Arbekacin

HCID 68682CAS 51025-85-5
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기본 정보

표준 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
분자식
C22H44N6O10
평균 분자량
552.6 g/mol
단동위원소 질량
552.31189161

개요

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.

이름 및 식별자

우선 이름
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
영어명
Arbekacin
분자식
C22H44N6O10
분자량
552.62

이름 및 동의어

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
이름 더 보기
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

데이터베이스 식별자

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

물성

구조 계산 물성

XLogP
-6.8
극성 표면적
297 Ų
수소 결합 공여자 수
11
수소 결합 수용자 수
15
회전 가능 결합 수
10
무거운 원자 수
38

실험 및 물리화학적 성질

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

물리화학적 성질

끓는 점
904 · 904.0±65.0 °C(Predicted)
밀도
1.47 · 1.47±0.1 g/cm3(Predicted)
산도 계수 (pKa)
13.07 · 13.07±0.70(Predicted)

안전 및 규제

독성 정보

Drug Induced Liver Injury · 4건

Drug-Induced Liver Injury Severity and Toxicity (DILIst)

Arbekacin

DILI Positive

DOI:10.1016/j.drudis.2019.09.022

화학 및 산업

약리 정보

ATC Code · 2건

J - Antiinfectives for systemic use

QJ - Antiinfectives for systemic use

Protein Binding3-12%
Pharmacodynamics · 1건

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 · 1건

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.
응용 분야 · 1건

개요Arbekacin 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.

상·하류 제품 정보

공급사32 곳

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]

추가 설명

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

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