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A8351

Sigma-Aldrich

Ampicillin sodium salt

BioXtra, suitable for cell culture

Synonym(s):

D-(−)-α-Aminobenzylpenicillin sodium salt

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About This Item

Empirical Formula (Hill Notation):
C16H18N3NaO4S
CAS Number:
69-52-3
Molecular Weight:
371.39
Beilstein:
4119211
EC Number:
200-708-1
MDL number:
MFCD00064313
UNSPSC Code:
51281716
PubChem Substance ID:
24891335
NACRES:
NA.76

product line

BioXtra

Quality Level

200

form

powder

technique(s)

cell culture | mammalian: suitable

impurities

endotoxin, tested

color

white to off-white

mp

215 °C (dec.) (lit.)

antibiotic activity spectrum

Gram-negative bacteria
Gram-positive bacteria

Mode of action

cell wall synthesis | interferes

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.

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.

Caution

This product has been reported stable as supplied at 25°C at 43% and 81% relative humidity for six weeks. 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, hygroscopic.

Pictograms

Health hazard
GHS08

Signal Word

Danger

Hazard Statements

H317 - H334

Hazard Classifications

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

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Sigma-Aldrich

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