| Catalog Number | I002237 |
| CAS Number | 171500-79-1 |
| Molecular Formula | C88H100Cl2N10O28 |
| Purity | ≥95% |
| Target | Antibiotic |
| Solubility | DMSO: ≥ 29 mg/mL |
| Storage | Store at -20°C |
| Related CAS |
247175-55-9
|
| IC50 | 0.06 mg/L(MIC50; B. anthracis) |
| 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 |
| 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)124-55-24-19-42(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)123-56-30-41(18-23-53(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 |
| InChIKey | KGPGQDLTDHGEGT-SZUNQUCBSA-N |
| 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 |
| Reference | 1. Expert Opin Investig Drugs. 2007 May;16(5):717-33. <br />
Review of dalbavancin, a novel semisynthetic lipoglycopeptide. <br />
Kim A(1), Kuti JL, Nicolau DP. <br />
Author information: <br />
(1)Center for Anti-Infective Research and Development, Connecticut, USA. <br />
Dalbavancin is a semisynthetic lipoglycopeptide that is derived from teicoplanin
with an extended half-life that enables once-weekly dosing. It has potent in
vitro activity against most gram-positive organisms, with lower minimum
inhibitory concentration values than vancomycin and other investigational
lipoglycopeptides. Dalbavancin is active against multi-drug-resistant pathogens
such as methicillin-resistant Staphylococcus aureus and vancomycin-resistant
enterococci, except for strains exhibiting vanA resistance. Several Phase II and
III trials have established similar efficacy and safety of dalbavancin with
comparator agents in the treatment of complicated skin and skin structure
infections and in catheter-related bloodstream infections. Dalbavancin may serve
as an appealing alternative agent in the treatment of gram-positive infections,
especially with its convenient once-weekly regimen. <br />
2. J Antimicrob Chemother. 2005 Mar;55 Suppl 2:ii25-30. <br />
Human pharmacokinetics and rationale for once-weekly dosing of dalbavancin, a
semi-synthetic glycopeptide. <br />
Dorr MB(1), Jabes D, Cavaleri M, Dowell J, Mosconi G, Malabarba A, White RJ,
Henkel TJ. <br />
Author information: <br />
(1)Vicuron Pharmaceuticals, 455 South Gulph Road, King of Prussia, PA, USA. <br />
The selection of a novel weekly dalbavancin dosage regimen was based on
pharmacokinetic and pharmacodynamic data from humans and an animal model of
infection. The results from the granuloma pouch model of infection suggested that
dalbavancin concentrations >/=5 mg/L are necessary for extended in vivo activity.
Serum bactericidal activity assessments demonstrated that dalbavancin serum
concentrations of approximately 20 mg/L were bactericidal upon two-fold dilution.
These data, coupled with simulations based on the pharmacokinetic profile derived
from a clinical study in healthy volunteers, were used to design the weekly
regimen studied in the initial efficacy trial. This efficacy study showed that a
two-dose weekly regimen was well tolerated and associated with a higher clinical
response rate than the comparator regimens. The data collectively support the
further study of dalbavancin as a once-weekly regimen for the treatment of
infections caused by Gram-positive bacteria. <br />
3. J Antimicrob Chemother. 2005 Mar;55 Suppl 2:ii15-20. <br />
Origin, structure, and activity in vitro and in vivo of dalbavancin. <br />
Malabarba A(1), Goldstein BP. <br />
Author information: <br />
(1)Vicuron Pharmaceuticals, Via R. Lepetit 34-21040, Gerenzano, Varese, Italy. <br />
Dalbavancin is a novel semi-synthetic lipoglycopeptide that was designed to
improve upon the natural glycopeptides currently available, vancomycin and
teicoplanin. Chemical modification of natural glycopeptides has produced
compounds with more potent antimicrobial activity and longer t(1/2), while
maintaining an excellent safety profile. Dalbavancin, prepared from a
teicoplanin-like glycopeptide, has better activity, in vitro and in animal
infection models, than vancomycin and teicoplanin. In particular, dalbavancin has
excellent activity against staphylococci, including coagulase-negatives. A unique
feature of dalbavancin is its pharmacokinetics, characterized by a long
elimination t(1/2) in humans which makes a once-weekly dosing regimen feasible.
Dalbavancin recently completed Phase 3 clinical trials in skin and skin structure
infection. <br />
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