Daptomycin
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| Clinical data | |
|---|---|
| Trade names | Cubicin |
| AHFS/Drugs.com | Monograph |
| Pregnancy category |
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| Routes of administration |
Intravenous |
| ATC code | |
| Legal status | |
| Legal status |
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| Pharmacokinetic data | |
| Bioavailability | n/a |
| Protein binding | 90–95% |
| Metabolism | Renal (speculative) |
| Biological half-life | 7–11 hours (up to 28 hours in renal impairment) |
| Excretion | Renal (78%; primarily as unchanged drug); faeces (5.7%) |
| Identifiers | |
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| CAS Number | |
| PubChem CID | |
| DrugBank | |
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| KEGG | |
| ChEBI | |
| ChEMBL | |
| ECHA InfoCard | 100.116.065 |
| Chemical and physical data | |
| Formula | C72H101N17O26 |
| Molar mass | 1619.7086 g/mol |
  (what is this?)
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| Daptomycin | |
|---|---|
| Identifiers | |
| Symbol | N/A |
| 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 multiple drug-resistant bacteria. It is marketed in the United States under the trade name Cubicin by Cubist Pharmaceuticals.
Daptomycin, originally designated as LY 146032, was discovered by researchers at Eli Lilly and Company in the late 1980s. LY 146032 showed promise in phase I/II clinical trials for treatment of infection caused by Gram-positive organisms. Lilly ceased development because high-dose therapy was associated with adverse effects on skeletal muscle, including myalgia and potential myositis.
The rights to LY 146032 were acquired by Cubist Pharmaceuticals in 1997, which following U.S. Food and Drug Administration (FDA) approval in September 2003 for use in people older than 18 years, began marketing the drug under the trade name Cubicin. Cubicin is marketed in the EU and in several other countries by Novartis following its purchase of Chiron Corporation, the previous licensee.
Daptomycin has a distinct mechanism of action, disrupting multiple aspects of bacterial cell membrane function. It inserts into the cell membrane in a phosphatidylglycerol-dependent fashion, where it then aggregates. The aggregation of daptomycin alters the curvature of the membrane, which creates holes that leak ions. This causes rapid depolarization, resulting in a loss of membrane potential leading to inhibition of protein, DNA, and RNA synthesis, which results in bacterial cell death.
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