dalbavancin

Also known as MDL-64397, A-A-1, VERO001, BI-397, 5,31-dichloro-38-de(methoxycarbonyl)-7-demethyl-19-deoxy-56-O [2-deoxy-2-[(10-methylundecanoyl)amino]-β-D-glucopyranuronosyl]-38-[[3-(dimethylamino)propyl] carbamoyl]-42-O-α-D-mannopyranosyl-15-N-methyl(ristomycin A aglycone) hydrochloride, dalbavancin B0, Zeven, BI 397

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).

Chemical data

Formula: C88H100Cl2N10O28
Molecular weight: 1816.7 g/mol
IUPAC name: (2S,3S,4R,5R,6S)-6-[[(1S,2R,19R,22R,34S,37R,40R,52S)-5,32-dichloro-52-[3-(dimethylamino)propylcarbamoyl]-2,26,31,44,49-pentahydroxy-22-(methylamino)-21,35,38,54,56,59-hexaoxo-47-[(2R,3S,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-7,13,28-trioxa-20,36,39,53,55,58-hexazaundecacyclo[38.14.2.23,6.214,17.219,34.18,12.123,27.129,33.141,45.010,37.046,51]hexahexaconta-3,5,8,10,12(64),14(63),15,17(62),23(61),24,26,29(60),30,32,41(57),42,44,46(51),47,49,65-henicosaen-64-yl]oxy]-3,4-dihydroxy-5-(10-methylundecanoylamino)oxane-2-carboxylic acid
SMILES: CC(C)CCCCCCCCC(=O)N[C@@H]1[C@H]([C@@H]([C@H](O[C@H]1OC2=C3C=C4C=C2OC5=C(C=C(C=C5)[C@H]([C@H]6C(=O)N[C@@H](C7=C(C(=CC(=C7)O)O[C@@H]8[C@H]([C@H]([C@@H]([C@H](O8)CO)O)O)O)C9=C(C=CC(=C9)[C@H](C(=O)N6)NC(=O)[C@@H]4NC(=O)[C@@H]1C2=C(C(=CC(=C2)OC2=C(C=CC(=C2)[C@H](C(=O)N[C@H](CC2=CC=C(O3)C=C2)C(=O)N1)NC)O)O)Cl)O)C(=O)NCCCN(C)C)O)Cl)C(=O)O)O)O
InChIKey: KGPGQDLTDHGEGT-SZUNQUCBSA-N
XLogP: 3.8
Polar surface area: 573 Å²
H-bond donors: 21
H-bond acceptors: 30
Formal charge: 0

via PubChem

Drug data · ChEMBL

Max clinical phase: Approved
Molecule type: Protein
First approval: 2014
Admin. routes: parenteral
Indications: osteomyelitis, pneumonia, bacteriemia, bacterial disease

via ChEMBL · EBI

Research

886 papers

Clinical Pharmacokinetics and Pharmacodynamics of Dalbavancin.Clinical pharmacokinetics · 2022
Dalbavancin as sequential therapy for infective endocarditis due to Gram-positive organisms: a review.International journal of antimicrobial agents · 2023
Dalbavancin.Revista espanola de quimioterapia : publicacion oficial de la Sociedad Espanola de Quimioterapia · 2021
A systematic review of dalbavancin efficacy as a sequential therapy for infective endocarditis.Infection · 2025
Dalbavancin.Drugs · 2008

via PubMed

Wikidata facts

Mass: 1814.609
Has use: medication

Show 7 more facts

chemical formula: C₈₈H₁₀₀Cl₂N₁₀O₂₈
isomeric SMILES: CC(C)CCCCCCCCC(=O)N[C@@H]1[C@H]([C@@H]([C@H](O[C@H]1OC2=C3C=C4C=C2OC5=C(C=C(C=C5)[C@H]([C@H]6C(=O)N[C@@H](C7=CC(=CC(=C7C8=C(C=CC(=C8)[C@H](C(=O)N6)NC(=O)[C@@H]4NC(=O)[C@@H]9C1=CC(=CC(=C1Cl)O)OC1=C(C=CC(=C1)[C@H](C(=O)N[C@H](CC1=CC=C(O3)C=C1)C(=O)N9)NC)O)O)O[C@@H]1[C@H]([C@H]([C@@H]([C@H](O1)CO)O)O)O)O)C(=O)NCCCN(C)C)O)Cl)C(=O)O)O)O
canonical SMILES: CC(C)CCCCCCCCC(=O)NC1C(C(C(OC1OC2=C3C=C4C=C2OC5=C(C=C(C=C5)C(C6C(=O)NC(C7=CC(=CC(=C7C8=C(C=CC(=C8)C(C(=O)N6)NC(=O)C4NC(=O)C9C1=CC(=CC(=C1Cl)O)OC1=C(C=CC(=C1)C(C(=O)NC(CC1=CC=C(O3)C=C1)C(=O)N9)NC)O)O)OC1C(C(C(C(O1)CO)O)O)O)O)C(=O)NCCCN(C)C)O)Cl)C(=O)O)O)O
World Health Organisation international non-proprietary name: dalbavancin
defined daily dose: 1.5
subject has role: bactericide
medical condition treated: cellulitis

Sources (4)

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Encyclopedic overview

10 sections

Contents

Medical uses
Contraindications
Side effects
Drug interactions
Pregnancy and lactation
Production and composition
Mechanism of action
Metabolism
History
References

{{Drugbox | Verifiedfields = changed | Watchedfields = changed | verifiedrevid = 385028149 | image = Dalbavancin_B0.svg | image_class = skin-invert-image | alt =

Excerpted from Wikipedia’s “dalbavancin” article, available under the CC BY-SA 4.0 licence.

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