Physicochemical properties of amphoteric β-lactam antibiotics. I

Stability, solubility, and dissolution behavior of amino penicillins as a function of pH

A. Tsuji, E. Nakashima, S. Hamano, T. Yamana

Research output: Contribution to journalArticle

118 Citations (Scopus)

Abstract

The degradation rate, solubility, and dissolution rate of amino penicillins, amoxicillin, ampicillin, epicillin, and cyclacillin, were determined quantitatively as a function of pH. In the pH range studied, 0.30-10.50, the degradation of amoxicillin and epicillin followed pseudo-first-order kinetics to give the same type of pH-rate profiles as those of ampicillin and cyclacillin. Cyclacillin anhydrate was the most soluble, followed in order by ampicillin anhydrate, ampicillin trihydrate, amoxicillin trihydrate, and epicillin anhydrate. These pH-solubility profiles showed U-shaped curves. The dissolution rate constants from the rotating disk were analyzed by the simultaneous chemical reaction and diffusion models. Their relative bioavailability after a single oral administration was assessed from their physicochemical properties determined in vitro.

Original languageEnglish
Pages (from-to)1059-1066
Number of pages8
JournalJournal of Pharmaceutical Sciences
Volume67
Issue number8
Publication statusPublished - 1978
Externally publishedYes

Fingerprint

Cyclacillin
Lactams
Ampicillin
Penicillins
Solubility
Amoxicillin
Dissolution
Anti-Bacterial Agents
Degradation
Rotating disks
Biological Availability
Oral Administration
Chemical reactions
Rate constants
Kinetics
epicillin

ASJC Scopus subject areas

  • Molecular Medicine
  • Chemistry(all)
  • Organic Chemistry
  • Drug Discovery
  • Pharmaceutical Science
  • Pharmacology

Cite this

Physicochemical properties of amphoteric β-lactam antibiotics. I : Stability, solubility, and dissolution behavior of amino penicillins as a function of pH. / Tsuji, A.; Nakashima, E.; Hamano, S.; Yamana, T.

In: Journal of Pharmaceutical Sciences, Vol. 67, No. 8, 1978, p. 1059-1066.

Research output: Contribution to journalArticle

@article{08477641804b4305b319bbf10d0c4afe,
title = "Physicochemical properties of amphoteric β-lactam antibiotics. I: Stability, solubility, and dissolution behavior of amino penicillins as a function of pH",
abstract = "The degradation rate, solubility, and dissolution rate of amino penicillins, amoxicillin, ampicillin, epicillin, and cyclacillin, were determined quantitatively as a function of pH. In the pH range studied, 0.30-10.50, the degradation of amoxicillin and epicillin followed pseudo-first-order kinetics to give the same type of pH-rate profiles as those of ampicillin and cyclacillin. Cyclacillin anhydrate was the most soluble, followed in order by ampicillin anhydrate, ampicillin trihydrate, amoxicillin trihydrate, and epicillin anhydrate. These pH-solubility profiles showed U-shaped curves. The dissolution rate constants from the rotating disk were analyzed by the simultaneous chemical reaction and diffusion models. Their relative bioavailability after a single oral administration was assessed from their physicochemical properties determined in vitro.",
author = "A. Tsuji and E. Nakashima and S. Hamano and T. Yamana",
year = "1978",
language = "English",
volume = "67",
pages = "1059--1066",
journal = "Journal of Pharmaceutical Sciences",
issn = "0022-3549",
publisher = "John Wiley and Sons Inc.",
number = "8",

}

TY - JOUR

T1 - Physicochemical properties of amphoteric β-lactam antibiotics. I

T2 - Stability, solubility, and dissolution behavior of amino penicillins as a function of pH

AU - Tsuji, A.

AU - Nakashima, E.

AU - Hamano, S.

AU - Yamana, T.

PY - 1978

Y1 - 1978

N2 - The degradation rate, solubility, and dissolution rate of amino penicillins, amoxicillin, ampicillin, epicillin, and cyclacillin, were determined quantitatively as a function of pH. In the pH range studied, 0.30-10.50, the degradation of amoxicillin and epicillin followed pseudo-first-order kinetics to give the same type of pH-rate profiles as those of ampicillin and cyclacillin. Cyclacillin anhydrate was the most soluble, followed in order by ampicillin anhydrate, ampicillin trihydrate, amoxicillin trihydrate, and epicillin anhydrate. These pH-solubility profiles showed U-shaped curves. The dissolution rate constants from the rotating disk were analyzed by the simultaneous chemical reaction and diffusion models. Their relative bioavailability after a single oral administration was assessed from their physicochemical properties determined in vitro.

AB - The degradation rate, solubility, and dissolution rate of amino penicillins, amoxicillin, ampicillin, epicillin, and cyclacillin, were determined quantitatively as a function of pH. In the pH range studied, 0.30-10.50, the degradation of amoxicillin and epicillin followed pseudo-first-order kinetics to give the same type of pH-rate profiles as those of ampicillin and cyclacillin. Cyclacillin anhydrate was the most soluble, followed in order by ampicillin anhydrate, ampicillin trihydrate, amoxicillin trihydrate, and epicillin anhydrate. These pH-solubility profiles showed U-shaped curves. The dissolution rate constants from the rotating disk were analyzed by the simultaneous chemical reaction and diffusion models. Their relative bioavailability after a single oral administration was assessed from their physicochemical properties determined in vitro.

UR - http://www.scopus.com/inward/record.url?scp=0018150036&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=0018150036&partnerID=8YFLogxK

M3 - Article

VL - 67

SP - 1059

EP - 1066

JO - Journal of Pharmaceutical Sciences

JF - Journal of Pharmaceutical Sciences

SN - 0022-3549

IS - 8

ER -