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Ampicillin

analytical standard

Synonym: D-(−)-α-Aminobenzylpenicillin

  • CAS Number 69-53-4

  • Empirical Formula (Hill Notation) C16H19N3O4S

  • Molecular Weight 349.40

  •  Beilstein/REAXYS Number 1090925

  •  EC Number 200-709-7

  •  MDL number MFCD00005175

  •  PubChem Substance ID 329758626

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Properties

Related Categories Additional Standards, Analytical Standards, Analytical/Chromatography, Antibiotics Standards, Chemical Structure,
grade   analytical standard
InChI Key   AVKUERGKIZMTKX-NJBDSQKTSA-N
assay   ≥95.0% anhydrous basis (NT)
form   neat
shelf life   limited shelf life, expiry date on the label
application(s)   HPLC: suitable
  gas chromatography (GC): suitable
impurities   ≤20% water
mp   208 °C (dec.) (lit.)
Featured Industry   Pharmaceutical (small molecule)
format   neat
storage temp.   2-8°C

Description

General description

Chemical structure: β-lactam
Ampicillin belongs to the β-lactum group of antibiotics. It is used to treat bacterial infections via penetrating gram positive and gram negative bacteria. Its mode of action basically involves the inhibition of bacterial cell wall synthesis, thus leading to cell lysis.

Application

Ampicillin has been used as a reference compound in the determination of ampicillin free drug concentration in standard solution of human serum albumin by micellar liquid chromatography method.

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.

Refer to the product′s Certificate of Analysis for more information on a suitable instrument technique. Contact Technical Service for further support.

Biochem/physiol Actions

Mode of Action: Ampicillin is a semisynthetic penicillin and 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: Effective against both Gram-positive (similar to benzylpenicillin) and Gram-negative bacteria (similar to tetracyclines and chloramphenicol.

Packaging

This product is packaged in a bottomless glass bottle with the contents inside an inserted fused cone.

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.

Safety & Documentation

Safety Information

Symbol 
Signal word 
Danger
Hazard statements 
Precautionary statements 
RIDADR 
NONH for all modes of transport
WGK Germany 
2
RTECS 
XH8350000

Documents

Certificate of Analysis (COA)

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Protocols & Articles

Articles

HPLC Analysis of β-Lactam Antibiotics on Discovery® RP-Amide C16

From our library of Articles, Sigma-Aldrich presents HPLC Analysis of β-Lactam Antibiotics on Discovery® RP-Amide C16
Keywords: Antibiotics, Chromatography, High performance liquid chromatography, Pharmaceutical

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