Large-scale synthesis and formulation of GMP-grade stampidine, a new anti-HIV agent.
The arylphosphoramidate derivative of stavudine (STV, d4T, 2,3'-didehydro-3'-deoxythymidine, CAS 3056-17-5), stampidine (STAMP, DDE-113, HI-113, N-[p-(4-bromophenyl)-2',3'-didehydro-3'-deoxy-5'-thymidylyl]-L-alanine methyl ester, CAS 217178-62-6), is a novel anti-HIV agent. STAMP was prepared under current Good Manufacturing Practice (cGMP) conditions on the scale of kilograms. Solid STAMP was subsequently formulated as a capsule under GMP conditions for oral administration.
DuMez
Darin
D
Parker Hughes Institute, Roseville, Minnesota, USA.
Venkatachalam
Taracad K
TK
Uckun
Fatih M
FM
D019380:Anti-HIV Agents / Q000008:administration & dosage / Q000138:chemical synthesis / Q000737:chemistry*; D055598:Chemical Phenomena; D002626:Chemistry, Pharmaceutical; D002627:Chemistry, Physical; D002849:Chromatography, Gas; D002851:Chromatography, High Pressure Liquid; D054306:Dideoxynucleotides; D004304:Dosage Forms; D004355:Drug Stability; D007202:Indicators and Reagents; D009682:Magnetic Resonance Spectroscopy; D013058:Mass Spectrometry; D008670:Metals / Q000737:chemistry; D013056:Spectrophotometry, Ultraviolet; D017550:Spectroscopy, Fourier Transform Infrared; D018119:Stavudine / Q000008:administration & dosage / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry; D013938:Thymidine Monophosphate / Q000008:administration & dosage / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry
D019380:Anti-HIV Agents; D054306:Dideoxynucleotides; D004304:Dosage Forms; D007202:Indicators and Reagents; D008670:Metals; C472384:stampidine; D013938:Thymidine Monophosphate; D018119:Stavudine