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安全信息

V2002

Sigma-Aldrich

万古霉素 盐酸盐 来源于东方链霉菌

≥900 μg per mg (as vancomycin base)

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别名:
Vancomycin
经验公式（希尔记法）:
C66H75Cl2N9O24 · HCl
CAS号:
1404-93-9
分子量:
1485.71
Beilstein:
3704657
PubChem化学物质编号:
24900723
NACRES:
NA.85

生物来源

Streptomyces orientalis

质量水平

200

形式

powder

储存条件

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

浓度

≥900 μg/mg (as vancomycin base)

颜色

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

抗生素抗菌谱

Gram-positive bacteria

作用机制

cell wall synthesis | interferes

储存温度

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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相关类别

一般描述

万古霉素是一种非核糖体糖肽抗生素，其特点是具有支链、三环和糖基化结构。与 β -内酰胺类抗生素不同，万古霉素在早期阶段通过抑制细菌细胞壁合成来起作用。它的活性谱主要针对好氧和厌氧革兰氏阳性细菌，包括广泛的分离株，包括对 β-内酰胺具有抗性的分离株。万古霉素对革兰氏阳性菌如艰难梭菌、单核增生李斯特菌、化脓性链球菌、肺炎链球菌、无乳链球菌、翠绿链球菌、牛链球菌、表皮葡萄球菌、放线菌和乳杆菌等均有显著疗效。它在对抗耐甲氧西林金黄色葡萄球菌 (MRSA) 方面表现出卓越的功效。此外，万古霉素在细胞生物学和生物化学研究中是防止细菌污染物增殖的宝贵工具。

应用

东方链霉菌的盐酸万古霉素已用于：
  • 研究抗生素诱导的厚壁菌门和拟杆菌门的消耗对肥胖患者能量稳态失调的影响
  • 研究牛养殖场非 o157 产志贺毒素大肠杆菌分离株
  • 研究双歧杆菌菌株在不同生物体内的抗菌敏感性

生化/生理作用

万古霉素是一种可在肽聚糖生物合成水平阻断细菌细胞壁生物合成的糖肽抗生素。 它会抑制NAM/NAG-肽的末端D-丙氨酰-D-丙氨酸部分插入。 它可有效用于革兰氏阳性菌。 万古霉素可改变细菌细胞膜的通透性和RNA合成。
万古霉素通过与十一戊烯基-(胞壁酰-葡萄糖胺基)-五肽形成非共价键发挥其抗菌作用，后者是细菌细胞壁生物合成的重要前体。这种相互作用破坏了肽聚糖的合成，干扰了对细菌细胞壁构建至关重要的转糖基化和转肽化过程。因此，细胞壁的完整性受到损害，导致细胞裂解。此外，万古霉素增加了细菌细胞壁的通透性，阻碍了 RNA 的合成。
作用机制：它会抑制 NAM/NAG-肽的末端 D-丙氨酰-D-丙氨酸部分插入。

抗菌谱：对革兰氏阳性细菌有活性。

特点和优势

  • 有效对抗多种革兰氏阳性细菌，包括耐甲氧西林金黄色葡萄球菌
  • 常用于细胞生物学和生物化学应用

包装

无底玻璃瓶。内含物装在插入的融合锥内。

其他说明

保持容器密闭并置于干燥通风处。
For additional information on our range of Biochemicals, please complete this form.

象形图

Health hazard
GHS08

警示用语：

Danger

危险声明

H317 - H334

危险分类

Resp. Sens. 1 - Skin Sens. 1

储存分类代码

11 - Combustible Solids

WGK

WGK 2

闪点(°F)

Not applicable

闪点(°C)

Not applicable

个人防护装备

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

法规信息

监管及禁止进口产品

分析证书(COA)

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索取COA

  1. Which document(s) contains shelf-life or expiration date information for a given product?

    If available for a given product, the recommended re-test date or the expiration date can be found on the Certificate of Analysis.

  2. How do I get lot-specific information or a Certificate of Analysis?

    The lot specific COA document can be found by entering the lot number above under the "Documents" section.

  3. What is Product V2002, Vancomycin, soluble in?

    This product is soluble in water (50 mg/ml), forming a clear, colorless to faint yellow solution. It is also moderately soluble in methanol, but insoluble in the higher alcohols, acetone, and ether. Low concentrations of urea increase the solubility in neutral aqueous solutions, and ammonium sulfate and sodium chloride precipitate the antibiotic from acidic solutions.

  4. How long are Product V2002, Vancomycin, solutions stable for?

    Solutions of vancomycin in physiological solutions such as 0.9% saline and 5% glucose are stable for 17 days at 24 °C and 63 days and 5 °C and -10 °C.

  5. What is the retest period for Product V2002, Vancomycin?

    At this time, Product No. V2002 is assigned a retest period of 2 years from the quality control release date. This interval may change if we are able to collect sufficient data from future retesting.

  6. How do I find price and availability?

    There are several ways to find pricing and availability for our products. Once you log onto our website, you will find the price and availability displayed on the product detail page. You can contact any of our Customer Sales and Service offices to receive a quote.  USA customers:  1-800-325-3010 or view local office numbers.

  7. What is the Department of Transportation shipping information for this product?

    Transportation information can be found in Section 14 of the product's (M)SDS.To access the shipping information for this material, use the link on the product detail page for the product. 

  8. My question is not addressed here, how can I contact Technical Service for assistance?

    Ask a Scientist here.

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
Serotypes and virulence profiles of non-O157 Shiga toxin-producing Escherichia coli isolates from bovine farms
Monaghan A et al.
Applied and Environmental Microbiology, 77, 8662-8668 (2011)
Antimicrobial susceptibility of Bifidobacterium strains from humans, animals and probiotic products
Masco et al.
The Journal of Antimicrobial Chemotherapy, 58, 85-94 (2006)
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)
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