Arbekacin

Arbekacin
Clinical data
Trade names	Habekacin
AHFS/Drugs.com	International Drug Names
Routes of; administration	Intramuscular, intravenous
Drug class	Aminoglycoside antibiotic
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-[(1R,2S,3R,4R,5S)-5-amino-2-{[(2S,3R,4S,5S,6R)-4-amino-3,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-4-{[(2R,3R,6S)-3-amino-6-(aminomethyl)oxan-2-yl]oxy}-3-hydroxycyclohexyl]-2-hydroxybutanamide;
CAS Number	51025-85-5 ;
PubChem CID	11398765;
DrugBank	DB06696 ;
ChemSpider	9573665 ;
UNII	G7V6SLI20L;
KEGG	D07462 ;
ChEMBL	ChEMBL426926 ;
PDB ligand	84G (PDBe, RCSB PDB);
CompTox Dashboard (EPA)	DTXSID8048319 ;
Chemical and physical data
Formula	C22H44N6O10
Molar mass	552.626 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES O=C(N[C@H]3[C@H](O[C@H]1O[C@@H]([C@@H](O)[C@H](N)[C@H]1O)CO)[C@H](O)[C@H](O[C@H]2O[C@H](CN)CC[C@H]2N)[C@@H](N)C3)[C@@H](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 which was derived from kanamycin. It is primarily used for the treatment of infections caused by multi-resistant bacteria including methicillin-resistant Staphylococcus aureus (MRSA).^[1]^[2] Arbekacin was originally synthesized from dibekacin in 1973 by Hamao Umezawa and collaborators.^[3] It has been registered and marketed in Japan since 1990 under the trade name Habekacin.^[4] Arbekacin is no longer covered by patent and generic versions of the drug are also available under such trade names as Decontasin and Blubatosine.

^ Inoue M, Nonoyama M, Okamoto R, Ida T (1994). "Antimicrobial activity of arbekacin, a new aminoglycoside antibiotic, against methicillin-resistant Staphylococcus aureus". Drugs Under Experimental and Clinical Research. 20 (6): 233–239. PMID 7758395.
^ Cordeiro JC, Reis AO, Miranda EA, Sader HS (June 2001). "In vitro antimicrobial activity of the aminoglycoside arbekacin tested against oxacillin-resistant Staphylococcus aureus isolated in Brazilian hospitals". The Brazilian Journal of Infectious Diseases. 5 (3). The Arbekacin Study Group: 130–135. doi:10.1590/s1413-86702001000300005. PMID 11506776.
^ Kondo S, Iinuma K, Yamamoto H, Maeda K, Umezawa H (July 1973). "Letter: Syntheses of 1-n-(S)-4-amino-2-hydroxybutyryl)-kanamycin B and -3', 4'-dideoxykanamycin B active against kanamycin-resistant bacteria". The Journal of Antibiotics. 26 (7): 412–415. doi:10.7164/antibiotics.26.412. PMID 4782059.
^ Kobayashi Y, Uchida H, Kawakami Y (July 1995). "Arbekacin". International Journal of Antimicrobial Agents. 5 (4): 227–230. doi:10.1016/0924-8579(95)00014-Y. PMID 18611673.

[1] Inoue M, Nonoyama M, Okamoto R, Ida T (1994). "Antimicrobial activity of arbekacin, a new aminoglycoside antibiotic, against methicillin-resistant Staphylococcus aureus". Drugs Under Experimental and Clinical Research. 20 (6): 233–239. PMID 7758395.

[2] Cordeiro JC, Reis AO, Miranda EA, Sader HS (June 2001). "In vitro antimicrobial activity of the aminoglycoside arbekacin tested against oxacillin-resistant Staphylococcus aureus isolated in Brazilian hospitals". The Brazilian Journal of Infectious Diseases. 5 (3). The Arbekacin Study Group: 130–135. doi:10.1590/s1413-86702001000300005. PMID 11506776.

[3] Kondo S, Iinuma K, Yamamoto H, Maeda K, Umezawa H (July 1973). "Letter: Syntheses of 1-n-(S)-4-amino-2-hydroxybutyryl)-kanamycin B and -3', 4'-dideoxykanamycin B active against kanamycin-resistant bacteria". The Journal of Antibiotics. 26 (7): 412–415. doi:10.7164/antibiotics.26.412. PMID 4782059.

[4] Kobayashi Y, Uchida H, Kawakami Y (July 1995). "Arbekacin". International Journal of Antimicrobial Agents. 5 (4): 227–230. doi:10.1016/0924-8579(95)00014-Y. PMID 18611673.

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