fialuridine
Fialuridine, or 1-(2-deoxy-2-fluoro-1-D-arabinofuranosyl)-5-iodouracil (FIAU), is a nucleoside analogue that was investigated as a potential therapy for hepatitis B virus infection. In a 1993 clinical study at the NIH, unexpected toxicity led to the death of 5 out of 15 patients from liver failure alongside lactic acidosis; two further participants required liver transplantation. It is suspected that the toxicity of fialuridine was a result of mitochondrial damage caused by the incorporation of fialuridine into mitochondrial DNA via its 3'-hydroxyl moiety, leading to impaired DNA synthesis. This toxicity was unusual in that it was not predicted by animal studies. — Wikipedia
Clinical trial activity
2 trials · 4 clinical orgs · 0 marketing orgs
Earliest trial started Nov 2, 1999 (NCT00000654)
Timeline
1990s
- Jan 1, 1999
Earliest Phase 2 Sponsor(trial)
Indications
Mechanism of action
- Hepatitis B virusINHIBITOR
Hepatitis B virus inhibitor
Chemistry & pharmacology
SMILES
O=c1[nH]c(=O)n([C@@H]2O[C@H](CO)[C@@H](O)[C@@H]2F)cc1I- Mol. weight
- 372.09 g/mol
- Lipinski Ro5
- Pass
- Rule of 3
- No
- Chirality
- Single Stereoisomer
- Inorganic
- No
- Polymer
- No
Oral
No
Parenteral
No
Topical
No
Sources
- WikipediaFialuridine ↗
- ChEMBLCHEMBL271475 ↗
Also known as
- 123i-fiau
- 1-(2-deoxy-2-fluoro-beta-arabinofuranosyl)-5-iodouracil
- 1-(2'fluoro-2'-deoxyarabinofuranosyl)-5-iodouracil
- 2'-fluoro-5-iodoarauracil
- fialuridine
- fialuridine
- fialuridine
- fialuridine
- fiau
- fiau
- fiau
Clinical trials
| NCT ID | Phase | Start date | Sponsor(s) |
|---|---|---|---|
| NCT00982449 | N/A | Dec 31, 2010 | Johns Hopkins University, National Cancer Institute (NCI) |
| NCT00000654 | Phase 2 | Nov 2, 1999 | National Institute of Allergy and Infectious Diseases (NIAID), Oclassen |
Organizations
Research & Development (4)
| Organization | Org type | Trials | As lead sponsor | Phases | Earliest year |
|---|---|---|---|---|---|
| Johns Hopkins University | Academic/Hospital | 1 | 1 | 1 | 2010 |
| National Cancer Institute (NCI) | Government | 1 | 0 | 1 | 2010 |
| National Institute of Allergy and Infectious Diseases (NIAID) | Government | 1 | 1 | 1 | 1999 |
| Oclassen | For profit | 1 | 0 | 1 | 1999 |