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Revision as of 20:08, 16 February 2012 editBeetstra (talk | contribs)Edit filter managers, Administrators172,031 edits Saving copy of the {{drugbox}} taken from revid 473572888 of page Adefovir for the Chem/Drugbox validation project (updated: 'DrugBank', 'CAS_number').  Latest revision as of 15:12, 20 November 2023 edit OAbot (talk | contribs)Bots439,234 editsm Open access bot: doi updated in citation with #oabot. 
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{{Short description|Chemical compound}}
{{ambox | text = This page contains a copy of the infobox ({{tl|drugbox}}) taken from revid of page ] with values updated to verified values.}}
{{Drugbox {{Drugbox
| Verifiedfields = changed | Verifiedfields = changed
| verifiedrevid = 456665883 | verifiedrevid = 477242223
| IUPAC_name = {methyl}phosphonic acid | IUPAC_name = {methyl}phosphonic acid
| image = Adefovir.svg | image = Adefovir.svg
| width = 208 | width = 215


<!--Clinical data--> <!--Clinical data-->
| tradename = | tradename = Hepsera
| Drugs.com = {{drugs.com|monograph|adefovir-dipivoxil}} | Drugs.com = {{drugs.com|monograph|adefovir-dipivoxil}}
| pregnancy_AU = B3
| pregnancy_US = C | pregnancy_US = C
| legal_status = Rx-only | legal_AU = S4
| legal_CA = Rx-only
| legal_UK = POM
| legal_US = Rx-only
| routes_of_administration = Oral | routes_of_administration = Oral


<!--Pharmacokinetic data--> <!--Pharmacokinetic data-->
| bioavailability = 59% | bioavailability = 59%
| protein_bound = | protein_bound = <4%
| metabolism = | metabolism =
| elimination_half-life = 7.5 hours | elimination_half-life = 7.5 hours
| excretion = Urine


<!--Identifiers--> <!--Identifiers-->
| CAS_number_Ref = {{cascite|changed|??}} | CAS_number_Ref = {{cascite|changed|??}}
| CAS_number = <!-- blanked - oldvalue: 106941-25-7 --> | CAS_number = 106941-25-7
| ATC_prefix = J05 | ATC_prefix = J05
| ATC_suffix = AF08 | ATC_suffix = AF08
| ATC_supplemental = | ATC_supplemental =
| PubChem = 60172 | PubChem = 60172
| DrugBank_Ref = {{drugbankcite|changed|drugbank}} | DrugBank_Ref = {{drugbankcite|correct|drugbank}}
| DrugBank = DB00718 | DrugBank = DB00718
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 54252 | ChemSpiderID = 54252
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| UNII_Ref = {{fdacite|correct|FDA}} | UNII_Ref = {{fdacite|correct|FDA}}
| UNII = 6GQP90I798 | UNII = 6GQP90I798
| ChEBI_Ref = {{ebicite|correct|EBI}}
| ChEBI = 2469
| KEGG_Ref = {{keggcite|correct|kegg}} | KEGG_Ref = {{keggcite|correct|kegg}}
| KEGG = D02768 | KEGG = D02768
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<!--Chemical data--> <!--Chemical data-->
| C=8 | H=12 | N=5 | O=4 | P=1 | C=8 | H=12 | N=5 | O=4 | P=1
| molecular_weight = 273.186 g/mol
| smiles = O=P(O)(O)COCCn1c2ncnc(c2nc1)N | smiles = O=P(O)(O)COCCn1c2ncnc(c2nc1)N
| InChI = 1/C8H12N5O4P/c9-7-6-8(11-3-10-7)13(4-12-6)1-2-17-5-18(14,15)16/h3-4H,1-2,5H2,(H2,9,10,11)(H2,14,15,16)
| InChIKey = SUPKOOSCJHTBAH-UHFFFAOYAL
| StdInChI_Ref = {{stdinchicite|correct|chemspider}} | StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 1S/C8H12N5O4P/c9-7-6-8(11-3-10-7)13(4-12-6)1-2-17-5-18(14,15)16/h3-4H,1-2,5H2,(H2,9,10,11)(H2,14,15,16) | StdInChI = 1S/C8H12N5O4P/c9-7-6-8(11-3-10-7)13(4-12-6)1-2-17-5-18(14,15)16/h3-4H,1-2,5H2,(H2,9,10,11)(H2,14,15,16)
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| StdInChIKey = SUPKOOSCJHTBAH-UHFFFAOYSA-N | StdInChIKey = SUPKOOSCJHTBAH-UHFFFAOYSA-N
}} }}

'''Adefovir''' is a prescription medicine used to treat (chronic) infections with hepatitis B virus. A prodrug form of adefovir was previously called '''bis-POM PMEA''', with trade names '''Preveon''' and '''Hepsera'''. It is an orally administered nucleotide analog ] (ntRTI). It can be formulated as the ] ] '''adefovir dipivoxil'''.

==Uses==
It is used for treatment of ].<ref name="pmid12606735">{{cite journal | vauthors = Marcellin P, Chang TT, Lim SG, Tong MJ, Sievert W, Shiffman ML, Jeffers L, Goodman Z, Wulfsohn MS, Xiong S, Fry J, Brosgart CL | display-authors = 6 | title = Adefovir dipivoxil for the treatment of hepatitis B e antigen-positive chronic hepatitis B | journal = The New England Journal of Medicine | volume = 348 | issue = 9 | pages = 808–16 | date = February 2003 | pmid = 12606735 | doi = 10.1056/NEJMoa020681 | url = https://scholarscompass.vcu.edu/cgi/viewcontent.cgi?article=1053&context=intmed_pubs | doi-access = free }}</ref><ref name="pmid17988233">{{cite journal | vauthors = Manolakopoulos S, Bethanis S, Koutsounas S, Goulis J, Vlachogiannakos J, Christias E, Saveriadis A, Pavlidis C, Triantos C, Christidou A, Papatheodoridis G, Karamanolis D, Tzourmakliotis D | display-authors = 6 | title = Long-term therapy with adefovir dipivoxil in hepatitis B e antigen-negative patients developing resistance to lamivudine | journal = Alimentary Pharmacology & Therapeutics | volume = 27 | issue = 3 | pages = 266–73 | date = February 2008 | pmid = 17988233 | doi = 10.1111/j.1365-2036.2007.03567.x | doi-access = free }}</ref><ref name="pmid12444940"/><ref>{{cite web|title=US Adefovir Dipivoxil label|url=http://www.accessdata.fda.gov/drugsatfda_docs/label/2013/202051Orig1s000lbl.pdf|publisher=FDA|access-date=12 February 2017|date=April 2013}}</ref>

Trials of adefovir in patients with ] have not shown any clear benefits.<ref name="pmid12444940">{{cite journal | author = ADHOC International Steering Committee | title = A randomized placebo-controlled trial of adefovir dipivoxil in advanced HIV infection: the ADHOC trial | journal = HIV Medicine | volume = 3 | issue = 4 | pages = 229–38 | date = October 2002 | pmid = 12444940 | doi = 10.1046/j.1468-1293.2002.00111.x | doi-access = free }}</ref><ref name="pmid11546945">{{cite journal | vauthors = Fisher EJ, Chaloner K, Cohn DL, Grant LB, Alston B, Brosgart CL, Schmetter B, El-Sadr WM, Sampson J | display-authors = 6 | title = The safety and efficacy of adefovir dipivoxil in patients with advanced HIV disease: a randomized, placebo-controlled trial | journal = AIDS | volume = 15 | issue = 13 | pages = 1695–700 | date = September 2001 | pmid = 11546945 | doi = 10.1097/00002030-200109070-00013 | s2cid = 9425407 | doi-access = free }}</ref>

==History==
Adefovir was invented in the Institute of Organic Chemistry and Biochemistry, ] by ], and the drug was developed by ] for HIV with the brand name Preveon. However, in November 1999, an expert panel advised the U.S. ] (FDA) not to approve the drug due to concerns about the severity and frequency of kidney toxicity when dosed at 60 or 120&nbsp;mg. The FDA followed that advice, refusing to approve adefovir as a treatment for HIV.{{cn|date=November 2022}}

Gilead Sciences discontinued its development for HIV treatment in December 1999, but continued to develop the drug for hepatitis B (HBV), where it is effective with a much lower dose of 10&nbsp;mg. FDA approval for use in the treatment of hepatitis B was granted on September 20, 2002, and adefovir is sold for this indication under the brand name Hepsera. Adefovir became an approved treatment for HBV in the European Union in March 2003.{{cn|date=November 2022}}

==Mechanism of action==
]
Adefovir works by blocking ], an enzyme crucial for the HBV to reproduce in the body. It is approved for the treatment of chronic hepatitis B in adults with evidence of active viral replication and either evidence of persistent elevations in serum ]s (primarily ALT) or histologically active disease.

The main benefit of adefovir over ] (the first NRTI approved for the treatment of HBV) is that it takes a much longer period of time for the virus to develop resistance to it.

Adefovir dipivoxil contains two ] units, making it a ] form of adefovir.

== References ==
{{Reflist}}

== External links ==
* {{PubChem}} - Adefovir dipivoxil

{{Antivirals}}

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