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A0166

Sigma-Aldrich

Ampicillin sodium salt

powder or crystals, BioReagent, suitable for cell culture

Synonym(s):
D-(−)-α-Aminobenzylpenicillin sodium salt
Empirical Formula (Hill Notation):
C16H18N3NaO4S
CAS Number:
Molecular Weight:
371.39
Beilstein:
4119211
EC Number:
MDL number:
PubChem Substance ID:
NACRES:
NA.76

Quality Level

biological source

synthetic

product line

BioReagent

form

powder or crystals

potency

845-988 μg per mg (C16H18N3O4S, Calculated on the anhydrous basis)

application(s)

cell culture | mammalian: suitable

color

white to off-white

mp

215 °C (dec.) (lit.)

solubility

H2O: 50 mg/mL (Stock solutions should be stored at −20 °C.)

Mode of action

cell wall synthesis | interferes

antibiotic activity spectrum

Gram-negative bacteria
Gram-positive bacteria

storage temp.

2-8°C

SMILES string

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

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

InChI key

KLOHDWPABZXLGI-YWUHCJSESA-M

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General description

Chemical structure: ß-lactam

Application

Ampicillin is a semi-synthetic derivative of penicillin that functions as a broad-spectrum antibiotic. It has been used to study antibiotic resistance and penetration limitations, the synergy between multiple antibiotics, certain bloodstream infections, and has been used to develop PCR assays to detect resistance genes in cerebrospinal fluid.

Recommended for antibacterial use in cell culture media at 100 mg/L.
Recommended for use in ampicillin-resistance studies at 20-125 μg/ml.

Biochem/physiol Actions

Mode of Action: This is a ß-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 ß-lactamase cleaves the ß-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.

Packaging

5g, 25g, 100g

Caution

This product has been reported stable as supplied at 25°C at 43% and 81% relative humidity for six weeks. It is stable at 37°C for three days. Additional studies have shown that the stability of Ampicillin in solution is a function of pH, temperature and the identity of the buffer. It′s activity is quickly lost when stored above pH 7. Optimal storage conditions are suggested as 2-8°C, and pH 3.8-5 where its activity was retained at 90%+ for a week.

Preparation Note

Ampicillin is reported as slightly soluble in water, practically insoluble in alcohol, chloroform, ether and fixed oils but soluble in dilute acids or bases. The solution should not be autoclaved; a stock solution should be sterilized through filtration and stored frozen, where it will be stable for months.

Other Notes

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

Pictograms

Health hazard

Signal Word

Danger

Hazard Statements

Precautionary Statements

Hazard Classifications

Resp. Sens. 1 - Skin Sens. 1

Storage Class Code

13 - Non Combustible Solids

WGK Germany

WGK 2

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US),Eyeshields,Gloves

Certificate of Analysis

Certificate of Origin

M Ashley Sobran et al.
Journal of bacteriology, 201(17) (2019-06-27)
To detect and respond to the diverse environments they encounter, bacteria often use two-component regulatory systems (TCS) to coordinate essential cellular processes required for survival. In pathogenic Bordetella species, the BvgAS TCS regulates expression of hundreds of genes, including those...
Alexander Frank et al.
Current biology : CB, 28(16), 2597-2606 (2018-08-07)
Synchronization of circadian clocks to the day-night cycle ensures the correct timing of biological events. This entrainment process is essential to ensure that the phase of the circadian oscillator is synchronized with daily events within the environment [1], to permit...
Duccio Conti et al.
eLife, 8 (2019-12-07)
Microtubules segregate chromosomes by attaching to macromolecular kinetochores. Only microtubule-end attached kinetochores can be pulled apart; how these end-on attachments are selectively recognised and stabilised is not known. Using the kinetochore and microtubule-associated protein, Astrin, as a molecular probe, we...
Wei Lin et al.
Molecular cell, 70(1), 60-71 (2018-04-03)
Fidaxomicin is an antibacterial drug in clinical use for treatment of Clostridium difficile diarrhea. The active ingredient of fidaxomicin, lipiarmycin A3 (Lpm), functions by inhibiting bacterial RNA polymerase (RNAP). Here we report a cryo-EM structure of Mycobacterium tuberculosis RNAP holoenzyme in...
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...

Protocols

USP HPLC Analysis of Ampicillin Sodium on Ascentis® Express C18

USP HPLC Analysis of Ampicillin Sodium on Ascentis® Express C18

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