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

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About This Item

실험식(Hill 표기법):

C₆₆H₇₅Cl₂N₉O₂₄ · HCl

CAS Number:

1404-93-9

Molecular Weight:

1485.71

Beilstein:

3704657

UNSPSC 코드:

51282703

PubChem Substance ID:

24900723

NACRES:

NA.85

기술 서비스

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도움 문의

생물학적 소스

Streptomyces orientalis

Quality Level

200

양식

powder

저장 조건

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

농도

≥900 μg/mg (as vancomycin base)

색상

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

항생제 활성 스펙트럼

Gram-positive bacteria

동작 모드

cell wall synthesis | interferes

저장 온도

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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일반 설명

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.

애플리케이션

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

생화학적/생리학적 작용

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.

특징 및 장점

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

포장

Bottomless glass bottle. Contents are inside inserted fused cone.

기타 정보

For additional information on our range of Biochemicals, please complete this form.

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

픽토그램

GHS08

신호어

Danger

유해 및 위험 성명서

H317,H334

예방조치 성명서

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

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

개인 보호 장비

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

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