Ramoplanin

Ramoplanin (INN) is a glycolipodepsipeptide antibiotic drug derived from strain ATCC 33076 of Actinoplanes. It is effective against Gram-positive bacteria.

In the Vinony graph

Within Vinony's link graph, Ramoplanin is referenced by 192 other articles, and connects out to antibiotic, ceftolozane/tazobactam and International Standard Book Number.

It sits within the topics Antibiotics, Chemical pages without DrugBank identifier and Drugboxes which contain changes to verified fields.

Its subject is documented across 8 Wikipedia language editions.

Chemical data

Formula: C106H170ClN21O30
Molecular weight: 2254.1 g/mol
IUPAC name: 2-[[(2R)-2-[[(2S)-2-[[2-[[2-[[(2S,3S)-2-[[2-[[(2R)-5-amino-2-[[(2S)-2-[[(2S,3S)-2-[[(2R)-2-[[(2R)-2-[[(2R,3S)-2-[[(2R)-5-amino-2-[[(2R)-2-[[4-amino-2-[[(2S)-4-amino-2-[[(2Z,4Z)-octa-2,4-dienoyl]amino]-4-oxobutanoyl]amino]-4-oxobutanoyl]amino]-2-(4-hydroxycyclohexyl)acetyl]amino]pentanoyl]amino]-3-hydroxybutanoyl]amino]-2-(4-hydroxycyclohexyl)acetyl]amino]-2-(4-hydroxycyclohexyl)acetyl]amino]-3-hydroxybutanoyl]amino]-3-phenylpropanoyl]amino]pentanoyl]amino]-2-(4-hydroxycyclohexyl)acetyl]amino]-3-hydroxybutanoyl]amino]-2-(4-hydroxycyclohexyl)acetyl]amino]acetyl]amino]-4-methylpentanoyl]amino]propanoyl]amino]-2-(3-chloro-4-hydroxycyclohexyl)acetic acid
SMILES: CCC/C=C\C=C/C(=O)N[C@@H](CC(=O)N)C(=O)NC(CC(=O)N)C(=O)N[C@H](C1CCC(CC1)O)C(=O)N[C@H](CCCN)C(=O)N[C@H]([C@H](C)O)C(=O)N[C@H](C2CCC(CC2)O)C(=O)N[C@H](C3CCC(CC3)O)C(=O)N[C@@H]([C@H](C)O)C(=O)N[C@@H](CC4=CC=CC=C4)C(=O)N[C@H](CCCN)C(=O)NC(C5CCC(CC5)O)C(=O)N[C@@H]([C@H](C)O)C(=O)NC(C6CCC(CC6)O)C(=O)NCC(=O)N[C@@H](CC(C)C)C(=O)N[C@H](C)C(=O)NC(C7CCC(C(C7)Cl)O)C(=O)O
InChIKey: FSBZBQUUCNYWOK-YIOPJBSBSA-N
XLogP: -4.8
Polar surface area: 852 Å²
H-bond donors: 31
H-bond acceptors: 32
Formal charge: 0

via PubChem

Research

197 papers

Ramoplanin: a lipoglycodepsipeptide antibiotic.The Annals of pharmacotherapy · 2005
Ramoplanin: a topical lipoglycodepsipeptide antibacterial agent.Expert review of anti-infective therapy · 2006
Ramoplanin as a novel therapy for Neisseria gonorrhoeae infection: an in vitro and in vivo study in Galleria mellonella.Journal of medical microbiology · 2024
Chemistry and biology of the ramoplanin family of peptide antibiotics.Biopolymers · 2002
Ramoplanin: a novel antimicrobial agent with the potential to prevent vancomycin-resistant enterococcal infection in high-risk patients.The Journal of antimicrobial chemotherapy · 2003

via PubMed

Wikidata facts

Subclass of: chemical compound
Mass: 2252.211100719999

Show 6 more facts

canonical SMILES: CCCC=CC=CC(=O)NC(CC(=O)N)C(=O)NC(CC(=O)N)C(=O)NC(C1CCC(CC1)O)C(=O)NC(CCCN)C(=O)NC(C(C)O)C(=O)NC(C2CCC(CC2)O)C(=O)NC(C3CCC(CC3)O)C(=O)NC(C(C)O)C(=O)NC(CC4=CC=CC=C4)C(=O)NC(CCCN)C(=O)NC(C5CCC(CC5)O)C(=O)NC(C(C)O)C(=O)NC(C6CCC(CC6)O)C(=O)NCC(=O)NC(CC(C)C)C(=O)NC(C)C(=O)NC(C7CCC(C(C7)Cl)O)C(=O)O
chemical formula: C₁₀₆H₁₇₀ClN₂₁O₃₀
isomeric SMILES: CCC/C=C\C=C/C(=O)N[C@@H](CC(=O)N)C(=O)NC(CC(=O)N)C(=O)N[C@H](C1CCC(CC1)O)C(=O)N[C@H](CCCN)C(=O)N[C@H]([C@H](C)O)C(=O)N[C@H](C2CCC(CC2)O)C(=O)N[C@H](C3CCC(CC3)O)C(=O)N[C@@H]([C@H](C)O)C(=O)N[C@@H](CC4=CC=CC=C4)C(=O)N[C@H](CCCN)C(=O)NC(C5CCC(CC5)O)C(=O)N[C@@H]([C@H](C)O)C(=O)NC(C6CCC(CC6)O)C(=O)NCC(=O)N[C@@H](CC(C)C)C(=O)N[C@H](C)C(=O)NC(C7CCC(C(C7)Cl)O)C(=O)O
subject has role: antibiotic
found in taxon: Actinoplanes
Commons category: Ramoplanin

Sources (1)

wikidata.org

via Wikidata · CC0

~3 min read

Encyclopedic overview

6 sections

Contents

Medical uses
Mechanism of action
Chemistry
Biosynthesis
Total synthesis
References

Ramoplanin (INN) is a glycolipodepsipeptide antibiotic drug derived from strain ATCC 33076 of Actinoplanes. It is effective against Gram-positive bacteria.

== Medical uses == Its development has been fast-tracked by the U.S. Food and Drug Administration as a treatment for multiple antibiotic-resistant Clostridioides difficile infection of the gastrointestinal tract, Unlike vancomycin, it is absorbed in the gastrointestinal tract, although it is unstable in the bloodstream, so can be taken only orally against Clostridioides difficile infections of the gastrointestinal tract.

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