‫ (عقار أزيثروميسين‬:‫الكلمات المفتاحية‬

1. Introduction
Azithromycin drugs are classified as macrolide antibiotics and are used to kill bacteria or inhibit
their growth. It’s a semi-synthetic antimicrobial compound derived from erythromycin, which falls
into the macrolide class of drugs. Macrolide antibiotics such as erythromycin, clarithromycin, and
roxithromycin were named after the presence of a macrocyclic lactone ring in their structure and were
originally isolated from cultures of Streptomyces erythraea in 1952. The first synthesis of
Azithromycin was in 1980 and was initially developed for the treatment of bacterial infections of the
upper and lower respiratory tracts, skin infections, and treatment of uncomplicated Chlamydial
infections [1,2].
Azithromycin (9-deoxo-9a-aza-9a-methyl-9a-homoerythromycin) consists of a 15 membered
macrolide ring with 2 basic amine groups (Fig 1), and can also be described as an azalide antibiotic.
Azithromycin generally is a white or almost white crystalline powder and the labeled water content of
its anhydrate form must not exceed 2.0 % of water [3]. It differs structurally from the other macrolide
antibiotics by methyl-substituted nitrogen in the macrolide ring, resulting in two basic amine groups,
rather than the one in erythromycin [4]. The unique structure of this ring prevents degradation in acidic
environments and improves the antibacterial spectrum and pharmacokinetics [5].

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Figure (1)
Structure of Azithromycin

Azithromycin, like other macrolide antibiotics, prevents bacterial protein synthesis by binding to
and interfering with the assembly of the 50S large ribosomal subunit and the growth of the nascent
polypeptide chain [6-8]. In comparison to larger macrocyclic antibiotics, azithromycin drug binds at
the polypeptide exit tunnel, near to the peptidyl transferase center (PTC) on the 23S rRNA, but does
not inhibit PT activity. The high pH of Azithromycin leads to rapid penetration of the outer membranes
and a more effective entrance into the bacteria, so improving activity against Gram-negative bacteria
[9]. Binding sites on the bacterial ribosome for the structurally different macrolides, lincosamides,
streptogramin B, and ketolides (MLSbK) overlap considerably so that modifications in a single
ribosomal region concurrently alter susceptibility to many MLSbK antibiotics. Even though
unsuccessful as a bactericidal agent against Pseudomonas aeruginosa at clinically appropriate
concentrations, Azithromycin stops the generation of both growth-stimulating, quorum-sensing
compounds, and alginate biofilm which protects the micro-organism from antibiotic actions [10-13].
Azithromycin may work in synergy with antiviral drugs. Some works have found that this
macrolide antibiotic can exert antiviral effects against rhinovirus, Ebola virus, and Zika virus [14-16].
Azithromycin perhaps acts alongside the word wild SARS-CoV-2 virus causes coronavirus
disease-19 in different points of the viral cycle. Its immunomodulatory properties consist of the
capability to downregulate cytokine production, retain epithelial cell integrity or stop lung fibrosis.
Azithromycin usage was linked with a decrease in mortality and ventilation days in other viral
infections. These properties might be beneficial throughout the COVID-19 [17-19].
On contrary to other Yemeni studies [20-22], the objective of the present work is to focus on the
importance and some physical characteristics of Azithromycin and compare three brands available in
Yemeni pharmacies.

2. Materials & Methods

Reagents: All materials used in this study had a high degree of purity. Azithromycin (99.5%
purity) (Globella Pharma, India).
Instruments: Analytical balance (RADWAG, model AS 220.B, Poland), FTIR spectroscopy
(PerkinElmer L1600400 Spectrum Two, UK). Pharma test tablet hardness, diameter, thickness
(PTB511, Germany).

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2.1 Samples collection

Three variably popular brands of Azithromycin were collected from selected community
pharmacies (Aden, Yemen). Approximately 28 tablets of each brand were collected randomly for the
analysis. The information of samples was properly checked (Table 1).
TABLE (1)
Detailed information on analyzed Azithromycin samples
Mnf. Exp.
Brand Symbol Manufacture Strength
date date
500 mg
Yemeni (Shaphaco
Azicure D1 film-coated 2/2021 2/2024
Pharmaceutical Ind.)
tablets
500 mg
Yemeni (RFA
Azicine D2 film-coated 4/2021 4/2024
Pharmaceutical Ind.)
tablets
500 mg
Indian (Unique
Zithrocin D3 film-coated 11/2020 11/2023
Pharmaceutical Labs)
tablets

3. Results & Discussions

3.1 Weight variation

This experiment was used to measure the weight variation of the tablets. Based on the obtained
results, the weight of the tablets (Table 2) for D1 had ranged between 707.4 mg and 745.5 mg with the
deviation ranging between 0.45 and 2.64. D2 drug had minimum-maximum weight between 862.3 mg
to 872.8 mg where the deviation rang found between 0- 0.70. Lastly, for the D3 drug the weight
minimum was 957.7 mg and the maximum weight was 998.4 mg with a deviation of 0.29- 2.65. The
result revealed that the tablets were uniform to each other and according to the results of the
experiment. Not exceeding the accepted limit of weight variation ±5, the tablet is identical to each
other [23]. The difference in the mean weights of all brands may be because of different excipients
used in the different brands.

3.2 Thickness
Based on the obtained results (Table 3), the thickness of D1 tablets ranged between 5.75 mm to
5.93 mm whereas the deviation felt between 0.2 to 1.02. The tablets of the D2 sample (5.56-5.80 mm)
had 0.58 to 2.78 deviation, while 0.10 to 1.20 variation for D3 drug with the thickness mean equals
5.306 mm. Thus, the thickness of the three brand tablets can be uninformed as they differ very little
from each other and each tablet is indistinguishable. In relation to Indian Pharmacopoeia, general tablet
thickness is controlled within 5% of a standard value where all the three brands of tablet Azithromycin
were found to be within their permissible limit (±5%) [24].
3.3 Diameter

Based on the results obtained, the diameter of the tablets is shown in Table 4. Whereas The variation
deviation ranges between 0.20-1.86 for D1, 0.10- 0.38 for D2, and 0- 0.34 for D3. The deviation of an
individual unit from the diameter mean ensured to not exceed ± 5% for tablets with a diameter of less
than 12.5 and ± 3% for a diameter of 12.5 mm or more where the results all the tablets have achieved

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percentage difference below than 3% which means that each tablet had obeyed the theoretical value of
standard diameter. By calculating the deviation of diameter, the uniformity of diameter of the tablets
can be proven. The results we obtained showed that all the tablets have achieved a percentage
difference below 3% which means that each tablet had obeyed the theoretical value of standard
diameter. [24,25].

3.4 Hardness
The results obtained in Table 5 proved that one tablet will have its hardness which is it might be
the same or different from other tablets. The coated tablets were generally more difficult to pulverize.
Commonly, the hardness of the individual tablet will be slightly different compared to others. Tablets
that have hardness more than 50 Newton (N) are generally considered acceptable. The hardness
average of D1, D2, and D3 was 152.9, 304.9, and 251.3 N, respectively which means this force is
needed to break a tablet. The hardness of studied brands is considered difficult to crush and it is not
fragile. [26-28].
TABLE (2)
Weight variation (n=10)

Weight, (mg)
Brand
Tablet No. 1 2 3 4 5 6 7 8 9 10
W (mg) 742.4 721.1 722.6 729.6 707.4 745.5 720.4 713.1 730.4 730.2
Mean ± SD = 726.3 ± 12.5
D1
Mean ± 726.3± 726.3± 726.3± 726.3± 726.3± 726.3± 726.3± 726.3± 726.3± 726.3
Deviation 2.2 0.70 0.50 0.45 2.60 2.64 0.81 1.81 0.56 ±0.53
W (mg) 862.3 871.7 866 866.5 872.8 870.7 867.5 868.4 871.1 867.0
Mean ± SD = 868.4 ± 3.203
D2
Mean ± 868.4 868.4± 868.4± 868.4± 868.4± 868.4± 868.4± 868.4± 868.4± 868.4 ±
Deviation ± 0.70 0.38 0.27 0.27 0.50 0.20 0.10 0 0.20 0.16
W (mg) 961.2 980.0 969.7 964.5 957.7 965.1 963.2 985.5 998.4 980.4
Mean ± SD = 972.6 ± 12.98
D3
Mean ± 972.6± 972.6± 972.6± 972.6± 972.6± 972.6± 972.6± 972.6± 972.6± 972.6
Deviation 1.17 0.76 0.29 0.83 1.50 0.77 0.96 1.32 2.65 ±0.80

TABLE (3)
The thickness of drug samples (n=6)

Thickness, (mm)
Brand
Tablet No. 1 2 3 4 5 6
T (mm) 5.90 5.83 5.75 5.90 5.93 5.91
D1 Mean ± SD = 5.87 ± 0.067
Mean ± Deviation 5.87±0.51 5.87±0.68 5.87±0.20 5.87±0.51 5.87±1.02 5.87±0.68
T (mm) 5.80 5.75 5.58 5.56 5.56 5.61
D2 Mean ± SD = 5.64 ± 0.104
Mean ± Deviation 5.64±2.78 5.64±1.89 5.64±1.11 5.64±1.47 5.64±1.47 5.64±0.58
T (mm) 5.31 5.27 5.30 5.37 5.26 5.33
D3 Mean ± SD = 5.306± 0.040
Mean ± Deviation 5.31±0.75 5.31±0.67 5.31±0.10 5.31±1.20 5.31±0.86 5.306±0.45

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TABLE (4)
Diameter values (n=6)

Diameter, (mm)
Brand
Tablet No. 1 2 3 4 5 6
D (mm) 9.45 9.39 9.24 9.48 9.43 9.46
D1 Mean ± SD = 9.408 ± 0.0879
Mean ± Deviation 9.408±0.46 9.408±0.20 9.408±1.86 9.408±0.79 9.408±0.24 9.408±0.57
D (mm) 8.20 8.18 8.15 8.16 8.18 8.14
D2 Mean ± SD = 8.168 ± 0.022
Mean ± Deviation 8.168±0.38 8.16±0.14 8.168±0.22 8.168±0.10 8.168±0.14 8.168±0.34
D (mm) 20.27 20.18 20.26 20.28 20.25 20.28
D3 Mean ± SD = 20.25 ± 0.0014
Mean ± Deviation 20.25±0.098 20.25±0.34 20.25±0.049 20.25±0.14 20.25±0 20.25±0.14

TABLE (5)
Results of hardness test (n=6)
Hardness, (N)
Brand
Tablet No. 1 2 3 4 5 6
H (N) 122.3 120.5 292.0 115.6 143.8 123.0
D1 Mean ± SD = 152.86 ± 68.85
Mean ± Deviation 152.86±19.9 152.86±21.3 152.86±91 152.86±24.3 152.86±6.45 152.86±19.5
H (N) 304.8 304.8 304.9 304.7 304.9 304.9
D2 Mean ± SD = 304.89 ± 0.081
Mean ± Deviation 304.8±0.03 304.9±0.03 304.9±0.0 304.9±0.065 304.9±0.0 304.8±0.0
H (N) 251.0 290.1 226.1 238.4 266.6 235.8
D3 Mean ± SD = 251.33± 23.58
Mean ± Deviation 251.33±0.13 251.3±15.4 251.3±10 251.3±5.14 251.3±6.07 251.3±6.17

3.5 Disintegration test

Table 6 implied that D2 and D3 brands have good values disintegration according to USP [29]
where the allowed range for film-coated tablets is between 5-30 min. On the other hand, Azithromycin
tablets labeled D1 brand did not have a standard disintegration value.

TABLE (6)
Disintegration values
Brand Final time
D1 1.30 min
D2 9.59 min
D3 20.9 min

3.6 FTIR peak of Azithromycin

The IR spectra for Azithromycin (Figures 2-5 and Table7) showed bands at 3560-3561 cm−1
represented -OH group. Wavenumbers 2972 -2971 cm−1 and 1376.89 cm−1 related to the axial

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stretching and bending of C-H of the methyl groups. The axial stretching of the C=O was observed at
1720 cm−1.
The value ~ 1188 cm−1 was appeared due to the absorption associated with the axial stretching of
C-O as R-O-R. Another important band in the spectrum was at 1081 cm−1 related to the axial stretching
and bending of C-N [30]. The spectra showed the three brands are pure and identical.

(2) Figure
FTIR spectrum of Azithromycin – (Pure)

Figure (3)
FTIR spectrum of Azithromycin - D1

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Figure (4)
FTIR spectrum of Azithromycin – D2

Figure (5)
FTIR spectrum of Azithromycin – D3

TABLE (7)
A comparison of FTIR peaks of Azithromycin
Pure-Observed D1-Observed D2-Observed D3- Observed
Reported Functional
peak in drug peak in drug peak in drug peak in drug
peak(cm-1) group
(cm-1) (cm-1) (cm-1) (cm-1)
3560.73 3560.16 3560.83 3560.53 3500-3700 -OH
2972.04 2971.69 2971.86 2971.80 2800-3200 -CH3
1720.61 1720.50 1720.57 1720.64 1705-1725 -C=O
1187.85 1188.03 1187.88 1187.91 1000-1300 R-O-R
1082.32 1082.33 1082.57 1081.89 1000-1350 -C-N

4. Conclusions
This research objected to characterizing three drug brands (i.e. Azicure, Azicine, and Zithrocin).
This research has provided quantitative evidence of the quality in recognized Yemeni markets of the

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randomly selected Azithromycin tablets (500mg). The drugs and excipients compatibility was carried
out by FT-IR studies. Whereas weight variation of tablets is important in process control evaluation of
tablets which is a valid indication of the corresponding variation in the drug content. The specification
of this weight variation test is given in pharmacopeias. All three brands of Azithromycin tablets passed
the weight variation uniformity, thickness, and diameter tests as specified in the pharmacopeia
according to which the acceptable limit for the deviation of weight for tablets averages does not exceed
5%. Regarding the results, average hardness for each brand was considered acceptable but the standard
deviation for D1 and D3 were largely supposed to be a little deviation. The standard disintegration
time for a film-coated tablet usually varies to 30 minutes. Results indicate that all three brands comply
with this limit where the time of Disintegration for D1, D2, and D3 brands was found to be within their
permissible limit. However, the D1 has a disintegration time lower than them and it has been assumed
that the D1 brand has uncoated tablets.

Conflict of Interest:
The authors declare that there are no conflicts of interest.

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