Oritavancin diphosphate
Catalog Number: BT-254314
CAS Number: 192564-14-0
Molecular Formula: C86H103Cl3N10O34P2
Molecular Weight: 1989.09
The product is for non-human research only. Not for therapeutic or veterinary use.
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Product Introduction
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.
Properties
CAS Number
192564-14-0
Product Name
Oritavancin diphosphate
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
Molecular Formula
C86H103Cl3N10O34P2
Molecular Weight
1989.09
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
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
Synonyms
LY333328; LY-333328; LY 333328; Oritavancin; Oritavancin diphosphate; brand name: Orbactiv.
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.
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.
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.
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.
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.
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.
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