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SML2378

Sigma-Aldrich

Dalbavancin

≥90% (HPLC)

Synonyme(s) :

5,31-dichloro-38-de(methoxycarbonyl)-7-demethyl-19-deoxy-56-O-[2-deoxy-2-[(10-methyl-1-oxoundecyl)amino]-β-Dglucopyranuronosyl]-38-[[[3-(dimethylamino)propyl]amino]carbonyl]-42-O-α-D-mannopyranosyl-N15-methyl- Ristomycin A aglycone, BI 397, BI-397, BI397, MDL 63,397, MDL 63397, MDL-63,397, MDL-63397, MDL63,397, MDL63397, Ristomycin A aglycone, VER 001, VER-001, VER001

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About This Item

Formule empirique (notation de Hill):
C88H100Cl2N10O28
Numéro CAS:
171500-79-1
Poids moléculaire :
1816.69
Code UNSPSC :
12352200
Nomenclature NACRES :
NA.77

Pureté

≥90% (HPLC)

Forme

powder

Couleur

white to beige

Solubilité

H2O: 2 mg/mL, clear

Température de stockage

−20°C

Chaîne SMILES 

O=C([C@@]1([H])NC([C@](C2)([H])NC([C@@H](C3=CC(OC4=CC1=C(Cl)C(O)=C4)=C(O)C=C3)NC)=O)=O)N[C@@](C5=CC(OC6=CC=C2C=C6)=C(O[C@H]7[C@H](NC(CCCCCCCCC(C)C)=O)[C@@H](O)[C@H](O)[C@@H](C(O)=O)O7)C(OC8=C(Cl)C=C([C@@]9([H])O)C=C8)=C5)([H])C(N[C@@]%10([H])C(N[C@]9([H])

InChI

1S/C88H100Cl2N10O28/c1-38(2)13-10-8-7-9-11-14-61(106)93-69-73(109)75(111)78(86(120)121)128-87(69)127-77-58-31-43-32-59(77)124-55-24-19-42(29-50(55)89)71(107)68-84(118)97-66(80(114)91-25-12-26-99(3)4)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)64(81(115)98-68)94-82(116)65(43)95-83(117)67-49-35-46(36-54(105)63(49)90)123-56-30-41(18-23-53(56)104)70(100(5)6)85(119)92-51(79(113)96-67)27-39-15-20-45(122-58)21-16-39/h15-24,28-36,38,51,60,64-76,78,87-88,101-105,107-112H,7-14,25-27,37H2,1-6H3,(H,91,114)(H,92,119)(H,93,106)(H,94,116)(H,95,117)(H,96,113)(H,97,118)(H,98,115)(H,120,121)/t51-,60-,64-,65-,66+,67+,68+,69-,70-,71-,72-,73-,74+,75+,76+,78+,87?,88+/m1/s1

Clé InChI

NECNEVHRBQBTTH-SOWMDMGUSA-N

Actions biochimiques/physiologiques

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 that 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.

Code de la classe de stockage

11 - Combustible Solids

Classe de danger pour l'eau (WGK)

WGK 3

Point d'éclair (°F)

Not applicable

Point d'éclair (°C)

Not applicable

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Katharina Neudorfer et al.
Diagnostic microbiology and infectious disease, 90(1), 58-63 (2017-12-03)
We tested the in vitro activity of dalbavancin, vancomycin and daptomycin against 83 enterococcal isolates in planktonic and biofilm states. The MIC90 for vancomycin-susceptible Enterococcus faecalis was 0.125 and 4μg/mL for dalbavancin and daptomycin, respectively. For vancomycin-resistant Enterococcus faecium, the
Helio S Sader et al.
Antimicrobial agents and chemotherapy, 62(3) (2017-12-22)
Dalbavancin activity was assessed against a large collection of Staphylococcus aureus isolates (n = 59,903), including isolates with decreased susceptibility to vancomycin (MIC, ≥2 mg/liter; n = 1,141), daptomycin (MIC, ≥2 mg/liter; n = 48), telavancin (MIC, ≥0.12 mg/liter; n
Zongru Guo
Acta pharmaceutica Sinica. B, 7(2), 119-136 (2017-03-18)
Drug innovation is characterized by painstaking molecular-level syntheses and modifications as the basic components of research and development. Similarly, natural products are chemically tailored and modified based upon their structural and biological properties. To some extent, the modification of natural
Michael A Pfaller et al.
International journal of antimicrobial agents, 51(4), 608-611 (2017-12-27)
Osteomyelitis is a difficult-to-treat infection that regularly involves prolonged use of systemic antibiotics. Dalbavancin has demonstrated activity against Gram-positive isolates, and has been considered as a candidate for the treatment of osteomyelitis in adults and children. This study evaluated the
Valentin Al Jalali et al.
Clinical pharmacokinetics, 57(7), 797-816 (2018-01-15)
Telavancin was discovered by modifying the chemical structure of vancomycin and belongs to the group of lipoglycopeptides. It employs its antimicrobial potential through two distinct mechanisms of action: inhibition of bacterial cell wall synthesis and induction of bacterial membrane depolarization
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