Skip to Content
Merck
All Photos(1)

Key Documents

View All Documentation

94747

Sigma-Aldrich

Vancomycin hydrochloride from Streptomyces orientalis

≥85% (Vancomycin B)

Synonym(s):

Vancomycin HCL

Sign Into View Organizational & Contract Pricing
All Photos(1)

About This Item

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

biological source

Streptomyces orientalis

Quality Level

100

Assay

≥85% (Vancomycin B)

form

powder

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

Looking for similar products? Visit Product Comparison Guide

General description

Chemical structure: glycopeptide

Application

Vancomycin has been used to study transcriptional induction of the penicillin-binding protein 2 gene in Staphylococcus aureus, the correlation of vancomycin and daptomycin susceptibility in Staphylococcus aureus, and the evaluation of telavancin activity in Staphylococcus aureus.

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

Packaging

250mg, 1g, 5g

Other Notes

Keep container tightly closed in a dry and well-ventilated place. Handle and store under inert gas.

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

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library

Warren E Rose et al.
The Journal of antimicrobial chemotherapy, 59(6), 1190-1193 (2007-04-17)
Recently, an association between the accessory gene regulator (agr) in Staphylococcus aureus and the development of vancomycin resistance secondary to suboptimal exposure has been demonstrated. We investigated the relationship of vancomycin with and without gentamicin or rifampicin, and daptomycin in
Gabriel A Russell et al.
STAR protocols, 2(4), 100946-100946 (2021-11-27)
The microbes indigenous to helminth species are a major obstacle to deciphering host-parasite interactions. Repurposing a system of reversible bacterial colonization, we have generated germ-free Heligomosomoides polygyrus bakeri (Hpb) larvae that maintain the sterility of axenic mice upon infection. This protocol
Helio S Sader et al.
The Journal of antimicrobial chemotherapy, 64(5), 1024-1028 (2009-09-12)
The bactericidal activities of vancomycin and daptomycin were evaluated in a large collection of methicillin-resistant Staphylococcus aureus (MRSA) bacteraemia strains from nine major USA medical centres. To evaluate the occurrence of heterogeneous vancomycin-intermediate S. aureus (hVISA) among MRSA strains tolerant
Susan Boyle-Vavra et al.
Antimicrobial agents and chemotherapy, 47(3), 1028-1036 (2003-02-27)
We found an increased abundance of pbpB-specific transcripts in vancomycin intermediate-resistant Staphylococcus aureus (VISA) isolates compared with that found in paired, genetically identical, susceptible isolates. This difference in expression cannot be explained by differences in the pbpB promoter sequence. Since
Oliver A Cornely et al.
Journal of clinical oncology : official journal of the American Society of Clinical Oncology, 31(19), 2493-2499 (2013-05-30)
Patients with cancer are at increased risk for Clostridium difficile-associated diarrhea (CDAD). Little is known about treatment response. Two double-blind trials randomly allocated 1,105 patients with CDAD to fidaxomicin or vancomycin treatment (modified intent-to-treat [mITT]), and 183 of these had
View All Related Papers

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.

Inhibition of Cell Wall Biosynthesis by Antibiotics

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

Inhibition of Cell Wall Biosynthesis by Antibiotics

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

Inhibition of Cell Wall Biosynthesis by Antibiotics

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

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service