Skip to Content
Merck
All Photos(2)

Key Documents

View All Documentation

D2446

Sigma-Aldrich

Daptomycin

cyclic lipopeptide antibiotic

Synonym(s):

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

Sign Into View Organizational & Contract Pricing
All Photos(2)

About This Item

Empirical Formula (Hill Notation):
C72H101N17O26
CAS Number:
103060-53-3
Molecular Weight:
1620.67
UNSPSC Code:
51102829
PubChem Substance ID:
329798741
NACRES:
NA.76

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

Related Categories

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.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library

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
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
Venkatesh Mayandi et al.
ACS infectious diseases, 5(8), 1411-1422 (2019-05-18)
Increased evolution of multidrug resistant pathogens necessitates the development of multifunctional antimicrobials. There is a perceived need for developing new antimicrobials that can interfere with acute inflammation after bacterial infections. Here, we investigated the therapeutic potential of linear polyethylenimine (LPEI)
Romain Guérillot et al.
Genome medicine, 10(1), 63-63 (2018-09-01)
Mutation acquisition is a major mechanism of bacterial antibiotic resistance that remains insufficiently characterised. Here we present RM-seq, a new amplicon-based deep sequencing workflow based on a molecular barcoding technique adapted from Low Error Amplicon sequencing (LEA-seq). RM-seq allows detection
View All Related Papers

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service