HomeSearch by AntimicrobialGentamicin (Gentamycin, Garamycin)
Antimicrobial Name: Gentamicin (Gentamycin, Garamycin)
CAS Number: 1403-66-3
Type of Antibiotic: Aminoglycosides
Origin: Fermentation
Functional Category: Antibiotic
Molecular Weight: 477.596
Mechanism of Action: Aminoglycosides like gentamicin “irreversibly” bind to specific 30S-subunit proteins and 16S rRNA. Specifically gentamicin binds to four nucleotides of 16S rRNA and a single amino acid of protein S12. This interferes with decoding site in the vicinity of nucleotide 1400 in 16S rRNA of 30S subunit. This region interacts with the wobble base in the anticodon of tRNA. This leads to interference with the initiation complex, misreading of mRNA so incorrect amino acids are inserted into the polypeptide leading to nonfunctional or toxic peptides and the breakup of polysomes into nonfunctional monosomes.
Chemical Formula:

C21H43N5O7

Solubility:

Freely sol in water; sol in pyridine, DMF, in acidic media with salt formation; moderately sol in methanol, ethanol, acetone. Practically insol in benzene, halogenated hydrocarbons.

Melting point:

102 - 108 °C

Resistance Genes:

aac2i: Aminoglycoside N-acetyltransferase, which modifies aminoglycosides by acetylation.

aac2ia: Aminoglycoside N-acetyltransferase, which modifies aminoglycosides by acetylation.

aac2ib: Aminoglycoside N-acetyltransferase, which modifies aminoglycosides by acetylation.

aac2ic: Aminoglycoside N-acetyltransferase, which modifies aminoglycosides by acetylation.

aac2id: Aminoglycoside N-acetyltransferase, which modifies aminoglycosides by acetylation.

aac3ia: Aminoglycoside N-acetyltransferase, which modifies aminoglycosides by acetylation.

aac3iia: Aminoglycoside N-acetyltransferase, which modifies aminoglycosides by acetylation.

aac3iib:Aminoglycoside N-acetyltransferase, which modifies aminoglycosides by acetylation.

aac3iii: Aminoglycoside N-acetyltransferase, which modifies aminoglycosides by acetylation.

aac3iv: Aminoglycoside N-acetyltransferase, which modifies aminoglycosides by acetylation.

aac3vi: Aminoglycoside N-acetyltransferase, which modifies aminoglycosides by acetylation.

aac6iia: Aminoglycoside N-acetyltransferase, which modifies aminoglycosides by acetylation.

aac6iib: Aminoglycoside N-acetyltransferase, which modifies aminoglycosides by acetylation.

ant2ia: Aminoglycoside O-nucleotidylyltransferase, which modifies aminoglycosides by adenylylation.

ant2ib: Aminoglycoside O-nucleotidylyltransferase, which modifies aminoglycosides by adenylylation.

Comments:

Gentamicin (Gentamycin, Garamycin) is an aminoglycoside antibiotic, used to treat many types of bacterial infections, particularly those caused by Gram-negative organisms.