Biexponential decomposition of a neuraminidase inhibitor prodrug (GS- 4104) in aqueous solution

Pharmaceutical Research

Volumn 15, Issue 8, 1998, Pages 1300-1304

  Oliyai, Reza ^a   Yuan, Lung Chi ^a   Dahl, Terrence C ^a   Swaminathan, S ^a   Wang, Ke Yu ^a   Lee, William A ^a  

^a GILEAD SCIENCES   (United States)

Author keywords

Biexponential kinetics; GS 4104; Heteronuclear multiple bond correlation NMR; N, N acyl migration; Neuraminidase inhibitor

Indexed keywords

ANTIVIRUS AGENT; ETHYL 4 ACETAMIDO 5 AZIDO 3 (1 ETHYLPROPOXY) 1 CYCLOHEXENE 1 CARBOXYLATE PHOSPHATE; PRODRUG; SIALIDASE INHIBITOR; UNCLASSIFIED DRUG;

ANTIVIRAL ACTIVITY; AQUEOUS SOLUTION; ARTICLE; DISSOCIATION CONSTANT; DRUG DECOMPOSITION; DRUG DEGRADATION; DRUG STRUCTURE; ENZYME INHIBITION; INFLUENZA; KINETICS; PH; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; REVERSED PHASE HIGH PERFORMANCE LIQUID CHROMATOGRAPHY;

AMINES; ANTIVIRAL AGENTS; ENZYME INHIBITORS; HYDROLYSIS; KINETICS; MAGNETIC RESONANCE SPECTROSCOPY; NEURAMINIDASE; OSELTAMIVIR; PRODRUGS; SOLUTIONS; WATER;

EID: 0031667225     PISSN: 07248741     EISSN: None     Source Type: Journal    
DOI: 10.1023/A:1011964529805     Document Type: Article

References (8)

1. C. U. Kim, W. Lew, M. A. Williams, L. Zhang, S. Swaminathan, N. Bischofberger, M. S. Chen, D. B. Mendel, W. Li, L. Tai, P. Escarpe, K. C. Cundy, E. J. Eisenberg, S. Lacy, R. W. Sidwell, R. C. Stevens, and W. G. Laver. New potent, orally active neuraminidase inhihitor as anti-influenza agents: in vitro and in vivo activity of GS-4071 and analogues. 36th ICAAC, New Orleans, Louisiana. Septemher, 1996.
2. C. U. Kim, W. Lew, M. A. Williams, H. Liu, L. Zhang, S. Swaminathan, N. Bischofberger, M. S. Chen, D. B. Mendel, L. Tai, W. G. Laver, and R. C. Stevens. Influenza neuraminidase inhibitors possessing a novel hydrophobic interaction in the enzyme active site: design, synthesis, and structural analysis of carbocyclic sialic acid analogues with potent anti-influenza activity. J. Am. Chem. Soc. 119:681-690 (1997).
3. W. Li, P. A. Escarpe, E. J. Eisenberg, K. C. Cundy, C. Sweet, K. J. Jakeman, J. Merson, W. Lew, M. Williams, L. Zhang, C. U. Kim, N. Bischofberger, M. S. Chen, and D. B. Mendel. Identification of GS-4104 as an orally bioavailable prodrug of the influenza virus neuraminidase inhihitor GS-4071. Antimicrob. Agents Chemother. 42:647-653 (1998).
4. D. D. Perrin, Boyd Dempsey, and E. P. Serjeant, "pKa prediction for organic acids and bases," Chapman and Hall, London, 1981.
5. L. V. Pavlova and F. Y. Rachinskii. Rearrangements connected with the migration of acyl and certain other groups. Russian Chem. Rev. 37:587-602 (1968).
6. B. Fernandez, I. Perillo, and S. Lamdan. Alkaline hydrolysis of 1,2,3-trisubstituted cyclic amidinium salts. Kinetic study of N,N′ acyl migration in alkaline solution in an ethylenediamine derivative. J. Chem. Soc. Perkin II 545-550 (1978).
7. R. F. Pratt and T. C. Bruce. Reactions of s-acylisothioureas. II. Effects of structure and stereochemistry on the rates of hydrolysis. thiol elimination, and S to N acyl migration in acyclic systems. J. Am. Chem. Soc. 94:2823-2837 (1972).
8. S. K. Chung and Y. T. Chang. Base-catalyzed acyl migrations in myo-inositol dibenzoates. J. Chem. Soc. Chem. Commun. 13-14 (1995).