Dalbavancin HCl
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MedKoo CAT#: 317136

CAS#: Unknown

Description: 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

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Dalbavancin HCl
CAS# Unknown

Theoretical Analysis

MedKoo Cat#: 317136
Name: Dalbavancin HCl
CAS#: Unknown
Chemical Formula: C88H101Cl3N10O28
Exact Mass:
Molecular Weight: 1853.17
Elemental Analysis: C, 57.04; H, 5.49; Cl, 5.74; N, 7.56; O, 24.17

Price and Availability

Size Price Availability Quantity
5.0mg USD 250.0 Same day
10.0mg USD 450.0 Same day
25.0mg USD 650.0 Same day
50.0mg USD 850.0 Same day
100.0mg USD 1450.0 Same day
200.0mg USD 2250.0 Same day
500.0mg USD 3250.0 Same day
1.0g USD 4950.0 2 Weeks
2.0g USD 7950.0 2 Weeks
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Related CAS #: 171500-79-1 (free base)  

Synonym: A-A 1; BI397; BI-397; BI 397; VER 001; VER-001; VER001; MDL63397; MDL-63397; MDL 63397; Dalbavancin. Dalbavancin B0; trade name: Dalvance in the US and Xydalba in Europe.

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]​-​β-​D-​glucopyranuronosyl]​-​38-​[[[3-​(dimethylamino)​propyl]​amino]​carbonyl]​-​42-​O-​α-​D-​mannopyranosyl-​N15-​methyl-

InChi Key: PEXPCJWLNBNBNT-AXKGEONOSA-N

InChi Code: InChI=1S/C88H100Cl2N10O28.ClH/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);1H/t51-,60-,64-,65-,66-,67+,68+,69+,70-,71-,72-,73-,74+,75+,76+,78+,87-,88+;/m1./s1

SMILES Code: CC(CCCCCCCCC(N[C@@H]1[C@@H](O)[C@H](O)[C@@H](C(O)=O)O[C@H]1OC2=C3C=C4C=C2OC5=C(Cl)C=C([C@@H](O)[C@H]6C(N[C@H](C(NCCCN(C)C)=O)C7=CC(O)=CC(O[C@@H]8[C@@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O8)=C7C9=C(O)C=CC([C@@H](NC([C@@H]4NC([C@@H]%10C%11=CC(OC%12=C(O)C=CC([C@@H](NC)C(N[C@@H](C(N%10)=O)CC%13=CC=C(C=C%13)O3)=O)=C%12)=CC(O)=C%11Cl)=O)=O)C(N6)=O)=C9)=O)C=C5)=O)C.Cl

Appearance: Off-white solid powder

Purity: >90% (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, not in water

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

Biological target: Dalbavancin hydrochloride (MDL-63397 hydrochloride) is a semisynthetic lipoglycopeptide antibiotic with potent bactericidal activity against Gram-positive bacteria.
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
Water 50.0 26.98
DMSO 24.0 12.95

Preparing Stock Solutions

The following data is based on the product molecular weight 1853.17 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. 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. 2. 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.

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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.



Additional Information

Dalbavancin is a lipoglycopeptide belonging in the same glycopeptide class as vancomycin. Similar to other glycopeptides, dalbavancin exerts its bactericidal effect by disrupting cell wall biosynthesis. It binds to the D-alanyl-D-alanyl residue on growing peptidoglycan chains and prevents transpeptidation from occurring, preventing peptidoglycan elongation and cell wall formation. Dalbavancin also dimerizes and anchors itself in the lipophilic bacterial membrane, thereby increasing its stability in the target environment and its affinity for peptidoglycan. Antimicrobial activity correlates with the ratio of area under the concentration-time curve to minimum inhibitory concentration for Staphylococcus aureus.

Dalbavancin free base:
Chemical Formula: C88H100Cl2N10O28
Exact Mass: 1814.60856
Molecular Weight: 1816.71000
Elemental Analysis: C, 58.18; H, 5.55; Cl, 3.90; N, 7.71; O, 24.66