PMID: 10079878Mar 18, 1999

Synthesis of dual function (5R,6R)- and (5S,6S)-5-bromo-6-methoxy-5,6-dihydro-AZT-5'-(para-bromophenyl methoxyalaninyl phosphate) as novel spermicidal and anti-HIV agents

Antiviral Chemistry & Chemotherapy
S T JanF M Uckun


We synthesized a novel compound, 5-bromo-6-methoxy-5,6-dihydro-AZT-5'- (p-bromophenyl methoxyalaninyl phosphate), which had an EC50 value of 5 microM in sperm motility assays. This is > 1 log10 better than that of the detergent spermicide nonoxynol-9 (EC50 81 microM). The compound also displayed a potent anti-human immunodeficiency virus (HIV) activity with an IC50 value of 0.005 microM in HIV replication assays, which was virtually identical to that of AZT (IC50 0.006 microM) and > 2 log10 more potent than that of nonoxynol-9 (IC50 2.2 microM). The promising results reported herein recommend the further development of the dual function 5-halo-6-alkoxyl-5,6-dihydro-AZT derivatives as a new class of vaginal contraceptives capable of preventing the sexual transmission of HIV while providing fertility control for women who are at high risk of acquiring HIV by heterosexual transmission. These dual function 5-halo-6-alkoxyl-5,6-dihydro-AZT derivatives may also have utility in curbing domestic and wildlife animal retroviral transmissions.


Jul 22, 1992·JAMA : the Journal of the American Medical Association·J KreissT R Fleming
Jul 1, 1991·Sexually Transmitted Diseases·S NiruthisardS Chutivongse
Jan 1, 1988·American Journal of Public Health·P J Feldblum, J A Fortney
May 20, 1988·JAMA : the Journal of the American Medical Association·P J FeldblumM J Rosenberg
Mar 1, 1984·Toxicology Letters·L Tryphonas, H S Buttar
Apr 1, 1995·Genitourinary Medicine·S S WeirP J Feldblum
Mar 1, 1995·The Veterinary Clinics of North America. Small Animal Practice·S C Kerwin
May 1, 1993·International Journal of STD & AIDS·R E RoddyJ A Fortney
Apr 16, 1993·Journal of Medicinal Chemistry·C McGuiganE De Clercq
Apr 12, 1997·Lancet·P M Rowe
Jun 12, 1998·Biology of Reproduction·O J D'CruzF M Uckun
Aug 14, 1998·Molecular Human Reproduction·O J D'CruzF M Uckun


Nov 28, 2001·Current Infectious Disease Reports·Christine K Mauck, Gustavo Doncel
Aug 11, 2005·Current HIV/AIDS Reports·Gustavo Doncel, Christine K Mauck
Jun 22, 2000·Biology of Reproduction·O J D'CruzF M Uckun

Related Concepts

5-bromo-6-methoxy-5,6-dihydro-AZT-5'-(4-bromophenyl methoxyalaninyl phosphate)
Vaginal Shield
Organopyrophosphorus Compounds
Vaginal Spermicides
Y-Chromosome-Bearing Sperm
Virus Replication
HIV Infections
Nonoxynol, 4-Sulfate, Ammonium Salt

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