Acid-catalyzed hydrolysis of BMS-582664: Degradation product identification and mechanism elucidation

Journal of Pharmaceutical Sciences

Volumn 101, Issue 9, 2012, Pages 3526-3530

  Zhao, Fang ^a,b   Derbin, George ^a   Miller, Scott ^a   Badawy, Sherif ^a   Hussain, Munir ^a  

^a BRISTOL MYERS SQUIBB   (United States)

^b ST JOHN FISHER COLLEGE   (United States)

Author keywords

Degradation; Diaryl ether; LC MS

Indexed keywords

BRIVANIB ALANINATE; ETHER; NITROGEN; OXYGEN 18; WATER;

ACIDITY; CATALYSIS; DRUG DEGRADATION; DRUG HYDROLYSIS; DRUG IDENTIFICATION; DRUG MECHANISM; ELECTROPHILICITY; LIQUID CHROMATOGRAPHY; MASS SPECTROMETRY; NOTE; PH; PROTON TRANSPORT; REVERSED PHASE HIGH PERFORMANCE LIQUID CHROMATOGRAPHY;

EID: 84864033046     PISSN: 00223549     EISSN: 15206017     Source Type: Journal    
DOI: 10.1002/jps.23028     Document Type: Article

References (8)

1. Bundgaard H, Larsen C, Arnold E. 1984. Prodrugs as drug delivery systems XXVII. Chemical stability and bioavailability of a water-soluble prodrug of metronidazole for parenteral administration. Int J Pharm 18:79-87.
2. Smith MB, March MJ. 2001. Advanced organic chemistry. Reactions, mechanisms and structure. 5th ed. New York: Wiley, pp 73-77and 465-468.
3. Morrison RT, Boyd RN. 1987. Organic chemistry. 5th ed. Boston: Allyn and Bacon, Inc., pp 707-708.
4. Connors KA, Amidon GL, Stella VJ. 1986. Hydrolysis and other acyl transfers. In Chemical stability of pharmaceuticals. A handbook for pharmacists. 2nd ed.New York: Wiley, pp 63-81.
5. Waterman KC, Adami RC, Alsante KM, Antipas AS, Arenson DR, Carrier R, Hong J, Landis MS, Lombardo F, Shah JC, Shalaev E, Smith SW, Wang H. 2002. Hydrolysis in pharmaceutical formulations. Pharm Dev Tech 7(2):113-146.
6. Rabel SR, Shinwari MK, Nemeth GA, Blom KF, Maurin MB. 1997. Characterization of the solution stability and degradation products of the novel neurotransmitter release enhancer 10, 10-bis(2-fluoro-4-pyridinylmethyl)-9(10H)-anthracenone. Drug Stability 1(4):224-230.
7. Chen J, Markovitz DA, Yang AY, Rabel SR, Pang J, Dolinsky O, Wu L, Alasandro M. 2000. Degradation of a fluoropyridinyl drug in capsule formulation: Degradant identification, proposed degradation mechanism, and formulation optimization. Pharm Dev Tech 5(4):561-570.
8. Clark HR, Beth LD, Burton RM, Garrett DL, Miller AL, Muscio OJ Jr. 1981. Kinetic study of the acid-promoted hydrolysis of some representative 2-fluoro nitrogen heterocycles. J Org Chem 46:4363-4369.