Dalbavancin HCl
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MedKoo CAT#: 317136

CAS#: 171500-79-1 (free base), CAS# of Dalbavancin HCl salt is 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).


Price and Availability

Size
Price

2mg
USD 90
10mg
USD 450
100mg
USD 1450
1g
USD 4950
Size
Price

3mg
USD 150
25mg
USD 650
200mg
USD 2250
2g
USD 6950
Size
Price

5mg
USD 250
50mg
USD 850
500mg
USD 3250
5g
Ask price

Dalbavancin HCl, purity > 90%, is in stock. Same day shipping after order is recieved. Shipping out time for order > 200mg is about 2 weeks.


Chemical Structure

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Theoretical Analysis

MedKoo Cat#: 317136
Name: Dalbavancin HCl
CAS#: 171500-79-1 (free base), CAS# of Dalbavancin HCl salt is 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


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


Technical Data

Appearance:
Off-white solid powder

Purity:
>90% (or refer to the Certificate of Analysis)

Certificate of Analysis:

Safety Data Sheet (MSDS):

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).

Harmonized System Code:
293490


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


References

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.