description a new lipoglycopeptide Mechanisms of action Side effects FDA approves Dalvance to treat skin infections Drug–drug interactions Drugbank Description
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Dalbavancin

description a new lipoglycopeptide Mechanisms of action Side effects FDA approves Dalvance to treat skin infections Drug–drug interactions Drugbank Description
Dalbavancin Structure
Dalbavancin
  • CAS No.171500-79-1
  • Chemical Name:Dalbavancin
  • CBNumber:CB41028737
  • Molecular Formula:C88H100Cl2N10O28
  • Formula Weight:1816.71
  • MOL File:171500-79-1.mol
Dalbavancin Property
  • Melting point >160°C (dec.)
  • Density 1.59
  • storage temp. -20°C
  • solubility Aqueous Base (Slightly), DMSO (Slightly, Heated), Water (Slightly)
  • form powder
  • pka 2.73±0.70(Predicted)
  • color white to beige
  • Water Solubility H2O: 2mg/mL, clear
  • FDA UNII DALBAVANCIN (808UI9MS5K)
    DALBAVANCIN B0 (B0U42518WL)
  • NCI Drug Dictionary dalbavancin
  • ATC code J01XA04
  • UNSPSC Code 12352200
  • NACRES NA.77
Hazard and Precautionary Statements (GHS)
  • Symbol(GHS)
  • Signal wordWarning
  • Hazard statements H315-H319-H335
  • Precautionary statements P261-P305+P351+P338
Dalbavancin Price More Price(1)
  • Brand: Sigma-Aldrich(India)
  • Product number: SML2378
  • Product name : Dalbavancin
  • Purity: ≥90% (HPLC)
  • Packaging: 5MG
  • Price: ₹7826.48
  • Updated: 2022/06/14
  • Buy: Buy

Dalbavancin Chemical Properties,Usage,Production

  • description Dalbavancin is a second generation, semi-synthetic lipoglycopeptide antibiotic that is active against gram-positive pathogens with a MIC90for Staphylococcus aureus of 0.06 μg/mL. Dalbavancin possesses more potent in vitro bactericidal activity than vancomycin or teicoplanin against many resistant Gram-positive organisms such as MRSA. Dalbavanacin displays prolonged terminal half-life in adults.Compared to existing glycopeptides anti-MRSA(Methicillin-Resistant Staphylococcus Aureus) antibiotics, it has better antibiotic strength and, because it only needs to be taken once a week, it will be easier for both patients and medical care providers. It also offers stable absorption and metabolism for patients with light to moderate kidney and liver dysfunction. We know that its interactions with other medications are extremely small, and it is proving to be very safe in clinical trials.

    Dalbavancin is specifically indicated for the treatment of adult patients with acute bacterial skin and skin structure infections (ABSSSI) caused by susceptible isolates of the following Gram-positive microorganisms: Staphylococcus aureus (including methicillin­susceptible and methicillin-resistant strains), Streptococcus pyogenes, Streptococcus agalactiae and Streptococcus anginosus group (including S. anginosus, S. intermedius, S. constellatus).

    Class    Glycopeptide anti-MRSA antibiotic
    Mechanism of Action    Cell Wall Peptidoglycan Synthesis Inhibitor
    Target Indication    MRSA Infections
  • a new lipoglycopeptide Dalbavancin is a new lipoglycopeptide that is active against Gram-positive pathogens, including methicillin-resistant Staphylococcus aureus. It has a half-life of 14.4 days, permitting intravenous treatment of acute bacterial skin and skin structure infections without the need for daily dosing.
    Dalbavancin was approved in 2014 by regulatory agencies in the United States (USA) and Europe for the treatment of skin and skin structure infections. The activity of dalbavancin was also widely assessed against Streptococcus pneumoniae clinical isolates collected from patients on six continents monitored during two time intervals (2011-2013 and 2014). A total of 18,186 pneumococci were obtained from 49 nations and submitted to a monitoring laboratory as part of the SENTRY Antimicrobial Surveillance Program for reference susceptibility testing. Dalbavancin potency against S. pneumoniae was consistent across the monitored years with a MIC50/90 of 0.015/0.03 μg/ml and all isolates were inhibited at ≤ 0.12 μg/ml. The activity for dalbavancin was not adversely influenced by non-susceptibility to β-lactams (ceftriaxone or penicillin), macrolides, clindamycin, fluoroquinolones, tetracyclines or multidrug-resistance (MDR). Regional variations of dalbavancin activity was not detected, but S. pneumoniae isolated in the Asia-Pacific region were more likely to be non-susceptible to penicillin and ceftriaxone as well as being MDR, compared to North or South America and Europe. Direct comparisons of potency illustrated dalbavancin (MIC50/90 of 0.015/0.03 μg/ml) to be 16-fold or more active than vancomycin (MIC50, 0.25 μg/ml), linezolid (MIC50, 1 μg/ml), levofloxacin (MIC50, 1 μg/ml), ceftriaxone (MIC90, 1 μg/ml), and penicillin (MIC90, 2 μg/ml). In conclusion, dalbavancin had potent and consistent activity against this contemporary (2011-2014) collection of S. pneumoniae isolates.
  • Mechanisms of action Dalbavancin is characterised as a second-generation bactericidal glycopeptide. Other examples of the glycopeptide class include vancomycin, teicoplanin, oritavancin (formerly LY-333328) and telavancin (formerly TD-6424). Like other glycopeptides, dalbavancin's mechanism of action involves the formation of a complex with the C-terminal d-alanyl-d-alanine of growing peptidoglycan chains, thereby inhibiting bacterial cell wall biosynthesis. In addition, dalbavancin appears to have the unique ability to dimerise and anchor its lipophilic side chain in the bacterial membranes. This is hypothesised to increase the affinity of dalbavancin for its target and to increase its antimicrobial potency. Consequently, dalbavancin possesses more potent in vitro bactericidal activity than vancomycin or teicoplanin against many resistant Gram-positive organisms such as MRSA.
    Originally developed by Vicuron Pharmaceuticals Inc., (Fremont, CA, USA) dalbavancin (Figure 1) was chemically derived from parent compound A-40926, a naturally occurring teicoplanin-like glycopeptide produced by the actinomycete Nonomuria spp. Modifications of the parent compound included derivatization of functional groups such as the C-terminus and N-terminus of the peptide, removal of sugars and the addition of acyl moieties.
  • Side effects Adverse effects associated with the use of Dalbavancin(Dalvance) may include, but are not limited to, the following:
    • nausea (4.7%)
    • headache (3.8%)
    • diarrhea (3.4%)
  • FDA approves Dalvance to treat skin infections May 23, 2014,The U.S. Food and Drug Administration approved Dalvance (dalbavancin), a new antibacterial drug used to treat adults with skin infections.
    Dalvance is intended to treat acute bacterial skin and skin structure infections (ABSSSI) caused by certain susceptible bacteria like Staphylococcus aureus (including methicillin-susceptible and methicillin-resistant strains) and Streptococcus pyogenes. The treatment is administered intravenously.
    Dalvance is the first drug designated as a Qualified Infectious Disease Product (QIDP) to receive FDA approval. Under the Generating Antibiotic Incentives Now (GAIN) title of the FDA Safety and Innovation Act, Dalvance was granted QIDP designation because it is an antibacterial or antifungal human drug intended to treat serious or life-threatening infections.
  • Drug–drug interactions Dalbavancin does not appear to be metabolised by the cytochrome P450 enzyme system. The administration of cytochrome P450 substrates, inhibitors or inducers do not affect dalbavancin's clearance rates. No drug–drug interactions have been identified. Furthermore, it is unknown whether dalbavancin has any cross-reactivity with glycopeptides as patients with a history of hypersensitivity have been excluded from these clinical trials. Recently, the in vitro drug interaction between dalbavancin in combination with nine different antimicrobial agents (clindamycin, daptomycin, gentamicin, levofloxacin, linezolid, oxacillin, quinupristin/dalfopristin, rifampin and vancomycin) was evaluated for either synergistic or antagonistic interactions. Antagonism was not observed between dalbavancin and any of the nine antimicrobials tested. In addition, there was no evidence of synergy observed between gentamicin and dalbavancin. However, dalbavancin and oxacillin appear to have some degree of synergy or partial synergy against staphylococci, including methicillin-resistant strains, VISA and enterococci. Further testing is needed to determine the clinical significance of these findings.
    References: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC1890846/
  • Drugbank Description Dalbavancin is a second-generation lipoglycopeptide antibiotic that was designed to improve on the natural glycopeptides currently available, such as vancomycin and teicoplanin. Modifications from these older glycoprotein classes allowed a similar mechanism of action with increased activity and once weekly dosing. Its use 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). Dalbavancin acts by interfering with cell wall synthesis by binding to the D-alanyl-D-alanine terminus of nascent cell wall peptidoglycan and preventing cross-linking.
    References: http://www.drugbank.ca/drugs/DB06219
  • Uses Dalbavancin is a second-generation lipoglycopeptide antibiotic. It is a semisynthetic lipoglycopeptide that was designed to improve upon the natural glycopeptides currently available, vancomycin and teicoplanin.
  • Uses Dalbavancin is a semi-synthetic glycopeptide prepared from A40926 by introducing a positively charged lipophilic moiety in a previously unexplored region of the natural glycopeptide. This modification provides a longer in vivo half life, and improved in vitro activity against a variety of Gram positive and multi-drug resistant isolates such as MRSA and MRSE.
  • Definition ChEBI: A semisynthetic glycopeptide used for the treatment of acute bacterial skin and skin structure infections caused or suspected to be caused by susceptible isolates of designated Gram-positive microorganisms including MRSA.
  • Biological Activity Dalbavancin is a semisynthetic, vancomycin class lipoglycopeptide with antibacterial activity against a variety of gram-positive pathogens, including methicillin-resistant S. aureus & S. epidermidis (MRSA & MRSE), but not gram-negative or vancomycin-resistant enterococci th at possess VanA gene. Similar to vancomycin and other class members (e.g. teicoplanin, telavancin, ramoplanin, and ritavancin), dalbavancin disrupts bateria cell wall formation and cell membrane integrity by targeting the D-alanyl-D-alanyl residues on the growing peptidoglycan chains, blocking transpeptidation and peptidoglycan elongation.
  • in vivo

    Dalbavancin (15-240 mg/kg; intraperitoneal injection; every 36 h or 72 h; for 14 days; female BALB/c mice) treatment has a survival rate of 80% to 100% of mice with all dose regimens[1].

    Animal Model:Female BALB/c mice (6-8 weeks) challenged with Ames strain of B. anthracis[1]
    Dosage:15 mg/kg, 30 mg/kg, 60 mg/kg, 120 mg/kg, 240 mg/kg
    Administration:Intraperitoneal injection; every 36 h or 72 h; for 14 days
    Result:The efficacy was 80 to 100%, as determined by the rate of survival at 42 days, when treatment was initiated 24 h postchallenge with regimens of 15 to 120 mg/kg every 36 h or 30 to 240 mg/kg every 72 h.
  • IC 50 Glycopeptide
Dalbavancin Preparation Products And Raw materials
Raw materials
Preparation Products
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Dalbavancin Spectrum
171500-79-1, DalbavancinRelated Search:
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  • 达巴万星原料 171500-79-1
  • 微生物代谢物
  • C88H100Cl2N10O28
  • 达巴万星B0
  • 达巴万星,10 MM DMSO 溶液
  • BI 397|||BI-397|||VER 001|||A-A 1|||BI397|||VER-001|||DALBAVANCIN HCL|||达巴万星
  • 盐酸达巴万星,道古霉素
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  • 达巴霉素
  • 道古霉素(达巴万星)
  • 道古霉素盐酸盐
  • 171500-79-1
  • Dalbavancin, 10 mM in DMSO
  • Dabavan Star.
  • BI 397|||BI-397|||VER 001|||A-A 1|||BI397|||VER-001|||Dalbavancin HCl
  • Dabavancin hydrochloride
  • Dabawan Star
  • Dalvance
  • 5,31-Dichloro-38-de(methoxycarbonyl)-7-demethyl-19-deoxy-56-O-[2-deoxy-2-(10-methylundecanamido)-beta-D-glucopyranuronosyl]-38-[N-[3-(dimethylamino)propyl]carbamoyl]-42-O-alpha-D-mannopyranosyl-N15-methylristomycin A aglycone
  • 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-
  • 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-Ristomy
  • TIANFUCHEM--171500-79-1---Dalbavancin
  • US-DMF No.: 035874
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  • albavancin
  • (3S,15R,18R,34R,35S,48S,50aR
  • MDL-63397;BI-397
  • VER001
  • A-A 1; BI397; VER001; MDL63397
  • DB/ QTH04
  • Antibotic Dalbavancin
  • Dalbavacin
  • DALBAVANCIN;MDL 63397;A-A-1; DALBAVANCIN AO; BI 397; MDL 63397;DALBAVANCIN(BI 397; MDL 63397)
  • Dalbavancin(BI 397

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