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Merck
CN

A2804

Ampicillin sodium salt

powder

Synonym(s):

D-(−)-α-Aminobenzylpenicillin sodium salt

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About This Item

Empirical Formula (Hill Notation):
C16H18N3NaO4S
CAS Number:
Molecular Weight:
371.39
EC Number:
200-708-1
UNSPSC Code:
12352200
PubChem Substance ID:
Beilstein/REAXYS Number:
4119211
MDL number:
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InChI key

KLOHDWPABZXLGI-YWUHCJSESA-M

InChI

1S/C16H19N3O4S.Na/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);/q;+1/p-1/t9-,10-,11+,14-;/m1./s1

SMILES string

[Na+].CC1(C)SC2[C@H](NC(=O)[C@H](N)c3ccccc3)C(=O)N2[C@H]1C([O-])=O

sterility

γ-irradiated

form

powder

color

white to slight yellow

mp

215 °C (dec.) (lit.)

solubility

sterile water: 5-20 mg/mL (as a stock solution)

antibiotic activity spectrum

Gram-negative bacteria, Gram-positive bacteria

storage temp.

2-8°C

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General description

Chemical structure: β-lactam

Application

Recommended for use in molecular biology applications at 20-50 μg/ml.

Biochem/physiol Actions

Mode of Action: This is a β-lactam antibiotic that inhibits bacterial cell-wall synthesis by inactivating transpeptidases on the inner surface of the bacterial cell membrane.

Mode of Resistance: Administration with β-lactamase cleaves the β-lactam ring of Ampicillin and inactivates it.

Antimicrobial Spectrum: Includes both gram-positive (similar to benzylpenicillin) and gram-negative bacteria (similar to tetracyclines and chloramphenicol.

Preparation Note

Prepare stock solutions directly in the vial at any concentration in the recommended range. Stock solutions should be stored at −20 °C. Stable at 37 °C for 3 days.

Analysis Note

USP potency testing is carried out on control vials after γ-irradiation to assure full biological activity (except where noted).

pictograms

Health hazard

signalword

Danger

hcodes

Hazard Classifications

Resp. Sens. 1A - Skin Sens. 1A

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

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

Regulatory Information

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Torbjörn Johansson et al.
Genesis (New York, N.Y. : 2000), 48(4), 264-280 (2010-02-10)
Transgenic mice are highly valuable tools for biological research as they allow cell type-specific expression of functionally instrumental genes. In this protocol, the generation of bacterial artificial chromosome (BAC) transgenic constructs is described. We give an overview of different transgenic
Xiaomei Chen et al.
Journal of natural products, 72(9), 1712-1715 (2009-08-28)
A study on the chemical constituents of the endophytic fungus Preussia sp. led to the isolation of three new spirobisnaphthalene analogues, spiropreussione A (1), spiropreussione B (2), and spiropreussomerin A (3). Compound 2 is a spirobisnaphthalene analogue with a cyclopenteno-naphthoindene
Nuria Fernández-Hidalgo et al.
Clinical infectious diseases : an official publication of the Infectious Diseases Society of America, 56(9), 1261-1268 (2013-02-09)
The aim of this study was to compare the effectiveness of the ampicillin plus ceftriaxone (AC) and ampicillin plus gentamicin (AG) combinations for treating Enterococcus faecalis infective endocarditis (EFIE). An observational, nonrandomized, comparative multicenter cohort study was conducted at 17
Jianhua Yin et al.
PloS one, 8(3), e60460-e60460 (2013-04-05)
Shewanella oneidensis is a facultative anaerobic γ-proteobacterium possessing remarkably diverse respiratory capacities for reducing various organic and inorganic substrates. As a veteran research model for investigating redox transformations of environmental contaminants the bacterium is well known to be a naturally
Yuanyuan Liu et al.
Science (New York, N.Y.), 339(6124), 1210-1213 (2013-03-09)
Recent observations have suggested that classic antibiotics kill bacteria by stimulating the formation of reactive oxygen species (ROS). If true, this notion might guide new strategies to improve antibiotic efficacy. In this study, the model was directly tested. Contrary to

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