Vancomycin hydrochloride
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| Category | Antibiotics |
| Catalog number | BBF-04073 |
| CAS | 1404-93-9 |
| Molecular Weight | 1485.72 |
| Molecular Formula | C66H75Cl2N9O24.HCl |
| Purity | >99% by HPLC |
Ordering Information
| Catalog Number | Size | Price | Stock | Quantity |
|---|---|---|---|---|
| BBF-04073 | 25 g | $249 | In stock |
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Add to cartDescription
The salt of a glycopeptide antibiotic isolated from amycolatopsis orientalis. Vancomycin hydrochloride exhibits potent activity against Gram-positive bacteria, and high effects against MRSA in vitro and in vivo. It interferes with cell wall synthesis by binding to D-alanine-D-alanine residues.
Specification
| Related CAS | 123409-00-7 (hydrate) 1404-90-6 (free base) |
| Synonyms | Vancomycin HCl; Vancomycin Monohydrochloride |
| Storage | Store at -20°C |
| IUPAC 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;hydrochloride |
| Canonical SMILES | CC1C(C(CC(O1)OC2C(C(C(OC2OC3=C4C=C5C=C3OC6=C(C=C(C=C6)C(C(C(=O)NC(C(=O)NC5C(=O)NC7C8=CC(=C(C=C8)O)C9=C(C=C(C=C9C(NC(=O)C(C(C1=CC(=C(O4)C=C1)Cl)O)NC7=O)C(=O)O)O)O)CC(=O)N)NC(=O)C(CC(C)C)NC)O)Cl)CO)O)O)(C)N)O.Cl |
| InChI | InChI=1S/C66H75Cl2N9O24.ClH/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);1H/t24-,34+,35-,42+,44-,46+,47+,48-,49+,50-,51+,52+,53+,54-,56+,57+,65-,66-;/m0./s1 |
| InChI Key | LCTORFDMHNKUSG-XTTLPDOESA-N |
Properties
| Appearance | White to Brown Powder |
| Antibiotic Activity Spectrum | Gram-positive bacteria |
| Density | 1.657 g/cm3 |
| Solubility | Soluble in ethanol, methanol, DMF, DMSO |
Reference Reading
1. Impact of urinary albumin excretion on the onset of adverse reactions to vancomycin hydrochloride
Hiroshi Kimura,Akihiro Tanaka,Shinichi Watanabe,Mamoru Tanaka,Noriaki Hidaka Int J Clin Pharmacol Ther . 2021 Jun;59(6):428-432. doi: 10.5414/CP203872.
Objective:Vancomycin dose needs to be reduced for decreased kidney function; however, impact of urinary albumin excretion (UAE) on serum vancomycin level is unknown. In this study, we examined the factors associated with the onset of renal impairment induced by vancomycin by focusing on UAE.Materials and methods:The study included 52 patients who received vancomycin for methicillin-resistantStaphylococcus aureusat Ehime University Hospital between April 2010 and March 2015. To determine the presence of renal impairment, patients whose common terminology criteria for adverse-events (CTCAE) grade worsened by 1 or more comprised the renal impairment group, and multivariate logistic regression analysis was performed.Results:13 patients (25%) had renal impairment as indicated by a CTCAE grade change by 1 or more. The results of multivariate logistic regression analysis only of UAE (OR = 18.03; 95% CI = 1.97 - 164.89) was identified as a significant factor.Conclusion:We investigated the factors associated with the onset of renal impairment induced by vancomycin and identified UAE as a potential risk factor.
2. Vancomycin
R Fekety Med Clin North Am . 1982 Jan;66(1):175-181. doi: 10.1016/s0025-7125(16)31451-1.
While vancomycin is thus not as nephrotoxic as once feared, its use by the parenteral route should be avoided if possible when other nephrotoxic drugs are being given. Used properly, vancomycin appears efficacious and can be given with safety to infants, children, and adults. Vancomycin is incompatible with many other drugs in intravenous solutions, especially chloramphenicol, adrenocorticosteroids, and methicillin.
3. Vancomycin
B A Cunha Med Clin North Am . 1995 Jul;79(4):817-31. doi: 10.1016/s0025-7125(16)30041-4.
Vancomycin is a nontoxic glycopeptide antibiotic most often used to treat serious gram-positive infections, C. difficile diarrhea/colitis, and endocarditis and hemodialysis shunt prophylaxis. Vancomycin should not be added to drug regimens for gram-positive coverage, and the empiric use of vancomycin should be discouraged to avoid the emergence of VRE. Vancomycin serum levels are no longer necessary or cost effective in most patients because vancomycin is not nephrotoxic.
4. Vancomycin hydrochloride-loaded stearic acid/lauric acid in situ forming matrix for antimicrobial inhibition in patients with joint infection after total knee arthroplasty
Wichai Santimaleeworagun,Patinya Sawangsri,Takron Chantadee,Thawatchai Phaechamud Mater Sci Eng C Mater Biol Appl . 2020 Oct;115:110761. doi: 10.1016/j.msec.2020.110761.
Knee joint infection following total knee arthroplasty (TKA) is a serious condition and the treatments are complicated. The intra-articular solvent exchange-induced in situ forming matrix is of interest for modulating the release of antibiotics with a high drug concentration and a long period of exposed time at the target site. Stearic acid (S) and lauric acid (L) at various ratios were used as matrix formers by dissolving them in biocompatible solvents such as N-methyl pyrrolidone (NMP) and dimethyl sulfoxide (DMSO). Their matrix formation behaviors in phosphate buffer (pH7.4) and hyaluronic acid (HA) solution were evaluated. Also, the density, viscosity, injectability, solvent diffusion, in vitro degradability and drug release using the dialysis tube method were investigated. The L:S ratio of 1:1 in DMSO exhibited rapid matrix formation and a remarkably low viscosity (7.67±0.03 cp) with acceptable injectability (0.608±0.027N and 0.867±0.010N through 18-G and 27-G, respectively). Vancomycin HCl (V)-loaded L/S in situ forming matrix still provided ease of injection (1.079±0.215N and 1.230±0.145N through 18-G and 27-G needle, respectively) with fatty acid matrix formation after solvent exchange within 1min, whilst V sustainably released over 6days. It also presented effective antimicrobial activities against standard Staphylococcus aureus and methicillin-resistant Staphylococcus aureus strains. Therefore, V-loaded solvent exchange-induced in situ forming matrix using L and S as the matrix formers may be a potential local delivery system for treating knee joint infections occurring after TKA in the future.
5. Comparative analysis of pharmacokinetics of vancomycin hydrochloride in rabbits after ocular, intragastric, and intravenous administration by LC-MS/MS
Qingsong Fei,Manman Dai,Luyu Bai,Huimin Zhang,Ning He,Rui Luo,Fang Lei,Qun Ma Xenobiotica . 2020 Dec;50(12):1461-1468. doi: 10.1080/00498254.2020.1774681.
The objective of this study was to compare the pharmacokinetics of vancomycin hydrochloride administered into rabbits through different routes and explore the feasibility of peptide drugs entering the systemic circulation through ocular administration. A convenient, accurate, and rapid liquid chromatography-trandem mass spectrometric (LC-MS/MS) method was established and used for the determination of vancomycin hydrochloride in rabbit plasma after intravenous administration (1.5 mg/kg), intragastric, and ocular administration (15 mg/kg). The pharmacokinetic parameters were analyzed using the DAS 2.0 software. We obtained a linear calibration curves vancomycin hydrochloride in plasma of rabbits over a concentration range of 0.05-10.0 μg/mL (R2> 0.9995), the interassay accuracy was within 5%, precision of 1.66-3.38%, and recovery of >85%. No matrix effects were observed. The absolute bioavailability of vancomycin hydrochloride after intragastric and ocular administration was 1.0 and 7.3%, with the half-life values of 63.1 and 138.5 min, respectively. Therefore, the LC-MS/MS method established in this experiment was suitable for the determination of vancomycin hydrochloride. Vancomycin hydrochloride was rapidly absorbed into the blood circulation after ocular administration. Ocular administration was linked to higher bioavailability compared with intragastric administration, suggesting that the former will become a route for the delivery of peptide drugs.
6. Transdermal delivery of vancomycin hydrochloride: Influence of chemical and physical permeation enhancers
Dhruvisha Sureshbhai Panchal,Venkata Vamsi Krishna Venuganti,Deepanjan Datta Int J Pharm . 2021 Jun 1;602:120663. doi: 10.1016/j.ijpharm.2021.120663.
Topical and transdermal delivery of vancomycin hydrochloride (VH), a broad-spectrum peptide antibiotic, is a challenge because of its high molecular weight (1485.7 Da) and hydrophilicity (log P -3.1). The objective of this study was to investigate the feasibility of delivering VH into and across the skin using permeation enhancement techniques. Skin permeation studies were performed using Franz diffusion cell apparatus in the excised porcine skin model. The influence of co-treatment and pre-treatment of chemical permeation enhancers (oleic acid and palmitic acid) on permeation of VH across intact and tape-stripped skin was evaluated. In addition, continuous anodal iontophoresis was applied to enhance the skin permeation of VH. The mechanism of skin permeation enhancement by palmitic acid was investigated using FTIR spectroscopy, impedance spectroscopy, and thermal analysis techniques. Pharmacokinetic analysis was performed after the topical application of VH formulations in Sprague Dawley rats. Results from permeation studies showed that VH did not passively permeate across the intact skin after 48 h, whereas the cumulative amount of VH permeated across the tape-stripped skin was found to be 854 ± 67 µg/cm2. A combination of tape-stripping and chemical enhancers resulted in enhancing the cumulative amount of VH permeated across the skin by 2- and 10-fold with oleic acid and palmitic acid application, respectively. Similarly, 2 and 12 h pre-treatment of tape-stripped skin with palmitic acid enhanced the flux of VH across the skin by 1.7- and 5-fold, respectively. It was found that tape-stripping and the palmitic acid application would provide greater VH permeation compared with 0.31 mA/cm2iontophoresis application. Thermal analysis and impedance spectroscopic analysis showed that palmitic acid interacts with epidermal lipids to enhance VH permeation. Pharmacokinetic analysis after topical application showed that the Cmaxand mean residence time increased by 3-fold with the application of VH and palmitic acid on tape-stripped skin compared with free VH on intact skin. Taken together, VH can be delivered through the topical route using a combination of chemical enhancer and tape-stripping to treat local and systemic bacterial infections.
7. Vancomycin Hydrochloride Loaded Hydroxyapatite Mesoporous Microspheres with Micro/Nano Surface Structure to Increase Osteogenic Differentiation and Antibacterial Ability
Xiaopei Wu,Zhiqing Mei,Yunhui Chai,Kai Huang,Beizhi Zhang,Honglian Dai,Xuejie Wei J Biomed Nanotechnol . 2021 Aug 1;17(8):1668-1678. doi: 10.1166/jbn.2021.3128.
As infection induced by the implant will lead to operation failure, the implant material must be endowed with certain antibacterial properties. Hydroxyapatite (HA) mesoporous microspheres have been widely used in bone repair due to their advantages, including simple synthesis, good osteogenic properties and drug loading capacity. In this study, vancomycin hydrochloride-loaded mesoporous hydroxyapatite microspheres with micro/nanosurface structures were synthesized to increase osteogenic differentiation and antibacterial ability. Phytic acid (IP6) was used as a template to prepare mesoporous hydroxyapatite microspheres composed of fibres, flakes and smooth surfaces by the hydrothermal homogeneous precipitation method, and the corresponding specific surface areas were 65.20 m²/g, 75.13 m²/g and 71.27 m²/g, respectively. Vancomycin hydrochloride (Van) was used as the drug model to study the drug loading and release characteristics of the microspheres, as well as thein vitroantibacterial properties after treatment. In addition, during cocultivation with MC3T3-E1 preosteoblasts, HA microspheres assembled via flakes exhibited better cell compatibility, which promoted cell proliferation, alkaline phosphatase (ALP) activity, and the formation of calcium nodules and increased the expression of osteogenic differentiation-related proteins such as Runx-2, osteopontin (OPN) and collagen I (COL I). These results indicated that the HA microspheres prepared in this experiment have broad application prospects in drug delivery systems and bone repair.
8. Vancomycin
M P Wilhelm Mayo Clin Proc . 1991 Nov;66(11):1165-70. doi: 10.1016/s0025-6196(12)65799-1.
Vancomycin is a glycopeptide antibiotic that is active against staphylococci, streptococci, and other gram-positive bacteria. It is the drug of choice for the treatment of infections due to methicillin-resistant staphylococci, Corynebacterium jeikeium, and multiply resistant strains of Streptococcus pneumoniae. Vancomycin is an alternative treatment for serious staphylococcal and streptococcal infections, including endocarditis, when allergy precludes the use of penicillins and cephalosporins. Vancomycin is bactericidal against most strains of staphylococci and nonenterococcal streptococci. Although rare strains of staphylococci and enterococci that are resistant to vancomycin have been reported, bacterial resistance has thus far not emerged as a major clinical problem despite widespread use of vancomycin. When therapy is monitored by periodic determinations of serum concentrations of the drug and rapid infusion rates are avoided, vancomycin is rarely associated with serious toxicity.
9. Vancomycin: a history
Donald P Levine Clin Infect Dis . 2006 Jan 1;42 Suppl 1:S5-12. doi: 10.1086/491709.
Vancomycin became available for clinical use >50 years ago but was soon discarded in favor of other antibiotics that were deemed to be more efficacious and less toxic. The advent of pseudomembranous enterocolitis, coupled with the spread of methicillin-resistant Staphylococcus aureus, led to a resurgence in the use of vancomycin. Almost immediately, concerns arose with regard to its therapeutic utility. In addition, resistance to vancomycin developed, first in enterococci and later in staphylococci. Several types of resistance have now been identified, each with a unique effect on infections treated with vancomycin. Recent studies have rekindled interest in the best way to administer the antibiotic. The findings of future studies may result in a return to measuring levels of vancomycin in serum, to assure a successful therapeutic outcome.
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Bio Calculators
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Concentration (start) x Volume (start) = Concentration (final) x Volume (final)
It is commonly abbreviated as: C1V1 = C2V2
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Tip: Chemical formula is case sensitive. C22H30N4O √ c22h30n40 ╳
