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Arbekacin

Clinical data
AHFS/Drugs.com	International Drug Names
Routes of administration	Intramuscular, intravenous
ATC code	J01GB12 (WHO)
Legal status
Legal status	In general: ℞ (Prescription only)
Pharmacokinetic data
Metabolism	minimal
Excretion	Renal
Identifiers
IUPAC name (2S)-4-amino-N-oxy}-4-{oxy}-3-hydroxycyclohexyl]-2-hydroxybutanamide
CAS Number	51025-85-5
PubChem CID	11398765
DrugBank	DB06696
ChemSpider	9573665
UNII	G7V6SLI20L
KEGG	D07462
ChEMBL	ChEMBL233430
CompTox Dashboard (EPA)	DTXSID8048319
Chemical and physical data
Formula	C22H44N6O10
Molar mass	552.62 g/mol g·mol
3D model (JSmol)	Interactive image
SMILES O=C(N3(O1O((O)(N)1O)CO)(O)(O2O(CN)CC2N)(N)C3)(O)CCN
InChI InChI=1S/C22H44N6O10/c23-4-3-12(30)20(34)28-11-5-10(26)18(37-21-9(25)2-1-8(6-24)35-21)17(33)19(11)38-22-16(32)14(27)15(31)13(7-29)36-22/h8-19,21-22,29-33H,1-7,23-27H2,(H,28,34)/t8-,9+,10-,11+,12-,13+,14-,15+,16+,17+,18+,19-,21+,22+/m0/s1 Key:MKKYBZZTJQGVCD-JLZDOWJMSA-N
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Arbekacin (INN) is a semisynthetic aminoglycoside antibiotic. It is primarily used for the treatment of infections caused by multi-resistant bacteria including methicillin-resistant Staphylococcus aureus (MRSA). Arbekacin was originally synthesized from dibekacin in 1973. It has been registered and marketed in Japan since 1990 under the trade name Habekacin. Arbekacin is no longer covered by patent and generic versions of the drug are also available under such trade names as Decontasin and Blubatosine.

Pharmacology

Arbekacin is used for the short term treatment of multi-resistant bacterial infections, such as methicillin-resistant Staphylococcus aureus (MRSA).

Pharmacodynamics

Aminoglycosides, such as Arbekacin, work by binding to the bacterial 30S ribosomal subunit, causing misreading of t-RNA which consequently, leaves the bacterium unable to synthesize proteins vital to its growth. Energy is needed for aminoglycoside uptake into the bacterial cell. Anaerobes have less energy available for this uptake, so aminoglycosides are less active against anaerobes. Aminoglycosides are useful primarily in infections involving aerobic, gram-negative bacteria, such as Pseudomonas, Acinetobacter, and Enterobacter.

Mechanism of action

Aminoglycosides, such as 'Arbekacin, inhibit protein synthesis in susceptible bacteria by irreversibly binding to bacterial 30S and 16S ribosomal subunits. Specifically Arbekacin 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 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.

Absorption

Aminoglycosides are not well absorbed from the gastrointestinal tract. Their absorption is markedly improved by parenteral administration.

Toxicity

Ototoxicity and nephrotoxicity are the most serious adverse effects of aminoglycoside therapy and are more likely to occur in patients with a history of renal impairment or who are receiving other ototoxic and/or nephrotoxic drugs. Normal duration of IM or IV aminoglycoside therapy is 7-10 days. Although a longer duration may be necessary in some cases, toxicity is more likely to occur when aminoglycoside treatment is continued for longer than 10 days.

Affected organisms

Enteric bacteria and other eubacteria

References

1. Inoue, M., M. Nonoyama, R. Okamoto, T. Ida (1994). "Antimicrobial activity of arbekacin, a new aminoglycoside antibiotic, against methicilin-resistant Staphylococcus aureus". Drugs Exp Clin Res. 20 (6): 233–240. PMID 7758395.{{cite journal}}: CS1 maint: multiple names: authors list (link)
2. Cordeiro, J. C. R., Reis, A. O., Miranda, E. A., Sader, H. S., The Arbekacin Study Group (2001). "In vitro antimicrobial activity of the aminoglycoside arbekacin tested against oxacillin-resistant Staphylococcus aureus isolated in Brazilian hospitals". Brazilian J Infectious Diseases. 5 (3): 130–135. PMID 11506776.{{cite journal}}: CS1 maint: multiple names: authors list (link)
3. Kobayashi, Y., Uchida, H., Kawakami, Y. (1995). "Arbekacin". Intl J Antimicrobial Agents. 5 (4): 227–230. doi:10.1016/0924-8579(95)00014-Y. PMID 18611673.{{cite journal}}: CS1 maint: multiple names: authors list (link)

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