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D2446

Daptomycin

Name: Daptomycin
Brand: SIGMA

cyclic lipopeptide antibiotic

Synonym(s):

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

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About This Item

Empirical Formula (Hill Notation):

C₇₂H₁₀₁N₁₇O₂₆

CAS Number:

103060-53-3

Molecular Weight:

1620.67

MDL number:

MFCD28968054

UNSPSC Code:

51102829

PubChem Substance ID:

329798741

NACRES:

NA.76

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Properties

Quality Level

100

assay

≥90% (HPLC)

form

powder

solubility

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

antibiotic activity spectrum

Gram-positive bacteria

mode of action

DNA synthesis | interferes, protein synthesis | interferes

storage temp.

−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

InChI key

DOAKLVKFURWEDJ-FAZHXZQASA-N

Description

Application

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 Actions

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).

Other Notes

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

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Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

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Certificates of Analysis (COA)

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Evaluation of Antibiotics Active against Methicillin-Resistant Staphylococcus aureus Based on Activity in an Established Biofilm.

Daniel G Meeker et al.

Antimicrobial agents and chemotherapy, 60(10), 5688-5694 (2016-07-13)

We used in vitro and in vivo models of catheter-associated biofilm formation to compare the relative activity of antibiotics effective against methicillin-resistant Staphylococcus aureus (MRSA) in the specific context of an established biofilm. The results demonstrated that, under in vitro

Is Implant Coating With Tyrosol- and Antibiotic-loaded Hydrogel Effective in Reducing Cutibacterium (Propionibacterium) acnes Biofilm Formation? A Preliminary In Vitro Study.

Konstantinos Tsikopoulos et al.

Clinical orthopaedics and related research, 477(7), 1736-1746 (2019-05-29)

Studies have suggested that Cutibacterium acnes (formerly known as Propionibacterium) is the most frequently isolated pathogen after shoulder arthroplasty. To address the burden of periprosthetic joint infections associated with this pathogen, new prevention methods are needed. Tyrosol has a promising

Bactericidal activity of daptomycin against Streptococcus pneumoniae compared with eight other antimicrobials.

Glenn A Pankuch et al.

The Journal of antimicrobial chemotherapy, 51(2), 443-446 (2003-02-04)

A spectrum of pneumococci with varying susceptibilities to beta-lactams, macrolides and quinolones was tested for susceptibility to nine antibiotics, including the novel lipopeptide daptomycin. Daptomycin was active against all strains (MIC range </=0.5 mg/L; MIC(50) 0.125 mg/L; MIC(90) 0.25 mg/L).

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