Daptomycin
Daptomycin is a natural antibiotic used to treat gram-positive bacterial infections.[1] A unique mechanism of action has allowed low rates of bacterial cross-resistance to daptomycin, making it an effective treatment to severe infection such as Vancomycin-resistant Enterococci (VRE) and Methicillin-reistant Staphlococcus aureus (MRSA).[2]
 Daptomycin. An antibiotic for gram-positive bacterial infection. | |
| Clinical data | |
|---|---|
| Routes of administration | intravenous |
| Identifiers | |
| DrugBank | |
| E number | {{#property:P628}} |
| ECHA InfoCard | {{#property:P2566}} |
| Chemical and physical data | |
| Formula | C72H101N17O26 |
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Nomenclature and structure
Daptomycin is also commonly referred to as Cubicin or abbreviated to DAP.[3][4] It is a lipopeptide, meaning that it is made of a combination of fatty acids and protein complexes.[5] Daptomycin is biosynthetic, first extracted from Streptomyces roseosporus.[5]
Medicine
Daptomycin is used to treat the following medical conditions:[2]
- right-handed myocarditis infection
- complicated skin and skin structure infections (cSSSIs)
- meningitis
- bacteraemia
- sepsis
- urinary tract infection
Mechanism of action
Daptomycin kills gram-positive bacteria by changing the structure of the cell membrane.[4] Daptomycin enters the bacterial cell membrane by chemical exchange with calcium ions and phospholipid phosphatidylglycerol (PG).[2][4]
Daptomycin Media
Figures 1–7. Biosynthesis of daptomycin
Figure 8. Structures of lipopeptide antibiotics*Colors highlight the positions in daptomycin that have been modified by genetic engineering, as well as the origins of modules or subunits from A54145 or calcium-dependent antibiotic (CDA).
Figure 9. Combinatorial biosynthesis of lipopeptide antibiotics related to daptomycin. Position 8, which typically has D-Ala in daptomycin, was modified by module exchanges to contain D-Ser, D-Asn or D-Lys; position 11, which naturally has D-Ser, was modified by module exchanges to consist of D-Ala or D-Asn; position 12, which normally has 3-methyl-L-Glu, was modified by deletion of the methyltransferase gene to possess L-Glu; position 13, which normally has L-kynurenine (L-Kyn), was modified by subunit exchanges to contain L-Trp, L-Ile or L-Val; position 1 usually includes the anteiso-undecanoyl, isododecanoyl and anteiso-tridecanoyl fatty acyl groups.
References
- ↑ Patel, Shivali; Saw, Stephen (2023), "Daptomycin", StatPearls, Treasure Island (FL): StatPearls Publishing, PMID 29261926, retrieved 2023-07-04
- ↑ 2.0 2.1 2.2 Heidary, Mohsen; Khosravi, Azar Dohkt; Khoshnood, Saeed; Nasiri, Mohammad Javad; Soleimani, Saleh; Goudarzi, Mehdi (2018-01-01). "Daptomycin". Journal of Antimicrobial Chemotherapy. 73 (1): 1–11. doi:10.1093/jac/dkx349. ISSN 0305-7453.
- ↑ PubChem. "Daptomycin". pubchem.ncbi.nlm.nih.gov. Retrieved 2023-07-04.
- ↑ 4.0 4.1 4.2 Miller, William R.; Bayer, Arnold S.; Arias, Cesar A. (November 2016). "Mechanism of Action and Resistance to Daptomycin in Staphylococcus aureus and Enterococci". Cold Spring Harbor Perspectives in Medicine. 6 (11): a026997. doi:10.1101/cshperspect.a026997. ISSN 2157-1422. PMC 5088507. PMID 27580748.
- ↑ 5.0 5.1 Micklefield, Jason (July 2004). "Daptomycin Structure and Mechanism of Action Revealed". Chemistry & Biology. 11 (7): 887–888. doi:10.1016/j.chembiol.2004.07.001. ISSN 1074-5521.