Dalbavancin Free Base
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MedKoo CAT#: 413452

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

Description: Dalbavancin Free Base is a derivative of A-40926; interferes with peptidoglycan synthesis.


Chemical Structure

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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
5.0mg USD 255.0 2 Weeks
25.0mg USD 591.0 2 Weeks
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Related CAS #: 171500-79-1 (free base)    

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

Product Data:

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/

Solubility Data

Solvent Max Conc. mg/mL Max Conc. mM
Solubility
DMSO 100.0 55.05
H2O 100.0 55.05

Preparing Stock Solutions

The following data is based on the product molecular weight 1816.71 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.

Recalculate based on batch purity %
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: 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.
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.

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1: Bouza E, Valerio M, Soriano A, Morata L, Carus EG, Rodríguez-González C, Hidalgo-Tenorio MC, Plata A, Muñoz P, Vena A; DALBUSE Study Group (Dalbavancina: Estudio de su uso clinico en España). Dalbavancin in the treatment of different gram-positive infections: a real-life experience. Int J Antimicrob Agents. 2018 Apr;51(4):571-577. doi: 10.1016/j.ijantimicag.2017.11.008. Epub 2017 Nov 24. PMID: 29180276.

2: Rappo U, Puttagunta S, Shevchenko V, Shevchenko A, Jandourek A, Gonzalez PL, Suen A, Mas Casullo V, Melnick D, Miceli R, Kovacevic M, De Bock G, Dunne MW. Dalbavancin for the Treatment of Osteomyelitis in Adult Patients: A Randomized Clinical Trial of Efficacy and Safety. Open Forum Infect Dis. 2018 Dec 10;6(1):ofy331. doi: 10.1093/ofid/ofy331. PMID: 30648126; PMCID: PMC6326511.

3: Almangour TA, Perry GK, Terriff CM, Alhifany AA, Kaye KS. Dalbavancin for the management of gram-positive osteomyelitis: Effectiveness and potential utility. Diagn Microbiol Infect Dis. 2019 Mar;93(3):213-218. doi: 10.1016/j.diagmicrobio.2018.10.007. Epub 2018 Oct 16. PMID: 30396697.

4: Lampejo T. Dalbavancin and telavancin in the treatment of infective endocarditis: a literature review. Int J Antimicrob Agents. 2020 Sep;56(3):106072. doi: 10.1016/j.ijantimicag.2020.106072. Epub 2020 Jul 3. PMID: 32629114.

5: Bork JT, Heil EL, Berry S, Lopes E, Davé R, Gilliam BL, Amoroso A. Dalbavancin Use in Vulnerable Patients Receiving Outpatient Parenteral Antibiotic Therapy for Invasive Gram-Positive Infections. Infect Dis Ther. 2019 Jun;8(2):171-184. doi: 10.1007/s40121-019-0247-0. Epub 2019 May 3. PMID: 31054088; PMCID: PMC6522607.

6: Tobudic S, Thalhammer F. Dalbavancin Dosage. Clin Infect Dis. 2019 Apr 24;68(9):1608. doi: 10.1093/cid/ciy941. PMID: 30380040.

7: Anderson VR, Keating GM. Dalbavancin. Drugs. 2008;68(5):639-48; discussion 649-51. doi: 10.2165/00003495-200868050-00006. PMID: 18370443.

8: Wunsch S, Krause R, Valentin T, Prattes J, Janata O, Lenger A, Bellmann- Weiler R, Weiss G, Zollner-Schwetz I. Multicenter clinical experience of real life Dalbavancin use in gram-positive infections. Int J Infect Dis. 2019 Apr;81:210-214. doi: 10.1016/j.ijid.2019.02.013. Epub 2019 Feb 19. PMID: 30794940.

9: Tobudic S, Forstner C, Burgmann H, Lagler H, Ramharter M, Steininger C, Vossen MG, Winkler S, Thalhammer F. Dalbavancin as Primary and Sequential Treatment for Gram-Positive Infective Endocarditis: 2-Year Experience at the General Hospital of Vienna. Clin Infect Dis. 2018 Aug 16;67(5):795-798. doi: 10.1093/cid/ciy279. PMID: 29659732.

10: Wang Y, Wang J, Wang R, Li Y, Cai Y. Efficacy and safety of dalbavancin in the treatment of Gram-positive bacterial infections. J Glob Antimicrob Resist. 2020 Dec 3;24:72-80. doi: 10.1016/j.jgar.2020.11.018. Epub ahead of print. PMID: 33279683.