Ampicillin trihydrate

• Catalog No.: 10045
• CAS Number: 7177-48-2
• M. F.: C16H25N3O7S
• M. W.: 403.4506
• Purity: ≥96.0% (NT)

SYNONYMS

• Title: 氨苄西林 三水合物
• IUPAC name: (2S,5R,6R)-6-[(2R)-2-amino-2-phenylacetamido]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid trihydrate
• IUPAC Traditional name: ampicillin trihydrate
• Synonyms: D-(-)-α-Aminobenzylpenicillin; 氨苄青霉素

DATABASE IDS

• CAS Number: 7177-48-2
• Beilstein Number: 5399534
• MDL Number: MFCD00072036
• EC Number: 200-709-7

PROPERTIES

• Empirical Formula (Hill Notation): C16H19N3O4S · 3H2O
• Ignition Residue: ≤0.05%
• Purity: ≥96.0% (NT)
• Melting Point: 198-200 °C (dec.)(lit.)
• Melting Point: 200-202 °C (dec.)
• Optical Rotation: [α]20/D +250±10°, c = 0.5% in H2O
• GHS Signal Word: Danger
• GHS Hazard statements: H315-H317-H319-H334-H335
• European Hazard Symbols: Harmful (Xn)
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Faceshields, Gloves
• GHS Precautionary statements: P261-P280-P305 + P351 + P338-P342 + P311
• Risk Statements: 36/37/38-42/43
• RTECS: XH8425000
• Safety Statements: 22-26-36/37
• Storage Temperature: 2-8°C
• German water hazard class: 2

DETAILS

Description (English)

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 1. Nanoparticle-bound ampicillin has been shown to be more effective than free ampicillin against Listeria monocytogenes in mouse peritoneal macrophages2. Ampicillin has been shown to cause Clostridium difficile-Associated ileocecitis in the hamster model3.

Description (简体中文)

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 1. Nanoparticle-bound ampicillin has been shown to be more effective than free ampicillin against Listeria monocytogenes in mouse peritoneal macrophages2. Ampicillin has been shown to cause Clostridium difficile-Associated ileocecitis in the hamster model3.