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50mg |
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250mg |
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500mg |
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10g |
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Purity: ≥98%
Vancomycin (Lyphocin) is a narrow-spectrum amphoteric glycopeptide antibacterial drug used to treat a number of bacterial infections. It acts by inhibiting bacterial cell wall synthesis by binding to peptidoglycan. Vancomycin is recommended intravenously as a treatment for complicated skin infections, bloodstream infections, endocarditis, bone and joint infections, and meningitis caused by methicillin-resistant Staphylococcus aureus. Blood levels may be measured to determine the correct dose. Vancomycin is also recommended by mouth as a treatment for severe Clostridium difficile colitis. When taken by mouth it is very poorly absorbed. Vancomycin acts by inhibiting proper cell wall synthesis in Gram-positive bacteria. Due to the different mechanism by which Gram-negative bacteria produce their cell walls and the various factors related to entering the outer membrane of Gram-negative organisms, vancomycin is not active against them (except some nongonococcal species of Neisseria).
Targets |
Glycopeptide
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ln Vitro |
In animal modeling, vancomycin can be used to create kidney injury models.
To reduce infusion-related side effects, vancomycin is infused intravenously for a minimum of one hour. Vancomycin has a β-elimination half-life of 6–12 hours and an α-distribution phase of 30 min to 1 h in subjects with normal creatinine clearance. 0.4–1 L/kg is the distribution volume. Vancomycin can bind to proteins 10%–50% of the time. Vancomycin's total activity is influenced by a number of factors, including its tissue distribution, inoculum size, and effects on protein binding[1]. Treatment with vancomycin for infected mice is linked to better scores in histopathology, clinical manifestations, and diarrhea[3].
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ln Vivo |
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Enzyme Assay |
Vancomycin is a unique glycopeptide structurally unrelated to any currently available antibiotic. It also has a unique mode of action inhibiting the second stage of cell wall synthesis of susceptible bacteria. There is also evidence that vancomycin alters the permeability of the cell membrane and selectively inhibits ribonucleic acid synthesis. Induction of bacterial L-phase variants from susceptible organisms with vancomycin is extremely difficult, and such variants are unstable. Stable L-phase variants induced by other agents are susceptible to vancomycin. Vancomycin is active against a large number of species of Gram-positive bacteria, such as Staphylococcus aureus (including methicillin-resistant strains), Staph. epidermidis (including multiple-resistant strains), Streptococcus pneumoniae (including multiple-resistant strains), Str. pyogenes, Str. agalactiae, Str. bovis, Str. mutans, viridans streptococci, enterococci, Clostridium species, diphtheroids, Listeria monocytogenes, Actinomyces species and Lactobacillus species. There has been no increase in resistance to vancomycin during the past three decades. Enhancement of antimicrobial activity has been demonstrated with the combination of vancomycin and an aminoglycoside against Staph. aureus, Str. bovis, enterococci and viridans streptococci. The combination of vancomycin and rifampicin are antagonistic to most strains of Staph. aureus, though indifference and occasionally synergism have been shown, but is synergistic against strains of Staph. epidermidis. It shows indifference against enterococci. Vancomycin and fusidic acid are indifferent against Staph. aureus [2].
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Cell Assay |
C. difficile toxin assay. C. difficile toxins A and B were detected using a modified protocol for the Tech Lab Toxin A/B II ELISA kit. Each stool sample was weighed and the amount of diluent per sample was normalized to provide the same stool mass-to-diluent ratio for each sample. The diluent-sample mixtures were homogenized by grinding and vortexing, and 1:10, 1:100, and 1:1,000 serial dilutions were made of the sample. A total of 150 μl of the 1:1,000 dilution of each sample was added to a precoated well provided in the kit. A negative control consisted of 150 μl of diluent, and a positive control consisted of 135 μl of diluent plus 3 drops of the positive control toxin A-B mixture provided in the kit. One drop of conjugate was added to each well, and the plate was incubated at 37°C for 50 min. Each well was washed three times with 150 μl of a 1× dilution of the wash buffer provided in the kit. Two drops of substrate were added to each well. After 10 min, 1 drop of stop solution was added to each well. The plate was allowed to sit for 2 min before being read in an ELISA reader [3].
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Animal Protocol |
Mice: In one series of studies, infected mice are given either vancomycin (20 mg/kg) daily for five or ten days and monitored for fifteen days after infection, or vancomycin (50 mg/kg) daily for one, two, three, or five days and monitored for twenty-one days after infection[3].
Murine model of C. difficile infection and treatment.[3] The infection model is a modification of the published protocol of Chen et al. This protocol has been approved by the Center for Comparative Medicine at University of Virginia. C57BL/6 mice, male, 8 weeks old, were used. From 6 to 4 days prior to infection, mice were given an antibiotic cocktail containing vancomycin (0.0045 mg/g), colistin (0.0042 mg/g), gentamicin (0.0035 mg/g), and metronidazole (0.0215 mg/g) in drinking water. One day prior to infection, clindamycin (32 mg/kg of body weight) was injected subcutaneously. The mice were divided into the following groups: control uninfected, control infected, infected and treated with vancomycin (20 mg/kg), and infected and treated with comparator drugs—nitazoxanide, fidaxomicin, and metronidazole (all drugs given at 20 mg/kg/day). Food and water were allowed ad libitum. Although each mouse or treatment group was housed in a separate cage, all mice were housed in the same pod of the vivarium. Infection was performed with VPI 10463 (ATCC) as an inoculum of 104 or 105 administered by oral gavage. This strain produces both C. difficile toxins A (TcdA) and B (TcdB). One day postinfection, treated mice were given either vancomycin or nitazoxanide at 20 mg/kg each by oral gavage daily for 5 days and monitored for either 1 or 2 weeks postinfection. One set of experiments was performed in which infected mice were treated with vancomycin (50 mg/kg) daily for 1, 2, 3, or 5 days and were observed for 21 days postinfection or with vancomycin (20 mg/kg) daily for either 5 or 10 days and monitoring for 15 days postinfection. In a separate experiment, mice given a preinfection antibiotic regimen described above were treated with either vancomycin, fidaxomicin, or metronidazole at 20 mg/kg/day for 5 days and infected another 5 days later. Except when indicated, all comparator drugs were administered using the same dosage (20 mg/kg/day for 5 days) to equally compare efficacies, outcomes, and effects on selected gut floras between treatment groups as previously described. From another study, a group of control mice was given vancomycin but was not infected. A clinical scoring system was developed on the basis of weight loss, diarrhea, activity level, and appearance of eyes and hair (each parameter scored from 0 to 3, where 0 is normal and 3 is the worst; maximum score of 20). Stool specimens were collected daily. Diarrhea was scored as follows: 1 for soft or color change (yellow), 2 for wet tail or mucoid, and 3 for liquid or no stool (ileus). Mice judged moribund by the clinical score (score of >14) at any day and all surviving mice at the end of the experiment were sacrificed, and intestinal tissues and cecal contents were collected as described below. A separate set of experiments was performed for harvesting cecal contents for clostridial bacterial and toxin burdens at days 3, 6, 9, and 12 to 13 postinfection to follow changes at different time points of the study. Histopathology. Upon euthanasia, cecal and colonic tissues were fixed in 10% zinc formalin overnight and then placed in 10% ethanol before being sent for paraffin embedding and hematoxylin and eosin (H&E) staining at the University of Virginia Histology Research Core. Histopathologic scoring was performed coded (C.A.W. and M.S.R.). H&E-stained tissues were scored for mucosal disruption, mucosal hypertrophy, inflammation, vascular congestion and exudates, and submucosal edema (each parameter was graded from 0 to 3, with 0 as normal and 3 worst; maximum score of 15) as we previously described in detail. |
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References |
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Molecular Formula |
C66H75CL2N9O24
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Molecular Weight |
1449.25
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Exact Mass |
1447.43
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CAS # |
1404-90-6
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Related CAS # |
Vancomycin hydrochloride;1404-93-9
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Appearance |
White to off-white solid powder
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LogP |
-2.6
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tPSA |
530.490
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SMILES |
C[C@H]1[C@H]([C@@](C[C@@H](O1)O[C@@H]2[C@H]([C@@H]([C@H](O[C@H]2OC3=C4C=C5C=C3OC6=C(C=C(C=C6)[C@H]([C@H](C(=O)N[C@H](C(=O)N[C@H]5C(=O)N[C@@H]7C8=CC(=C(C=C8)O)C9=C(C=C(C=C9O)O)[C@H](NC(=O)[C@H]([C@@H](C1=CC(=C(O4)C=C1)Cl)O)NC7=O)C(=O)O)CC(=O)N)NC(=O)[C@@H](CC(C)C)NC)O)Cl)CO)O)O)(C)N)O
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InChi Key |
MYPYJXKWCTUITO-LYRMYLQWSA-N
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InChi Code |
InChI=1S/C66H75Cl2N9O24/c1-23(2)12-34(71-5)58(88)76-49-51(83)26-7-10-38(32(67)14-26)97-40-16-28-17-41(55(40)101-65-56(54(86)53(85)42(22-78)99-65)100-44-21-66(4,70)57(87)24(3)96-44)98-39-11-8-27(15-33(39)68)52(84)50-63(93)75-48(64(94)95)31-18-29(79)19-37(81)45(31)30-13-25(6-9-36(30)80)46(60(90)77-50)74-61(91)47(28)73-59(89)35(20-43(69)82)72-62(49)92/h6-11,13-19,23-24,34-35,42,44,46-54,56-57,65,71,78-81,83-87H,12,20-22,70H2,1-5H3,(H2,69,82)(H,72,92)(H,73,89)(H,74,91)(H,75,93)(H,76,88)(H,77,90)(H,94,95)/t24-,34+,35-,42+,44-,46+,47+,48-,49+,50-,51+,52+,53+,54-,56+,57+,65-,66-/m0/s1
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Chemical Name |
(1S,2R,18R,19R,22S,25R,28R,40S)-48-[(2S,3R,4S,5S,6R)-3-[(2S,4S,5S,6S)-4-amino-5-hydroxy-4,6-dimethyloxan-2-yl]oxy-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-22-(2-amino-2-oxoethyl)-5,15-dichloro-2,18,32,35,37-pentahydroxy-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(48),9,11,14,16,29(45),30,32,34(39),35,37,46,49-pentadecaene-40-carboxylic acid
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Synonyms |
Vancocin;Vancoled; Vancomicina; Vancomycine; Vancomycinum; VANCOR
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HS Tariff Code |
3004209090
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Storage |
Powder -20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month Note: Please store this product in a sealed and protected environment, avoid exposure to moisture. |
Shipping Condition |
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
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Solubility (In Vitro) |
DMSO : ~125 mg/mL (~86.25 mM)
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Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 4.17 mg/mL (2.88 mM) (saturation unknown) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 41.7 mg/mL clear DMSO stock solution to 400 μL PEG300 and mix evenly; then add 50 μL Tween-80 to the above solution and mix evenly; then add 450 μL normal saline to adjust the volume to 1 mL. Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution. Solubility in Formulation 2: ≥ 4.17 mg/mL (2.88 mM) (saturation unknown) in 10% DMSO + 90% (20% SBE-β-CD in Saline) (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 41.7 mg/mL clear DMSO stock solution to 900 μL of 20% SBE-β-CD physiological saline solution and mix evenly. Preparation of 20% SBE-β-CD in Saline (4°C,1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution.  (Please use freshly prepared in vivo formulations for optimal results.) |
Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
1 mM | 0.6900 mL | 3.4501 mL | 6.9001 mL | |
5 mM | 0.1380 mL | 0.6900 mL | 1.3800 mL | |
10 mM | 0.0690 mL | 0.3450 mL | 0.6900 mL |
*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.
Calculation results
Working concentration: mg/mL;
Method for preparing DMSO stock solution: mg drug pre-dissolved in μL DMSO (stock solution concentration mg/mL). Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug.
Method for preparing in vivo formulation::Take μL DMSO stock solution, next add μL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH2O,mix and clarify.
(1) Please be sure that the solution is clear before the addition of next solvent. Dissolution methods like vortex, ultrasound or warming and heat may be used to aid dissolving.
(2) Be sure to add the solvent(s) in order.
Effect of vancomycin on Clostridium difficile-infected mice during acute infection and posttreatment.[3].Antimicrob Agents Chemother. 2013 Feb;57(2):689-96. td> |
Intestinal histopathology. Shown are representative H&E-stained cecal tissues from infected mice treated or not with vancomycin for 5 days.[3].Antimicrob Agents Chemother. 2013 Feb;57(2):689-96. td> |
Clostridial and toxin burdens in cecal contents at peak of infection, post-vancomycin treatment, and at relapse.[3].Antimicrob Agents Chemother. 2013 Feb;57(2):689-96. td> |
Effect of duration of vancomycin treatment on disease and survival in mice with CDI. [3].Antimicrob Agents Chemother. 2013 Feb;57(2):689-96. td> |
Effect of vancomycin, fidaxomicin, or metronidazole on Clostridium difficile-infected mice during acute infection and posttreatment.[3].Antimicrob Agents Chemother. 2013 Feb;57(2):689-96.. td> |
Effect of preexposure to vancomycin, fidaxomicin, or metronidazole on C.[3].Antimicrob Agents Chemother. 2013 Feb;57(2):689-96. td> |