Stavudine
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Missing image Stavudine.png Chemical structure of stavudine. d4T | |
| 2'-3'-didehydro-2'-3'-dideoxythymidine | |
| Molecular Weight | 224.21 |
| Empiric Formula | C10H12N2O4 |
| ATC code | J05AF04 |
| Metabolism | Renal elimination (ca.40%) |
| Pregnancy category | C (USA) B3 (Aus) |
Stavudine (2'-3'-didehydro-2'-3'-dideoxythymidine, d4T) is a thymidine analogue active against HIV. It is phosphorylated by cellular kinases into active triphosphate. Stavudine triphosphate inhibits the reverse transcriptase by competing with natural substrate, thymidine triphosphate. It also causes termination of DNA synthesis by incorporating into it.
The oral absorption rate of stavudine is over 80 %. Approximately half of stavudine is actively secreted unchanged into the urine and the other half is eliminated through endogenic pathways. Simultaneous use of AZT is not recommended, for AZT can inhibit the intracellular phosphorylation of stavudine. Other anti-HIV drugs do not possess this property. The main severe side effect is peripheral neuropathy, which can be corrected by reducing dosage. Stavudine has been shown in laboratory test to be genotoxic, but with clinical doses its carcinogenic effects are non-existent.