Cidofovir

Cidofovir

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Systematic (IUPAC) name
({[(S)-1-(4-amino-2-oxo-1,2-dihydropyrimidin-1-yl)-3-hydroxypropan-2-yl]oxy}methyl)phosphonic acid
Clinical data
Routes of administration	intravenous
Pharmacokinetic data
Bioavailability	complete
Protein binding	6%
Biological half-life	2.4 to 3.2 hours
Excretion	renal
Identifiers
CAS Number	113852-37-2
ATC code	J05AB12 (WHO)
PubChem	CID 60613
DrugBank	APRD00148
ChemSpider	54636
Chemical data
Formula	C8H14N3O6P
Molar mass	279.187 g/mol[[]]
Specific rotation	-97.3
Physical data
Melting point	260 °C (500 °F)
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Cidofovir is an injectable antiviral medication for the treatment of cytomegalovirus (CMV) retinitis in patients with AIDS. It suppresses CMV replication by selective inhibition of viral DNA polymerase and therefore prevention of viral replication and transcription. It is an acyclic nucleoside phosphonate, and is therefore independent of phosphorylation by viral enzymes, in contrast to, for instance, acyclovir.

Administration

Maintenance therapy with cidofovir involves an infusion only once every two weeks, making it a convenient treatment option. Because dosing is relatively infrequent, a permanent catheter is not necessary for infusions.

Side effects

The major side effect of cidofovir is that it can be nephrotoxic.

Uses

DNA virus

Cidofovir demonstrated a statistically significant effect in delaying the progression of CMV retinitis lesions in newly diagnosed patients, as well as in previously treated patients who had failed other therapies.

Cidofovir has also shown efficacy in the treatment of acyclovir resistant herpes

Cidofovir has also been investigated as a treatment for progressive multifocal leukoencephalopathy, but as of 2005 studies are inconclusive.

Cidofovir might have anti-smallpox efficacy and might be used on a limited basis in the event of a bioterror incident involving smallpox cases.

Cidofovir shows anti-BK virus activity in a subgroup of transplant patients.

Cidofovir is being investigated as a complementary intralesional therapy against papillomatosis caused by HPV.

Other

It has been suggested as an antitumor agent, due to its suppression of FGF2.

History

Cidofovir was discovered at the Institute of Organic Chemistry and Biochemistry, Prague, by Antonín Holý, and developed by Gilead Sciences and is marketed with the brand name Vistide by Gilead in the USA, and by Pfizer elsewhere.

Chem

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Brodfuehrer, P (1994). "A practical synthesis of (S)-HPMPC". Tetrahedron Letters. 35: 3243. doi:10.1016/S0040-4039(00)76875-4. 

References

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