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Merck
CN

D2446

Daptomycin

cyclic lipopeptide antibiotic

别名:

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

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关于此项目

经验公式（希尔记法）:
C72H101N17O26
化学文摘社编号:
103060-53-3
分子量:
1620.67
MDL number:
MFCD28968054
UNSPSC Code:
51102829
PubChem Substance ID:
329798741
NACRES:
NA.76

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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

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

Quality Level

100

相关类别

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.

存储类别

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

法规信息

涉药品监管产品
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历史批次信息供参考:

分析证书(COA)

Lot/Batch Number
0000417606
0000417606
0000395351
0000311947
0000395351

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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
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
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
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
Muhd Haziq F Abdul Momin et al.
Journal of medical microbiology, 66(11), 1554-1561 (2017-10-07)
A selective chromogenic culture medium for the laboratory isolation and differentiation of colistin resistant Acinetobacter, Pseudomonas, Stenotrophomonas and Enterobacteriaceae spp. (CHROMagar COL-APSE) was developed, evaluated and compared to an existing selective bacterial culture medium (SuperPolymyxin). The medium was challenged with
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