Arbekacin
Explore a selection of our essential drug information below, or:
Overview
- DrugBank ID
- DB06696
- Type
- Small Molecule
- Clinical Trials
- Phase 0
- 0
- Phase 1
- 4
- Phase 2
- 1
- Phase 3
- 0
- Phase 4
- 0
- Mechanism of Action
Identification
- Generic Name
- Arbekacin
- DrugBank Accession Number
- DB06696
- Background
An semisynthetic aminoglycoside antibiotic. Often used for treatment of multi-resistant bacterial infection such as methicillin-resistant Staphylococcus aureus (MRSA).
- Type
- Small Molecule
- Groups
- Experimental, Investigational
- Structure
- Weight
- Average: 552.619
Monoisotopic: 552.311891658 - Chemical Formula
- C22H44N6O10
- Synonyms
- ABK
- Arbekacin
- Arbekacina
- Arbekacine
- Arbekacinum
- Haberacin
- External IDs
- 1665-RB
- AHB-DBK
- HABA-Dibekacin
- HABA-DKB
- HBK
- ME-1100
- ME1100
Pharmacology
- Indication
Arbekacin is used for the short term treatment of multi-resistant bacterial infections, such as methicillin-resistant Staphylococcus aureus (MRSA).
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- Pharmacodynamics
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
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.
Target Actions Organism A30S ribosomal protein S12 inhibitorEscherichia coli (strain K12) - Absorption
Aminoglycosides are not well absorbed from the gastrointestinal tract. Their absorption is markedly improved by parenteral administration.
- Volume of distribution
Not Available
- Protein binding
3-12%
- Metabolism
- Not Available
- Route of elimination
Not Available
- Half-life
3 hours
- Clearance
Not Available
- Adverse Effects
- Improve decision support & research outcomesWith structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates. View sample adverse effects data in our new Data Library!Improve decision support & research outcomes with our structured adverse effects data.
- Toxicity
Patients with renal impairment or those taking ototoxic and nephrotoxic drugs are at the highest risk for ototoxicity and nephrotoxicity associated with aminoglycoside use. 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.
- Pathways
Pathway Category Arbekacin Action Pathway Drug action - Pharmacogenomic Effects/ADRs
- Not Available
Interactions
- Drug Interactions
- This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
Drug Interaction Integrate drug-drug
interactions in your softwareAbacavir Abacavir may decrease the excretion rate of Arbekacin which could result in a higher serum level. Aceclofenac Aceclofenac may decrease the excretion rate of Arbekacin which could result in a higher serum level. Acemetacin Acemetacin may decrease the excretion rate of Arbekacin which could result in a higher serum level. Acenocoumarol The risk or severity of bleeding can be increased when Arbekacin is combined with Acenocoumarol. Acetaminophen Acetaminophen may decrease the excretion rate of Arbekacin which could result in a higher serum level. - Food Interactions
- Not Available
Products
- Drug product information from 10+ global regionsOur datasets provide approved product information including:dosage, form, labeller, route of administration, and marketing period.Access drug product information from over 10 global regions.
- Product Ingredients
Ingredient UNII CAS InChI Key Arbekacin sulfate G7395HZ992 104931-87-5 UTUVRPOLEMRKQC-XDJMXTNXSA-N
Categories
- ATC Codes
- J01GB12 — Arbekacin
- Drug Categories
- Agents that produce neuromuscular block (indirect)
- Aminoglycoside Antibacterials
- Anti-Bacterial Agents
- Anti-Infective Agents
- Antibacterials for Systemic Use
- Antiinfectives for Systemic Use
- Carbohydrates
- Drugs that are Mainly Renally Excreted
- Drugs that are Mainly Renally Excreted with a Narrow Therapeutic Index
- Glycosides
- Narrow Therapeutic Index Drugs
- Nephrotoxic agents
- Chemical TaxonomyProvided by Classyfire
- Description
- This compound belongs to the class of organic compounds known as 4,6-disubstituted 2-deoxystreptamines. These are 2-deoxystreptamine aminoglycosides that a glycosidically linked to a pyranose of furanose unit at the C4- and C6-positions.
- Kingdom
- Organic compounds
- Super Class
- Organic oxygen compounds
- Class
- Organooxygen compounds
- Sub Class
- Carbohydrates and carbohydrate conjugates
- Direct Parent
- 4,6-disubstituted 2-deoxystreptamines
- Alternative Parents
- O-glycosyl compounds / Aminocyclitols and derivatives / Cyclohexanols / Cyclohexylamines / Oxanes / Monosaccharides / 1,3-aminoalcohols / 1,2-aminoalcohols / Propargyl-type 1,3-dipolar organic compounds / Acetals show 6 more
- Substituents
- 1,2-aminoalcohol / 1,3-aminoalcohol / 4,6-disubstituted 2-deoxystreptamine / Acetal / Alcohol / Aliphatic heteromonocyclic compound / Amine / Aminocyclitol or derivatives / Carboximidic acid / Carboximidic acid derivative show 20 more
- Molecular Framework
- Aliphatic heteromonocyclic compounds
- External Descriptors
- aminoglycoside, kanamycins (CHEBI:37922)
- Affected organisms
- Enteric bacteria and other eubacteria
- Escherichia coli
- Staphylococcus aureus
- Acinetobacter
Chemical Identifiers
- UNII
- G7V6SLI20L
- CAS number
- 51025-85-5
- InChI Key
- MKKYBZZTJQGVCD-XTCKQBCOSA-N
- 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
- IUPAC Name
- (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
- 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
References
- Synthesis Reference
Shinichi Kondo, Seiji Shibahara, Takayuki Usui, Toshiaki Kudo, Shuichi Gomi, Atsushi Tamura, Yoko Ikeda, Daishiro Ikeda, Tomio Takeuchi, "Dibekacin derivatives and arbekacin derivatives active against resistant bacteria, and the production thereof." U.S. Patent US5618795, issued October, 1989.
US5618795- General References
- Inoue M, Nonoyama M, Okamoto R, Ida T: Antimicrobial activity of arbekacin, a new aminoglycoside antibiotic, against methicillin-resistant Staphylococcus aureus. Drugs Exp Clin Res. 1994;20(6):233-9. [Article]
- Morikawa K, Nonaka M, Yoshikawa Y, Torii I: Synergistic effect of fosfomycin and arbekacin on a methicillin-resistant Staphylococcus aureus-induced biofilm in a rat model. Int J Antimicrob Agents. 2005 Jan;25(1):44-50. [Article]
- Doi Y, Yokoyama K, Yamane K, Wachino J, Shibata N, Yagi T, Shibayama K, Kato H, Arakawa Y: Plasmid-mediated 16S rRNA methylase in Serratia marcescens conferring high-level resistance to aminoglycosides. Antimicrob Agents Chemother. 2004 Feb;48(2):491-6. [Article]
- Antimicrobial agents and Chemotherapy [Link]
- External Links
- Human Metabolome Database
- HMDB0015642
- KEGG Drug
- D07462
- PubChem Compound
- 68682
- PubChem Substance
- 99443250
- ChemSpider
- 61936
- 26397
- ChEBI
- 37922
- ChEMBL
- CHEMBL426926
- ZINC
- ZINC000009575047
- PharmGKB
- PA165958370
- PDBe Ligand
- 84G
- Drugs.com
- Drugs.com Drug Page
- Wikipedia
- Arbekacin
- PDB Entries
- 6cgg / 8ifc / 8ife / 8q4f
Clinical Trials
- Clinical Trials
Clinical Trial & Rare Diseases Add-on Data Package
Explore 4,000+ rare diseases, orphan drugs & condition pairs, clinical trial why stopped data, & more. Preview package Phase Status Purpose Conditions Count Start Date Why Stopped 100+ additional columns Unlock 175K+ rows when you subscribe.View sample dataNot Available No Longer Available Not Available Infection Due to Resistant Organism 1 somestatus stop reason just information to hide 2 Unknown Status Treatment Duchenne Muscular Dystrophy (DMD) 1 somestatus stop reason just information to hide 1 Completed Treatment Bacterial Pneumonia 1 somestatus stop reason just information to hide 1 Completed Treatment Healthy Volunteers (HV) 2 somestatus stop reason just information to hide
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage Forms
- Not Available
- Prices
- Not Available
- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
Property Value Source melting point (°C) 178 Not Available - Predicted Properties
Property Value Source Water Solubility 41.0 mg/mL ALOGPS logP -2.9 ALOGPS logP -6.9 Chemaxon logS -1.1 ALOGPS pKa (Strongest Acidic) 12.49 Chemaxon pKa (Strongest Basic) 9.99 Chemaxon Physiological Charge 5 Chemaxon Hydrogen Acceptor Count 15 Chemaxon Hydrogen Donor Count 11 Chemaxon Polar Surface Area 297.27 Å2 Chemaxon Rotatable Bond Count 10 Chemaxon Refractivity 129.08 m3·mol-1 Chemaxon Polarizability 56.58 Å3 Chemaxon Number of Rings 3 Chemaxon Bioavailability 0 Chemaxon Rule of Five No Chemaxon Ghose Filter No Chemaxon Veber's Rule No Chemaxon MDDR-like Rule Yes Chemaxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption - 0.9365 Blood Brain Barrier - 0.9659 Caco-2 permeable - 0.7588 P-glycoprotein substrate Substrate 0.5786 P-glycoprotein inhibitor I Non-inhibitor 0.7254 P-glycoprotein inhibitor II Non-inhibitor 0.8424 Renal organic cation transporter Non-inhibitor 0.8676 CYP450 2C9 substrate Non-substrate 0.8204 CYP450 2D6 substrate Non-substrate 0.8289 CYP450 3A4 substrate Non-substrate 0.559 CYP450 1A2 substrate Non-inhibitor 0.933 CYP450 2C9 inhibitor Non-inhibitor 0.9392 CYP450 2D6 inhibitor Non-inhibitor 0.909 CYP450 2C19 inhibitor Non-inhibitor 0.9122 CYP450 3A4 inhibitor Non-inhibitor 0.9564 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.9002 Ames test Non AMES toxic 0.7048 Carcinogenicity Non-carcinogens 0.9617 Biodegradation Not ready biodegradable 0.6627 Rat acute toxicity 1.8593 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.9902 hERG inhibition (predictor II) Non-inhibitor 0.5444
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
- Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 248.0974632 predictedDarkChem Lite v0.1.0 [M-H]- 215.209 predictedDeepCCS 1.0 (2019) [M+H]+ 248.1856632 predictedDarkChem Lite v0.1.0 [M+H]+ 216.93271 predictedDeepCCS 1.0 (2019) [M+Na]+ 247.2710632 predictedDarkChem Lite v0.1.0 [M+Na]+ 223.26167 predictedDeepCCS 1.0 (2019)
Targets
- Kind
- Protein
- Organism
- Escherichia coli (strain K12)
- Pharmacological action
- Yes
- Actions
- Inhibitor
- General Function
- With S4 and S5 plays an important role in translational accuracy.
- Specific Function
- misfolded RNA binding
- Gene Name
- rpsL
- Uniprot ID
- P0A7S3
- Uniprot Name
- 30S ribosomal protein S12
- Molecular Weight
- 13736.995 Da
References
- Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [Article]
- Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [Article]
- Funatsu G, Yaguchi M, Wittmann-Liebold B: Primary stucture of protein S12 from the small Escherichia coli ribosomal subunit. FEBS Lett. 1977 Jan 15;73(1):12-7. [Article]
- Carter AP, Clemons WM, Brodersen DE, Morgan-Warren RJ, Wimberly BT, Ramakrishnan V: Functional insights from the structure of the 30S ribosomal subunit and its interactions with antibiotics. Nature. 2000 Sep 21;407(6802):340-8. [Article]
Drug created at May 05, 2010 16:31 / Updated at November 09, 2024 06:19