Daptomycin | CAS#103060-53-3 | MedKoo Biosciences

MedKoo Cat#: 300143 | Name: Daptomycin

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Description:

WARNING: This product is for research use only, not for human or veterinary use.

Daptomycin is a novel lipopeptide antibiotic used in the treatment of certain infections caused by Gram-positive organisms. It is a naturally occurring compound found in the soil saprotroph Streptomyces roseosporus. Its distinct mechanism of action means that it may be useful in treating infections caused by multi-resistant bacteria. It is marketed in the United States under the trade name Cubicin by Cubist Pharmaceuticals.

Chemical Structure

Daptomycin

CAS#103060-53-3

Theoretical Analysis

MedKoo Cat#: 300143

Name: Daptomycin

CAS#: 103060-53-3

Chemical Formula: C72H101N17O26

Exact Mass: 1619.7104

Molecular Weight: 1620.67

Elemental Analysis: C, 53.36; H, 6.28; N, 14.69; O, 25.67

Price and Availability

Size	Price	Availability
10mg	USD 150.00	Ready to ship
25mg	USD 250.00	Ready to ship
50mg	USD 450.00	Ready to ship
1g	USD 2,950.00	2 Weeks

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Related CAS #

No Data

Synonym

LY 146032; LY-146032; LY146032; Daptomycin; Cidecin; Cubicin;

IUPAC/Chemical Name

2,2'-((3S,6S,9R,15S,18R,21S,24S)-30-((S)-2-((S)-4-amino-2-((S)-2-decanamido-3-(1H-indol-3-yl)propanamido)-4-oxobutanamido)-3-carboxypropanamido)-3-(2-(2-aminophenyl)-2-oxoethyl)-24-(3-aminopropyl)-6-((R)-1-carboxypropan-2-yl)-9-(hydroxymethyl)-18,31-dimethyl-2,5,8,11,14,17,20,23,26,29-decaoxo-1-oxa-4,7,10,13,16,19,22,25,28-nonaazacyclohentriacontane-15,21-diyl)diacetic acid

InChi Key

DOAKLVKFURWEDJ-AVSAZHKKSA-N

InChi Code

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

SMILES Code

O=C1NCC(N[C@@H](CCCN)C(N[C@@H](CC(O)=O)C(N[C@H](C)C(N[C@@H](CC(O)=O)C(NCC(N[C@H](CO)C(N[C@@H]([C@H](C)CC(O)=O)C(N[C@@H](CC(C2=CC=CC=C2N)=O)C(OC(C)C1NC([C@@H](NC([C@@H](NC([C@@H](NC(CCCCCCCCC)=O)CC3=CNC4=C3C=CC=C4)=O)CC(N)=O)=O)CC(O)=O)=O)=O)=O)=O)=O)=O)=O)=O)=O)=O

Appearance

solid powder

Purity

>94% (or refer to the Certificate of Analysis)

Shipping Condition

Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition

Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility

Soluble in DMSO.

Shelf Life

>2 years if stored properly

Drug Formulation

This drug may be formulated in DMSO

Stock Solution Storage

0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code

2934.99.9001

More Info

Product Data

Product Data

Certificate of Analysis

View CoA: current batch, Lot#T7C06I13

Safety Data Sheet (SDS)

View Safety Data Sheet (SDS)

Instruction

View handling instruction

Biological target:

Daptomycin is a lipopeptide antibiotic with rapid in vitro bactericidal activity against gram-positive organisms.

In vitro activity:

To analyze how the clustering of fluid lipids by daptomycin affects the overall fluidity of the cell membrane, the membrane fluiditysensitive dye laurdan was used. As shown in Fig. 5A, daptomycin induces a rapid increase in laurdan general polarization (GP) values, reflecting rapid membrane rigidification. The decrease in membrane fluidity occurs in less than 2 min, suggesting that it is a direct effect of daptomycin insertion into the bilayer rather than a cellular adaptation. Laurdan GP also can be used to visualize differences in membrane fluidity microscopically in bacterial cells. Indeed, laurdan GP microscopy of daptomycin-treated cells showed a clear decrease in overall membrane fluidity (Fig. 5B). Interestingly, the large fluorescent membrane patches, indicative of fluid lipids clustered together by daptomycin, showed a clearly reduced laurdan GP. This observation suggests that the interaction of the lipids with daptomycin reduces their acyl chain mobility, resulting in relatively rigid membrane domains. Reference: Proc Natl Acad Sci U S A. 2016 Nov 8; 113(45): E7077–E7086. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5111643/

In vivo activity:

This study used a rat model to study the in vivo efficacy of daptomycin in the treatment of burn wound infections by S. aureus, and the wound healing process was evaluated through morphological and immunohistochemical analysis. The study included two uninfected control groups with and without daptomycin treatment, an infected control group that did not receive any treatment, and two infected groups treated, respectively, with intraperitoneal daptomycin and teicoplanin. The highest inhibition of the bacterial load was obtained in the group that received daptomycin (2.0 ×103 ± 0.4 × 103 CFU/g) (P < 0.01). Biopsy specimens from uninfected rats treated or not treated with daptomycin showed robust epidermal coverage: we observed a reconstitution of the regular epidermal lining with evident keratinization, a substantial reduction of fibrinous exudation, and regular collagen deposition. In particular, rats treated with daptomycin displayed better epithelialization than rats treated with teicoplanin because they showed less hypertrophic epithelium. Treatment with daptomycin produced a significantly increased rate of positivity for FGF-2 in the dermis (P < 0.05), while the regenerated keratinocytes showed moderate and focal positivity for FGF-2 in the cytoplasm in the epithelium. In conclusion, these results support the hypothesis that daptomycin is an important modulator of wound repair by possibly reducing hypertrophic burn scar formation. Reference: Antimicrob Agents Chemother. 2017 Sep; 61(9): e00606-17. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5571319/

	Solvent	mg/mL	mM
Solubility
	DMSO	90.0	55.53
	H2O	77.0	47.51

Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 1,620.67 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Concentration / Solvent Volume / Mass	1 mg	5 mg	10 mg
1 mM	1.15 mL	5.76 mL	11.51 mL
5 mM	0.23 mL	1.15 mL	2.3 mL
10 mM	0.12 mL	0.58 mL	1.15 mL
50 mM	0.02 mL	0.12 mL	0.23 mL

Formulation protocol:

1. Müller A, Wenzel M, Strahl H, Grein F, Saaki TNV, Kohl B, Siersma T, Bandow JE, Sahl HG, Schneider T, Hamoen LW. Daptomycin inhibits cell envelope synthesis by interfering with fluid membrane microdomains. Proc Natl Acad Sci U S A. 2016 Nov 8;113(45):E7077-E7086. doi: 10.1073/pnas.1611173113. Epub 2016 Oct 24. PMID: 27791134; PMCID: PMC5111643. 2. Tantibhedhyangkul W, Wongsawat E, Matamnan S, Inthasin N, Sueasuay J, Suputtamongkol Y. Anti-Mycoplasma Activity of Daptomycin and Its Use for Mycoplasma Elimination in Cell Cultures of Rickettsiae. Antibiotics (Basel). 2019 Aug 21;8(3):123. doi: 10.3390/antibiotics8030123. PMID: 31438510; PMCID: PMC6784056. 3. Barichello T, Gonçalves JC, Generoso JS, Milioli GL, Silvestre C, Costa CS, Coelho Jda R, Comim CM, Quevedo J. Attenuation of cognitive impairment by the nonbacteriolytic antibiotic daptomycin in Wistar rats submitted to pneumococcal meningitis. BMC Neurosci. 2013 Apr 2;14:42. doi: 10.1186/1471-2202-14-42. PMID: 23548182; PMCID: PMC3616840. 4. Simonetti O, Lucarini G, Orlando F, Pierpaoli E, Ghiselli R, Provinciali M, Castelli P, Guerrieri M, Di Primio R, Offidani A, Giacometti A, Cirioni O. Role of Daptomycin on Burn Wound Healing in an Animal Methicillin-Resistant Staphylococcus aureus Infection Model. Antimicrob Agents Chemother. 2017 Aug 24;61(9):e00606-17. doi: 10.1128/AAC.00606-17. PMID: 28696234; PMCID: PMC5571319.

In vitro protocol:

In vivo protocol:

1. Barichello T, Gonçalves JC, Generoso JS, Milioli GL, Silvestre C, Costa CS, Coelho Jda R, Comim CM, Quevedo J. Attenuation of cognitive impairment by the nonbacteriolytic antibiotic daptomycin in Wistar rats submitted to pneumococcal meningitis. BMC Neurosci. 2013 Apr 2;14:42. doi: 10.1186/1471-2202-14-42. PMID: 23548182; PMCID: PMC3616840. 2. Simonetti O, Lucarini G, Orlando F, Pierpaoli E, Ghiselli R, Provinciali M, Castelli P, Guerrieri M, Di Primio R, Offidani A, Giacometti A, Cirioni O. Role of Daptomycin on Burn Wound Healing in an Animal Methicillin-Resistant Staphylococcus aureus Infection Model. Antimicrob Agents Chemother. 2017 Aug 24;61(9):e00606-17. doi: 10.1128/AAC.00606-17. PMID: 28696234; PMCID: PMC5571319.

1: Tirilomis T. Daptomycin and Its Immunomodulatory Effect: Consequences for Antibiotic Treatment of Methicillin-Resistant Staphylococcus aureus Wound Infections after Heart Surgery. Front Immunol. 2014 Mar 11;5:97. doi: 10.3389/fimmu.2014.00097. eCollection 2014. Review. PubMed PMID: 24653723; PubMed Central PMCID: PMC3949290. 2: Kelesidis T. The Interplay between Daptomycin and the Immune System. Front Immunol. 2014 Feb 12;5:52. doi: 10.3389/fimmu.2014.00052. eCollection 2014. Review. PubMed PMID: 24575098; PubMed Central PMCID: PMC3921582. 3: Humphries RM, Pollett S, Sakoulas G. A current perspective on daptomycin for the clinical microbiologist. Clin Microbiol Rev. 2013 Oct;26(4):759-80. doi: 10.1128/CMR.00030-13. Review. PubMed PMID: 24092854; PubMed Central PMCID: PMC3811228. 4: Whang DW, Miller LG, Partain NM, McKinnell JA. Systematic review and meta-analysis of linezolid and daptomycin for treatment of vancomycin-resistant enterococcal bloodstream infections. Antimicrob Agents Chemother. 2013 Oct;57(10):5013-8. doi: 10.1128/AAC.00714-13. Epub 2013 Jul 29. Review. PubMed PMID: 23896468; PubMed Central PMCID: PMC3811395. 5: Shukla BS, Gauthier TP, Correa R, Smith L, Abbo L. Treatment considerations in vancomycin-resistant enterococcal bacteremia: daptomycin or linezolid? A review. Int J Clin Pharm. 2013 Oct;35(5):697-703. doi: 10.1007/s11096-013-9825-5. Epub 2013 Jul 27. Review. PubMed PMID: 23893061. 6: Gould IM, MirÃ³ JM, Rybak MJ. Daptomycin: the role of high-dose and combination therapy for Gram-positive infections. Int J Antimicrob Agents. 2013 Sep;42(3):202-10. doi: 10.1016/j.ijantimicag.2013.05.005. Epub 2013 Jul 8. Review. PubMed PMID: 23845504. 7: Gilmore JF, Kim M, LaSalvia MT, Mahoney MV. Treatment of enterococcal peritonitis with intraperitoneal daptomycin in a vancomycin-allergic patient and a review of the literature. Perit Dial Int. 2013 Jul-Aug;33(4):353-7. doi: 10.3747/pdi.2012.00277. Review. PubMed PMID: 23843587; PubMed Central PMCID: PMC3707710. 8: Phillips J, Cardile AP, Patterson TF, Lewis JS 2nd. Daptomycin-induced acute eosinophilic pneumonia: analysis of the current data and illustrative case reports. Scand J Infect Dis. 2013 Oct;45(10):804-8. doi: 10.3109/00365548.2013.805427. Epub 2013 Jul 5. Review. PubMed PMID: 23826793. 9: Di Carlo P, D'Alessandro N, Guadagnino G, Bonura C, Mammina C, Lunetta M, Novo S, Giarratano A. High dose of trimethoprim-sulfamethoxazole and daptomycin as a therapeutic option for MRSA endocarditis with large vegetation complicated by embolic stroke: a case report and literature review. Infez Med. 2013 Mar;21(1):45-9. Review. PubMed PMID: 23524901. 10: Kanzler I, Weis F, Beiras-Fernandez A. Current use of daptomycin in cardiac surgery and postoperative intensive care. Expert Rev Anti Infect Ther. 2013 Mar;11(3):309-20. doi: 10.1586/eri.13.3. Review. PubMed PMID: 23458770.