(2R)-daptomycin

Also known as N-decanoyl-L-tryptophyl-L-asparaginyl-L-aspartyl-L-threonylglycyl-L-ornithyl-L-aspartyl-D-alanyl-L-aspartylglycyl-D-seryl-threo-3-methyl-L-glutamyl-3-anthraniloyl-L-alanine epsilon(1)-lactone, N-decanoyl-L-tryptophyl-L-asparaginyl-L-aspartyl-L-threonylglycyl-L-ornithyl-L-aspartyl-D-alanyl-L-aspartylglycyl-D-seryl-threo-3-methyl-L-glutamyl-3-anthraniloyl-L-alanine 1.13-3.4-lactone, LY 146032, daptomycin, CBC134

Daptomycin, sold under the brand name Cubicin among others, is a lipopeptide antibiotic used in the treatment of systemic and life-threatening infections caused by Gram-positive organisms.

Key facts

Drug.ChEBI: 600103
Drug.ChEMBL: 508162
Drug.O: 26
Drug.Verifiedfields: changed
Drug.Watchedfields: changed
Drug.verifiedrevid: 457630808
Drug.image: Daptomycin Ball et al.svg
Drug.image_class: skin-invert-image
Drug.width: 300
Drug.tradename: Cubicin, Cubicin RF, Dapzura RT
Drug.DailyMedID: Daptomycin
Drug.pregnancy_AU: B1
Drug.routes_of_administration: Intravenous
Drug.ATC_prefix: J01
Drug.ATC_suffix: XX09
Drug.legal_AU: S4
Drug.legal_UK: POM
Drug.legal_US: Rx-only

via Wikipedia infobox

Chemical data

Formula: C72H101N17O26
Molecular weight: 1620.7 g/mol
IUPAC name: (3S)-4-[[(3S,6S,9R,15S,18R,21S,24S,30S,31R)-3-[2-(2-aminophenyl)-2-oxoethyl]-24-(3-aminopropyl)-15,21-bis(carboxymethyl)-6-[(2R)-1-carboxypropan-2-yl]-5,8,11,14,17,20,23,26,29-nonahydroxy-9-(hydroxymethyl)-18,31-dimethyl-2-oxo-1-oxa-4,7,10,13,16,19,22,25,28-nonazacyclohentriaconta-4,7,10,13,16,19,22,25,28-nonaen-30-yl]imino]-3-[[(2R)-1,4-dihydroxy-2-[[(2S)-1-hydroxy-2-(1-hydroxydecylideneamino)-3-(1H-indol-3-yl)propylidene]amino]-4-iminobutylidene]amino]-4-hydroxybutanoic acid
SMILES: CCCCCCCCCC(=N[C@@H](CC1=CNC2=CC=CC=C21)C(=N[C@H](CC(=N)O)C(=N[C@@H](CC(=O)O)C(=N[C@H]3[C@H](OC(=O)[C@@H](N=C([C@@H](N=C([C@H](N=C(CN=C([C@@H](N=C([C@H](N=C([C@@H](N=C([C@@H](N=C(CN=C3O)O)CCCN)O)CC(=O)O)O)C)O)CC(=O)O)O)O)CO)O)[C@H](C)CC(=O)O)O)CC(=O)C4=CC=CC=C4N)C)O)O)O)O
InChIKey: DOAKLVKFURWEDJ-QCMAZARJSA-N
XLogP: 0.7
Polar surface area: 748 Å²
H-bond donors: 23
H-bond acceptors: 42
Formal charge: 0

via PubChem

Research

3 papers

The Chiral Target of Daptomycin Is the 2R,2'S Stereoisomer of Phosphatidylglycerol.Angewandte Chemie (International ed. in English) · 2022
A54145 Factor D Is Not Less Susceptible to Inhibition by Lung Surfactant than Daptomycin.ACS infectious diseases · 2022
A Versatile Boc Solid Phase Synthesis of Daptomycin and Analogues Using Site Specific, On-Resin Ozonolysis to Install the Kynurenine Residue.Chemistry (Weinheim an der Bergstrasse, Germany) · 2019

via PubMed

Wikidata facts

Mass: 1619.710366
Manufacturer: Pfizer
Has use: medication

Show 12 more facts

chemical formula: C₇₂H₁₀₁N₁₇O₂₆
Commons category: Daptomycin
defined daily dose: 0.28
canonical SMILES: CCCCCCCCCC(=O)NC(CC1=CNC2=CC=CC=C21)C(=O)NC(CC(=O)N)C(=O)NC(CC(=O)O)C(=O)NC3C(OC(=O)C(NC(=O)C(NC(=O)C(NC(=O)CNC(=O)C(NC(=O)C(NC(=O)C(NC(=O)C(NC(=O)CNC3=O)CCCN)CC(=O)O)C)CC(=O)O)CO)C(C)CC(=O)O)CC(=O)C4=CC=CC=C4N)C
isomeric SMILES: CCCCCCCCCC(=O)N[C@@H](CC1=CNC2=C1C=CC=C2)C(=O)N[C@H](CC(N)=O)C(=O)N[C@@H](CC(O)=O)C(=O)N[C@H]3[C@@H](C)OC(=O)[C@H](CC(=O)C4=C(N)C=CC=C4)NC(=O)[C@@H](NC(=O)[C@@H](CO)NC(=O)CNC(=O)[C@H](CC(O)=O)NC(=O)[C@@H](C)NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](CCCN)NC(=O)CNC3=O)[C@H](C)CC(O)=O
medical condition treated: bacterial infectious disease
World Health Organisation international non-proprietary name: daptomycin
NCI Thesaurus ID: C47470
subject has role: bactericide
stylized name: DAPTOmycin
has characteristic: biopharmaceutical
significant drug interaction: pravastatin

Sources (8)

via Wikidata · CC0

~16 min read

Encyclopedic overview

12 sections

Contents

Medical uses
Adverse effects
Pharmacology
Mechanism of action
Microbiology
Daptomycin resistance
Efficacy
Biosynthesis
History
References
Further reading
External links

Daptomycin, sold under the brand name Cubicin among others, is a lipopeptide antibiotic used in the treatment of systemic and life-threatening infections caused by Gram-positive organisms.

Daptomycin was removed from the World Health Organization's List of Essential Medicines in 2019. The World Health Organization classifies daptomycin as critically important for human medicine.

Excerpted from Wikipedia’s “(2R)-daptomycin” article, available under the CC BY-SA 4.0 licence.