Daptomycin

Title: Daptomycin
CAS Registry Number: 103060-53-3
Manufacturers' Codes: LY-146032
Trademarks: Cidecin (Cubist); Cubicin (Cubist)
Molecular Formula: C72H101N17O26
Molecular Weight: 1620.67
Percent Composition: C 53.36%, H 6.28%, N 14.69%, O 25.67%
Literature References: Cyclic lipopeptide antibiotic derived from a fermentation product of Streptomyces roseosporus; disrupts plasma membrane function in gram-positive bacteria. Prepn: B. J. Abbott et al., US 4537717 (1985 to Eli Lilly); M. Debono et al., J. Antibiot. 41, 1093 (1988). Mechanism of action study: N. E. Allen et al., Antimicrob. Agents Chemother. 31, 1093 (1987); and structure determn: D. Jung et al., Chem. Biol. 11, 949 (2004). Comparative in vitro antibacterial spectrum: I. A. Critchley et al., J. Antimicrob. Chemother. 51, 639 (2003). Clinical pharmacokinetics: J. R. Woodworth et al., Antimicrob. Agents Chemother. 36, 318 (1992). Clinical trial in skin infections: R. D. Arbeit et al., Clin. Infect. Dis. 38, 1673 (2004). Review of pharmacology and clinical evaluations: F. P. Tully et al., Expert Opin. Invest. Drugs 8, 1223-1238 (1999); L. P. Kotra Curr. Opin. Anti-Infect. Invest. Drugs 2, 185-205 (2000).
Properties: uv max (ethanol): 220, 260 nm (e 46500, 10000). LD50 i.v. in mice: 600 mg/kg (Debono).
Absorption maximum: uv max (ethanol): 220, 260 nm (e 46500, 10000)
Toxicity data: LD50 i.v. in mice: 600 mg/kg (Debono)
Therap-Cat: Antibacterial.
Keywords: Antibacterial (Antibiotics); Polypeptides.
D-Araboflavin Darbepoetin Alfa Darifenacin Darunavir Darvan?

Daptomycin
Daptomycin Ball et al.svg
Systematic (IUPAC) name
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[egr]1-lactone
Clinical data
Trade names Cubicin
AHFS/Drugs.com monograph
Pregnancy cat. B (US)
Legal status -only (US)
Routes Intravenous
Pharmacokinetic data
Bioavailability n/a
Protein binding 90–95%
Metabolism Renal (speculative)[1]
Half-life 7–11 hours (up to 28 hours in renal impairment)
Excretion Renal (78%; primarily as unchanged drug); Faeces (5.7%)
Identifiers
CAS number 103060-53-3 YesY
ATC code J01XX09
PubChem CID 16129629
DrugBank DB00080
ChemSpider 10482098 YesY
UNII NWQ5N31VKK YesY
KEGG D01080 N
ChEMBL CHEMBL508162 N
Chemical data
Formula C72H101N17O26 
Mol. mass 1619.7086 g/mol
 N (what is this?)  (verify)
Identifiers
TCDB 1.D.15
OPM superfamily 172
OPM protein 1t5n

Daptomycin is a lipopeptide antibiotic used in the treatment of systemic and life-threatening infections caused by Gram-positive organisms. It is a naturally occurring compound found in the soil saprotroph Streptomyces roseosporus. Its distinct mechanism of action makes it useful in treating infections caused by multi-resistant bacteria. It is marketed in the United States under the trade name Cubicin by Cubist Pharmaceuticals.