Ampicillin

Description

Ampicillin, CAS # 69-53-4, is structurally related to penicillin and is considered to be a semi-synthetic antibiotic with antibacterial activity. | CAS: 69-53-4 | C16H19N3O4S | 349.405 g/mol

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

• 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

• Type: Ampicillin
• Physical Form: Powder
• Melting Point: 208°C (decomposition)
• Color: White
• Quantity: 5 g
• Beilstein: 1090925
• Merck Index: 14,586
• Solubility Information: In 1 M NH4OH,50mg/ml
• Formula Weight: 349.4
• Chemical Name or Material: Ampicillin

Safety and Handling

Hazard Category	H315-H317-H319-H334-H335
Hazard Statement	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.
Precautionary Statement	P261-P264b-P271-P272-P280-P285-P302+P352-P304+P340-P305+P351+P338-P333+P313-P342+P311-P362-P501c
EINECSNumber	200-709-7
RTECSNumber	XH8350000
TSCA	No
Recommended Storage	Keep cold

SDS

RUO – Research Use Only