Dalbavancin

Dalbavancin
Clinical data
Trade namesDalvance, Xydalba, others
AHFS/Drugs.comMonograph
MedlinePlusa614036
License data
Routes of
administration		Intravenous
ATC code
Legal status
Legal status
Pharmacokinetic data
Elimination half-life14.4 d[5]
Identifiers
IUPAC name
  • 2-deoxy-1-O-[(3S,15R,18R,34R,35S,38S,48R,50aR)-5,31-dichloro-38-{[3-(dimethylamino)propyl]carbamoyl}-6,11,34,40,44-pentahydroxy-42-(α-D-mannopyranosyloxy)-15-(methylamino)-2,16,36,50,51,59-hexaoxo-2,3,16,17,18,19,35,36,37,38,48,49,50,50a-tetradecahydro-1H,15H,34H-20,23:30,33-dietheno-3,18:35,48-bis(iminomethano) 4,8:10,14:25,28:43,47-tetrametheno[1,14,6,22]dioxadiazacyclooctacosino[4,5-m] [10,2,16]benzoxadiazacyclohexacosin-56-yl]-2-[(10-methylundecanoyl)amino]-β-D-glucopyranuronic acid [6]
CAS Number
PubChem CID
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.308.391
Chemical and physical data
FormulaC88H100Cl2N10O28
Molar mass1816.71 g·mol−1
3D model (JSmol)
SMILES
  • CC(C)CCCCCCCCC(=O)N[C@@H]1[C@H]([C@@H]([C@H](O[C@H]1Oc2c3cc4cc2Oc5ccc(cc5Cl)[C@H]([C@H]6C(=O)N[C@@H](c7cc(cc(c7-c8cc(ccc8O)[C@H](C(=O)N6)NC(=O)[C@@H]4NC(=O)[C@@H]9c1cc(cc(c1Cl)O)Oc1ccc(cc1O)[C@H](C(=O)N[C@H](Cc1ccc(cc1)O3)C(=O)N9)NC)O[C@@H]1[C@H]([C@H]([C@@H]([C@H](O1)CO)O)O)O)O)C(=O)NCCCN(C)C)O)C(=O)O)O)O
InChI
  • 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)124-55-23-19-42(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)123-56-24-18-41(30-53(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 N
  • Key:IZJRUXNZMRDQJI-SZUNQUCBSA-N N
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Dalbavancin, sold under the brand names Dalvance in the US and Xydalba in the EU (both by AbbVie) among others, is a second-generation lipoglycopeptide antibiotic medication. It belongs to the same class as vancomycin, the most widely used and one of the treatments available to people infected with methicillin-resistant Staphylococcus aureus (MRSA).[7]

Dalbavancin is a semisynthetic lipoglycopeptide that was designed to improve upon the natural glycopeptides vancomycin and teicoplanin.[8] It is derived from a complex of glycopeptide antibiotics, referred to as A-40926, that is produced by a new strain of Actinomadura. Dalbavancin has been referred to in the scientific literature by a series of names: MDL-63397, A-!-1, BI-397, VER-001. These different labels reflected where the research had been carried out: MDL representing Merrell-Dow-Lepetit, where the initial complex was discovered; BI referring to BioSearch Italia where Dalbavancin itself was first synthesized; VER referring to Versicor (which Biosearch Italia merged with to create Vicuron Pharmaceuticals). The phase I, II and III clinical trials were carried out of by Vicuron and the initial NDA filed. Vicuron was acquired by Pfizer in 2005, which decided to not further develop Dalbavancin at that time, subsequently selling the rights to Durata Therapeutics in 2009.

It possesses in vitro activity against a variety of Gram-positive pathogens[9][10] including MRSA and methicillin-resistant Staphylococcus epidermidis (MRSE).[11] It is a once-weekly, two-dose antibiotic, the rights to which Actavis acquired when it bought Durata Therapeutics in 2014.[12]

The U.S. Food and Drug Administration (FDA) approved dalbavancin in May 2014, for the treatment of acute bacterial skin and skin structure infections (ABSSSIs) caused by certain susceptible bacteria such as Staphylococcus aureus including methicillin-susceptible and methicillin-resistant strains of Streptococcus pyogenes, in intravenous dosage form.[13][14][15]

  1. ^ "Summary Basis of Decision (SBD) for Xydalba". Health Canada. 23 October 2014. Retrieved 29 May 2022.
  2. ^ "Drug and medical device highlights 2018: Helping you maintain and improve your health". Health Canada. 14 October 2020. Retrieved 17 April 2024.
  3. ^ "Dalvance- dalbavancin injection, powder, for solution". DailyMed. Retrieved 12 February 2022.
  4. ^ "Xydalba EPAR". European Medicines Agency. 17 September 2018. Retrieved 12 February 2022.
  5. ^ Cite error: The named reference pmid38075413 was invoked but never defined (see the help page).
  6. ^ Cite error: The named reference EMA_assessment was invoked but never defined (see the help page).
  7. ^ "Vicuron Pharmaceuticals Submits New Drug Application for Dalbavancin to U.S. Food and Drug Administration". Drugs.com.
  8. ^ Scheinfeld N (May 2006). "Dalbavancin: a review for dermatologists". Dermatology Online Journal. 12 (4): 6. doi:10.5070/D30WN7D4Q9. PMID 17083861.
  9. ^ Chen AY, Zervos MJ, Vazquez JA (May 2007). "Dalbavancin: a novel antimicrobial". International Journal of Clinical Practice. 61 (5): 853–63. doi:10.1111/j.1742-1241.2007.01318.x. PMC 1890846. PMID 17362476.
  10. ^ Das B, Sarkar C, Biswas R, Pandey S (January 2008). "Review: dalbavancin--a novel lipoglycopeptide antimicrobial for gram positive pathogens". Pakistan Journal of Pharmaceutical Sciences. 21 (1): 78–87. PMID 18166524.
  11. ^ "Dalbavancin: A Novel Lipoglycopeptide Antibacterial". Medscape.
  12. ^ UPDATE 1-Pfizer says US FDA wants more data on antibiotic. December 2007
  13. ^ Cite error: The named reference FDA PR was invoked but never defined (see the help page).
  14. ^ "Drug Approval Package: Dalvance (dalbavancin hydrochloride) Lyophilized Powder for Injection NDA #021883". U.S. Food and Drug Administration (FDA). 24 June 2014. Retrieved 21 May 2022.
  15. ^ Summary evaluation
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