ANTIBIOTIKA

AMINOGLIKOSIDA
KIMIA FARMASI I
Aminoglycosides are a group of
antibiotics that are effective against:

Aminoglycoside
(AGL)

Aerobic gram( - )bacteria

Some mycobacteria
e.g.: pseudomonas,
e.g.:
Acinetobacter, Some gram ( + ) bacteria
bacteria that cause
enterobacter
tuberculosis
 Aminoglycoside
(AGL)

Stretomyces Micromonospora
Suffix -mycin Suffix -micin

Streptomycin Paromomycin Gentamicin Amikacin

Neomycin Tobramycin Netilmicin

Antibiotik Aminoglikosida
antibiotika dengan struktur kimia yang bervariasi , yang
mengandung:
• basa deoksistreptamin atau streptidin
• Gula amino: 3-aminoglukosa, 6-aminoglukosa, 2,6
diaminoglukosa, garosamin, D-glukosamin,L-N-
metilglukosamin, neosamin dan purpurosamin

• Bakterisid menghambat sintesis protein

• Spektrum sempit  gram negatif
• Turunan aminoglikosida adalah antibiotika dengan
spectrum luas
• FIG. 1.(A) Natural aminoglycoside antibiotics that target
the bacterial ribosomal decoding site. The natural
products are derived from 2-DOS by glycosidic
substitutions at positions 4 and 5 (paromomycin) or 4 and
6 (gentamicin). Gentamicin is a mixture of gentamicin C1
(R1 = R2 = CH3), gentamicin C1A (R1 = R2 = H), and
gentamicin C2 (R1 = CH3, R2 = H). (B) Secondary
structure of the bacterial decoding site (A-site) within 16S
rRNA. Residues that are involved in aminoglycoside
interactions are labeled. (C) Scaffolds that were designed
and studied as structural mimetics of the aminoglycoside
2-DOS core (2, 22, 28). 3,5-Diaminopiperidines are
described in this report. (D) Structure of DAPT
antibacterials (compounds designated by the number 1).
Compounds 1a to 1c contain at least one cis-3,5-diamino-
piperidinyl group.
Mekanisme Aksi &
Farmakokinetik:
• Mekanisme Aksi : Berikatan pada unit
ribosom (30S & 50S) pada bakteri dan
menghambat sintesis protein
• Farmakokinetik:
– Absorbsi lemah ; Pemberian intravena
& Injeksi Intramuscular lebih baik
– Distribusi: Hidrofilik, CFS buruk, Cross
plasenta
– Metabolisme: Excreted unchanged,
special dosing for renal failure
Drug Use

Streptomycin  Second-choice medications: for

(Streptomycin Sulfate ® ) tuberculosis (TB)
 streptococcal endocarditis (with B- lactam)

 enterococcal endocarditis ( with penicillins )

Paromomycin  Intestinal infections

Ttt of hepatic encephalopathy
( Humatin ®)
 Ttt of amebiasis

Neomycin  prophylaxis GI surgery

 prevention of hepatic encephalopathy &
( mycifrdish ®)
hypercholesterolemia

Tobramycin  Ttt of systemic infection

 respiratory tract infection
( Nebcin ®) , (Tobi®)
Ttt of systemic infection
Gentamicin
 life threatening infection
( garamycin ®)
 eye infection

Amikacin  Respiratory tract infection

 Skin infection
( Amikin ® )
 Urinary tract infection

 Blood, abdomen or bones infection

Netilmicin  septicemia
 Lower respiratory tract infection
( NETROMYCIN ®)
 Urinary tract infection

 peritonitis and endometritis

Tugas Kelompok
• Cari Golongan Aminoglycosida yang
beredar di Indonesia! (nama
dagang, zat aktif, sturktur kimia,
gambar produk, kegunaan)
 Identifikasi Neomycin
Beberapa milligram sampel dilarutkan dalam 1ml
air. 1 ml reagen ninhidrin (0.2% ninhidrin dalam
n-butanol) dan 0.5 ml pyridine ditambahkan dan
campuran dipanaskan dalam penangas air selama 5
menit. Warna ungu gelap dihasilkan.

Sebanyak 5mg sampel dilarutkan dalam 2ml asam

sulfat, larutannya tidak berwarna. Larutan akan
jernih ketika diencerkan dengan 3-4 volume air.
 Identifikasi Streptomisin
Beberapa milligram sampel dilarutkan dalam 5ml water,
1ml natrium hidroksida 1N ditambahkan, dan larutan
dipanaskan pada penangas air selama 3 menit.

Setelah larutan dingin, 2ml dari larutan ferri ammonium

sulfat 2% dalam asam sulfat 1N ditambahkan. Warna
merah keunguan mengindikasikan mengandung
streptomisin.