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Merck
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安全信息

A9393

Sigma-Aldrich

氨苄西林

anhydrous, 96.0-102.0% (anhydrous basis)

别名:

D-(−)-α-氨苄青霉素

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About This Item

经验公式（希尔记法）:
C16H19N3O4S
CAS号:
69-53-4
分子量:
349.40
Beilstein:
1090925
EC 号:
200-709-7
MDL编号:
MFCD00005175
UNSPSC代码:
51101500
PubChem化学物质编号:
24891442
NACRES:
NA.85

质量水平

200

检测方案

96.0-102.0% (anhydrous basis)

形式

solid

pKa (25 °C)

2.5 (COOH)
7.3 (NH2)

mp

208 °C (dec.) (lit.)

抗生素抗菌谱

Gram-negative bacteria
Gram-positive bacteria

作用机制

cell wall synthesis | interferes

储存温度

2-8°C

SMILES字符串

[H][C@]12SC(C)(C)[C@@H](N1C(=O)[C@H]2NC(=O)[C@H](N)c3ccccc3)C(O)=O

InChI

1S/C16H19N3O4S/c1-16(2)11(15(22)23)19-13(21)10(14(19)24-16)18-12(20)9(17)8-6-4-3-5-7-8/h3-7,9-11,14H,17H2,1-2H3,(H,18,20)(H,22,23)/t9-,10-,11+,14-/m1/s1

InChI key

AVKUERGKIZMTKX-NJBDSQKTSA-N

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相关类别

一般描述

化学结构:β-内酰胺

应用

氨苄西林已被用于研究抗生素的耐药性和渗透性限制、多种抗生素之间的协同作用、某些血液感染，并已被用于开发检测脑脊液耐药基因的 PCR 检测法。

生化/生理作用

ββ-内酰胺被 β-内酰胺酶灭活，因此氨苄青霉素与 β-内酰胺酶抑制剂一起使用。
作用机制：氨苄西林是一种半合成的青霉素和ß-内酰胺抗生素，其通过灭活位于细菌的细胞膜内表面的转肽酶从而抑制细菌细胞壁合成。

耐药性机制：ß-内酰胺酶切开氨苄青霉素的ß-内酰胺环,使其失去活性。

抗菌谱：对革兰氏阳性菌（类似于苄青霉素）和革兰氏阴性菌（类似于四环素和氯霉素）均有效。

注意

据报道，该产品在25°C、43%和81%相对湿度下可稳定6周。 另外的研究表明氨苄青霉素在溶液中的稳定性与pH、温度和缓冲液的性质有关。 当储存在 pH 值 7 以上时，它′的活性很快就会丧失。 推荐最佳保存条件为2-8℃，pH 3.8-5，一周内其活性可保留90%。

制备说明

据报道，氨苄青霉素微溶于水，几乎不溶于酒精、氯仿、醚和固定油脂，但溶于稀酸或稀碱。 该溶液不应高压灭菌;原液应通过过滤消毒并冷冻保存，可稳定数月。

其他说明

在氩气环境中储存。保存于密闭容器内，置于干燥通风处，吸湿性。

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

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)

输入产品批号来搜索 分析证书(COA) 。批号可以在产品标签上"批“ （Lot或Batch）字后找到。

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  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. Is Ampicillin product stable in solution?

    We recommend using freshly prepared solutions. A concentrated solution of sodium ampicillin in water (approximately 330 mg/mL) may be expected to lose about 10% potency in 20 hours at -20°C.

  3. How do I use Ampicllin in agar plates?

    For plates, add ampicillin to autoclaved media cooled to 48°C, to a final concentration of 35-50 μg/mL. Pour the plates, and allow them to cool completely. Plates may be stored at 2-8°C for up to only 1-2 weeks before use.

  4. 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.

  5. What is the solubility of Product A9393, Ampicillin?

    The solubility of ampicillin is tested at 50 mg/mL in 1M ammonium hydroxide. Additional solubility information can be found on the product information sheet (under Documents, above).

  6. Which Ampicillin product has higher water solubility, Product A9393 or Product A9518?

    Product No. A9518 (Ampicillin, sodium salt) is soluble at 50 mg/mL in water.

  7. 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.

  8. 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. 

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

    Ask a Scientist here.

Comparative evaluation of a new beta-lactamase inhibitor, YTR 830, combined with different beta-lactam antibiotics against bacteria harboring known beta-lactamases.
Antimicrobial Agents and Chemotherapy, 29, 955-957 (1986)
Laurent Poirel et al.
Antimicrobial agents and chemotherapy, 52(5), 1613-1617 (2008-02-27)
The basis of the beta-lactam resistance of 39 multidrug-resistant Acinetobacter baumannii isolates recovered from hospitalized patients was studied. These isolates were collected from 2001 to 2005 at the Sahloul Hospital in Sousse, Tunisia. They belonged to two distinct clones. One
J N Anderl et al.
Antimicrobial agents and chemotherapy, 44(7), 1818-1824 (2000-06-20)
The penetration of two antibiotics, ampicillin and ciprofloxacin, through biofilms developed in an in vitro model system was investigated. The susceptibilities of biofilms and corresponding freely suspended bacteria to killing by the antibiotics were also measured. Biofilms of Klebsiella pneumoniae
Kenneth H Rand et al.
The Journal of antimicrobial chemotherapy, 53(3), 530-532 (2004-02-14)
We used a novel screening method to look for synergy between daptomycin and 18 other antibiotics against 19 strains of high-level vancomycin-resistant enterococci (VRE) (vancomycin MIC > or = 256 mg/L). In this approach, daptomycin was incorporated into Ca(2+)-supplemented Mueller-Hinton
M R Jacobs et al.
Antimicrobial agents and chemotherapy, 29(6), 980-985 (1986-06-01)
The in vitro synergistic activities of the beta-lactamase inhibitors YTR 830, clavulanate, and sulbactam, combined with ampicillin, ticarcillin, mezlocillin, azlocillin, piperacillin, and apalcillin, were determined against 34 strains of members of the Enterobacteriaceae family, Pseudomonas aeruginosa, Aeromonas hydrophila, and Haemophilus
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