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Volumn 99, Issue 7, 2010, Pages 3030-3040

Elucidating the pathways of degradation of denagliptin

Author keywords

Chemical stability; Formulation; Mass spectrometry; NMR spectroscopy; Preformulation; Solid state stability; Stability

Indexed keywords

AMIDINE; DENAGLIPTIN; PIPERAZINEDIONE;

EID: 77953303299     PISSN: 00223549     EISSN: 15206017     Source Type: Journal    
DOI: 10.1002/jps.22069     Document Type: Article
Times cited : (5)

References (31)
  • 1
    • 3242703886 scopus 로고    scopus 로고
    • Q1A (R2) November
    • Q1A (R2) Stability testing of new drug substances and products, November 2003. http://www.fda.gov/downloads/Drugs/ GuidanceComplianceRegulatoryInformation/Guidances/ucm073369.pdf.
    • (2003) Stability Testing of New Drug Substances and Products
  • 2
    • 38549168121 scopus 로고    scopus 로고
    • Q3B (R) (revision 2), August
    • Q3B (R) Impurities in new drug products (revision 2), August 2006. http://www.fda.gov/downloads/Drugs/Guidance-ComplianceRegulatoryInformation/ Guidances/ucm073389.pdf.
    • (2006) Impurities in New Drug Products
  • 3
    • 0031897939 scopus 로고    scopus 로고
    • Kinetics of diketopiperazine formation using model peptides
    • Goolcharan C, Borchardt RT. 1998. Kinetics of diketopiperazine formation using model peptides. J Pharm Sci 87:283-287.
    • (1998) J Pharm Sci , vol.87 , pp. 283-287
    • Goolcharan, C.1    Borchardt, R.T.2
  • 4
    • 0030636829 scopus 로고    scopus 로고
    • Solid state stability studies of model dipeptides: Aspartame and aspartylphenylalanine
    • Leung SS, Grant DJW. 1997. Solid state stability studies of model dipeptides: Aspartame and aspartylphenylalanine. J Pharm Sci 86:64-71.
    • (1997) J Pharm Sci , vol.86 , pp. 64-71
    • Leung, S.S.1    Grant, D.J.W.2
  • 5
    • 0023481924 scopus 로고
    • Diketopiperazine formation, hydrolysis, and epimerization of the new dipeptide angiotensinconverting enzyme inhibitor RS-10085
    • Gu L, Strickley RG. 1987. Diketopiperazine formation, hydrolysis, and epimerization of the new dipeptide angiotensinconverting enzyme inhibitor RS-10085. Pharm Res 4:392-397.
    • (1987) Pharm Res , vol.4 , pp. 392-397
    • Gu, L.1    Strickley, R.G.2
  • 6
    • 0024825988 scopus 로고
    • An unexpected pH effect on the stability of moexipril lyophilized powder
    • Strickley RG, Visor GC, Lin L, Gu L. 1989. An unexpected pH effect on the stability of moexipril lyophilized powder. Pharm Res 6:971-975. (Pubitemid 20078450)
    • (1989) Pharmaceutical Research , vol.6 , Issue.11 , pp. 971-975
    • Strickley, R.G.1    Visor, G.C.2    Lin, L.-H.3    Gu, L.4
  • 7
    • 0025024417 scopus 로고
    • Drug-excipient incompatibility studies of the dipeptide angiotensin-converting enzyme inhibitor, moexipril hydrochloride: Dry powder vs wet granulation
    • DOI 10.1023/A:1015871406549
    • Gu L, Strickley RG, Chi L, Chowan ZT. 1990. Drug-excipient incompatibility studies of the dipeptide angiotensin-converting enzyme inhibitor, moexipril hydrochloride: Dry powder vs wet granulation. Pharm Res 7:379-383. (Pubitemid 20266593)
    • (1990) Pharmaceutical Research , vol.7 , Issue.4 , pp. 379-383
    • Gu, L.1    Strickley, R.G.2    Chi, L.-H.3    Chowhan, Z.T.4
  • 8
    • 0025337292 scopus 로고
    • A profound solvent effect on the diketopiperazine formation of the new dipeptide angiotensin-converting enzyme inhibitor, Moexipril
    • DOI 10.1016/0378-5173(90)90295-F
    • Gu L, Strickley RG. 1990. A profound solvent effect on the diketopiperazine formation of the new dipeptide angiotensin-converting enzyme inhibitor, moexipril. Int J Pharm 60:99-107. (Pubitemid 20171033)
    • (1990) International Journal of Pharmaceutics , vol.60 , Issue.2 , pp. 99-107
    • Gu, L.1    Strickley, R.G.2
  • 9
    • 0033971208 scopus 로고    scopus 로고
    • Physical characteristics and chemical degradation of amorphous quinapril hydrochloride
    • DOI 10.1002/(SICI)1520-6017(200001)89:1<128::AID-JPS13>3.0.CO;2-Z
    • Guo Y, Byrn SR, Zografi G. 2000. Physical characteristics and chemical degradation of amorphous quinapril hydrochloride. J Pharm Sci 89:128-143. (Pubitemid 30080161)
    • (2000) Journal of Pharmaceutical Sciences , vol.89 , Issue.1 , pp. 128-143
    • Guo, Y.1    Byrn, S.R.2    Zografi, G.3
  • 10
    • 0033795715 scopus 로고    scopus 로고
    • Effects of lyophilization on the physical characteristics and chemical stability of amorphous quinapril hydrochloride
    • Guo Y, Byrn SR, Zografi G. 2000. Effects of lyophilization on the physical characteristics and chemical stability of amorphous quinapril hydrochloride. Pharm Res 17:930-935.
    • (2000) Pharm Res , vol.17 , pp. 930-935
    • Guo, Y.1    Byrn, S.R.2    Zografi, G.3
  • 11
    • 0036143366 scopus 로고    scopus 로고
    • The solid-state stability of amorphous quinapril in the presence of b-cyclodextrins
    • DOI 10.1002/jps.10014
    • Li J, Guo Y, Zografi G. 2002. The solid-state stability of amorphous quinapril in the presence of b-cyclodextrins. J Pharm Sci 91:229-243. (Pubitemid 34074481)
    • (2002) Journal of Pharmaceutical Sciences , vol.91 , Issue.1 , pp. 229-243
    • Li, J.1    Guo, Y.2    Zografi, G.3
  • 12
    • 0036145187 scopus 로고    scopus 로고
    • Effects of a citrate buffer system on the solid-state chemical stability of lyophilized quinapril preparations
    • DOI 10.1023/A:1013695030082
    • Li J, Guo Y, Zografi G. 2002. Effects of a citrate buffer system on the solid-state chemical stability of lyophilized quinapril preparations. Pharm Res 19:20-26. (Pubitemid 34075102)
    • (2002) Pharmaceutical Research , vol.19 , Issue.1 , pp. 20-26
    • Li, J.1    Guo, Y.2    Zografi, G.3
  • 13
    • 0035064335 scopus 로고    scopus 로고
    • Reaction kinetics of solid-state cyclization of enalapril maleate investigated by isothermal FT-IR microscopic system
    • DOI 10.1248/cpb.49.402
    • Wang S, Lin S, Chen T. 2001. Reaction kinetics of solid-state cyclization of enalapril maleate investigated by isothermal FT-IR microscopic system. Chem Pharm Bull 49:402-406. (Pubitemid 32367671)
    • (2001) Chemical and Pharmaceutical Bulletin , vol.49 , Issue.4 , pp. 402-406
    • Wang, S.-L.1    Lin, S.-Y.2    Chen, T.-F.3
  • 14
    • 0141523555 scopus 로고
    • Drug-excipient interaction study of enalapril maleate using thermal analysis and scanning electron microscopy
    • Cotton ML, Wu DW, Vadas EB. 1987. Drug-excipient interaction study of enalapril maleate using thermal analysis and scanning electron microscopy. Int J Pharm 40:129-142.
    • (1987) Int J Pharm , vol.40 , pp. 129-142
    • Cotton, M.L.1    Wu, D.W.2    Vadas, E.B.3
  • 15
    • 21644446693 scopus 로고    scopus 로고
    • Eudragit e accelerated the diketopiperazine formation of enalapril maleate determined by thermal FTIR microspectroscopic technique
    • DOI 10.1023/B:PHAM.0000048206.62093.4e
    • Wang S, Lin S, Chen T, Cheng W. 2004. Eudragit E accelerated the diketopiperazine formation of enalapril maleate determined by thermal FTIR microspectroscopic technique. Pharm Res 21:2127-2132. (Pubitemid 40941235)
    • (2004) Pharmaceutical Research , vol.21 , Issue.11 , pp. 2127-2132
    • Wang, S.-L.1    Lin, S.-Y.2    Chen, T.-F.3    Cheng, W.-T.4
  • 16
    • 0034532789 scopus 로고    scopus 로고
    • Thermal-dependent dehydration process and intramolecular cyclization of lisinopril dihydrate in solid state
    • Wang S, Lin S, Chen T. 2000. Thermal dependant dehydration process and intramolecular cyclization of lisinopril dihydrate in the solid state. Chem Pharm Bull 48:1890-1893. (Pubitemid 32011514)
    • (2000) Chemical and Pharmaceutical Bulletin , vol.48 , Issue.12 , pp. 1890-1893
    • Wang, S.-L.1    Lin, S.-Y.2    Chen, T.-F.3
  • 17
    • 0032507276 scopus 로고    scopus 로고
    • Mechanism of 2,5-dioxopiperazine formation
    • Capasso S, Vergara A, Mazzarella L. 1998. Mechanism of 2,5-dioxopiperazine formation. J Am Chem Soc 120:1990-1995.
    • (1998) J Am Chem Soc , vol.120 , pp. 1990-1995
    • Capasso, S.1    Vergara, A.2    Mazzarella, L.3
  • 18
    • 37049133921 scopus 로고
    • Piperazinedione formation from esters of dipeptides containing glycine, alanine, and sarcosine: The kinetics in aqueous solution
    • Purdie JE, Benoiton NL. 1973. Piperazinedione formation from esters of dipeptides containing glycine, alanine, and sarcosine: The kinetics in aqueous solution. J Chem Soc II 1845-1852.
    • (1973) J Chem Soc , vol.2 , pp. 1845-1852
    • Purdie, J.E.1    Benoiton, N.L.2
  • 19
    • 0001382259 scopus 로고
    • N-Alkylation of nitriles: I
    • Fuks R. 1973. N-Alkylation of nitriles: I. Tetrahedron 29:2147-2151.
    • (1973) Tetrahedron , vol.29 , pp. 2147-2151
    • Fuks, R.1
  • 21
    • 0000535768 scopus 로고
    • Solvent effects on the energetics of prolyl peptide bond isomerization
    • Eberhardt ES, Loh SN, Hinck AP, Raines RT. 1992. Solvent effects on the energetics of prolyl peptide bond isomerization. J Am Chem Soc 114:5437-5439.
    • (1992) J Am Chem Soc , vol.114 , pp. 5437-5439
    • Eberhardt, E.S.1    Loh, S.N.2    Hinck, A.P.3    Raines, R.T.4
  • 22
    • 0034419296 scopus 로고    scopus 로고
    • Chemical aspects of peptide bond isomerisation
    • Fischer G. 2000. Chemical aspects of peptide bond isomerisation. Chem Soc Rev 29:119-127.
    • (2000) Chem Soc Rev , vol.29 , pp. 119-127
    • Fischer, G.1
  • 23
    • 84985715908 scopus 로고
    • NMR studies of the rates of proline cis-trans isomerization in oligopeptides
    • Grathwohl C, Wuthrich K. 1981. NMR studies of the rates of proline cis-trans isomerization in oligopeptides. Biopolymers 20:2623-2633.
    • (1981) Biopolymers , vol.20 , pp. 2623-2633
    • Grathwohl, C.1    Wuthrich, K.2
  • 24
    • 34848845825 scopus 로고    scopus 로고
    • Kinetics and equilibria of cis/trans isomerization of backbone amide bonds in peptoids
    • DOI 10.1021/ja0740925
    • Sui Q, Borchardt D, Rabenstein DL. 2007. Kinetics and equilibria of cis/trans isomerization of backbone amide bonds in peptoids. J Am Chem Soc 129:12042-12048. (Pubitemid 47512033)
    • (2007) Journal of the American Chemical Society , vol.129 , Issue.39 , pp. 12042-12048
    • Sui, Q.1    Borchardt, D.2    Rabenstein, D.L.3
  • 25
    • 0031710830 scopus 로고
    • Surface acidity of solid pharmaceutical excipients. III. Excipients for solid dosage forms
    • Scheef CA, Oelkrug D, Schmidt PC. 1995. Surface acidity of solid pharmaceutical excipients. III. Excipients for solid dosage forms. Eur J Pharm Biopharm 46:209-213.
    • (1995) Eur J Pharm Biopharm , vol.46 , pp. 209-213
    • Scheef, C.A.1    Oelkrug, D.2    Schmidt, P.C.3
  • 26
    • 67650084888 scopus 로고    scopus 로고
    • Role of salt and excipient properties on disproportionation in the solid-state
    • Guerrieri P, Taylor LS. 2009. Role of salt and excipient properties on disproportionation in the solid-state. Pharm Res 26:2015-2026.
    • (2009) Pharm Res , vol.26 , pp. 2015-2026
    • Guerrieri, P.1    Taylor, L.S.2
  • 27
    • 0004039575 scopus 로고
    • 2nd edition. Washington DC: American Pharmaceutical Association and. Royal Pharmaceutical Society of Great Britain
    • Wade A, Weller PJ. 1994. Handbook of pharmaceutical excipients. 2nd edition. Washington DC: American Pharmaceutical Association and. Royal Pharmaceutical Society of Great Britain. pp. 494-497.
    • (1994) Handbook of Pharmaceutical Excipients , pp. 494-497
    • Wade, A.1    Weller, P.J.2
  • 28
    • 0000799827 scopus 로고
    • Aspartame decomposition and epimerization in the diketopiperazine and dipeptide products as a function of pH and temperature
    • Gaines SM, Bada JL. 1988. Aspartame decomposition and epimerization in the diketopiperazine and dipeptide products as a function of pH and temperature. J Org Chem 53:2757-2764.
    • (1988) J Org Chem , vol.53 , pp. 2757-2764
    • Gaines, S.M.1    Bada, J.L.2
  • 29
    • 0006910983 scopus 로고
    • Origin of the ring-ring interaction in cyclic dipeptides incorporating an aromatic amino acid
    • Liwo R, Ciarkowski J. 1985. Origin of the ring-ring interaction in cyclic dipeptides incorporating an aromatic amino acid. Tett Lett 26:1873-1876.
    • (1985) Tett Lett , vol.26 , pp. 1873-1876
    • Liwo, R.1    Ciarkowski, J.2
  • 30
    • 0032506324 scopus 로고    scopus 로고
    • Stereochemical investigations on the diketopiperazine derivatives of enalapril and lisinopril by NMR spectroscopy
    • Demeter A, Fodor T, Fischer J. 1998. Stereochemical investigations on the diketopiperazine derivatives of enalapril and lisinopril by NMR spectroscopy. J Mol Struct 471:161-174.
    • (1998) J Mol Struct , vol.471 , pp. 161-174
    • Demeter, A.1    Fodor, T.2    Fischer, J.3
  • 31
    • 33750024512 scopus 로고    scopus 로고
    • Effects of steric bulk and stereochemistry on the rates of diketopiperazine formation from N-aminoacyl-2,2-dimethylthiazolidine-4- carboxamides (Dmt dipeptide amides)-A model for a new prodrug linker system
    • Suaifan GA, Mahon MF, Arafat T, Threadgill MD. 2006. Effects of steric bulk and stereochemistry on the rates of diketopiperazine formation from N-aminoacyl-2,2-dimethylthiazolidine-4-carboxamides (Dmt dipeptide amides)-A model for a new prodrug linker system. Tetrahedron 62:11245-11266.
    • (2006) Tetrahedron , vol.62 , pp. 11245-11266
    • Suaifan, G.A.1    Mahon, M.F.2    Arafat, T.3    Threadgill, M.D.4


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.