Vancomycin
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| Category | Antibiotics |
| Catalog number | BBF-03437 |
| CAS | 1404-90-6 |
| Molecular Weight | 1449.25 |
| Molecular Formula | C66H75Cl2N9O24 |
| Purity | >98% |
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Description
Tricyclic glycopeptide antibiotic. Inhibits cell wall synthesis in Gram-positive bacteria. Pharmacologically active in vivo.
Specification
| Related CAS | 1404-93-9 (hydrochloride) 64685-75-2 (sulfate) |
| Synonyms | Vancocin; Vancomycinum; Vancomicina; Vancomycine; (S)-3,6-Diamino-hexanoic acid {(3S,9S,12S,15S)-3-((S)-6-hydroxy-2-imino-hexahydro-pyrimidin-4-yl)-9,12-bis-hydroxymethyl-2,5,8,11,14-pentaoxo-6-[1-ureido-meth-(Z)-ylidene]-1,4,7,10,13pentaaza-cyclohexadec-15-yl}-amide |
| Storage | Store at 2-8°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 |
| 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=C9O)O)C(NC(=O)C(C(C1=CC(=C(O4)C=C1)Cl)O)NC7=O)C(=O)O)CC(=O)N)NC(=O)C(CC(C)C)NC)O)Cl)CO)O)O)(C)N)O |
| InChI | 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 |
| InChI Key | MYPYJXKWCTUITO-LYRMYLQWSA-N |
| Source | Streptomyces orientalis |
Properties
| Appearance | White to Off-white Powder |
| Antibiotic Activity Spectrum | Gram-positive bacteria |
| Density | 1.65 g/cm3 |
| Solubility | Soluble in water |
| LogP | -3.1 |
Toxicity
| Carcinogenicity | No indication of carcinogenicity to humans (not listed by IARC). |
| Mechanism Of Toxicity | The bactericidal action of vancomycin results primarily from inhibition of cell-wall biosynthesis. Specifically, vancomycin prevents incorporation of N-acetylmuramic acid (NAM)- and N-acetylglucosamine (NAG)-peptide subunits from being incorporated into the peptidoglycan matrix; which forms the major structural component of Gram-positive cell walls. The large hydrophilic molecule is able to form hydrogen bond interactions with the terminal D-alanyl-D-alanine moieties of the NAM/NAG-peptides. Normally this is a five-point interaction. This binding of vancomycin to the D-Ala-D-Ala prevents the incorporation of the NAM/NAG-peptide subunits into the peptidoglycan matrix. In addition, vancomycin alters bacterial-cell-membrane permeability and RNA synthesis. There is no cross-resistance between vancomycin and other antibiotics. Vancomycin is not active in vitro against gram-negative bacilli, mycobacteria, or fungi. |
| Toxicity | LD50: 5000 mg/kg (Oral, Mouse); LD50: 319 mg/kg (Intravenous, Rat); LD50: 400 mg/kg (Intravenous, Mouse). |
Reference Reading
1.Characterization and rapid control of a vancomycin-resistant Enterococcus faecium (VREF) outbreak in a renal transplant unit in Spain: The environment matters.
Herrera S1, Sorlí L2, Pérez-Sáez MJ3, Ruiz-Garbajosa P4, Barrios C3, Plasencia V5, Montero M2, Terradas R6, Crespo M3, Castells X6, Cantón R4, Pascual J3, Horcajada JP2. Enferm Infecc Microbiol Clin. 2016 May 4. pii: S0213-005X(16)30081-7. doi: 10.1016/j.eimc.2016.04.002. [Epub ahead of print]
OBJECTIVE: To describe a clonal outbreak due to vancomycin-resistant Enterococcus faecium (VREF) in the nephrology and renal transplant unit of a tertiary teaching hospital in Barcelona, Spain, and to highlight how active patient and environment surveillance cultures, as well as prompt and directed intervention strategies, mainly environmental, helped to successfully bring it under control.
2.Draft Genome Sequence of Vancomycin-Susceptible, Ampicillin-Intermediate Enterococcus faecium Strain D344RRF.
García-Solache M1, Rice LB2. Genome Announc. 2016 May 5;4(3). pii: e01720-15. doi: 10.1128/genomeA.01720-15.
Enterococcus faecium is an important nosocomial pathogen, causing a substantial health burden due to high resistance to antibiotics and its ability to colonize the gastrointestinal tract. Here, we present the draft genome of vancomycin-susceptible, ampicillin-intermediate strain D344RRF, a rifampicin/fusidic acid-resistant and commonly used laboratory strain, which is useful in studying the transfer of antibiotic resistance.
3.Identification of subclinical transmission of vancomycin-resistant enterococcus within an intensive care unit in Taiwan.
Lee SC1, Lee CW2, Shih TC3, See LC4, Chu CM5, Liu YC5. J Microbiol Immunol Infect. 2016 Jan 18. pii: S1684-1182(16)00012-8. doi: 10.1016/j.jmii.2015.11.002. [Epub ahead of print]
BACKGROUND/PURPOSE: Colonization, infection, and clonal dissemination of vancomycin-resistant enterococcus (VRE) have been reported in the literature. We aimed to investigate the incidence rate of VRE acquisition and route of transmission of VRE within the medical intensive care unit (ICU) to prove whether subclinical transmission occurs in medical ICUs.
4.Resistance Mechanisms, Epidemiology, and Approaches to Screening for Vancomycin Resistant Enterococcus (VRE) in the Health Care Setting.
Faron ML1, Ledeboer NA2, Buchan BW3. J Clin Microbiol. 2016 May 4. pii: JCM.00211-16. [Epub ahead of print]
Infections attributable to vancomycin resistant Enterococcus (VRE) have become increasingly prevalent over the past decade. Prompt identification of colonized patients combined with effective multifaceted infection control practices can reduce transmission of VRE and aid in prevention of hospital acquired infections (HAIs). Increasingly, the clinical microbiology laboratory is being asked to support infection control efforts through early identification of potential patient or environmental reservoirs. This review discusses the factors that contribute to the rise of VRE as an important healthcare associated pathogen, the utility of laboratory screening and various infection control strategies and the available laboratory methods to identify VRE in clinical specimens.
Spectrum
LC-MS/MS Spectrum - DI-ESI-Ion Trap , Positive
Experimental Conditions
Instrument Type: DI-ESI-Ion Trap
Ionization Mode: Positive
Ionization Mode: Positive
Predicted LC-MS/MS Spectrum - 10V, Positive
Experimental Conditions
Ionization Mode: Positive
Collision Energy: 10 eV
Instrument Type: QTOF (generic), spectrum predicted by CFM-ID
Mass Resolution: 0.0001 Da
Molecular Formula: C66H75Cl2N9O24
Molecular Weight (Monoisotopic Mass): 1447.4302 Da
Molecular Weight (Avergae Mass): 1449.254 Da
Collision Energy: 10 eV
Instrument Type: QTOF (generic), spectrum predicted by CFM-ID
Mass Resolution: 0.0001 Da
Molecular Formula: C66H75Cl2N9O24
Molecular Weight (Monoisotopic Mass): 1447.4302 Da
Molecular Weight (Avergae Mass): 1449.254 Da
13C NMR Spectrum
Experimental Conditions
Solvent: D2O
Nucleus: 13C
Frequency: 100
Nucleus: 13C
Frequency: 100
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Bio Calculators
* Our calculator is based on the following equation:
Concentration (start) x Volume (start) = Concentration (final) x Volume (final)
It is commonly abbreviated as: C1V1 = C2V2
* Total Molecular Weight:
g/mol
Tip: Chemical formula is case sensitive. C22H30N4O √ c22h30n40 ╳
