Cidofovir

Cidofovir
Systematic (IUPAC) name
({[(S)-1-(4-amino-2-oxo-1,2-dihydropyrimidin-1-yl)-3-hydroxypropan-2-yl]oxy}methyl)phosphonic acid
Clinical data
Trade names Vistide
AHFS/Drugs.com monograph
Pregnancy cat.  ?
Legal status  ?
Routes intravenous
Pharmacokinetic data
Bioavailability complete
Protein binding 6%
Half-life 2.4 to 3.2 hours
Excretion renal
Identifiers
CAS number 113852-37-2
ATC code J05AB12
PubChem CID 60613
DrugBank APRD00148
ChemSpider 54636 YesY
NIAID ChemDB 001049
UNII 768M1V522C YesY
ChEBI CHEBI:3696 YesY
ChEMBL CHEMBL152 YesY
Chemical data
Formula C8H14N3O6P 
Mol. mass 279.187 g/mol
SMILES eMolecules & PubChem
Physical data
Melt. point 260 °C (500 °F)
Spec. rot -97.3
 YesY(what is this?)  (verify)

Cidofovir is an injectable antiviral medication for the treatment of cytomegalovirus (CMV) retinitis[1] in patients with AIDS. It suppresses CMV replication by selective inhibition of viral DNA polymerase and therefore prevention of viral replication and transcription.[2] It is an acyclic nucleoside phosphonate, and is therefore independent of phosphorylation by viral enzymes,[3] in contrast to, for instance, acyclovir.

Contents

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.[4]

Probenecid (a uricosuric drug) is usually prescribed to prevent this nephrotoxicity.

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 shown efficacy as an anti-HSV, anti-VZV and as an anti-CMV

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

Cidofovir has also been investigated as a treatment for progressive multifocal leukoencephalopathy,[5] but as of 2005 studies are inconclusive.

Cidofovir might have anti-smallpox efficacy[6] and might be used on a limited basis in the event of a bioterror incident involving smallpox cases.In fact, it is a extremely high chance for Cidofovir to work against smallpox.

Cidofovir shows anti-BK virus activity in a subgroup of transplant patients.[7]

Cidofovir is being investigated as a complementary intralesional therapy against papillomatosis caused by HPV.[8][9]

Other

It has been suggested as an antitumor agent, due to its suppression of FGF2.[10][11]

History

Cidofovir was discovered at the Institute of Organic Chemistry and Biochemistry, Prague, by Antonín Holý, and developed by Gilead Sciences[12] and is marketed with the brand name Vistide by Gilead in the USA, and by Pfizer elsewhere.

Synthesis

Cidofovir syn.png

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

References

  1. ^ Becker MN, Obraztsova M, Kern ER, et al. (2008). "Isolation and characterization of cidofovir resistant vaccinia viruses". Virol. J. 5: 58. doi:10.1186/1743-422X-5-58. PMC 2397383. PMID 18479513. http://www.virologyj.com/content/5//58. 
  2. ^ Cidofovir VIRUSES, HIV, PRIONS, AND RELATED TOPICS. Human Virology at Stanford University
  3. ^ The mechanism of action of cidofovir and HSV helicase–primase complex inhibitors. Nature reviews
  4. ^ Kazory A, Singapuri S, Wadhwa A, Ejaz AA (July 2007). "Simultaneous development of Fanconi syndrome and acute renal failure associated with cidofovir". J. Antimicrob. Chemother. 60 (1): 193–4. doi:10.1093/jac/dkm143. PMID 17496056. http://jac.oxfordjournals.org/cgi/pmidlookup?view=long&pmid=17496056. 
  5. ^ Segarra-Newnham M, Vodolo KM (June 2001). "Use of cidofovir in progressive multifocal leukoencephalopathy". Ann Pharmacother 35 (6): 741–4. doi:10.1345/aph.10338. PMID 11408993. http://www.theannals.com/cgi/pmidlookup?view=long&pmid=11408993. 
  6. ^ De Clercq E (July 2002). "Cidofovir in the treatment of poxvirus infections". Antiviral Res. 55 (1): 1–13. doi:10.1016/S0166-3542(02)00008-6. PMID 12076747. http://linkinghub.elsevier.com/retrieve/pii/S0166354202000086. 
  7. ^ Araya CE, Lew JF, Fennell RS, Neiberger RE, Dharnidharka VR (February 2006). "Intermediate-dose cidofovir without probenecid in the treatment of BK virus allograft nephropathy". Pediatr Transplant 10 (1): 32–7. doi:10.1111/j.1399-3046.2005.00391.x. PMID 16499584. http://www3.interscience.wiley.com/resolve/openurl?genre=article&sid=nlm:pubmed&issn=1397-3142&date=2006&volume=10&issue=1&spage=32. 
  8. ^ Broekema FI, Dikkers FG (August 2008). "Side-effects of cidofovir in the treatment of recurrent respiratory papillomatosis". Eur Arch Otorhinolaryngol 265 (8): 871–9. doi:10.1007/s00405-008-0658-0. PMC 2441494. PMID 18458927. http://www.pubmedcentral.nih.gov/articlerender.fcgi?tool=pmcentrez&artid=2441494. 
  9. ^ Soma MA, Albert DM (February 2008). "Cidofovir: to use or not to use?". Curr Opin Otolaryngol Head Neck Surg 16 (1): 86–90. doi:10.1097/MOO.0b013e3282f43408. PMID 18197029. http://meta.wkhealth.com/pt/pt-core/template-journal/lwwgateway/media/landingpage.htm?an=00020840-200802000-00019. 
  10. ^ Liekens S, Gijsbers S, Vanstreels E, Daelemans D, De Clercq E, Hatse S (March 2007). "The nucleotide analog cidofovir suppresses basic fibroblast growth factor (FGF2) expression and signaling and induces apoptosis in FGF2-overexpressing endothelial cells". Mol. Pharmacol. 71 (3): 695–703. doi:10.1124/mol.106.026559. PMID 17158200. http://molpharm.aspetjournals.org/cgi/pmidlookup?view=long&pmid=17158200. 
  11. ^ Liekens S (2008). "Regulation of cancer progression by inhibition of angiogenesis and induction of apoptosis". Verh. K. Acad. Geneeskd. Belg. 70 (3): 175–91. PMID 18669159. 
  12. ^ "Press Releases: Gilead". http://www.gilead.com/pr_881577. Retrieved 2007-12-05. 

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