| Revision as of 12:04, 17 November 2011 editBeetstra (talk | contribs)Edit filter managers, Administrators172,074 edits Saving copy of the {{drugbox}} taken from revid 456543537 of page Famciclovir for the Chem/Drugbox validation project (updated: 'DrugBank'). |
Latest revision as of 04:11, 2 April 2024 edit Whywhenwhohow (talk | contribs)Autopatrolled, Extended confirmed users, Pending changes reviewers49,324 edits add template |
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{{Short description|Chemical compound}} |
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{{ambox | text = This page contains a copy of the infobox ({{tl|drugbox}}) taken from revid of page ] with values updated to verified values.}} |
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{{Drugbox |
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{{Drugbox |
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| verifiedrevid = 443750270 |
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| verifiedrevid = 461098816 |
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| image = Famciclovir.svg |
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| IUPAC_name = 2--4-(2-amino-9''H''-purin-9-yl)butyl acetate |
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| width = 225 |
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| image = Famciclovir structure.svg |
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| alt = |
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<!--Clinical data--> |
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<!-- Clinical data --> |
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| tradename = Famvir |
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| tradename = Famvir |
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| pronounce = {{IPAc-en|ˌ|f|æ|m|ˈ|s|aɪ|k|l|oʊ|ˌ|v|ɪər}}{{refn|{{MerriamWebsterDictionary|access-date=2016-01-22|Famciclovir}}}} |
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| Drugs.com = {{drugs.com|monograph|famciclovir}} |
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| Drugs.com = {{drugs.com|monograph|famciclovir}} |
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| MedlinePlus = a694038 |
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| MedlinePlus = a694038 |
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| pregnancy_AU = B1 |
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| pregnancy_category = B1 <small>(])</small>, B <small>(])</small> |
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| pregnancy_category = |
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| legal_status = S4 <small>(Au)</small>, POM <small>(])</small>, â-only <small>(U.S.)</small> |
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| routes_of_administration = Oral |
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| routes_of_administration = ] |
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| ATC_prefix = J05 |
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| ATC_suffix = AB09 |
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| ATC_supplemental = {{ATC|S01|AD07}} |
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| legal_AU = S4 |
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| legal_AU_comment = <ref>{{cite web | title=Prescription medicines: registration of new generic medicines and biosimilar medicines, 2017 | website=Therapeutic Goods Administration (TGA) | date=21 June 2022 | url=https://www.tga.gov.au/resources/publication/publications/prescription-medicines-registration-new-generic-medicines-and-biosimilar-medicines-2017 | access-date=30 March 2024}}</ref> |
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| legal_CA = |
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| legal_UK = POM |
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| legal_US = Rx-only |
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| legal_status = |
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<!--Pharmacokinetic data--> |
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<!--Pharmacokinetic data--> |
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| bioavailability = 75â77% |
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| bioavailability = 75–77% |
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| protein_bound = 20-25% |
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| protein_bound = 20–25% |
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| metabolism = Hepatic, circulation, intestinal wall (to ]) |
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| metabolism = ], circulation, intestinal wall (to ]) |
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| elimination_half-life = 2â2.3 hours |
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| elimination_half-life = 2–2.3 hours |
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| excretion = Renal, faecal |
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| excretion = ], faecal |
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<!--Identifiers--> |
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<!--Identifiers--> |
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| CASNo_Ref = {{cascite|correct|CAS}} |
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| CAS_number_Ref = {{cascite|correct|??}} |
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| CAS_number_Ref = {{cascite|correct|??}} |
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| CAS_number = 104227-87-4 |
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| CAS_number = 104227-87-4 |
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| ATC_prefix = J05 |
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| ATC_suffix = AB09 |
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| ATC_supplemental = {{ATC|S01|AD07}} |
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| PubChem = 3324 |
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| PubChem = 3324 |
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| DrugBank_Ref = {{drugbankcite|correct|drugbank}} |
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| DrugBank_Ref = {{drugbankcite|correct|drugbank}} |
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| ChEMBL = 880 |
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| ChEMBL = 880 |
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<!--Chemical data--> |
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<!-- Chemical data --> |
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| IUPAC_name = 2--4-(2-amino-9''H''-purin-9-yl)butyl acetate |
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| C=14 | H=19 | N=5 | O=4 |
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| C=14 | H=19 | N=5 | O=4 |
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| molecular_weight = 321.332 g/mol |
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| smiles = O=C(OCC(COC(=O)C)CCn1c2nc(ncc2nc1)N)C |
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| smiles = O=C(OCC(COC(=O)C)CCn1c2nc(ncc2nc1)N)C |
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| InChI = 1/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) |
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| InChIKey = GGXKWVWZWMLJEH-UHFFFAOYAH |
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| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChI = 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) |
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| StdInChI = 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) |
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| melting_point = 103 |
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| melting_point = 103 |
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}} |
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'''Famciclovir''' is a ] analogue ] used for the treatment of various ] infections, most commonly for ] (shingles). It is a ] form of ] with improved oral ]. Famciclovir is marketed under the trade name '''Famvir''' (]). |
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<!-- Society and culture --> |
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Famciclovir was patented in 1983 and approved for medical use in 1994.<ref>{{cite book| vauthors = Long SS, Pickering LK, Prober CG |title=Principles and Practice of Pediatric Infectious Disease|date=2012|publisher=Elsevier Health Sciences|isbn=978-1437727029|page=1502 |url=https://books.google.com/books?id=nQ7-o8JAH7kC&pg=PA1502 }}</ref><ref name=Fis2006>{{cite book | vauthors = Fischer J, Ganellin CR |title=Analogue-based Drug Discovery |date=2006 |publisher=John Wiley & Sons |isbn=9783527607495 |page=504 |url=https://books.google.com/books?id=FjKfqkaKkAAC&pg=PA504 |language=en}}</ref> In 2007, the ] ] approved the first generic version of famciclovir. Generic tablets are manufactured by ] and ].<ref>{{cite web| url=http://www.tevausa.com/default.aspx?pageid=75| title=Recent Product Launches, Teva Pharmaceuticals USA| access-date=2008-02-21| archive-url= https://web.archive.org/web/20111108014430/http://www.tevausa.com/default.aspx?pageid=75| archive-date=2011-11-08| url-status=dead}}{{better source|date=March 2016}}</ref><ref>{{cite press release|title=Mylan Launches Generic Version of Famvir® Tablets |publisher=Mylan |date=20 April 2011 |url=http://investor.mylan.com/releasedetail.cfm?ReleaseID=570428 |access-date=21 April 2011 |url-status=dead |archive-url=https://web.archive.org/web/20110723062658/http://investor.mylan.com/releasedetail.cfm?ReleaseID=570428 |archive-date=July 23, 2011 }}</ref> |
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==Medical uses== |
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Famciclovir is indicated for the treatment of herpes zoster (shingles),<ref name=Tyring1995>{{cite journal | vauthors = Tyring S, Barbarash RA, Nahlik JE, Cunningham A, Marley J, Heng M, Jones T, Rea T, Boon R, Saltzman R | display-authors = 6 | title = 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 | journal = Annals of Internal Medicine | volume = 123 | issue = 2 | pages = 89–96 | date = July 1995 | pmid = 7778840 | doi = 10.7326/0003-4819-123-2-199507150-00002 | s2cid = 35498460 }}</ref> treatment of herpes simplex virus 2 (genital herpes),<ref name=Luber1995>{{cite journal | vauthors = Luber AD, Flaherty JF | title = Famciclovir for treatment of herpesvirus infections | journal = The Annals of Pharmacotherapy | volume = 30 | issue = 9 | pages = 978–85 | date = September 1996 | pmid = 8876860 | doi = 10.1177/106002809603000913 | s2cid = 27057728 }}</ref> herpes labialis (cold sores) in immunocompetent patients<ref name=Spraunce2006>{{cite journal | vauthors = Spruance SL, Bodsworth N, Resnick H, Conant M, Oeuvray C, Gao J, Hamed K | title = Single-dose, patient-initiated famciclovir: a randomized, double-blind, placebo-controlled trial for episodic treatment of herpes labialis | journal = Journal of the American Academy of Dermatology | volume = 55 | issue = 1 | pages = 47–53 | date = July 2006 | pmid = 16781291 | doi = 10.1016/j.jaad.2006.02.031 }}</ref> 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.{{cn|date=November 2022}} |
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==Adverse effects== |
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Side effects: mild to extreme stomach upset, headaches, mild fever. |
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==Herpes== |
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=== Early treatment === |
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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 ].<ref name="pmid10993926">{{cite journal | vauthors = Thackray AM, Field HJ | title = 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 | journal = The Journal of General Virology | volume = 81 | issue = Pt 10 | pages = 2385–2396 | date = October 2000 | pmid = 10993926 | doi = 10.1099/0022-1317-81-10-2385 | doi-access = free }}</ref><ref name="pmid9660982">{{cite journal | vauthors = Thackray AM, Field HJ | title = Famciclovir and valaciclovir differ in the prevention of herpes simplex virus type 1 latency in mice: a quantitative study | journal = Antimicrobial Agents and Chemotherapy | volume = 42 | issue = 7 | pages = 1555–62 | date = July 1998 | pmid = 9660982 | pmc = 105644 | doi = 10.1128/AAC.42.7.1555}}</ref><ref name="pmid10602729">{{cite journal | vauthors = Thackray AM, Field HJ | title = Persistence of infectious herpes simplex virus type 2 in the nervous system in mice after antiviral chemotherapy | journal = Antimicrobial Agents and Chemotherapy | volume = 44 | issue = 1 | pages = 97–102 | date = January 2000 | pmid = 10602729 | pmc = 89634 | doi = 10.1128/aac.44.1.97-102.2000 }}</ref> 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.<ref>{{cite web | title = Observation May Indicate A Possible Clinical Effect On Latency | url = http://www.pslgroup.com/dg/D29E.htm | work = Doctor's Guide Publishing Limited | archive-url = https://web.archive.org/web/20120216215210/http://www.pslgroup.com/dg/D29E.htm | archive-date = 2012-02-16 }}</ref> Neither drug affected latency if treatment was delayed for several months.<ref name=Thackray>{{cite journal | vauthors = Thackray AM, Field HJ | title = Differential effects of famciclovir and valaciclovir on the pathogenesis of herpes simplex virus in a murine infection model including reactivation from latency | journal = The Journal of Infectious Diseases | volume = 173 | issue = 2 | pages = 291–9 | date = February 1996 | pmid = 8568288 | doi = 10.1093/infdis/173.2.291 | doi-access = free }}</ref> |
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{{Clear}} |
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== References == |
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{{Reflist}} |
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{{Antivirals}} |
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{{Ophthalmological anti-infectives}} |
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{{Schering-Plough|state=autocollapse}} |
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