Famciclovir

Last updated
Famciclovir
Famciclovir.svg
Clinical data
Pronunciation /ˌfæmˈsklˌvɪər/ [1]
Trade names Famvir
AHFS/Drugs.com Monograph
MedlinePlus a694038
Pregnancy
category
  • AU:B1
Routes of
administration
Oral
ATC code
Legal status
Legal status
Pharmacokinetic data
Bioavailability 75–77%
Protein binding 20–25%
Metabolism Hepatic, circulation, intestinal wall (to penciclovir)
Elimination half-life 2–2.3 hours
Excretion Renal, 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. [2] [3] 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. [4] [5]

Medical uses

Famciclovir is indicated for the treatment of herpes zoster (shingles), [6] treatment of herpes simplex virus 2 (genital herpes), [7] herpes labialis (cold sores) in immunocompetent patients [8] 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. [9] [10] [11] 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. [12] Neither drug affected latency if treatment was delayed for several months. [13]

See also

Related Research Articles

<span class="mw-page-title-main">Varicella zoster virus</span> Herpes virus that causes chickenpox and shingles

Varicella zoster virus (VZV), also known as human herpesvirus 3 or Human alphaherpesvirus 3 (taxonomically), is one of nine known herpes viruses that can infect humans. It causes chickenpox (varicella) commonly affecting children and young adults, and shingles in adults but rarely in children. VZV infections are species-specific to humans. The virus can survive in external environments for a few hours.

<span class="mw-page-title-main">Shingles</span> Viral disease caused by the varicella zoster virus

Shingles, also known as herpes zoster, is a viral disease characterized by a painful skin rash with blisters in a localized area. Typically the rash occurs in a single, wide mark either on the left or right side of the body or face. Two to four days before the rash occurs there may be tingling or local pain in the area. Other common symptoms are fever, headache, and tiredness. The rash usually heals within two to four weeks; however, some people develop ongoing nerve pain which can last for months or years, a condition called postherpetic neuralgia (PHN). In those with poor immune function the rash may occur widely. If the rash involves the eye, vision loss may occur.

<span class="mw-page-title-main">Aciclovir</span> Antiviral medication used against herpes, chickenpox and shingles

Aciclovir (ACV), also known as acyclovir, is an antiviral medication. It is primarily used for the treatment of herpes simplex virus infections, chickenpox, and shingles. Other uses include prevention of cytomegalovirus infections following transplant and severe complications of Epstein–Barr virus infection. It can be taken by mouth, applied as a cream, or injected.

<span class="mw-page-title-main">Valaciclovir</span> Anti-herpes virus drug

Valaciclovir, also spelled valacyclovir, is an antiviral medication used to treat outbreaks of herpes simplex or herpes zoster (shingles). It is also used to prevent cytomegalovirus following a kidney transplant in high risk cases. It is taken by mouth.

<span class="mw-page-title-main">Ganciclovir</span> Chemical compound

Ganciclovir, sold under the brand name Cytovene among others, is an antiviral medication used to treat cytomegalovirus (CMV) infections.

<span class="mw-page-title-main">Nucleoside analogue</span> Biochemical compound

Nucleoside analogues are structural analogues of a nucleoside, which normally contain a nucleobase and a sugar. Nucleotide analogues are analogues of a nucleotide, which normally has one to three phosphates linked to a nucleoside. Both types of compounds can deviate from what they mimick in a number of ways, as changes can be made to any of the constituent parts. They are related to nucleic acid analogues.

<span class="mw-page-title-main">Herpetic gingivostomatitis</span> Medical condition

Gingivostomatitis is a combination of gingivitis and stomatitis, or an inflammation of the oral mucosa and gingiva. Herpetic gingivostomatitis is often the initial presentation during the first ("primary") herpes simplex infection. It is of greater severity than herpes labialis which is often the subsequent presentations. Primary herpetic gingivostomatitis is the most common viral infection of the mouth.

Virus latency is the ability of a pathogenic virus to lie dormant within a cell, denoted as the lysogenic part of the viral life cycle. A latent viral infection is a type of persistent viral infection which is distinguished from a chronic viral infection. Latency is the phase in certain viruses' life cycles in which, after initial infection, proliferation of virus particles ceases. However, the viral genome is not eradicated. The virus can reactivate and begin producing large amounts of viral progeny without the host becoming reinfected by new outside virus, and stays within the host indefinitely.

<span class="mw-page-title-main">Brivudine</span> Chemical compound

Brivudine is an antiviral drug used in the treatment of herpes zoster ("shingles"). Like other antivirals, it acts by inhibiting replication of the target virus.

<span class="mw-page-title-main">Herpes simplex virus</span> Species of virus

Herpes simplex virus1 and 2, also known by their taxonomic names Human alphaherpesvirus 1 and Human alphaherpesvirus 2, are two members of the human Herpesviridae family, a set of viruses that produce viral infections in the majority of humans. Both HSV-1 and HSV-2 are very common and contagious. They can be spread when an infected person begins shedding the virus.

<span class="mw-page-title-main">Genital herpes</span> Infection by herpes simplex viruses of the genitals

Genital herpes is a herpes infection of the genitals caused by the herpes simplex virus (HSV). Most people either have no or mild symptoms and thus do not know they are infected. When symptoms do occur, they typically include small blisters that break open to form painful ulcers. Flu-like symptoms, such as fever, aching, or swollen lymph nodes, may also occur. Onset is typically around 4 days after exposure with symptoms lasting up to 4 weeks. Once infected further outbreaks may occur but are generally milder.

<span class="mw-page-title-main">Sorivudine</span> Chemical compound

Sorivudine (INN), is a nucleoside analogue antiviral drug, marketed under trade names such as Usevir and Brovavir (BMS). It is used for the treatment of varicella zoster virus infections.

<span class="mw-page-title-main">Mollaret's meningitis</span> Medical condition

Mollaret's meningitis is a recurrent or chronic inflammation of the protective membranes covering the brain and spinal cord, known collectively as the meninges. Since Mollaret's meningitis is a recurrent, benign (non-cancerous), aseptic meningitis, it is also referred to as benign recurrent lymphocytic meningitis. It was named for Pierre Mollaret, the French neurologist who first described it in 1944.

<span class="mw-page-title-main">Thymidine kinase from herpesvirus</span>

Thymidine kinase from herpesvirus is a sub-family of thymidine kinases that catalyses the transfer of phospho group of ATP to thymidine to generate thymidine monophosphate, which serves as a substrate during viral DNA replication.

<span class="mw-page-title-main">Herpes</span> Viral disease caused by herpes simplex viruses

Herpes simplex, often known simply as herpes, is a viral infection caused by the herpes simplex virus. Herpes infections are categorized by the area of the body that is infected. The two major types of herpes are oral herpes and genital herpes, though other forms also exist.

<span class="mw-page-title-main">Cold sore</span> Herpes simplex virus infection of the lip

A cold sore is a type of herpes infection caused by the herpes simplex virus that affects primarily the lip. Symptoms typically include a burning pain followed by small blisters or sores. The first attack may also be accompanied by fever, sore throat, and enlarged lymph nodes. The rash usually heals within ten days, but the virus remains dormant in the trigeminal ganglion. The virus may periodically reactivate to create another outbreak of sores in the mouth or lip.

<span class="mw-page-title-main">Herpes esophagitis</span> Medical condition

Herpes esophagitis is a viral infection of the esophagus caused by Herpes simplex virus (HSV).

FV-100, also known as Cf1743, is an orally available nucleoside analogue drug with antiviral activity. It may be effective against shingles.

Herpes simplex research includes all medical research that attempts to prevent, treat, or cure herpes, as well as fundamental research about the nature of herpes. Examples of particular herpes research include drug development, vaccines and genome editing. HSV-1 and HSV-2 are commonly thought of as oral and genital herpes respectively, but other members in the herpes family include chickenpox (varicella/zoster), cytomegalovirus, and Epstein-Barr virus. There are many more virus members that infect animals other than humans, some of which cause disease in companion animals or have economic impacts in the agriculture industry.

HSV epigenetics is the epigenetic modification of herpes simplex virus (HSV) genetic code.

References

  1. "Famciclovir". Merriam-Webster.com Dictionary . Retrieved 2016-01-22.
  2. Long SS, Pickering LK, Prober CG (2012). Principles and Practice of Pediatric Infectious Disease. Elsevier Health Sciences. p. 1502. ISBN   978-1437727029.
  3. Fischer J, Ganellin CR (2006). Analogue-based Drug Discovery. John Wiley & Sons. p. 504. ISBN   9783527607495.
  4. "Recent Product Launches, Teva Pharmaceuticals USA". Archived from the original on 2011-11-08. Retrieved 2008-02-21.[ better source needed ]
  5. "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.
  6. 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.
  7. 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.
  8. Spruance SL, Bodsworth N, Resnick H, Conant M, Oeuvray C, Gao J, Hamed K (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.
  9. 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.
  10. 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.
  11. 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.
  12. "Observation May Indicate A Possible Clinical Effect On Latency". Doctor's Guide Publishing Limited. Archived from the original on 2012-02-16.
  13. 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.