Amikacin

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Amikacin
Systematic (IUPAC) name
(2S)-4-amino-N-[(2S,3S,4R,5S)-5-amino-2- [(2S,3R,4S,5S,6R)-4-amino-3,5-dihydroxy- 6-(hydroxymethyl)oxan-2-yl]oxy-4-[(2R,3R, 4S,5R,6R)-6-(aminomethyl)-3,4,5-trihydroxy- oxan-2-yl]oxy-3-hydroxy-cyclohexyl]-2-hydroxy- butanamide
Identifiers
CAS number	37517-28-5
ATC code	D06AX12 J01GB06, S01AA21
PubChem	441188
DrugBank	APRD00550
Chemical data
Formula	C22H43N5O13
Mol. mass	585.603 g/mol
Pharmacokinetic data
Bioavailability	?
Protein binding	0-11%
Metabolism	?
Half life	2-3 hours
Excretion	Renal
Therapeutic considerations
Pregnancy cat.	D(AU) C(US)
Legal status	POM(UK) ℞-only(US)
Routes	Intramuscular, intravenous

Amikacin is an aminoglycoside antibiotic used to treat different types of bacterial infections. Amikacin works by binding to the bacterial 30S ribosomal subunit, causing misreading of mRNA and leaving the bacterium unable to synthesize proteins vital to its growth.

Contents 1 Administration 2 Uses 3 Resistance 4 Side effects 5 References

[edit] Administration

Amikacin may be administered once or twice a day but must be given by the intravenous or intramuscular route, which tends to be painful. There is no oral form available. Dosage must be adjusted in people with kidney failure.

[edit] Uses

Amikacin is most often used for treating severe, hospital-acquired infections with multidrug resistant Gram negative bacteria such as Pseudomonas aeruginosa, Acinetobacter, and Enterobacter.

Amikacin may be combined with a beta-lactam antibiotic for empiric therapy for people with neutropenia and fever.

[edit] Resistance

Amikacin has high resistance againt bacterial inactivation. It resists attacks by most bacterial inactivating enzymes, this is accomplished by the L-hydroxyaminobuteroyl amide (L-HABA) moiety attached to N-3 which inhibits acetylation, phosphorylation and adenylation in the distant amino sugar ring (C-2,C-3,C-4). Due to the fact that this is a very powerful anti-biotic. Its use is tightly regulated to prevent bacterial resistance developing.

[edit] Side effects

Side effects of amikacin are similar to other aminoglycosides. Kidney damage and hearing loss are the most important effects. Because of this potential, blood levels of the drug and markers of kidney function (creatinine) may be monitored.

[edit] References

• Edson RS, Terrell CL. The aminoglycosides. Mayo Clin Proc. 1999 May;74(5):519-28. Review. PMID 10319086

v • d • e Antibiotics and chemotherapeutics for dermatological use (D06) Antibiotics: tetracycline and derivatives Demeclocycline - Chlortetracycline - Oxytetracycline - Tetracycline Antibiotics: other Fusidic acid - Chloramphenicol - Neomycin - Bacitracin - Gentamicin - Tyrothricin - Mupirocin - Nadifloxacin - Virginiamycin - Rifaximin - Amikacin Chemotherapeutics: sulfonamides Silver sulfadiazine - Sulfathiazole - Mafenide - Sulfamethizole - Sulfanilamide - Sulfamerazine Chemotherapeutics: antivirals Idoxuridine - Tromantadine - Aciclovir - Podophyllotoxin - Inosine - Penciclovir - Lysozyme - Ibacitabine - Edoxudine - Imiquimod - Docosanol Chemotherapeutics: other Metronidazole

v • d • e Antibacterials for systemic use: aminoglycosides (J01G) -mycin (Streptomyces) Streptomycin • Neomycin (Framycetin, Paromomycin, Ribostamycin) • Kanamycin (Amikacin, Dibekacin, Tobramycin) • Hygromycin B • Spectinomycin -micin (Micromonospora) Gentamicin (Netilmicin, Sisomicin, Isepamicin) • Verdamicin