Ribostamycin

Identification

Summary

Ribostamycin is a broad spectrum aminoglycoside antibiotic on the list of WHO critical antimicrobials for human medicine.

Generic Name
Ribostamycin
DrugBank Accession Number
DB03615
Background

Ribostamycin is an aminoglycoside antibiotic1 isolated from Streptomyces ribosidificus2 listed as one of the World Health Organization's critically important antimicrobials.3

Type
Small Molecule
Groups
Approved, Experimental
Structure
Thumb
Weight
Average: 454.4727
Monoisotopic: 454.227493328
Chemical Formula
C17H34N4O10
Synonyms
  • Ribostamicina
  • Ribostamycin
  • Ribostamycin A
  • Ribostamycine
  • Ribostamycinum
  • Vistamycin
External IDs
  • Antibiotic SF 733
  • Bu 1709
  • SF-733

Pharmacology

Indication

Not Available

Pharmacology
Reduce drug development failure rates
Build, train, & validate machine-learning models
with evidence-based and structured datasets.
See how
Build, train, & validate predictive machine-learning models with structured datasets.
See how
Contraindications & Blackbox Warnings
Contraindications
Avoid life-threatening adverse drug events
Improve clinical decision support with information on contraindications & blackbox warnings, population restrictions, harmful risks, & more.
Learn more
Avoid life-threatening adverse drug events & improve clinical decision support.
Learn more
Pharmacodynamics

Not Available

Mechanism of action

Aminoglycosides work by binding to the bacterial 30S ribosomal subunit (some work by binding to the 50S subunit), inhibiting the translocation of the peptidyl-tRNA from the A-site to the P-site and also causing misreading of mRNA, leaving the bacterium unable to synthesize proteins vital to its growth. However, their exact mechanism of action is not fully known.

TargetActionsOrganism
UAminoglycoside N(6')-acetyltransferase type 1Not AvailableSalmonella enteritidis
UAminoglycoside 2'-N-acetyltransferaseNot AvailableMycobacterium tuberculosis
UProtein disulfide-isomeraseNot AvailableHumans
U30S ribosomal protein S12Not AvailableEscherichia coli (strain K12)
Absorption

Not Available

Volume of distribution

Not Available

Protein binding

Not Available

Metabolism
Not Available
Route of elimination

Not Available

Half-life

Not Available

Clearance

Not Available

Adverse Effects
Adverseeffects
Improve decision support & research outcomes
With structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates.
Learn more
Improve decision support & research outcomes with our structured adverse effects data.
Learn more
Toxicity

Not Available

Pathways
Not Available
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.
DrugInteraction
AbacavirAbacavir may decrease the excretion rate of Ribostamycin which could result in a higher serum level.
AceclofenacAceclofenac may decrease the excretion rate of Ribostamycin which could result in a higher serum level.
AcemetacinAcemetacin may decrease the excretion rate of Ribostamycin which could result in a higher serum level.
AcenocoumarolThe risk or severity of bleeding can be increased when Ribostamycin is combined with Acenocoumarol.
AcetaminophenAcetaminophen may decrease the excretion rate of Ribostamycin which could result in a higher serum level.
AcetylcholineThe therapeutic efficacy of Acetylcholine can be decreased when used in combination with Ribostamycin.
AcetyldigitoxinThe risk or severity of adverse effects can be increased when Ribostamycin is combined with Acetyldigitoxin.
Acetylsalicylic acidAcetylsalicylic acid may decrease the excretion rate of Ribostamycin which could result in a higher serum level.
AclidiniumAclidinium may decrease the excretion rate of Ribostamycin which could result in a higher serum level.
AcrivastineAcrivastine may decrease the excretion rate of Ribostamycin which could result in a higher serum level.
Interactions
Identify potential medication risks
Easily compare up to 40 drugs with our drug interaction checker.
Get severity rating, description, and management advice.
Learn more
Food Interactions
Not Available

Products

Products2
Drug product information from 10+ global regions
Our datasets provide approved product information including:
dosage, form, labeller, route of administration, and marketing period.
Access now
Access drug product information from over 10 global regions.
Access now
Product Ingredients
IngredientUNIICASInChI Key
Ribostamycin sulfateQFN1QU7PEN53797-35-6RTCDDYYZMGGHOE-YMSVYGIHSA-N

Categories

ATC Codes
J01GB10 — Ribostamycin
Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as 4,5-disubstituted 2-deoxystreptamines. These are 2-deoxystreptamine aminoglycosides that a glycosidically linked to a pyranose of furanose unit at the C4- and C5-positions.
Kingdom
Organic compounds
Super Class
Organic oxygen compounds
Class
Organooxygen compounds
Sub Class
Carbohydrates and carbohydrate conjugates
Direct Parent
4,5-disubstituted 2-deoxystreptamines
Alternative Parents
O-glycosyl compounds / Aminocyclitols and derivatives / Cyclohexylamines / Cyclohexanols / Oxanes / Monosaccharides / Tetrahydrofurans / 1,2-aminoalcohols / Oxacyclic compounds / Acetals
show 4 more
Substituents
1,2-aminoalcohol / 4,5-disubstituted 2-deoxystreptamine / Acetal / Alcohol / Aliphatic heteromonocyclic compound / Amine / Aminocyclitol or derivatives / Cyclic alcohol / Cyclitol or derivatives / Cyclohexanol
show 16 more
Molecular Framework
Aliphatic heteromonocyclic compounds
External Descriptors
aminoglycoside antibiotic, amino cyclitol glycoside (CHEBI:45257)
Affected organisms
  • Humans and other mammals
  • Enteric bacteria and other eubacteria

Chemical Identifiers

UNII
2Q5JOU7T53
CAS number
25546-65-0
InChI Key
NSKGQURZWSPSBC-VVPCINPTSA-N
InChI
InChI=1S/C17H34N4O10/c18-2-6-10(24)12(26)8(21)16(28-6)30-14-5(20)1-4(19)9(23)15(14)31-17-13(27)11(25)7(3-22)29-17/h4-17,22-27H,1-3,18-21H2/t4-,5+,6-,7-,8-,9+,10-,11-,12-,13-,14-,15-,16-,17+/m1/s1
IUPAC Name
(2R,3S,4R,5R,6R)-5-amino-2-(aminomethyl)-6-{[(1R,2R,3S,4R,6S)-4,6-diamino-2-{[(2S,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]oxy}-3-hydroxycyclohexyl]oxy}oxane-3,4-diol
SMILES
[H][C@@]1(O[C@@H]2[C@@H](O)[C@H](N)C[C@H](N)[C@H]2O[C@H]2O[C@H](CN)[C@@H](O)[C@H](O)[C@H]2N)O[C@H](CO)[C@@H](O)[C@H]1O

References

Synthesis Reference

Eiichi Akita, Tsutomu Tsuchiya, Shinichi Kondo, Shuntaro Yasuda, Sumio Umezawa, Hamao Umezawa, "1-N-((S)-.alpha.-substituted-.omega.-aminoacyl)-neamine or -ribostamycin and the production thereof." U.S. Patent US4008218, issued February, 1974.

US4008218
General References
  1. Baud H, Betencourt A, Peyre M, Penasse L: Ribostamycin, as an intermediate in the biosynthesis of neomycin. J Antibiot (Tokyo). 1977 Sep;30(9):720-3. doi: 10.7164/antibiotics.30.720. [Article]
  2. Zachman-Brockmeyer TR, Thoden JB, Holden HM: The structure of RbmB from Streptomyces ribosidificus, an aminotransferase involved in the biosynthesis of ribostamycin. Protein Sci. 2017 Sep;26(9):1886-1892. doi: 10.1002/pro.3221. Epub 2017 Jul 23. [Article]
  3. WHO: Critically Important Antimicrobials for Human Medicine 6th Revision [Link]
KEGG Drug
D08478
KEGG Compound
C01759
PubChem Compound
33042
PubChem Substance
46505351
ChemSpider
30581
ChEBI
45257
ChEMBL
CHEMBL221572
ZINC
ZINC000053255716
Therapeutic Targets Database
DNC001211
PDBe Ligand
RIO
Wikipedia
Ribostamycin
PDB Entries
1m4g / 1s3z / 2bue / 2et5 / 2fcz / 2kxm / 2n0j / 3c3z / 3dvv / 5iqd
show 2 more

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage Forms
FormRouteStrength
Capsule
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)193.5 °CPhysProp
pKa7.7MERCK INDEX (1996)
Predicted Properties
PropertyValueSource
Water Solubility88.7 mg/mLALOGPS
logP-2.9ALOGPS
logP-6.4ChemAxon
logS-0.71ALOGPS
pKa (Strongest Acidic)12.19ChemAxon
pKa (Strongest Basic)9.67ChemAxon
Physiological Charge4ChemAxon
Hydrogen Acceptor Count14ChemAxon
Hydrogen Donor Count10ChemAxon
Polar Surface Area262.38 Å2ChemAxon
Rotatable Bond Count6ChemAxon
Refractivity100.17 m3·mol-1ChemAxon
Polarizability44.9 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability0ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption-0.8617
Blood Brain Barrier-0.9659
Caco-2 permeable-0.7502
P-glycoprotein substrateNon-substrate0.5164
P-glycoprotein inhibitor INon-inhibitor0.8023
P-glycoprotein inhibitor IINon-inhibitor0.8764
Renal organic cation transporterNon-inhibitor0.7886
CYP450 2C9 substrateNon-substrate0.8231
CYP450 2D6 substrateNon-substrate0.8041
CYP450 3A4 substrateNon-substrate0.6473
CYP450 1A2 substrateNon-inhibitor0.9157
CYP450 2C9 inhibitorNon-inhibitor0.9147
CYP450 2D6 inhibitorNon-inhibitor0.9231
CYP450 2C19 inhibitorNon-inhibitor0.9034
CYP450 3A4 inhibitorNon-inhibitor0.9471
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.8446
Ames testNon AMES toxic0.6934
CarcinogenicityNon-carcinogens0.9505
BiodegradationNot ready biodegradable0.8587
Rat acute toxicity1.4850 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9728
hERG inhibition (predictor II)Non-inhibitor0.81
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available

Targets

Drugtargets2
Build, predict & validate machine-learning models
Use our structured and evidence-based datasets to unlock new
insights and accelerate drug research.
Learn more
Use our structured and evidence-based datasets to unlock new insights and accelerate drug research.
Learn more
Kind
Protein
Organism
Salmonella enteritidis
Pharmacological action
Unknown
General Function
Protein homodimerization activity
Specific Function
Catalyzes the transfer of an acetyl group from acetyl-CoA to the 6'-amino group of aminoglycoside molecules conferring resistance to antibiotics containing the purpurosamine ring including amikacin...
Gene Name
Not Available
Uniprot ID
Q9R381
Uniprot Name
Aminoglycoside N(6')-acetyltransferase type 1
Molecular Weight
16361.42 Da
Kind
Protein
Organism
Mycobacterium tuberculosis
Pharmacological action
Unknown
General Function
May catalyze the coenzyme A-dependent acetylation of the 2' hydroxyl or amino group of a broad spectrum of aminoglycosides and confer resistance to aminoglycosides (By similarity). In vitro assays show no significant increase of resistance to aminoglycosides, possibly due to low expression in a heterologous system (PubMed:9159528).
Specific Function
Aminoglycoside 2'-n-acetyltransferase activity
Gene Name
aac
Uniprot ID
P9WQG9
Uniprot Name
Aminoglycoside 2'-N-acetyltransferase
Molecular Weight
20037.53 Da
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Protein heterodimerization activity
Specific Function
This multifunctional protein catalyzes the formation, breakage and rearrangement of disulfide bonds. At the cell surface, seems to act as a reductase that cleaves disulfide bonds of proteins attach...
Gene Name
P4HB
Uniprot ID
P07237
Uniprot Name
Protein disulfide-isomerase
Molecular Weight
57115.795 Da
References
  1. Horibe T, Nagai H, Sakakibara K, Hagiwara Y, Kikuchi M: Ribostamycin inhibits the chaperone activity of protein disulfide isomerase. Biochem Biophys Res Commun. 2001 Dec 21;289(5):967-72. [Article]
Kind
Protein
Organism
Escherichia coli (strain K12)
Pharmacological action
Unknown
General Function
Trna binding
Specific Function
With S4 and S5 plays an important role in translational accuracy.Interacts with and stabilizes bases of the 16S rRNA that are involved in tRNA selection in the A site and with the mRNA backbone. Lo...
Gene Name
rpsL
Uniprot ID
P0A7S3
Uniprot Name
30S ribosomal protein S12
Molecular Weight
13736.995 Da

Enzymes

Kind
Protein
Organism
Mycobacterium tuberculosis
Pharmacological action
Unknown
Actions
Substrate
General Function
May catalyze the coenzyme A-dependent acetylation of the 2' hydroxyl or amino group of a broad spectrum of aminoglycosides and confer resistance to aminoglycosides (By similarity). In vitro assays show no significant increase of resistance to aminoglycosides, possibly due to low expression in a heterologous system (PubMed:9159528).
Specific Function
Aminoglycoside 2'-n-acetyltransferase activity
Gene Name
aac
Uniprot ID
P9WQG9
Uniprot Name
Aminoglycoside 2'-N-acetyltransferase
Molecular Weight
20037.53 Da
References
  1. Vong K, Auclair K: Understanding and overcoming aminoglycoside resistance caused by N-6'-acetyltransferase. Medchemcomm. 2012 Apr 1;3(4):397-407. doi: 10.1039/C2MD00253A. [Article]
  2. Zarate SG, De la Cruz Claure ML, Benito-Arenas R, Revuelta J, Santana AG, Bastida A: Overcoming Aminoglycoside Enzymatic Resistance: Design of Novel Antibiotics and Inhibitors. Molecules. 2018 Jan 30;23(2). pii: molecules23020284. doi: 10.3390/molecules23020284. [Article]
  3. Shi K, Caldwell SJ, Fong DH, Berghuis AM: Prospects for circumventing aminoglycoside kinase mediated antibiotic resistance. Front Cell Infect Microbiol. 2013 Jun 25;3:22. doi: 10.3389/fcimb.2013.00022. eCollection 2013. [Article]

Drug created on June 13, 2005 13:24 / Updated on February 21, 2021 18:51