Dalbavancin Free Base | CAS# 171500-79-1 (free base) | Antibiotic

MedKoo Cat#: 413452 | Name: Dalbavancin Free Base

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Description:

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

Dalbavancin Free Base is a derivative of A-40926; interferes with peptidoglycan synthesis. Dalbavancin is a novel second-generation lipoglycopeptide antibiotic. It belongs to the same class as vancomycin, the most widely used and one of the few treatments available to patients infected with methicillin-resistant Staphylococcus aureus (MRSA). Dalbavancin is a semisynthetic lipoglycopeptide that was designed to improve upon the natural glycopeptides currently available, vancomycin and teicoplanin. It possesses in vitro activity against a variety of Gram-positive pathogens including MRSA and methicillin-resistant Staphylococcus epidermidis (MRSE).

Chemical Structure

Dalbavancin Free Base

CAS#171500-79-1 (free base)

Theoretical Analysis

MedKoo Cat#: 413452

Name: Dalbavancin Free Base

CAS#: 171500-79-1 (free base)

Chemical Formula: C88H100Cl2N10O28

Exact Mass: 1814.6086

Molecular Weight: 1816.71

Elemental Analysis: C, 58.18; H, 5.55; Cl, 3.90; N, 7.71; O, 24.66

Price and Availability

Size	Price	Availability	Quantity
10mg	USD 350.00	2 Weeks
25mg	USD 700.00	2 Weeks

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Related CAS #

171500-79-1 (free base) Dalbavancin HCl

Synonym

Dalbavancin Free Base; BI397; BI-397; BI 397

IUPAC/Chemical Name

Ristomycin A aglycone, 5,31-dichloro-38-de(methoxycarbonyl)-7-demethyl-19-deoxy-56-O-(2-deoxy-2-((10-methyl-1-oxoundecyl)amino)-beta-D-glucopyranuronosyl)-38-(((3-(dimethylamino)propyl)amino)carbonyl)-42-O-alpha-D-mannopyranosyl-N15-methyl-

InChi Key

KGPGQDLTDHGEGT-SZUNQUCBSA-N

InChi Code

InChI=1S/C88H100Cl2N10O28/c1-38(2)13-10-8-6-7-9-11-14-61(106)94-70-73(109)75(111)78(86(120)121)128-87(70)127-77-58-31-43-32-59(77)124-55-24-19-42(29-50(55)89)71(107)69-85(119)98-67(80(114)92-25-12-26-100(4)5)48-33-44(102)34-57(125-88-76(112)74(110)72(108)60(37-101)126-88)62(48)47-28-40(17-22-52(47)103)65(82(116)99-69)95-83(117)66(43)96-84(118)68-49-35-46(36-54(105)63(49)90)123-56-30-41(18-23-53(56)104)64(91-3)81(115)93-51(79(113)97-68)27-39-15-20-45(122-58)21-16-39/h15-24,28-36,38,51,60,64-76,78,87-88,91,101-105,107-112H,6-14,25-27,37H2,1-5H3,(H,92,114)(H,93,115)(H,94,106)(H,95,117)(H,96,118)(H,97,113)(H,98,119)(H,99,116)(H,120,121)/t51-,60-,64-,65-,66-,67+,68+,69+,70-,71-,72-,73-,74+,75+,76+,78+,87-,88+/m1/s1

SMILES Code

CN[C@H]1C(N[C@@H]2Cc3ccc(Oc4c(O[C@@H]5O[C@H](C(O)=O)[C@H]([C@@H]([C@H]5NC(CCCCCCCCC(C)C)=O)O)O)c(Oc6c(Cl)cc([C@H]([C@@H]7NC([C@@H](c8cc(c9c([C@@H](C(NCCCN(C)C)=O)NC7=O)cc(O)cc9O[C@H]%10O[C@@H]([C@H]([C@@H]([C@@H]%10O)O)O)CO)c(O)cc8)NC([C@@H]%11NC([C@H](c%12c(Cl)c(O)cc(Oc%13c(O)ccc1c%13)c%12)NC2=O)=O)=O)=O)O)cc6)cc%11c4)cc3)=O

Appearance

Solid powder

Purity

>98% (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

Instruction

View handling instruction

Biological target:

Dalbavancin (MDL-63397) is a semisynthetic lipoglycopeptide antibiotic with potent bactericidal activity against Gram-positive bacteria that inhibits Staphylococcus aureus and Bacillus anthracis with MIC90s of 0.06 μg/mL and 0.25 μg/mL, respectively.

In vitro activity:

Dalbavancin showed potent in vitro activity against S. aureus (MIC range < 0.007–0.125 mg/L), with MIC50/MIC90 values within the susceptibility breakpoints. Remarkably, its activity was retained against the most refractory MDR-MRSA isolates belonging to the major MRSA clones: ST228-SCCmec I, ST8-SCCmec IV, ST239-SCCmec III, ST5-SCCmec II, and ST22-SCCmec-IVh. Dalbavancin also demonstrated activity against DNS isolates, making it a valuable tool against these periodically reported strains. Reference: Antibiotics (Basel). 2020 Dec 3;9(12):865. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7761838/

In vivo activity:

Mice infected with SARS-CoV-2 displayed transient infection and viral replication, but little virus was found at 72 hpi. At 24 hpi and 72 hpi, the viral load in the lungs of the control group was ~107 and ~105 copies/μg total RNA, respectively, whereas that in mice treated with a single dose of dalbavancin (130 mg/kg intraperitoneal administration at day 0) decreased to ~103 and ~102 copies, respectively (Fig. 4a). Thus, dalbavancin administration almost completely inhibited viral replication. Histopathological examination of the lungs indicated that most of mice in the control group showed typical interstitial pneumonia, characterized by infiltration of significant macrophages and lymphocytes into the alveolar interstitium, and accumulation of macrophages in alveolar cavities. In contrast, dalbavancin administration showed significant protective effects and prevented histopathological injuries caused by virus infection, with only mild histopathological injuries (Fig. 4b). Viral infection caused a decrease in mouse body weight, while dalbavancin administration rescued this decrease (Fig. 4c), with little effect on body temperature (Supplementary information, Fig. S2). Reference: Cell Res. 2021 Jan;31(1):17-24. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7705431/

	Solvent	mg/mL	mM
Solubility
	DMSO	100.0	55.05
	H2O	100.0	55.05

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 1,816.71 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. Neudorfer K, Schmidt-Malan SM, Patel R. Dalbavancin is active in vitro against biofilms formed by dalbavancin-susceptible enterococci. Diagn Microbiol Infect Dis. 2018 Jan;90(1):58-63. doi: 10.1016/j.diagmicrobio.2017.09.015. Epub 2017 Sep 27. PMID: 29195766. 2. Bongiorno D, Lazzaro LM, Stefani S, Campanile F. In Vitro Activity of Dalbavancin against Refractory Multidrug-Resistant (MDR) Staphylococcus aureus Isolates. Antibiotics (Basel). 2020 Dec 3;9(12):865. doi: 10.3390/antibiotics9120865. PMID: 33287376; PMCID: PMC7761838. 3. Wang G, Yang ML, Duan ZL, Liu FL, Jin L, Long CB, Zhang M, Tang XP, Xu L, Li YC, Kamau PM, Yang L, Liu HQ, Xu JW, Chen JK, Zheng YT, Peng XZ, Lai R. Dalbavancin binds ACE2 to block its interaction with SARS-CoV-2 spike protein and is effective in inhibiting SARS-CoV-2 infection in animal models. Cell Res. 2021 Jan;31(1):17-24. doi: 10.1038/s41422-020-00450-0. Epub 2020 Dec 1. PMID: 33262453; PMCID: PMC7705431. 4. Silva V, Antão HS, Guimarães J, Prada J, Pires I, Martins Â, Maltez L, Pereira JE, Capelo JL, Igrejas G, Poeta P. Efficacy of dalbavancin against MRSA biofilms in a rat model of orthopaedic implant-associated infection. J Antimicrob Chemother. 2020 Aug 1;75(8):2182-2187. doi: 10.1093/jac/dkaa163. PMID: 32417903.

In vitro protocol:

In vivo protocol:

1. Silva V, Antão HS, Guimarães J, Prada J, Pires I, Martins Â, Maltez L, Pereira JE, Capelo JL, Igrejas G, Poeta P. Efficacy of dalbavancin against MRSA biofilms in a rat model of orthopaedic implant-associated infection. J Antimicrob Chemother. 2020 Aug 1;75(8):2182-2187. doi: 10.1093/jac/dkaa163. PMID: 32417903. 2. Wang G, Yang ML, Duan ZL, Liu FL, Jin L, Long CB, Zhang M, Tang XP, Xu L, Li YC, Kamau PM, Yang L, Liu HQ, Xu JW, Chen JK, Zheng YT, Peng XZ, Lai R. Dalbavancin binds ACE2 to block its interaction with SARS-CoV-2 spike protein and is effective in inhibiting SARS-CoV-2 infection in animal models. Cell Res. 2021 Jan;31(1):17-24. doi: 10.1038/s41422-020-00450-0. Epub 2020 Dec 1. PMID: 33262453; PMCID: PMC7705431.

1: Scoble PJ, Owens RC Jr, Puttagunta S, Yen M, Dunne MW. Pharmacokinetics, Safety, and Tolerability of a Single 500-mg or 1000-mg Intravenous Dose of Dalbavancin in Healthy Japanese Subjects. Clin Drug Investig. 2015 Oct 12. [Epub ahead of print] PubMed PMID: 26458939. 2: Mendes RE, Castanheira M, Farrell DJ, Flamm RK, Sader HS, Jones RN. Update on dalbavancin activity tested against Gram-positive clinical isolates responsible for documented skin and skin-structure infections in US and European hospitals (2011-13). J Antimicrob Chemother. 2015 Oct 7. pii: dkv303. [Epub ahead of print] PubMed PMID: 26451012. 3: Lepak A, Marchillo K, VanHecker J, Andes D. Impact of Glycopeptide Resistance in Staphylococcus aureus on the Dalbavancin In Vivo Pharmacodynamic Target. Antimicrob Agents Chemother. 2015 Sep 21. pii: AAC.01717-15. [Epub ahead of print] PubMed PMID: 26392492. 4: Koeth LM, DiFranco-Fisher JM, McCurdy S. A Reference Broth Microdilution Method for Dalbavancin In Vitro Susceptibility Testing of Bacteria that Grow Aerobically. J Vis Exp. 2015 Sep 9;(103). doi: 10.3791/53028. PubMed PMID: 26381422. 5: Smith JR, Roberts KD, Rybak MJ. Dalbavancin: A Novel Lipoglycopeptide Antibiotic with Extended Activity Against Gram-Positive Infections. Infect Dis Ther. 2015 Sep;4(3):245-58. doi: 10.1007/s40121-015-0077-7. Epub 2015 Sep 4. PubMed PMID: 26341488; PubMed Central PMCID: PMC4575294. 6: Ramdeen S, Boucher HW. Dalbavancin for the treatment of acute bacterial skin and skin structure infections. Expert Opin Pharmacother. 2015;16(13):2073-81. Epub 2015 Aug 4. PubMed PMID: 26239321; PubMed Central PMCID: PMC4600683. 7: Cho JC, Estrada SJ, Beltran AJ, Revuelta MP. Treatment of methicillin-sensitive Staphylococcus aureus bacteremia secondary to septic phlebitis using dalbavancin. J Clin Pharm Ther. 2015 Jul 16. doi: 10.1111/jcpt.12306. [Epub ahead of print] PubMed PMID: 26183753. 8: Scott LJ. Dalbavancin: A Review in Acute Bacterial Skin and Skin Structure Infections. Drugs. 2015 Jul;75(11):1281-91. doi: 10.1007/s40265-015-0430-x. PubMed PMID: 26105117. 9: McCurdy SP, Jones RN, Mendes RE, Puttagunta S, Dunne MW. In Vitro Activity of Dalbavancin against Drug-Resistant Staphylococcus aureus Isolates from a Global Surveillance Program. Antimicrob Agents Chemother. 2015 Aug;59(8):5007-9. doi: 10.1128/AAC.00274-15. Epub 2015 May 18. PubMed PMID: 25987636; PubMed Central PMCID: PMC4505194. 10: Dunne MW, Sahm D, Puttagunta S. Use of vancomycin as a surrogate for dalbavancin in vitro susceptibility testing: results from the DISCOVER studies. Ann Clin Microbiol Antimicrob. 2015 Apr 2;14:19. doi: 10.1186/s12941-015-0081-5. PubMed PMID: 25885674; PubMed Central PMCID: PMC4389583. 11: Gupta AK, Foley KA, Abramovits W, Rosen T. Dalbavancin (Dalvance) for the treatment of acute bacterial skin infection. Skinmed. 2014 Nov-Dec;12(6):366-9. PubMed PMID: 25823083. 12: Jones RN, Farrell DJ, Flamm RK, Sader HS, Dunne MW, Mendes RE. Surrogate analysis of vancomycin to predict susceptible categorization of dalbavancin. Diagn Microbiol Infect Dis. 2015 May;82(1):73-7. doi: 10.1016/j.diagmicrobio.2015.01.017. Epub 2015 Feb 7. PubMed PMID: 25724854. 13: Dunne MW, Zhou M, Darpo B. A thorough QT study with dalbavancin: a novel lipoglycopeptide antibiotic for the treatment of acute bacterial skin and skin-structure infections. Int J Antimicrob Agents. 2015 Apr;45(4):393-8. doi: 10.1016/j.ijantimicag.2014.12.021. Epub 2015 Jan 22. PubMed PMID: 25681068. 14: Leuthner KD, Yuen A, Mao Y, Rahbar A. Dalbavancin (BI-387) for the treatment of complicated skin and skin structure infection. Expert Rev Anti Infect Ther. 2015 Feb;13(2):149-59. doi: 10.1586/14787210.2015.995633. PubMed PMID: 25578881. 15: Dunne MW, Puttagunta S, Sprenger CR, Rubino C, Van Wart S, Baldassarre J. Extended-duration dosing and distribution of dalbavancin into bone and articular tissue. Antimicrob Agents Chemother. 2015 Apr;59(4):1849-55. doi: 10.1128/AAC.04550-14. Epub 2015 Jan 5. PubMed PMID: 25561338; PubMed Central PMCID: PMC4356775. 16: Bradley JS, Puttagunta S, Rubino CM, Blumer JL, Dunne M, Sullivan JE. Pharmacokinetics, Safety and Tolerability of Single Dose Dalbavancin in Children 12-17 Years of Age. Pediatr Infect Dis J. 2015 Jul;34(7):748-52. doi: 10.1097/INF.0000000000000646. PubMed PMID: 25551831. 17: Cada DJ, Ingram K, Baker DE. Dalbavancin. Hosp Pharm. 2014 Oct;49(9):851-61. doi: 10.1310/hpj4909-851. PubMed PMID: 25477617; PubMed Central PMCID: PMC4252189. 18: Hussar DA, Nguyen A. Dalbavancin, tedizolid phosphate, oritavancin diphosphate, and vedolizumab. J Am Pharm Assoc (2003). 2014 Nov-Dec;54(6):658-62. doi: 10.1331/JAPhA.2014.14543. PubMed PMID: 25379985. 19: Zervou FN, Zacharioudakis IM, Mylonakis E. Weekly dalbavancin was noninferior to daily vancomycin for acute bacterial skin infection in adults. Ann Intern Med. 2014 Oct 21;161(8):JC9. doi: 10.7326/0003-4819-161-8-201410210-02009. PubMed PMID: 25329226. 20: Corey GR, Jiang H, Moeck G. Dalbavancin or oritavancin for skin infections. N Engl J Med. 2014 Sep 18;371(12):1162-3. PubMed PMID: 25243251.