| Supplier |
Creative Peptides |
| Product # |
10-101-78 |
| CAS # |
171500-79-1 |
| Pricing |
Inquire
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| Synonyms |
Dalbavancin; Zeven; D03640
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| MolecularFormula |
C88H100Cl2N10O28
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| MolecularWeight |
1816.69
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| Source |
Synthetic
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| ShippingCondition |
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
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| Explanation |
Dalbavancin (INN, trade name Dalvance) is a novel second-generation lipoglycopeptide antibiotic. It belongs to the same class as vancomycin.The Food and Drug Administration approved dalbavancin for the treatment of acute bacterial skin and skin structure infections caused by certain susceptible bacteria.
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| ChemicalName |
(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
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| Application |
Dalbavancin can treat patients infected with methicillin-resistant Staphylococcus aureus (MRSA).
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| 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+/m0/s1
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| InChIKey |
KGPGQDLTDHGEGT-CUIWZYKSSA-N
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| CanonicalSMILES |
CC(C)CCCCCCCCC(=O)NC1C(C(C(OC1OC2=C3C=C4C=C2OC5=C(C=C(C=C5)C(C6C(=O)NC(C7=C(C(=CC(=C7)O)OC8C(C(C(C(O8)CO)O)O)O)C9=C(C=CC(=C9)C(C(=O)N6)NC(=O)C4NC(=O)C1C2=C(C(=CC(=C2)OC2=C(C=CC(=C2)C(C(=O)NC(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
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| Solubility |
Soluble in DMSO, not in water
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| IsomericSMILES |
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)NC(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
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| Appearance |
Off-white solid powder
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| BiologicalActivity |
Dalbavancin (MDL-63397) is a semisynthetic lipoglycopeptide antibiotic with potent bactericidal activity against Gram-positive bacteria that inhibits Staphylococcus aureus and Bacillus anthracis with MIC90s of 0.06 μg/mL and 0.25 μg/mL, respectively.
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| Target |
Gram-positive bacteria
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| Reference |
- The increasing incidence of serious infections because of Gram-positive pathogens and the rising cost in parenteral administration of antimicrobials has inspired the development of a novel antibiotic. Dalbavancin is the first once a week antibiotic with activity against a broad range of Gram-positive pathogens. A large multicentre, pivotal, Phase III clinical trial, which included 854 patients with complicated skin and skin structure infections, compared 1–2 doses of dalbavancin vs. linezolid. The results demonstrated non-inferiority and a comparable safety profile. With its unique pharmacokinetic profile, ease of use and excellent safety profile, dalbavancin should provide a valuable addition to the armamentarium used to treat infections because of Gram-positive cocci.
- Chen, A. Y., Zervos, M. J., & Vazquez, J. A. (2007). Dalbavancin: a novel antimicrobial. International journal of clinical practice, 61(5), 853-863.
- Health care-associated infections, especially those caused by multidrug-resistant gram-positive organisms, such as methicillin-resistant Staphylococcus aureus (MRSA), are a growing public health threat. In 2014, the U.S. Food and Drug Administration approved two new lipoglycopeptides, oritavancin and dalbavancin, for the treatment of acute bacterial skin and skin structure infections. The rationale for the development of these antimicrobials was partly to aid in the battle against vancomycin resistance in both Staphylococcus and Enterococcus. Considered a subclass of the glycopeptide antibiotics, the new lipoglycopeptides have similar mechanisms of action of binding to the carboxyl terminal d-alanyl-d-alanine residue of the growing peptide chains but differ from their parent glycopeptides by the addition of lipophilic tails. This addition allows for these agents to have prolonged half-lives, giving them unique dosing profiles. In addition, by concentrating at the site of action, they have increased potency against MRSA compared with vancomycin, the current mainstay of therapy. In this review, we focus on comparing and contrasting these two new agents with regard to their pharmacology, mechanisms of action, spectrum of activity, safety profiles, dosage and administration, and drug and laboratory interactions, and we review the clinical trials evaluating their use.
- Roberts, K. D., Sulaiman, R. M., & Rybak, M. J. (2015). Dalbavancin and Oritavancin: An Innovative Approach to the Treatment of Gram‐Positive Infections. Pharmacotherapy: The Journal of Human Pharmacology and Drug Therapy, 35(10), 935-948.
- Acute bacterial skin and skin structure infections (ABSSSI) have increased in incidence and severity. The involvement of resistant organisms, particularly methicillin-resistant Staphylococcus aureus, presents additional challenges. The lipoglycopeptide dalbavancin has a prolonged half-life, high protein binding, and excellent tissue levels which led to its development as a once-weekly treatment for ABSSSI. In the pivotal DISCOVER 1 and DISCOVER 2 trials, dalbavancin proved non-inferior to vancomycin followed by linezolid when used sequentially for ABSSSI, forming the basis for its recent approval in the US and Europe for ABSSSI.
- Ramdeen, S., & Boucher, H. W. (2015). Dalbavancin for the treatment of acute bacterial skin and skin structure infections. Expert opinion on pharmacotherapy, 16(13), 2073-2081.
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| Purity |
>90% (or refer to the Certificate of Analysis)
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| AreasOfInterest |
Infection
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| ShortTermStorageConditions |
Dry, dark and at 0 - 4 °C
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| LongTermStorageConditions |
-20 °C
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| Disease |
- Infection of skin AND/OR subcutaneous tissue;
- Bacterial infection of skin;
- Staphylococcal infection of skin
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| LabelingTarget |
Bacterial
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