Structure via PubChem · Public domain (PubChem)
داپتومایسین
Sign in to saveAlso 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 Ų
- 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