アルベカシン
Wikipedia preview
出典(authority):フリー百科事典『ウィキペディア（Wikipedia）』「2014/01/20 16:31:46」(JST)
[Wiki en表示]
Arbekacin
|
| Systematic (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 |
| Clinical data |
| AHFS/Drugs.com |
International Drug Names |
| Legal status |
℞ Prescription only |
| Routes |
Intramuscular, intravenous |
| Pharmacokinetic data |
| Metabolism |
minimal |
| Excretion |
Renal |
| Identifiers |
| CAS number |
51025-85-5 Y |
| ATC code |
J01GB12 |
| PubChem |
CID 11398765 |
| DrugBank |
DB06696 |
| ChemSpider |
9573665 Y |
| UNII |
G7V6SLI20L Y |
| KEGG |
D07462 Y |
| ChEMBL |
CHEMBL233430 Y |
| Chemical data |
| Formula |
C22H44N6O10 |
| Mol. mass |
552.62 g/mol |
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 Y
Key:MKKYBZZTJQGVCD-JLZDOWJMSA-N Y
|
| Y (what is this?) (verify) |
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).[1][2] Arbekacin was originally synthesized from dibekacin in 1973. It has been registered and marketed in Japan since 1990 under the trade name Habekacin.[3] Arbekacin is no longer covered by patent and generic versions of the drug are also available under such trade names as Decontasin and Blubatosine.
Contents
- 1 Pharmacology
- 1.1 Pharmacodynamics
- 1.2 Mechanism of action
- 1.3 Absorption
- 1.4 Toxicity
- 2 References
Pharmacology[edit]
Arbekacin is used for the short term treatment of multi-resistant bacterial infections, such as methicillin-resistant Staphylococcus aureus (MRSA).
Pharmacodynamics[edit]
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[edit]
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[edit]
Aminoglycosides are not well absorbed from the gastrointestinal tract. Their absorption is markedly improved by parenteral administration.
Toxicity[edit]
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[edit]
Enteric bacteria and other eubacteria
References[edit]
- ^ 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.
- ^ 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.
- ^ 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.
|
Antibacterials: protein synthesis inhibitors (J01A, J01B, J01F, J01G, QJ01XQ)
|
|
| 30S |
Aminoglycosides
(initiation inhibitors) |
| -mycin (Streptomyces) |
- Streptomycin#
- Dihydrostreptomycin
- Neomycin#
- Framycetin
- Paromomycin
- Ribostamycin
- Kanamycin#
- Amikacin
- Arbekacin
- Bekanamycin
- Dibekacin
- Tobramycin
- Spectinomycin#
- Hygromycin B
|
|
| -micin (Micromonospora) |
- Gentamicin#
- Netilmicin
- Sisomicin
- Isepamicin
|
|
|
Tetracycline antibiotics
(tRNA binding) |
| Tetracyclines |
- Doxycycline#
- Chlortetracycline
- Clomocycline
- Demeclocycline
- Lymecycline
- Meclocycline
- Metacycline
- Minocycline
- Oxytetracycline
- Penimepicycline
- Rolitetracycline
- Tetracycline
|
|
| Glycylcyclines |
|
|
|
|
| 50S |
Oxazolidinone
(initiation inhibitors) |
- Eperezolid
- Linezolid
- Posizolid
- Radezolid
- Ranbezolid
- Sutezolid
- Tedizolid
|
|
| Peptidyl transferase |
| Amphenicols |
- Chloramphenicol#
- Azidamfenicol
- Thiamphenicol
- Florfenicol
|
|
| Pleuromutilins |
- Retapamulin
- Tiamulin
- Valnemulin
|
|
|
| MLS (transpeptidation/translocation) |
| Macrolides |
- Azithromycin#
- Clarithromycin
- Dirithromycin
- Erythromycin#
- Flurithromycin
- Josamycin
- Midecamycin
- Miocamycin
- Oleandomycin
- Rokitamycin
- Roxithromycin
- Spiramycin
- Troleandomycin
- Tylosin
- Ketolides
- Telithromycin
- Cethromycin
- Solithromycin†
|
|
| Lincosamides |
- Clindamycin#
- Lincomycin
- Pirlimycin
|
|
| Streptogramins |
- Pristinamycin
- Quinupristin/dalfopristin
- Virginiamycin
|
|
|
|
| EF-G |
|
|
- #WHO-EM
- ‡Withdrawn from market
- Clinical trials:
- †Phase III
- §Never to phase III
|
|
|
gr+f/gr+a (t)/gr-p (c)/gr-o
|
drug (J1p, w, n, m, vacc)
|
|
|
|
English Journal
- In Vitro Combination Effects of Aztreonam and Aminoglycoside against Multidrug-Resistant Pseudomonas aeruginosa in Japan.
- Araoka H, Baba M, Tateda K, Ishii Y, Oguri T, Okuzumi K, Oishi T, Mori S, Mitsuda T, Moriya K, Nakamori Y, Ohmagari N, Yamaguchi K, Yoneyama A; ABX Combination Therapy Study Group.SourceDepartment of Infectious Diseases, Toranomon Hospital, Tokyo 105-8470, Japan.
- Japanese journal of infectious diseases.Jpn J Infect Dis.2012 Jan;65(1):84-7.
- The aim of this study was to evaluate the in vitro combination effects of aztreonam (AZT) and aminoglycosides against multidrug-resistant (MDR) Pseudomonas aeruginosa strains in Japan. We investigated 47 MDR P. aeruginosa strains collected from 8 facilities. We selected the aminoglycosides amikac
- PMID 22274165
- Clinical efficacy of arbekacin for Gram-negative bacteria.
- Hamada Y, Tamura K, Koyama I, Kuroyama M, Yago K, Sunakawa K.SourceDepartment of Pharmacy, Kitasato East University Hospital, 2-1-1, Asamizodai, Minami-ku, Sagamihara, Kanagawa 252-0380, Japan. yuki@kitasato-u.ac.jp
- Journal of infection and chemotherapy : official journal of the Japan Society of Chemotherapy.J Infect Chemother.2011 Dec;17(6):876-9. Epub 2011 Jun 11.
- In an analysis of methicillin-resistant Staphylococcus aureus (MRSA) infected patients treated with arbekacin (ABK) only, Gram-negative bacteria (GNB) that were inhibited by low minimal inhibitory concentrations (MICs) of amikacin (AMK) or gentamycin (GM) were eradicated by the end of the ABK treatm
- PMID 21667069
Japanese Journal
- Aranorosin circumvents arbekacin-resistance in MRSA by inhibiting the bifunctional enzyme AAC(6')/APH(2")
- SUGA Takuya,ISHII Takahiro,IWATSUKI Masato,YAMAMOTO Tsuyoshi,NONAKA Kenichi,MASUMA Rokuro,MATSUI Hidehito,HANAKI Hideaki,OMURA Satoshi,SHIOMI Kazuro
- Journal of antibiotics 65(10), 527-529, 2012-10-25
- NAID 10031121426
- Cmax/MICからみたアルベカシンの有効性に関する検討
- 木村 匡男,山岸 由佳,川澄 紀代 [他]
- The Japanese journal of antibiotics 65(4), 263-269, 2012-08-00
- NAID 40019417642
- Evaluation of arbekacin anti-MRSA agents for adult in Japan
- HAMADA YUKIHIRO,TAMURA KAZUYOSHI,KOYAMA IKUMI [他]
- The Japanese journal of antibiotics 65(4), 221-234, 2012-08-00
- NAID 40019417607
Related Links
- アルベカシン（日局アルベカシン硫酸塩、Arbekacin, ABK）は、アミノグリコシド系抗生 物質の一つである。硫酸塩（硫酸アルベカシン）が明治製菓より「ハベカシン®」という 商品名で上市されているほか、後発品にデコンタシン®、ブルバトシン®などがある。
- 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 ...
Related Pictures
★リンクテーブル★
[★]
- 英
- arbekacin ABK
- 化
- 硫酸アルベカシン アルベカシン硫酸塩 arbekacin sulfate
- 商
- ハベカシン Habekacin
- 関
- ジベカシン、アミカシン、アミノグリコシド系抗菌薬
[★]
アルベカシン arbekacin
[★]
- 関
- arbekacin