Arbekacin

HCID 68682CAS 51025-85-5
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Grundinformationen

Standard-SMILES
NCC[C@H](O)C(=O)N[C@@H]1C[C@H](N)[C@@H](O[C@H]2O[C@H](CN)CC[C@H]2N)[C@H](O)[C@H]1O[C@H]1O[C@H](CO)[C@@H](O)[C@H](N)[C@H]1O
InChIKey
MKKYBZZTJQGVCD-XTCKQBCOSA-N
Summenformel
C22H44N6O10
Durchschnittliche Molmasse
552,6 g/mol
Monoisotopische Masse
552,31189161

Überblick

Arbekacin is a kanamycin that is kanamycin B bearing an N-(2S)-4-amino-2-hydroxybutyryl group on the aminocyclitol ring. It has a role as an antimicrobial agent, an antibacterial agent, an antibacterial drug and a protein synthesis inhibitor. It is a member of kanamycins and an aminoglycoside. It is functionally related to a kanamycin B.

Namen und Bezeichner

Bevorzugter Name
Arbekacin
IUPAC
(2S)-4-amino-N-[(1R,2S,3S,4R,5S)-5-amino-4-[(2R,3R,6S)-3-amino-6-(aminomethyl)oxan-2-yl]oxy-2-[(2S,3R,4S,5S,6R)-4-amino-3,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-3-hydroxycyclohexyl]-2-hydroxybutanamide
Englischer Name
Arbekacin
Summenformel
C22H44N6O10
Molmasse
552.62

Namen und Synonyme

Arbekacin51025-85-5ArbekacinaHaberacinArbekacineArbekacinumG7V6SLI20LME1100ME-1100(2S)-4-amino-N-[(1R,2S,3S,4R,5S)-5-amino-4-[(2R,3R,6S)-3-amino-6-(aminomethyl)oxan-2-yl]oxy-2-[(2S,3R,4S,5S,6R)-4-amino-3,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-3-hydroxycyclohexyl]-2-hydroxybutanamideNPC-14DTXSID8048319
Weitere Namen anzeigen
1665RBAHB-DKBAHB[1KBHABA-DKBhabekacinDecontasinBlubatosineArbekacin USP/EP/BP
CHEBI:37922(2S)-4-amino-N-[(1R,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,6S)-3-amino-6-(aminomethyl)oxan-2-yl]oxy}-3-hydroxycyclohexyl]-2-hydroxybutanamide(2S)-4-amino-N-((1R,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,6S)-3-amino-6-(aminomethyl)oxan-2-yl)oxy)-3-hydroxycyclohexyl)-2-hydroxybutanamide(2S)-4-amino-N-((1R,2S,3S,4R,5S)-5-amino-4-((2R,3R,6S)-3-amino-6-(aminomethyl)oxan-2-yl)oxy-2-((2S,3R,4S,5S,6R)-4-amino-3,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl)oxy-3-hydroxycyclohexyl)-2-hydroxybutanamideRefChem:113718DTXCID00282944-amino-2-hydroxybutylyldibekacinJ01GB12

Datenbank-Bezeichner

CAS
51025-85-5
PubChem CID
68682
DTXSID
DTXSID8048319
ChEMBL
CHEMBL426926
ChEBI
CHEBI:37922
UNII
G7V6SLI20L
Nikkaji
J33.173B

Eigenschaften

Berechnete Struktureigenschaften

XLogP
-6,8
Polarare Oberfläche (TPSA)
297 Ų
H-Brücken-Donoren
11
H-Brücken-Akzeptoren
15
Frei drehbare Bindungen
10
Schwere Atome
38

Experimentelle und physikochemische Eigenschaften

DrugsPharmaceuticals -> Listed in ZINC15
Solubility4.10e+01 g/L
Melting Point178 °C
Physical DescriptionSolid

Physikochemische Eigenschaften

Siedepunkt
904 · 904.0±65.0 °C(Predicted)
Dichte
1.47 · 1.47±0.1 g/cm3(Predicted)
pka
13.07 · 13.07±0.70(Predicted)
CAS Datenbank
51025 · 51025-85-5(CAS DataBase Reference)

Sicherheit und Regulatorisches

Toxikologische Informationen

Drug Induced Liver Injury · 4 Einträge

Drug-Induced Liver Injury Severity and Toxicity (DILIst)

Arbekacin

DILI Positive

DOI:10.1016/j.drudis.2019.09.022

Chemie und Industrie

Pharmakologische Informationen

ATC Code · 2 Einträge

J - Antiinfectives for systemic use

QJ - Antiinfectives for systemic use

Protein Binding3-12%
Pharmacodynamics · 1 Eintrag

Arbekacin is an aminoglycoside. Aminoglycosides function by binding to bacterial 30S ribosomal subunits, causing t-RNA misreads, and preventing the production of proteins. Anaerobes are less susceptible to aminoglycosides because they do not spend as much energy as aerobes on taking up chemicals like aminoglycosides. Aminoglycosides are useful primarily in infections involving aerobic, gram-negative bacteria, such as Pseudomonas, Acinetobacter, and Enterobacter.

Mechanism of Action · 1 Eintrag

Arbekacin irreversibly binds bacterial 30S and 16S ribosomal subunits inhibiting protein synthesis. Arbekacin binds to 4 nucleotides of the 16S subunit and 1 amino acid of protein S12 to interfere with the decoding site around nucleotide 1400 in the 16S subunit. Interference with the decoding site interferes with its interaction with the wobble base of tRNA. This hindered interaction causes mRNA to be misread and the incorrect amino acids are inserted into protein. These error filled proteins are not able to function or may even be toxic.

Biological Half-Life3 hours
MeSH Pharmacological ClassificationSubstances that inhibit the growth or reproduction of BACTERIA.
Anwendungen · 1 Eintrag

BeschreibungArbekacin is a semi-synthetic derivative of dibekacin useful in the treatment of bacterial infections. This aminoglycoside is active against a broad spectrum of bacteria, including some of the gentamycin-, kanamycin-, and tobramycin-resistant pathogens. Compared to amikacin and dibekacin, ototoxicity is reportedly milder.

Vor- und nachgelagerte Produkte

Anbieter32 Anbieter

北京华美互利生物化工010-56205725 · [email protected]
China Kouting Group Limited+86 (21) 5811-6473 5811-6475 · [email protected]
深圳市恩赞生物医药有限公司0755-25325458 13602565027 · [email protected]
杭州璟皓生物科技有限公司（原河南辛迪加生物）17513242016 · [email protected]
重庆乾泰医药研究院有限公司17864179792 · [email protected]

Ergänzende Hinweise

DefinitionChEBI: A kanamycin that is kanamycin B bearing an N-(2S)-4-amino-2-hydroxybutyryl group on the aminocyclitol ring.

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