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10045 Sigma-Aldrich

Ampicillin trihydrate

≥96.0% (NT)

Synonym: D-(−)-α-Aminobenzylpenicillin

  • CAS Number 7177-48-2

  • Empirical Formula (Hill Notation) C16H19N3O4S · 3H2O

  • Molecular Weight 403.45

  •  Beilstein Registry Number 5399534

  •  EC Number 200-709-7

  •  MDL number MFCD00072036

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Properties

InChI Key   RXDALBZNGVATNY-CWLIKTDRSA-N
assay   ≥96.0% (NT)
optical activity   [α]20/D +250±10°, c = 0.5% in H2O
ign. residue   ≤0.05%
mp   198-200 °C (dec.) (lit.)
  200-202 °C (dec.)
Mode of action   cell wall synthesis | interferes
storage temp.   2-8°C

Description

Biochem/physiol Actions

A β-lactam antibiotic with an amino group side chain attached to the penicillin structure. Penicillin derivative that inhibits bacterial cell-wall synthesis (peptidoglycan cross-linking) by inactivating transpeptidases on the inner surface of the bacterial cell membrane. Bactericidal only to growing Escherichia coli . Mode of resistance: Cleavage of β-lactam ring of ampicillin by β-lactamase. Antimicrobial spectrum: Gram-negative and Gram-positive bacteria.

Application

Ampicillin Trihydrate is commonly used to select for ampicillin resistance in mutated and transformed cells. It is used in intracellular targeting of antibiotics on biodegradable polymeric carriers . Nanoparticle-bound ampicillin has been shown to be more effective than free ampicillin against Listeria monocytogenes in mouse peritoneal macrophages. Ampicillin has been shown to cause Clostridium difficile-Associated ileocecitis in the hamster model.

General description

Chemical structure: ß-lactam

Safety & Documentation

Safety Information

Symbol 
Signal word 
Danger
Hazard statements 
Precautionary statements 
Personal Protective Equipment 
WGK Germany 
2
RTECS 
XH8425000

Documents

Certificate of Analysis

Protocols & Articles
Peer-Reviewed Papers
15

References

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Description

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A6140 Ampicillin trihydrate, 96.0-100.5% anhydrous basis (HPLC)

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