Ampicillin; Chemical name, Molecular Formula, Molar mass, Chemical Structure
Автор: Sokoto Pharmacology
Загружено: 2026-02-01
Просмотров: 2
Описание:
Ampicillin is a broad‑spectrum β‑lactam antibiotic of the aminopenicillin family, with the molecular formula C₁₆H₁₉N₃O₄S and a molar mass of about 349.4 g/mol. Its chemical structure is based on the penicillin nucleus (β‑lactam fused to thiazolidine) with an amino‑phenylacetyl side chain that enhances activity against Gram‑negative bacteria.
🔬 Chemical Details of Ampicillin
Chemical Name (IUPAC):
(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
Molecular Formula:
C₁₆H₁₉N₃O₄S
Molar Mass:
349.40 g/mol
🧩 Chemical Structure
Core Framework:
Ampicillin is derived from 6‑aminopenicillanic acid (6‑APA), the common penicillin nucleus. It consists of a β‑lactam ring fused to a thiazolidine ring.
Key Features:
β‑lactam ring: responsible for antibacterial activity by inhibiting bacterial cell wall synthesis.
Thiazolidine ring fused to the β‑lactam.
Side chain: a D‑(–)‑α‑phenylglycine moiety with an amino group, which improves penetration into Gram‑negative bacteria compared to penicillin G.
Carboxylic acid group at position 2, contributing to solubility and ionic interactions.
Functional Groups Present:
Amide linkage (between β‑lactam and side chain).
Carboxylic acid (-COOH).
Phenyl ring.
Primary amine (-NH₂).
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