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861987

Sigma-Aldrich

Vancomycin hydrochloride hydrate

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About This Item

Empirical Formula (Hill Notation):
C66H75Cl2N9O24 · HCl · xH2O
CAS Number:
123409-00-7
Molecular Weight:
1485.71 (anhydrous basis)
MDL number:
MFCD00151026
UNSPSC Code:
12352005
PubChem Substance ID:
329769449

optical activity

[α]21/D −28.5°, c = 1 in H2O

storage temp.

2-8°C

SMILES string

O.Cl.CN[C@H](CC(C)C)C(=O)N[C@@H]1[C@H](O)c2ccc(Oc3cc4cc(Oc5ccc(cc5Cl)[C@@H](O)[C@@H]6NC(=O)[C@H](NC(=O)[C@@H]4NC(=O)[C@H](CC(N)=O)NC1=O)c7ccc(O)c(c7)-c8c(O)cc(O)cc8[C@H](NC6=O)C(O)=O)c3O[C@@H]9O[C@H](CO)[C@@H](O)[C@H](O)[C@H]9O[C@H]%10CC(C)(N)[C@H](O)[C@H](C)O%10)c(Cl)c2

InChI

1S/C66H75Cl2N9O24.ClH.H2O/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;1H2/t24-,34+,35-,42+,44-,46+,47+,48-,49+,50-,51+,52+,53+,54-,56+,57+,65-,66-;;/m0../s1

InChI key

ZMJRZOPYYSQOFX-MHDRKALASA-N

Application

Used as selective membrane mergers to study the functional determinants of synthetic vesicle fusion

Used as an antibiotic for a variety of different studies including:
  • Impact to intestinal flora with prolonged exposure to antibiotics
  • Usefulness against antibiotic resistant bacterial strains
  • Transport of nanoparticles across phospholipid membranes

pictograms

Health hazard
GHS08

signalword

Danger

hcodes

H317,H334

Hazard Classifications

Resp. Sens. 1 - Skin Sens. 1

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

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

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Certificates of Analysis (COA)

Lot/Batch Number
WXBC7235V
WXBC1728V
WXBC4992V
WXBC3045V
WXBC3046V

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David J Tennent et al.
Journal of orthopaedic trauma, 30(10), 531-537 (2016-04-29)
To evaluate the effectiveness of locally applied vancomycin powder at different times postinfection in a contaminated traumatic animal model. This study used an established segmental defect rat femur model contaminated with Staphylococcus aureus UAMS-1 followed by treatment at 6 or
Jan Gessmann et al.
Tissue engineering. Part A, 24(9-10), 809-818 (2017-11-04)
Platelet-free blood plasma clots were loaded either with antibiotics (vancomycin, gentamicin, or linezolid) at concentrations of 5-300 μg/mL or with silver ions (silver acetate) at concentrations of 3.3-129 μg/mL. The release of antibiotics or silver from the clot matrix was analyzed after
Freija Van den Driessche et al.
International journal of antimicrobial agents, 49(3), 315-320 (2017-02-06)
Staphylococcus aureus biofilms are involved in a wide range of infections that are extremely difficult to treat with conventional antibiotic therapy. We aimed to identify potentiators of antibiotics against mature biofilms of S. aureus Mu50, a methicillin-resistant and vancomycin-intermediate-resistant strain.
Mu Cheng et al.
Antimicrobial agents and chemotherapy, 58(11), 6819-6827 (2014-09-04)
Ramoplanin is an actinomycetes-derived antibiotic with broad-spectrum activity against Gram-positive bacteria that has been evaluated in clinical trials for the treatment of gastrointestinal vancomycin-resistant enterococci (VRE) and Clostridium difficile infections. Recent studies have proposed that ramoplanin binds to bacterial membranes
Mia M Kiamco et al.
Biotechnology and bioengineering, 115(6), 1594-1603 (2018-02-21)
Biofilms alter their metabolism in response to environmental stress. This study explores the effect of a hyperosmotic agent-antibiotic treatment on the metabolism of Staphylococcus aureus biofilms through the use of nuclear magnetic resonance (NMR) techniques. To determine the metabolic activity
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