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Safety Information

V2002

Sigma-Aldrich

Vancomycin hydrochloride from Streptomyces orientalis

≥900 μg per mg (as vancomycin base)

Synonym(s):

Vancomycin, Vancomycin HCL

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About This Item

Empirical Formula (Hill Notation):
C66H75Cl2N9O24 · HCl
CAS Number:
1404-93-9
Molecular Weight:
1485.71
Beilstein:
3704657
UNSPSC Code:
51282703
PubChem Substance ID:
24900723
NACRES:
NA.85

biological source

Streptomyces orientalis

Quality Level

200

form

powder

storage condition

(Keep container tightly closed in a dry and well-ventilated place.)

concentration

≥900 μg/mg (as vancomycin base)

color

, off-white to brown or White to orange-brown

antibiotic activity spectrum

Gram-positive bacteria

Mode of action

cell wall synthesis | interferes

storage temp.

2-8°C

SMILES string

Cl[H].CO[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@@H]1O[C@H]2C[C@](C)(N)[C@@H](O)[C@@H](C)O2.CN[C@H](CC(C)C)C(=O)NC3[C@H](O)c4ccc(Oc5cc6Oc7ccc(cc7Cl)[C@@H](O)[C@H]8NC(=O)[C@H](NC(=O)[C@H](NC(=O)[C@H](CC(N)=O)NC3=O)c(c5)c6)c9ccc(O)c(c9)-c%10c(O)cc(O)cc%10[C@@H](NC8=O)C(O)=O)c(Cl)c4

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 nonribosomal glycopeptide antibiotic characterized by its branched, tricyclic, and glycosylated structure. Unlike beta-lactam antibiotics, vancomycin operates by inhibiting bacterial cell wall synthesis at an earlier stage. Its spectrum of activity is primarily directed against aerobic and anaerobic gram-positive bacteria, encompassing a wide range of isolates, including those that exhibit resistance to β-lactams. Vancomycin is notably effective against Gram-positive organisms such as Clostridium difficile, Listeria monocytogenes, Streptococcus pyogenes, Streptococcus pneumoniae, Streptococcus agalactiae, Streptococcus viridans, Streptococcus bovis, Staphylococcus epidermidis, Actinomyces species, and Lactobacillus species. It demonstrates exceptional efficacy in combating methicillin-resistant Staphylococcus aureus (MRSA). Furthermore, vancomycin is a valuable tool for preventing the proliferation of bacterial contaminants in studies related to cell biology and biochemistry.

Application

Vancomycin hydrochloride from Streptomyces orientalis has been used:
  • in the research the effects of antibiotic-induced depletion of Firmicutes and Bacteroidetes on dysregulation of energy homeostasis in obesity
  • in the research of non-O157 Shiga toxin-producing Escherichia coli Isolates from Bovine Farms
  • to research the antimicrobial susceptibility of Bifidobacterium strains in various organisms

Biochem/physiol Actions

Mode of action: Inhibits incorporation of terminal D-alanyl-D-alanine moieties of the NAM/NAG-peptides.

Antimicrobial Spectrum: Active against Gram-positive bacteria
Vancomycin exerts its antibacterial effects by forming noncovalent bonds with undecaprenyl-(muramyl-glucosaminyl)-pentapeptide, a crucial precursor in the biosynthesis of bacterial cell walls. This interaction disrupts the synthesis of peptidoglycan, interfering with the transglycosylation and transpeptidation processes that are essential for bacterial cell wall construction. Consequently, the cell wall′s integrity is compromised, leading to cell lysis. Furthermore, Vancomycin augments the permeability of the bacterial cell wall and hinders RNA synthesis.
Vancomycin is a glycopeptide antibiotic that blocks bacterial cell wall biosynthesis at the level of peptidoglycan biosynthesis. It inhibits incorporation of terminal D-alanyl-D-alanine moieties of the NAM/NAG-peptides. It is effective against Gram-positive bacteria. Vancomycin also alters bacterial-cell-membrane permeability and RNA synthesis.

Features and Benefits

  • Effective against a wide range of Gram-positive bacteria, including MRSA
  • Commonly used in Cell Biology and Biochemical applications

Packaging

Bottomless glass bottle. Contents are inside inserted fused cone.

Other Notes

For additional information on our range of Biochemicals, please complete this form.
Keep container tightly closed in a dry and well-ventilated place.

Pictograms

Health hazard
GHS08

Signal Word

Danger

Hazard Statements

H317,H334

Hazard Classifications

Resp. Sens. 1 - Skin Sens. 1

Storage Class Code

11 - Combustible Solids

WGK

WGK 2

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Regulatory Information

监管及禁止进口产品

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Certificates of Analysis (COA)

Lot/Batch Number
0000406483
0000405932
0000395352
0000367076
0000405932

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  1. Which document(s) contains shelf-life or expiration date information for a given product?

    If available for a given product, the recommended re-test date or the expiration date can be found on the Certificate of Analysis.

  2. How do I get lot-specific information or a Certificate of Analysis?

    The lot specific COA document can be found by entering the lot number above under the "Documents" section.

  3. What is Product V2002, Vancomycin, soluble in?

    This product is soluble in water (50 mg/ml), forming a clear, colorless to faint yellow solution. It is also moderately soluble in methanol, but insoluble in the higher alcohols, acetone, and ether. Low concentrations of urea increase the solubility in neutral aqueous solutions, and ammonium sulfate and sodium chloride precipitate the antibiotic from acidic solutions.

  4. How long are Product V2002, Vancomycin, solutions stable for?

    Solutions of vancomycin in physiological solutions such as 0.9% saline and 5% glucose are stable for 17 days at 24 °C and 63 days and 5 °C and -10 °C.

  5. What is the retest period for Product V2002, Vancomycin?

    At this time, Product No. V2002 is assigned a retest period of 2 years from the quality control release date. This interval may change if we are able to collect sufficient data from future retesting.

  6. How do I find price and availability?

    There are several ways to find pricing and availability for our products. Once you log onto our website, you will find the price and availability displayed on the product detail page. You can contact any of our Customer Sales and Service offices to receive a quote.  USA customers:  1-800-325-3010 or view local office numbers.

  7. What is the Department of Transportation shipping information for this product?

    Transportation information can be found in Section 14 of the product's (M)SDS.To access the shipping information for this material, use the link on the product detail page for the product. 

  8. My question is not addressed here, how can I contact Technical Service for assistance?

    Ask a Scientist here.

Serotypes and virulence profiles of non-O157 Shiga toxin-producing Escherichia coli isolates from bovine farms
Monaghan A et al.
Applied and Environmental Microbiology, 77, 8662-8668 (2011)
Ashraf Zarkan et al.
Scientific reports, 7(1), 4893-4893 (2017-07-09)
Vancomycin is known to bind to Zn(II) and can induce a zinc starvation response in bacteria. Here we identify a novel polymerization of vancomycin dimers by structural analysis of vancomycin-Zn(II) crystals and fibre X-ray diffraction. Bioassays indicate that this structure
Antimicrobial susceptibility of Bifidobacterium strains from humans, animals and probiotic products
Masco et al.
The Journal of Antimicrobial Chemotherapy, 58, 85-94 (2006)
Shasha Rao et al.
The Journal of antibiotics, 69(12), 879-884 (2016-05-18)
Antibiotic-resistant bacteria is a major threat to human health and is predicted to become the leading cause of death from disease by 2050. Despite the recent resurgence of research and development in the area, few antibiotics have reached the market
Aβeβment of vancomycin use in chronic haemodialysis patients: room for improvement
Keyserling HL, et al.
Nephrology, Dialysis, and Transplantation, 112, e104-e111 (2003)
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Inhibition of Cell Wall Biosynthesis by Antibiotics

β-lactam antibacterials inhibit transpeptidase enzymes, preventing peptidoglycan assembly in both Gram-positive and Gram-negative bacteria.

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