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SBR00001

Sigma-Aldrich

Vancomycin hydrochloride

Ready Made Solution, 100 mg/mL in DMSO

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Synonym(s):
Vancomycin HCL
Empirical Formula (Hill Notation):
C66H75Cl2N9O24 · xHCl
CAS Number:
1404-93-9
Molecular Weight:
1449.25 (free base basis)
NACRES:
NA.85

biological source

Streptomyces orientalis

Quality Level

200

form

liquid

storage condition

(Keep container tightly closed in a dry and well-ventilated place. Storage class (TRGS 510) Combustible liquids.)

concentration

100 mg/mL in DMSO

color

colorless to faint tan

antibiotic activity spectrum

Gram-positive bacteria

Mode of action

cell wall synthesis | interferes

storage temp.

−20°C

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

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General description

Vancomycin is a glycopeptide antibiotic, which was initially isolated from Streptomyces orientalis. It is effective against multidrug-resistant MRSA strain (methicillin-resistant Staphylococcus aureus). However, it is nephrotoxic as it is mainly excreted by the kidneys. It has a core heptapeptide having aliphatic amino acids at positions 1 and 3. It is mainly effective against gram-positive bacteria.

Application

Vancomycin hydrochloride may be used-
  • for the assessment of the antimicrobial activity of vancomycin hydrochloride against Mycobacterium tuberculosis in nonreplicating persistence (NRP) using low-oxygen-recovery assay (LORA) and against a luciferase reporter strain of M. tuberculosis in a fermentor-grown culture adapted to low oxygen conditions
  • for the estimation of biomass in a culture of various strains of bacteria
  • as a positive control for E. coli and Staphylococcus aureus in antibacterial activity assay.

Biochem/physiol Actions

Vancomycin is bactericidal in nature, where it inhibits the synthesis of peptidoglycan. It forms hydrogen bond with the peptidoglycan precursor UDP-N-acetylmuramylpentapeptide, and forms a stoichiometric 1:1 complex. Thus, it prevents the growth of the glycan polymer of peptidoglycan by transglycosylase enzyme.

Packaging

10ML

Other Notes

Keep container tightly closed in a dry and well-ventilated place. Storage class (TRGS 510): Combustible liquids

Pictograms

Health hazard
GHS08

Signal Word

Danger

Hazard Statements

H317 - H334

Hazard Classifications

Resp. Sens. 1 - Skin Sens. 1

Storage Class Code

10 - Combustible liquids

WGK

WGK 2

Flash Point(F)

188.6 °F - closed cup

Flash Point(C)

87 °C - closed cup

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Antibacterial activities and modes of action of vancomycin and related glycopeptides.
R Nagarajan
Antimicrobial agents and chemotherapy, 35(4), 605-609 (1991-04-01)
S L Kinniment et al.
Microbiology (Reading, England), 142 ( Pt 3), 631-638 (1996-03-01)
The complexity of biofilm communities like dental plaque suggests that laboratory model biofilm growth systems may help to understand their structure and function. This study describes the use of a constant-depth film fermenter (CDFF) to investigate biofilm formation by a
Naoko Hodoshima et al.
Drug metabolism and pharmacokinetics, 19(1), 68-75 (2004-10-23)
A generic form of vancomycin for I.V. infusion (MEEK) is more soluble and stable than the brand-name form of vancomycin hydrochloride (VCM) due to the addition of two inactive ingredients: D-mannitol and Macrogol400 (PEG400). The aim of the present study
Ayda Sarikaya et al.
Tissue engineering, 8(1), 63-71 (2002-03-12)
Materials derived from extracellular matrices (ECMs) are being evaluated as scaffolds for surgical reconstruction of damaged or missing tissues. It is important to understand the susceptibility of these biological materials to bacterial infections. ECMs derived from porcine small intestinal submucosa
R C Evans et al.
Antimicrobial agents and chemotherapy, 31(6), 889-894 (1987-06-01)
Peritonitis is a major complication of continuous ambulatory peritoneal dialysis. Relapsing peritonitis after the cessation of antimicrobial therapy is frequently reported and often involves Staphylococcus epidermidis. To investigate the potential role of catheter-associated biofilm in the pathogenesis of relapsing peritonitis
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