Oritavancin diphosphate Solid powder Others Oritavancin diphosphate is a semi-synthetic lipoglycopeptide antibiotic that is used to treat serious bacterial infections. It was first approved by the US Food and Drug Administration (FDA) in 2014 for the treatment of acute bacterial skin and skin structure infections (ABSSSI) caused by susceptible Gram-positive bacteria. Oritavancin diphosphate is a derivative of vancomycin, which is a glycopeptide antibiotic that has been used for several decades to treat infections caused by Gram-positive bacteria.
1989.09
$ $99 In stock
Formulation: 1989.09
Source:
Usage:
Oritavancin diphosphate - 192564-14-0

Oritavancin diphosphate

The product is for non-human research only. Not for therapeutic or veterinary use.

Catalog Number: BT-254314

CAS Number: 192564-14-0

Molecular Formula: C86H103Cl3N10O34P2

Molecular Weight: 1989.09

Purity: ≥ 99%

Inventory: In Stock

Size SKU Price
2mg bt-254314-2mg $364.62
5mg bt-254314-5mg $576.92

CAS Number 192564-14-0
Product Name Oritavancin diphosphate
Molecular Formula C86H103Cl3N10O34P2
Molecular Weight 1989.09
Appearance Solid powder
InChI InChI=1S/C86H97Cl3N10O26.2H3O4P/c1-35(2)22-51(92-7)77(110)98-67-69(105)42-15-20-55(49(88)24-42)120-57-26-44-27-58(73(57)125-84-74(71(107)70(106)59(34-100)122-84)124-62-32-86(6,76(109)37(4)119-62)93-33-38-8-10-39(11-9-38)40-12-17-45(87)18-13-40)121-56-21-16-43(25-50(56)89)72(123-61-31-85(5,91)75(108)36(3)118-61)68-82(115)97-66(83(116)117)48-28-46(101)29-54(103)63(48)47-23-41(14-19-53(47)102)64(79(112)99-68)96-80(113)65(44)95-78(111)52(30-60(90)104)94-81(67)114;2*1-5(2,3)4/h8-21,23-29,35-37,51-52,59,61-62,64-72,74-76,84,92-93,100-103,105-109H,22,30-34,91H2,1-7H3,(H2,90,104)(H,94,114)(H,95,111)(H,96,113)(H,97,115)(H,98,110)(H,99,112)(H,116,117);2*(H3,1,2,3,4)/t36-,37-,51+,52-,59+,61-,62-,64+,65+,66-,67+,68-,69+,70+,71-,72+,74+,75-,76-,84-,85-,86-;;/m0../s1
InChI Key PWTROOMOPLCZHB-BHYQHFGMSA-N
IUPAC Name (1S,2R,18R,19R,22S,25R,28R,40S)-2-[(2R,4S,5R,6S)-4-amino-5-hydroxy-4,6-dimethyloxan-2-yl]oxy-22-(2-amino-2-oxoethyl)-5,15-dichloro-48-[(2S,3R,4S,5S,6R)-3-[(2S,4S,5R,6S)-4-[[4-(4-chlorophenyl)phenyl]methylamino]-5-hydroxy-4,6-dimethyloxan-2-yl]oxy-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-18,32,35,37-tetrahydroxy-19-[[(2R)-4-methyl-2-(methylamino)pentanoyl]amino]-20,23,26,42,44-pentaoxo-7,13-dioxa-21,24,27,41,43-pentazaoctacyclo[26.14.2.23,6.214,17.18,12.129,33.010,25.034,39]pentaconta-3,5,8,10,12(48),14,16,29(45),30,32,34(39),35,37,46,49-pentadecaene-40-carboxylic acid;phosphoric acid
Description Oritavancin diphosphate is a semi-synthetic lipoglycopeptide antibiotic that is used to treat serious bacterial infections. It was first approved by the US Food and Drug Administration (FDA) in 2014 for the treatment of acute bacterial skin and skin structure infections (ABSSSI) caused by susceptible Gram-positive bacteria. Oritavancin diphosphate is a derivative of vancomycin, which is a glycopeptide antibiotic that has been used for several decades to treat infections caused by Gram-positive bacteria.
Method of Synthesis or Extraction Oritavancin diphosphate is synthesized from vancomycin through a series of chemical modifications. The most commonly used method for the synthesis of oritavancin diphosphate involves the modification of the vancomycin molecule at the C-6 position. This modification involves the addition of a lipophilic side chain, which enhances the lipophilicity of the molecule and improves its pharmacokinetic properties. The yield of this method is typically around 10-15%, and the process is relatively complex and time-consuming.
Another method for the synthesis of oritavancin diphosphate involves the modification of the vancomycin molecule at the C-9 position. This modification involves the addition of a hydrophobic group, which also enhances the lipophilicity of the molecule. The yield of this method is typically around 5-10%, and the process is also complex and time-consuming.
Environmental and safety considerations for the synthesis of oritavancin diphosphate include the use of hazardous chemicals and solvents, which can pose a risk to human health and the environment. The use of these chemicals and solvents should be minimized, and appropriate safety measures should be taken to prevent exposure.
Chemical Structure and Biological Activity The chemical structure of oritavancin diphosphate is similar to that of vancomycin, with the addition of a lipophilic side chain at the C-6 position. The molecule has a molecular weight of 1079.2 g/mol and a complex three-dimensional structure.
The mechanism of action of oritavancin diphosphate is similar to that of vancomycin, which involves the inhibition of bacterial cell wall synthesis. Oritavancin diphosphate binds to the D-alanyl-D-alanine terminus of the peptidoglycan precursor, preventing its incorporation into the growing cell wall. This results in the inhibition of bacterial cell wall synthesis and ultimately leads to bacterial cell death.
Oritavancin diphosphate has a broad spectrum of activity against Gram-positive bacteria, including methicillin-resistant Staphylococcus aureus (MRSA) and vancomycin-resistant enterococci (VRE). The potency of oritavancin diphosphate is higher than that of vancomycin, with a minimum inhibitory concentration (MIC) of 0.06-0.12 μg/mL for most Gram-positive bacteria.
Biological Effects Oritavancin diphosphate has been shown to have a number of biological effects on cell function and signal transduction. These effects include the inhibition of bacterial cell wall synthesis, the induction of autolysis in some bacterial species, and the modulation of host immune responses.
Potential therapeutic and toxic effects of oritavancin diphosphate include the treatment of serious bacterial infections, such as ABSSSI, pneumonia, and endocarditis. However, like all antibiotics, oritavancin diphosphate can also have potential side effects, such as gastrointestinal disturbances, allergic reactions, and the development of antibiotic resistance.
Applications In medical research, oritavancin diphosphate has been used to study the role of bacterial cell wall synthesis in the pathogenesis of bacterial infections. It has also been used in clinical trials to evaluate its efficacy and safety in the treatment of various bacterial infections.
In environmental research, oritavancin diphosphate has been studied for its effects on ecosystems and its role in pollution management. It has also been evaluated for its sustainability and environmental impact.
In industrial research, oritavancin diphosphate has been used in manufacturing processes to improve product quality and efficiency. Health and safety considerations are important in the use of oritavancin diphosphate in industrial settings.
Future Perspectives and Challenges Current limitations in the use and study of oritavancin diphosphate include the development of antibiotic resistance, the potential for adverse effects on human health and the environment, and the high cost of production. Possible solutions and improvements include the development of new antibiotics with novel mechanisms of action, the use of combination therapies to reduce the risk of resistance, and the optimization of production processes to reduce costs and environmental impact.
Future trends and prospects in the application of oritavancin diphosphate in scientific research include the development of new formulations and delivery methods, the evaluation of its efficacy in the treatment of emerging bacterial infections, and the study of its potential role in the modulation of host immune responses.
Shelf Life >2 years if stored properly
SMILES CC1C(C(CC(O1)OC2C3C(=O)NC(C4=C(C(=CC(=C4)O)O)C5=C(C=CC(=C5)C(C(=O)N3)NC(=O)C6C7=CC(=C(C(=C7)OC8=C(C=C2C=C8)Cl)OC9C(C(C(C(O9)CO)O)O)OC1CC(C(C(O1)C)O)(C)NCC1=CC=C(C=C1)C1=CC=C(C=C1)Cl)OC1=C(C=C(C=C1)C(C(C(=O)NC(C(=O)N6)CC(=O)N)NC(=O)C(CC(C)C)NC)O)Cl)O)C(=O)O)(C)N)O.OP(=O)(O)O.OP(=O)(O)O
Solubility Soluble in DMSO, not in water
Storage Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Synonyms LY333328; LY-333328; LY 333328; Oritavancin; Oritavancin diphosphate; brand name: Orbactiv.
Reference

Kmeid J, Kanafani ZA. Oritavancin for the treatment of acute bacterial skin and skin structure infections: an evidence-based review. Core Evid. 2015 Feb 11;10:39-47. doi: 10.2147/CE.S51284. eCollection 2015. Review. PubMed PMID: 25709561; PubMed Central PMCID: PMC4334198.

Das B, Sarkar C, Schachter J. Oritavancin - a new semisynthetic lipoglycopeptide agent to tackle the challenge of resistant gram positive pathogens. Pak J Pharm Sci. 2013 Sep;26(5):1045-55. Review. PubMed PMID: 24035967.

Karaoui LR, El-Lababidi R, Chahine EB. Oritavancin: an investigational lipoglycopeptide antibiotic. Am J Health Syst Pharm. 2013 Jan 1;70(1):23-33. doi: 10.2146/ajhp110572. Review. PubMed PMID: 23261897.

Bouza E, Burillo A. Oritavancin: a novel lipoglycopeptide active against Gram-positive pathogens including multiresistant strains. Int J Antimicrob Agents. 2010 Nov;36(5):401-7. doi: 10.1016/j.ijantimicag.2010.06.048. Epub 2010 Aug 21. Review. PubMed PMID: 20729040.

Zhanel GG, Calic D, Schweizer F, Zelenitsky S, Adam H, Lagacé-Wiens PR, Rubinstein E, Gin AS, Hoban DJ, Karlowsky JA. New lipoglycopeptides: a comparative review of dalbavancin, oritavancin and telavancin. Drugs. 2010 May 7;70(7):859-86. doi: 10.2165/11534440-000000000-00000. Review. Erratum in: Drugs. 2011 Mar 26;71(5):526. PubMed PMID: 20426497.

Guskey MT, Tsuji BT. A comparative review of the lipoglycopeptides: oritavancin, dalbavancin, and telavancin. Pharmacotherapy. 2010 Jan;30(1):80-94. doi: 10.1592/phco.30.1.80. Review. PubMed PMID: 20030476.

Anderson DL. Oritavancin for skin infections. Drugs Today (Barc). 2008 Aug;44(8):563-75. doi: 10.1358/dot.2008.44.8.1250078. Review. PubMed PMID: 18846268.

Crandon J, Nicolau DP. Oritavancin: a potential weapon in the battle against serious Gram-positive pathogens. Future Microbiol. 2008 Jun;3(3):251-63. doi: 10.2217/17460913.3.3.251. Review. PubMed PMID: 18505390.

Poulakou G, Giamarellou H. Oritavancin: a new promising agent in the treatment of infections due to Gram-positive pathogens. Expert Opin Investig Drugs. 2008 Feb;17(2):225-43. doi: 10.1517/13543784.17.2.225. Review. PubMed PMID: 18230056.

Ward KE, Mersfelder TL, LaPlante KL. Oritavancin--an investigational glycopeptide antibiotic. Expert Opin Investig Drugs. 2006 Apr;15(4):417-29. Review. PubMed PMID: 16548791.

Jones, R.N., Barrett, M.S., and Erwin, M.E. In vitro activity and spectrum of LY333328, a novel glycopeptide derivative. Antimicrob. Agents Chemother. 41(2), (1997).

Zhanel, G.G., Schweizer, F., and Karlowsky, J.A. Oritavancin: Mechanism of action. Clin. Infect. Dis. 54(Suppl 3), S214-S219 (2012).

Belley, A., McKay, G.A.A., F.F., Sarmiento, I., et al. Oritavancin disrupts membrane integrity of Staphylococcus aureus and vancomycin-resistant enterococci to effect rapid bacterial killing. Antimicrob. Agents Chemother. 54(12), 5369-5371 (2010).

Mendes, R.E., Farrell, D.J., Sader, H.S., et al. Activity of oritavancin against Gram-positive clinical isolates responsible for documented skin and soft-tissue infections in European and US hospitals (2010-13). J. Antimicrob. Chemother. 70(2), 498-504 (2015).

Boylan, C.J., Campanale, K., Iversen, P.W., et al. Pharmacodynamics of oritavancin (LY333328) in a neutropenic-mouse thigh model of Staphylococcus aureus infection. Antimicrob. Agents Chemother. 47(5), 1700-1706 (2003).

Heine, H.S., Bassett, J., Miller, L., et al. Efficacy of oritavancin in a murine model of Bacillus anthracis spore inhalation anthrax. Antimicrob. Agents Chemother. 52(9), 3350-3357 (2008).

PubChem Compound Oritavancin diphosphate
Last Modified May 30 2023