Famciclovir

Last updated

Famciclovir
Famciclovir.svg
Clinical data
Pronunciation /ˌfæmˈsaɪkloʊˌvɪər/ [1]
Trade names Famvir
AHFS/Drugs.com Monograph
MedlinePlus a694038
Pregnancy
category
  • AU:B1
Routes of
administration 		By mouth
ATC code
Legal status
Legal status
Pharmacokinetic data
Bioavailability 75–77%
Protein binding 20–25%
Metabolism Liver, circulation, intestinal wall (to penciclovir)
Elimination half-life 2–2.3 hours
Excretion Kidney, faecal
Identifiers
  • 2-[(acetyloxy)methyl]-4-(2-amino-9H-purin-9-yl)butyl acetate
CAS Number
PubChem CID
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard 100.158.713 OOjs UI icon edit-ltr-progressive.svg
Chemical and physical data
Formula C14H19N5O4
Molar mass 321.337 g·mol−1
3D model (JSmol)
Melting point 103 °C (217 °F)
  • O=C(OCC(COC(=O)C)CCn1c2nc(ncc2nc1)N)C
  • InChI=1S/C14H19N5O4/c1-9(20)22-6-11(7-23-10(2)21)3-4-19-8-17-12-5-16-14(15)18-13(12)19/h5,8,11H,3-4,6-7H2,1-2H3,(H2,15,16,18) Yes check.svgY
  • Key:GGXKWVWZWMLJEH-UHFFFAOYSA-N Yes check.svgY
   (verify)

Famciclovir is a guanosine analogue antiviral drug used for the treatment of various herpesvirus infections, most commonly for herpes zoster (shingles). It is a prodrug form of penciclovir with improved oral bioavailability. Famciclovir is marketed under the trade name Famvir (Novartis).

Contents

Famciclovir was patented in 1983 and approved for medical use in 1994. [3] [4] In 2007, the United States Food and Drug Administration approved the first generic version of famciclovir. Generic tablets are manufactured by TEVA Pharmaceuticals and Mylan Pharmaceuticals. [5] [6]

Medical uses

Famciclovir is indicated for the treatment of herpes zoster (shingles), [7] treatment of herpes simplex virus 2 (genital herpes), [8] herpes labialis (cold sores) in immunocompetent patients [9] and for the suppression of recurring episodes of herpes simplex virus 2. It is also indicated for treatment of recurrent episodes of herpes simplex in HIV patients.[ citation needed ]

Adverse effects

Side effects: mild to extreme stomach upset, headaches, mild fever.

Herpes

Early treatment

Several studies in humans and mice provide evidence that early treatment with famciclovir soon after the first infection with herpes can significantly lower the chance of future outbreaks. Use of famciclovir in this manner has been shown to reduce the amount of latent virus in the neural ganglia compared to no treatment or treatment with valaciclovir. [10] [11] [12] A review of human subjects treated for five days with famciclovir 250 mg three times daily during their first herpes episode found that only 4.2 percent experienced a recurrence within six months after the first outbreak, a fivefold decrease compared to the 19 percent recurrence in acyclovir-treated patients. [13] Neither drug affected latency if treatment was delayed for several months. [14]

History

Initially studied as compound BRL 42810, famciclovir grew out of the study of "several potential prodrugs of penciclovir", that were synthesized by M. R. Harnden and R. L. Jarvest from the Beecham Group plc. in the late 1980s. After showing promise on studies with mice, BRL 42810 (famciclovir) was selected for further evaluation and progression to studies in humans. [15]

References

  1. ↑ "Famciclovir". Merriam-Webster.com Dictionary . Merriam-Webster. Retrieved 2016-01-22.
  2. ↑ "Prescription medicines: registration of new generic medicines and biosimilar medicines, 2017". Therapeutic Goods Administration (TGA). 21 June 2022. Retrieved 30 March 2024.
  3. ↑ Long SS, Pickering LK, Prober CG (2012). Principles and Practice of Pediatric Infectious Disease. Elsevier Health Sciences. p. 1502. ISBN   978-1437727029.
  4. ↑ Fischer J, Ganellin CR (2006). Analogue-based Drug Discovery. John Wiley & Sons. p. 504. ISBN   9783527607495.
  5. ↑ "Recent Product Launches, Teva Pharmaceuticals USA". Archived from the original on 2011-11-08. Retrieved 2008-02-21.[ better source needed ]
  6. ↑ "Mylan Launches Generic Version of Famvir® Tablets" (Press release). Mylan. 20 April 2011. Archived from the original on July 23, 2011. Retrieved 21 April 2011.
  7. ↑ Tyring S, Barbarash RA, Nahlik JE, Cunningham A, Marley J, Heng M, et al. (July 1995). "Famciclovir for the treatment of acute herpes zoster: effects on acute disease and postherpetic neuralgia. A randomized, double-blind, placebo-controlled trial. Collaborative Famciclovir Herpes Zoster Study Group". Annals of Internal Medicine. 123 (2): 89–96. doi:10.7326/0003-4819-123-2-199507150-00002. PMID   7778840. S2CID   35498460.
  8. ↑ Luber AD, Flaherty JF (September 1996). "Famciclovir for treatment of herpesvirus infections". The Annals of Pharmacotherapy. 30 (9): 978–85. doi:10.1177/106002809603000913. PMID   8876860. S2CID   27057728.
  9. ↑ Spruance SL, Bodsworth N, Resnick H, Conant M, Oeuvray C, Gao J, et al. (July 2006). "Single-dose, patient-initiated famciclovir: a randomized, double-blind, placebo-controlled trial for episodic treatment of herpes labialis". Journal of the American Academy of Dermatology. 55 (1): 47–53. doi:10.1016/j.jaad.2006.02.031. PMID   16781291.
  10. ↑ Thackray AM, Field HJ (October 2000). "The effects of antiviral therapy on the distribution of herpes simplex virus type 1 to ganglionic neurons and its consequences during, immediately following and several months after treatment". The Journal of General Virology. 81 (Pt 10): 2385–2396. doi: 10.1099/0022-1317-81-10-2385 . PMID   10993926.
  11. ↑ Thackray AM, Field HJ (July 1998). "Famciclovir and valaciclovir differ in the prevention of herpes simplex virus type 1 latency in mice: a quantitative study". Antimicrobial Agents and Chemotherapy. 42 (7): 1555–62. doi:10.1128/AAC.42.7.1555. PMC   105644 . PMID   9660982.
  12. ↑ Thackray AM, Field HJ (January 2000). "Persistence of infectious herpes simplex virus type 2 in the nervous system in mice after antiviral chemotherapy". Antimicrobial Agents and Chemotherapy. 44 (1): 97–102. doi:10.1128/aac.44.1.97-102.2000. PMC   89634 . PMID   10602729.
  13. ↑ "Observation May Indicate A Possible Clinical Effect On Latency". Doctor's Guide Publishing Limited. Archived from the original on 2012-02-16.
  14. ↑ Thackray AM, Field HJ (February 1996). "Differential effects of famciclovir and valaciclovir on the pathogenesis of herpes simplex virus in a murine infection model including reactivation from latency". The Journal of Infectious Diseases. 173 (2): 291–9. doi: 10.1093/infdis/173.2.291 . PMID   8568288.
  15. ↑ Vere Hodge RA, Sutton D, Boyd MR, Harnden MR, Jarvest RL (October 1989). "Selection of an oral prodrug (BRL 42810; famciclovir) for the antiherpesvirus agent BRL 39123 [9-(4-hydroxy-3-hydroxymethylbut-l-yl)guanine; penciclovir]". Antimicrobial Agents and Chemotherapy. 33 (10): 1765–1773. doi:10.1128/AAC.33.10.1765. PMC   172752 . PMID   2589844.
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