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94747

Sigma-Aldrich

Vancomicina hydrochloride from Streptomyces orientalis

≥85% (Vancomycin B)

Sinónimos:

Vancomycin HCL

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About This Item

Fórmula empírica (notación de Hill):
C66H75Cl2N9O24 · HCl
Número de CAS:
1404-93-9
Peso molecular:
1485.71
Beilstein/REAXYS Number:
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

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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

Modo de acción: inhibe la incorporación de los restos de D-alanil-D-alanina terminales de los NAM/NAG-péptidos.

Espectro antimicrobiano: activo contra las bacterias grampositivas

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

signalword

Danger

hcodes

H317,H334

Hazard Classifications

Resp. Sens. 1 - Skin Sens. 1

Storage Class

11 - Combustible Solids

wgk_germany

WGK 2

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

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

Certificados de análisis (COA)

Busque Certificados de análisis (COA) introduciendo el número de lote del producto. Los números de lote se encuentran en la etiqueta del producto después de las palabras «Lot» o «Batch»

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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
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
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
Kerri A Miller et al.
Proceedings of the National Academy of Sciences of the United States of America, 116(13), 5955-5960 (2019-03-10)
Copper is a critical enzyme cofactor in the body but also a potent cellular toxin when intracellularly unbound. Thus, there is a delicate balance of intracellular copper, maintained by a series of complex interactions between the metal and specific copper
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