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V2002

Vancomycin hydrochloride from Streptomyces orientalis

Name: Vancomycin hydrochloride from <I>Streptomyces orientalis</I>
Brand: SIGMA

≥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

NACRES:

NA.85

PubChem Substance ID:

24900723

UNSPSC Code:

51282703

Beilstein/REAXYS Number:

3704657

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Properties

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

Description

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.

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pictograms

GHS08

signalword

Danger

hcodes

H317,H334

pcodes

P261 - P272 - P280 - P284 - P302 + P352 - P333 + P313

Hazard Classifications

Resp. Sens. 1 - Skin Sens. 1

Storage Class

11 - Combustible Solids

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Faceshields, Gloves

Regulatory Information

涉药品监管产品

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Articles

Inhibition of Cell Wall Biosynthesis by Antibiotics

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

Zn(II) mediates vancomycin polymerization and potentiates its antibiotic activity against resistant bacteria.

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

Preclinical development of Ramizol, an antibiotic belonging to a new class, for the treatment of Clostridium difficile colitis.

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)

View All Related Papers

Global Trade Item Number

SKU	GTIN
V2002-100G	04061833306956
V2002-1G	04061835550487
V2002-100MG	04061835550470
V2002-250MG	04061835514335
V2002-5G	04061835516964