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CAS No: 171500-79-1
AHFC code: 8:12.28.16
Synonyms: 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-(alpha-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-20,23:30,33-dietheno-3,18:35,48-bis(iminomethano)-1H,15H-4,8:10,14:25,28:43,47-tetrametheno-34H-(1,14,6,22)dioxadiazacyclooctacosino(4,5-m)(10,2,16)benzoxadiazacyclotetracosin-56-yl)-2-((10-methylundecanoyl)amino)-beta-D-glucopyranuronic acid (main component), A-A-1, BI 397, BI397, Dalbavancin, Dalvance, MDL 63,397, MDL 64,397, 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-N(sup 15)-methyl-, UNII-B0U42518WL, VER 001, VER001
ATC Code: J01XA04
Chemical Formula: C88-H100-Cl2-N10-O28
Molecular Weight: 1816.706
Assay/Purity: Typically NLT 98%
IUPAC: 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-
Dalbavancin is indicated for the treatment of acute bacterial skin and skin structure infections (ABSSSI) caused by the following gram-positive microorganisms: Staphylococcus aureus (including methicillin-susceptible and methicillin-resistant strains), S. pyogenes, S. agalactiae, and S. anginosus group (including S. anginosus, S. intermedius, and S. constellatus). It is administered as a 30 minute IV infusion in a two-dose regimen of 1000 mg followed by 500 mg one week later.
Mode of Action:
Dalbavancin has a spectrum and mechanism of action similar to vancomycin, a naturally formed glycopeptide antimicrobial. The bactericidal action of dalbavancin results primarily from inhibition of cell-wall biosynthesis. Specifically, dalbavancin prevents incorporation of N-acetylmuramic acid (NAM)- and N-acetylglucosamine (NAG)-peptide subunits from being incorporated into the peptidoglycan matrix; which forms the major structural component of Gram-positive cell walls. The large hydrophilic molecule is able to form hydrogen bond interactions with the terminal D-alanyl-D-alanine moieties of the NAM/NAG-peptides, which is normally a five-point interaction. Binding of dalbavancin to the D-Ala-D-Ala prevents the incorporation of the NAM/NAG-peptide subunits into the peptidoglycan matrix. In addition, dalbavancin alters bacterial-cell-membrane permeability and RNA synthesis.
Dalbavancin is not a substrate, inhibitor, or inducer of CYP450 isoenzymes. A minor hydroxy metabolite has been observed in the urine of healthy subjects.
Treatment with antibacterial agents can alter the normal flora of the colon leading to growth of C. difficile and commonly occurs in the development of C. difficile-associated diarrhea. Other common side effects include nausea, vomiting, diarrhea, headache, rash, and pruritis. Side effects that occurred in less than 2% of patients during clinical trials include blood and lymphatic system disorders, gastrointestinal disorders, hepatotoxicity, anaphylactoid reactions, hepatic enzyme elevation, hypoglycaemia, dizziness, bronchospasm, urticaria, and vascular disorders. There have been no adequate or well-controlled studies to conclude that use of dalbavancin is safe during pregnancy or breastfeeding.
Bailey J, Summers KM: Dalbavancin: a new lipoglycopeptide antibiotic. Am J Health Syst Pharm. 2008 Apr 1;65(7):599-610. PubmedBennett JW, Lewis JS, Ellis MW: Dalbavancin in the treatment of complicated skin and soft-tissue infections: a review. Ther Clin Risk Manag. 2008 Feb;4(1):31-40. PubmedBailey J, Summers KM: Dalbavancin: a new lipoglycopeptide antibiotic. Am J Health Syst Pharm. 2008 Apr 1;65(7):599-610. doi: 10.2146/ajhp070255. PubmedLeuthner 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
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