Stavudine

Stavudine (trade name Zerit) is an anti-HIV treatment in the class of drugs called Nucleoside Reverse Transcriptase Inhibitors (NRTIs).

• Chemical IUPAC Name: 1-[(2R,5S)-5-(hydroxymethyl)-2,5-dihydrofuran-2-yl]-5-methylpyrimidine-2,4-dione
• Synonyms: D4T, DHT, Ddethd, Ddetyd, Estavudina, STV, Sanilvudine, Stavudine, Zerit
• Chemical Formula: C₁₀H₁₂N₂O₄
• Molecular Weight: 224.216 g/mol
• CAS Registry Number: 3056-17-5
• Melting Point: 159 – 160 °C
• Solubility in water: 5-10 g/100 mL at 21 °C
• Canonical SMILES: CC1=CN(C(=O)NC1=O)C2C=CC(O2)CO
• Isomeric SMILES: CC1=CN(C(=O)NC1=O)[C@H]2C=C[C@H](O2)CO
• InChIKey Identifier: XNKLLVCARDGLGL-ATTKCSSXDC
• Safety (MSDS) data for stavudine: http://physchem.ox.ac.uk/MSDS/ST/stavudine.html

Stavudine has the following structural formula:

Stavudine is a nucleoside analogue of thymidine. It is phosphorylated by cellular kinases into active triphosphate. Stavudine triphosphate inhibits the HIV reverse transcriptase by competing with natural substrate, thymidine triphosphate. It also causes termination of viral DNA synthesis by incorporating into it.

Synthesis Reference:

1. J. P. Horwitz, J. Org. Chem. (1996) 31, 205
2. Joshi, Bhalchandra V. et al.; J.Chem.Soc.Perkin Trans.1; 19; 2537-2544 (1992)