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Ampicillin, Thermo Scientific Chemicals

Ampicillin, CAS # 69-53-4, is structurally related to penicillin and is considered to be a semi-synthetic antibiotic with antibacterial activity.

$244.71 - $686.64

Chemical Identifiers

CAS 69-53-4
Molecular Formula C16H19N3O4S
Molecular Weight (g/mol) 349.405
MDL Number MFCD00005175
InChI Key AVKUERGKIZMTKX-NJBDSQKTSA-N
PubChem CID 6249
ChEBI CHEBI:28971
IUPAC Name (2S,5R,6R)-6-[[(2R)-2-amino-2-phenylacetyl]amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
SMILES CC1(C(N2C(S1)C(C2=O)NC(=O)C(C3=CC=CC=C3)N)C(=O)O)C
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Products 2
Catalog Number Mfr. No. Quantity Price Quantity  
Catalog Number Mfr. No. Quantity Price Quantity  
AAJ6097706
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Thermo Scientific Chemicals
J6097706
5 g
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AAJ6097714
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Thermo Scientific Chemicals
J6097714
25 g
Each for $686.64
 
Description

Description

Ampicillin is used as asemi-synthetic antibiotic which has antibacterial activity structurally related to penicillin. It is widely used selection reagent for transformed cells expressing β-lactamase. It is also used to prevent and treat a number of bacterial infections. It may also be used to prevent group B streptococcal infection in newborns.

This Thermo Scientific Chemicals brand product was originally part of the Alfa Aesar product portfolio. Some documentation and label information may refer to the legacy brand. The original Alfa Aesar product / item code or SKU reference has not changed as a part of the brand transition to Thermo Scientific Chemicals.

General Description

  • Ampicillin is a broad-spectrum, semi-synthetic, β-lactam penicillin with bactericidal activity. It acts against several gram-positive and -negative infections
  • This compound binds to and inactivates penicillin-binding proteins (PBP) located on the inner membrane of the bacterial cell wall. This inactivation interferes with the cross-linkage of peptidoglycan chains essential for bacterial cell wall strength and rigidity. Consequently, there is an interruption in the bacterial cell wall synthesis which results in the weakening of the bacterial cell wall causing cell lysis

Application

  • In laboratory experiments, it is commonly used as a selector reagent for transformed cells expressing β-lactamase. The ampicillin-resistant gene (ampR) catalyzes the hydrolysis of the β-lactam ring of ampicillin and naturally detoxifies the drug
  • Ampicillin is commonly used as a selection marker for E. coli and other bacteria during plasmid DNA isolation, protein expression, and gene cloning
Specifications

Chemical Identifiers

69-53-4
349.405
AVKUERGKIZMTKX-NJBDSQKTSA-N
CHEBI:28971
CC1(C(N2C(S1)C(C2=O)NC(=O)C(C3=CC=CC=C3)N)C(=O)O)C
C16H19N3O4S
MFCD00005175
6249
(2S,5R,6R)-6-[[(2R)-2-amino-2-phenylacetyl]amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid

Specifications

Ampicillin
69-53-4
White
C16H19N3O4S
1090925
In 1 M NH4OH,50mg/ml
CC1(C(N2C(S1)C(C2=O)NC(=O)C(C3=CC=CC=C3)N)C(=O)O)C
349.405
CHEBI:28971
Ampicillin
Powder
208°C (decomposition)
5 g
MFCD00005175
14,586
AVKUERGKIZMTKX-NJBDSQKTSA-N
(2S,5R,6R)-6-[[(2R)-2-amino-2-phenylacetyl]amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
6249
349.4
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Safety and Handling

Safety and Handling

GHS H Statement
H334-H335-H315-H319-H317
May cause allergy or asthma symptoms or breathing difficulties if inhaled.
May cause respiratory irritation.
Causes skin irritation.
Causes serious eye irritation.
May cause an allergic skin reaction.

P261-P264b-P271-P272-P280-P285-P302+P352-P304+P340-P305+P351+P338-P333+P313-P342+P311-P362-P501c

H315-H317-H319-H334-H335

EINECSNumber : 200-709-7

RTECSNumber : XH8350000

TSCA : No

Recommended Storage : Keep cold

SDS
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RUO – Research Use Only