ribostamycin

Ribostamycin is an aminoglycoside-aminocyclitol antibiotic isolated from a streptomycete, Streptomyces ribosidificus, originally identified in a soil sample from Tsu City of Mie Prefecture in Japan. It is made up of 3 ring subunits: 2-deoxystreptamine (DOS), neosamine C, and ribose. Ribostamycin, along with other aminoglycosides with the DOS subunit, is an important broad-spectrum antibiotic with important use against human immunodeficiency virus and is considered a critically important antimicrobial by the World Health Organization., Resistance against aminoglycoside antibiotics, such as ribo

In the Vinony graph

Within Vinony's link graph, ribostamycin is referenced by 116 other articles, and connects out to neomycin, World Health Organization and International Standard Book Number.

It is catalogued under topics including Aminoglycoside antibiotics, Chemical pages without DrugBank identifier and Drugboxes which contain changes to verified fields.

Its subject is documented across 9 Wikipedia language editions.

Chemical data

Formula: C17H34N4O10
Molecular weight: 454.5 g/mol
IUPAC name: 5-amino-2-(aminomethyl)-6-[4,6-diamino-2-[3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]oxy-3-hydroxycyclohexyl]oxyoxane-3,4-diol
SMILES: C1C(C(C(C(C1N)OC2C(C(C(C(O2)CN)O)O)N)OC3C(C(C(O3)CO)O)O)O)N
InChIKey: NSKGQURZWSPSBC-UHFFFAOYSA-N
XLogP: -6.3
Polar surface area: 262 Å²
H-bond donors: 10
H-bond acceptors: 14
Formal charge: 0

via PubChem

Drug data · ChEMBL

Molecule type: Small molecule

via ChEMBL · EBI

Research

211 papers

Characterization of ribostamycin and its impurities using a nano-quantity analyte detector: Systematic comparison of performance among three different aerosol detectors.Talanta · 2024
Biosynthesis of ribostamycin derivatives by reconstitution and heterologous expression of required gene sets.Applied biochemistry and biotechnology · 2011
Synthesis of (+)-ribostamycin by catalytic, enantioselective hydroamination of benzene.Nature synthesis · 2022
Pharmacokinetics of ribostamycin in paediatric patients.Clinical pharmacokinetics · 1992
Ribostamycin inhibits the chaperone activity of protein disulfide isomerase.Biochemical and biophysical research communications · 2001

via PubMed

Wikidata facts

Mass: 454.2274932879999

Show 4 more facts

chemical formula: C₁₇H₃₄N₄O₁₀
canonical SMILES: C1C(C(C(C(C1N)OC2C(C(C(C(O2)CN)O)O)N)OC3C(C(C(O3)CO)O)O)O)N
subject has role: antibiotic
isomeric SMILES: C1[C@H]([C@@H]([C@H]([C@@H]([C@H]1N)O[C@@H]2[C@@H]([C@H]([C@@H]([C@H](O2)CN)O)O)N)O[C@H]3[C@@H]([C@@H]([C@H](O3)CO)O)O)O)N

Sources (3)

via Wikidata · CC0

~3 min read

Encyclopedic overview

2 sections

Contents

Biosynthesis
References

{{Drugbox | Verifiedfields = changed | Watchedfields = changed | verifiedrevid = 376278091 | IUPAC_name = (1R,2R,3S,4R,6S)-4,6-diamino-3-hydroxy-2-(β-D-ribofuranosyloxy)cyclohexyl 2,6-diamino-2,6-dideoxy-α-D-glucopyranoside | image = Ribostamycin.svg | image_class = skin-invert-image

Excerpted from Wikipedia’s “ribostamycin” article, available under the CC BY-SA 4.0 licence.