Stampidine

Stampidine
Skeletal formula of stampidine
Ball-and-stick model of the stampidine molecule
Clinical data
ATC code
  • none
Identifiers
  • methyl N-((4-bromophenoxy){[(2S,5R)-5-(5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-2,5-dihydrofuran-2-yl]methoxy}phosphoryl)-D-alaninate
CAS Number
PubChem CID
ChemSpider
UNII
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC20H23BrN3O8P
Molar mass544.295 g·mol−1
3D model (JSmol)
  • Cc1cn(c(=O)[nH]c1=O)[C@H]2C=C[C@H](O2)COP(=O)(N[C@H](C)C(=O)OC)Oc3ccc(cc3)Br
  • InChI=1S/C20H23BrN3O8P/c1-12-10-24(20(27)22-18(12)25)17-9-8-16(31-17)11-30-33(28,23-13(2)19(26)29-3)32-15-6-4-14(21)5-7-15/h4-10,13,16-17H,11H2,1-3H3,(H,23,28)(H,22,25,27)/t13-,16+,17-,33?/m1/s1
  • Key:VPABMVYNSQRPBD-AOJMVMDXSA-N
  (verify)

Stampidine is an experimental nucleoside reverse transcriptase inhibitor (NRTI) with anti-HIV activity.[1][2]

It is a derivative of stavudine (d4T, brand name Zerit), and has been designed to avoid dependence on the rate limiting step of phosphorylation of stavudine to stavudine monophosphate. This is governed by the supply of thymidine kinase that is available, and stavudine is poorly phosphorylated to its monophosphate form in thymidine kinase-deficient cells.[1]

  1. ^ a b Uckun FM (February 2006). "Stampidine as a novel nucleoside reverse transcriptase inhibit with potent anti-HIV activity". Arzneimittelforschung. 56 (2A): 121–35. doi:10.1055/s-0031-1296800. PMID 16570821. S2CID 37628532.
  2. ^ Uckun FM, Cahn P, Qazi S, D'Cruz O (April 2012). "Stampidine as a promising antiretroviral drug candidate for pre-exposure prophylaxis against sexually transmitted HIV/AIDS". Expert Opin Investig Drugs. 21 (4): 489–500. doi:10.1517/13543784.2012.664635. PMID 22360744. S2CID 8037238.