PMID: 39159Aug 1, 1979

Kinetics and mechanism of chlorambucil hydrolysis

Journal of Pharmaceutical Sciences
W R Owen, P J Stewart

Abstract

The kinetics and mechanism of hydrolysis of the cytotoxic drug chlorambucil were investigated. A study of the reaction order and of the pH, dielectric constant, and ionic strength effects on the reaction rate revealed that the hydrolysis was a limiting unimolecular nucleophilic substitution, the rate-determining step being the ionization of the first 2-chloroethylamine chlorine. The hydrolysis rate was markedly dependent on the protonation degree of the chlorambucil basic group. indicating that a cyclic ethyleneimmonium ion may be involved in the rate-determining step.

References

Nov 1, 1994·Pharmacology, Biochemistry, and Behavior·G C KunduI B Wilson
Jan 1, 1987·Pharmacology & Therapeutics·P B Farmer
Feb 24, 2015·AAPS PharmSciTech·Iqbal AhmadAmbreen Hafeez
Jun 6, 1997·Chemico-biological Interactions·M P GamcsikT G Hamill
Jul 17, 2016·Journal of Hazardous Materials·Helena Franquet-GriellSilvia Lacorte
Jul 1, 1982·Journal of Pharmaceutical Sciences·H Ehrsson, U Lönroth
Jul 23, 2009·Chemistry & Biodiversity·Diana Florea-WangJari Hovinen
May 1, 1981·The Journal of Pharmacy and Pharmacology·H EhrssonS O Nilsson

Related Concepts

Ethanol
NSC-3088
Hydrolysis
Hydrogen-Ion Concentration
Cytotoxic agent
Chlorambucil
2-chloroethylamine
Osmolality

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