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Merck

D2446

Sigma-Aldrich

Daptomycin

cyclic lipopeptide antibiotic

Synonym(e):

Cubicin, Daptomycin, 9-L beta-Aspartic Acid, Dapcin

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About This Item

Empirische Formel (Hill-System):
C72H101N17O26
CAS-Nummer:
Molekulargewicht:
1620.67
UNSPSC-Code:
51102829
PubChem Substanz-ID:
NACRES:
NA.76

Qualitätsniveau

Assay

≥90% (HPLC)

Form

powder

Löslichkeit

methanol: 5 mg/mL
DMSO: soluble
ethanol: soluble
methanol: soluble

Wirkungsspektrum von Antibiotika

Gram-positive bacteria

Wirkungsweise

DNA synthesis | interferes
protein synthesis | interferes

Lagertemp.

−20°C

SMILES String

CCCCCCCCCC(=O)N[C@@H](Cc1c[nH]c2ccccc12)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)c4ccccc4N)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

InChI

1S/C72H101N17O26/c1-5-6-7-8-9-10-11-22-53(93)81-44(25-38-31-76-42-20-15-13-17-39(38)42)66(108)84-45(27-52(75)92)67(109)86-48(30-59(102)103)68(110)89-61-37(4)115-72(114)49(26-51(91)40-18-12-14-19-41(40)74)87-71(113)60(35(2)24-56(96)97)88-69(111)50(34-90)82-55(95)32-77-63(105)46(28-57(98)99)83-62(104)36(3)79-65(107)47(29-58(100)101)85-64(106)43(21-16-23-73)80-54(94)33-78-70(61)112/h12-15,17-20,31,35-37,43-50,60-61,76,90H,5-11,16,21-30,32-34,73-74H2,1-4H3,(H2,75,92)(H,77,105)(H,78,112)(H,79,107)(H,80,94)(H,81,93)(H,82,95)(H,83,104)(H,84,108)(H,85,106)(H,86,109)(H,87,113)(H,88,111)(H,89,110)(H,96,97)(H,98,99)(H,100,101)(H,102,103)/t35-,36-,37-,43-,44+,45-,46+,47+,48+,49+,50-,60+,61+/m1/s1

InChIKey

DOAKLVKFURWEDJ-FAZHXZQASA-N

Anwendung

Daptomycin has been studied as a potential therapy for Streptococcus pneumoniae infections. It has also been used to study the impact of sarA on daptomycin susceptibility of Staphylococcus aureus.

Biochem./physiol. Wirkung

Daptomycin is a cyclic lipopeptide antibiotic. isolated from Streptomyces sp. It is effective against Gram-positive bacteria. It disrupts the plasma membrane causes rapid depolarization and inhibits the synthesis of protein, RNA and DNA. It is potent against Staphylococcus aureus infections, including MRSA (methicillin-resistant Staphylococcus aureus).

Sonstige Hinweise

Keep container tightly closed in a dry and well-ventilated place.

Lagerklassenschlüssel

11 - Combustible Solids

WGK

WGK 3

Flammpunkt (°F)

Not applicable

Flammpunkt (°C)

Not applicable


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Elizabeth C Weiss et al.
Antimicrobial agents and chemotherapy, 53(10), 4096-4102 (2009-08-05)
We used a murine model of catheter-associated biofilm formation to determine whether the mutation of the staphylococcal accessory regulator (sarA) has an impact on the susceptibility of established Staphylococcus aureus biofilms to treatment with daptomycin in vivo. The experiments were
Lucia Grassi et al.
Frontiers in microbiology, 8, 1917-1917 (2017-10-20)
Persister cells (PCs) are a subset of dormant, phenotypic variants of regular bacteria, highly tolerant to antibiotics. Generation of PCs
Romney M Humphries et al.
Clinical microbiology reviews, 26(4), 759-780 (2013-10-05)
Daptomycin is a lipopeptide antimicrobial with in vitro bactericidal activity against Gram-positive bacteria that was first approved for clinical use in 2004 in the United States. Since this time, significant data have emerged regarding the use of daptomycin for the
Nigam M Mishra et al.
Frontiers in microbiology, 9, 1175-1175 (2018-06-23)
Vancomycin is a glycopeptide antibiotic that inhibits transpeptidation during cell wall synthesis by binding to the D-Ala-D-Ala termini of lipid II. For long, it has been used as a last resort antibiotic. However, since the emergence of the first vancomycin-resistant
Abiodun D Ogunniyi et al.
PloS one, 12(9), e0183457-e0183457 (2017-09-06)
The spread of multidrug resistance among bacterial pathogens poses a serious threat to public health worldwide. Recent approaches towards combating antimicrobial resistance include repurposing old compounds with known safety and development pathways as new antibacterial classes with novel mechanisms of

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