Proton Magnetic Resonance Studies of the Decomposition of 4-Hydroxycyclophosphamide, a Microsomal Metabolite of Cyclophosphamide
dc.contributor.author | Servis, Kenneth L. | en_US |
dc.contributor.author | Valente, Edward J. | en_US |
dc.contributor.author | Chan, Kenneth K. | en_US |
dc.date.accessioned | 2006-09-08T19:14:30Z | |
dc.date.available | 2006-09-08T19:14:30Z | |
dc.date.issued | 1984-03 | en_US |
dc.identifier.citation | Valente, Edward J.; Chan, Kenneth K.; Servis, Kenneth L.; (1984). "Proton Magnetic Resonance Studies of the Decomposition of 4-Hydroxycyclophosphamide, a Microsomal Metabolite of Cyclophosphamide." Pharmaceutical Research 1(2): 89-92. <http://hdl.handle.net/2027.42/41423> | en_US |
dc.identifier.issn | 0724-8741 | en_US |
dc.identifier.issn | 1573-904X | en_US |
dc.identifier.uri | https://hdl.handle.net/2027.42/41423 | |
dc.description.abstract | The proposed tautomeric equilibrium between the microsomal metabolite of cyclophosphamide, 4-hydroxycyclophosphamide, and the open chain aldophosphamide, and the subsequent facile β-elimination to generate acrolein and phosphoramide mustard have been confirmed by proton magnetic resonance studies. When 4-hydroxycyclophosphamide, initially maintained in CDC1 3 at −20°C, was allowed to equilibrate at 15°C, a singlet at 9.76 δ and a triplet at 2.88 δ appeared concomitantly which were assigned to the aldehydic proton and the protons α to the carbonyl of aldophosphamide, respectively. Further reaction led to the appearance of several NMR signals that indicated the irreversible formation of acrolein (multiplet at 9.55 δ) and phosphoramide mustard. Polymerization occurred approximately 2 hours after the initiation of the reaction. The kinetic data of the reaction sequence are discussed. | en_US |
dc.format.extent | 674067 bytes | |
dc.format.extent | 3115 bytes | |
dc.format.mimetype | application/pdf | |
dc.format.mimetype | text/plain | |
dc.language.iso | en_US | |
dc.publisher | Kluwer Academic Publishers-Plenum Publishers; Plenum Publishing Corporation ; Springer Science+Business Media | en_US |
dc.subject.other | Biomedical Engineering | en_US |
dc.subject.other | Biomedicine | en_US |
dc.subject.other | Biochemistry, General | en_US |
dc.subject.other | Medical Law | en_US |
dc.subject.other | Pharmacy | en_US |
dc.subject.other | Pharmacology/Toxicology | en_US |
dc.title | Proton Magnetic Resonance Studies of the Decomposition of 4-Hydroxycyclophosphamide, a Microsomal Metabolite of Cyclophosphamide | en_US |
dc.type | Article | en_US |
dc.subject.hlbsecondlevel | Pharmacy and Pharmacology | en_US |
dc.subject.hlbtoplevel | Health Sciences | en_US |
dc.description.peerreviewed | Peer Reviewed | en_US |
dc.contributor.affiliationum | School of Pharmacy, University of Southern California, Los Angeles, Califorinia, 90033; Department of Chemistry, University of Michigan, Ann Arbor, MI, 48104 | en_US |
dc.contributor.affiliationother | School of Pharmacy, University of Southern California, Los Angeles, Califorinia, 90033 | en_US |
dc.contributor.affiliationother | Department of Chemistry, University of Southern California, Los Angeles, California, 90007 | en_US |
dc.contributor.affiliationumcampus | Ann Arbor | en_US |
dc.identifier.pmid | 24277218 | en_US |
dc.description.bitstreamurl | http://deepblue.lib.umich.edu/bitstream/2027.42/41423/1/11095_2004_Article_307226.pdf | en_US |
dc.identifier.doi | http://dx.doi.org/10.1023/A:1016307515811 | en_US |
dc.identifier.source | Pharmaceutical Research | en_US |
dc.owningcollname | Interdisciplinary and Peer-Reviewed |
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