80734-02-7

Basic information

• Product Name: LENAMPICILLIN
• Synonyms: (5-methyl-2-oxo-1,3-dioxolen-4-yl)methyl-d-alpha-aminobenzylpenicillinatehyd;-2-carboxylicacid,hydrochloride;-amino-2-phenylacetamido)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo(3.2.0)heptane;ampicillin,(5-methyl-2-oxo-1,3-dioxolen-4-yl)methylester,hydrochloride;carbonicacid,cyclic1-(hydroxymethyl)-2-methylethyleneester,esterwith6-(2;kb1585;kbt1585;kbt-1585
• CAS NO: 80734-02-7
• Molecular Formula: C₂₁H₂₃N₃O₇S*ClH
• Molecular Weight: 461.49
• Product Categories: Amines;Drug Analogues;Heterocycles;Intermediates & Fine Chemicals;Pharmaceuticals;Sulfur & Selenium Compounds
• Mol File: 80734-02-7.mol
• Article Data: 2

Chemical Properties

• Melting Point: 145° (dec)
• Boiling Point: 717.4°C at 760 mmHg
• Flash Point: 387.7°C
• Appearance: /
• Vapor Pressure: 7.54E-21mmHg at 25°C
• CAS DataBase Reference: LENAMPICILLIN(CAS DataBase Reference)
• NIST Chemistry Reference: LENAMPICILLIN(80734-02-7)
• EPA Substance Registry System: LENAMPICILLIN(80734-02-7)

Safety Data

• Hazardous Substances Data: 80734-02-7(Hazardous Substances Data)

Usage

Description

Lenampicillin, also known as an oral ampicillin prodrug, is a semi-synthetic antibiotic derived from the penicillin group. It possesses broad-spectrum antimicrobial properties and is effective against a wide range of both gram-positive and gram-negative bacteria. Its unique structure allows for better absorption in the gastrointestinal tract, making it a suitable oral antibiotic.
Source:
Lenampicillin is synthesized through a chemical modification of ampicillin, which involves the addition of a phenethanolamine side chain to the molecule.
Production Methods:
The production of lenampicillin involves the esterification of ampicillin with phenethanolamine, resulting in a more stable and bioavailable prodrug.

Uses

Used in Pharmaceutical Industry:
Lenampicillin is used as an antibiotic for the treatment of various bacterial infections, particularly those affecting the respiratory and urinary tracts. Its effectiveness is attributed to its ability to inhibit bacterial cell wall synthesis, leading to the disruption of cell division and ultimately, bacterial cell death.
Used in Respiratory Tract Infections:
Lenampicillin is used as a therapeutic agent for respiratory tract infections, such as bronchitis, pneumonia, and sinusitis. Its broad-spectrum activity allows it to target multiple bacterial pathogens, providing effective treatment for these infections.
Used in Urinary Tract Infections:
Lenampicillin is also used as a treatment for urinary tract infections, including those affecting the bladder, kidneys, and urethra. Its ability to concentrate in the urine and maintain effective levels makes it a suitable choice for treating these types of infections.

InChI:InChI=1/C21H23N3O7S.ClH/c1-10-12(31-20(28)30-10)9-29-19(27)15-21(2,3)32-18-14(17(26)24(15)18)23-16(25)13(22)11-7-5-4-6-8-11;/h4-8,13-15,18H,9,22H2,1-3H3,(H,23,25);1H/t13-,14-,15+,18-;/m1./s1

Upstream product

• 80715-22-6 4-bromomethyl-1,3-dioxa-5-methylcyclopentene-2-one 
• 37830-90-3 4,5-Dimethyl-1,3-dioxole-2-one 
• 80715-31-7 (5-methyl-2-oxo-1,3-dioxolen-4-yl)methyl 6β-aminopenicillanate p-toluenesulfonate 
• 40966-78-7 2-(R)-2-phenyl-2-aminoacetyl chloride hydrochloride 

Relevant articles and documents

Studies on prodrugs. II. Preparation and characterization of (5-substituted 2-oxo-1,3-dioxolen-4-yl)methyl esters of ampicillin

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