| Revision as of 11:01, 17 November 2011 editBeetstra (talk | contribs)Edit filter managers, Administrators172,031 edits Saving copy of the {{drugbox}} taken from revid 460581959 of page Emtricitabine for the Chem/Drugbox validation project (updated: 'DrugBank'). |
Latest revision as of 10:21, 24 August 2023 edit Vaccinationist (talk | contribs)Extended confirmed users4,733 edits different structural formula better demonstrating similarity to lamivudineTag: 2017 wikitext editor |
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{{short description|Antiretroviral drug used to treat HIV infection}} |
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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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{{Infobox drug |
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{{Drugbox |
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| Watchedfields = changed |
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| verifiedrevid = 443722379 |
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| verifiedrevid = 461093388 |
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| drug_name = |
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| IUPAC_name = 4-amino-5-fluoro-1--1,2-dihydropyrimidin-2-one |
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| INN = |
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| image = Emtricitabine skeletal.svg |
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| type = <!-- empty --> |
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| width = 160 |
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| image = Emtricitabine structure.svg |
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| width = 155 |
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| alt = |
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| caption = |
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<!--Clinical data--> |
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<!-- Clinical data --> |
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| pronounce = {{IPAc-en|ˌ|ɛ|m|t|r|ə|ˈ|s|aɪ|t|ə|b|iː|n}}<br />{{respell|EM|trə|SY|tə|been}} |
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| tradename = Emtriva |
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| tradename = Emtriva |
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| Drugs.com = {{drugs.com|monograph|emtricitabine}} |
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| Drugs.com = {{drugs.com|monograph|emtricitabine}} |
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| MedlinePlus = a604004 |
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| MedlinePlus = a604004 |
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| licence_EU = yes |
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| DailyMedID = Emtricitabine |
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| licence_US = <!-- FDA may use generic or brand name (generic name preferred) --> |
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| pregnancy_AU = B1 |
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| pregnancy_AU = B1 |
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| pregnancy_US = B |
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| pregnancy_US = B |
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| routes_of_administration = ] |
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| class = |
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| ATC_prefix = J05 |
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| ATC_suffix = AF09 |
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<!-- Legal status --> |
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| legal_AU = <!-- S2, S3, S4, S5, S6, S7, S8, S9 or Unscheduled --> |
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| legal_AU_comment = |
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| legal_BR = <!-- OTC, A1, A2, A3, B1, B2, C1, C2, C3, C4, C5, D1, D2, E, F --> |
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| legal_BR_comment = |
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| legal_CA = <!-- OTC, Rx-only, Schedule I, II, III, IV, V, VI, VII, VIII --> |
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| legal_CA_comment = |
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| legal_DE = <!-- Anlage I, II, III or Unscheduled --> |
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| legal_DE_comment = |
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| legal_NZ = <!-- Class A, B, C --> |
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| legal_NZ_comment = |
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| legal_UK = POM |
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| legal_UK = POM |
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| legal_UK_comment = |
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| legal_US = Rx-only |
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| legal_US = Rx-only |
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| legal_US_comment = |
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| routes_of_administration = Oral |
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| legal_EU = Rx-only |
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| legal_EU_comment = |
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| legal_UN = <!-- N I, II, III, IV / P I, II, III, IV --> |
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| legal_UN_comment = |
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| legal_status = <!-- For countries not listed above --> |
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<!--Pharmacokinetic data--> |
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<!-- Pharmacokinetic data --> |
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| bioavailability = 93% |
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| bioavailability = 93% |
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| protein_bound = Very low (less than 4%) |
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| protein_bound = Very low (less than 4%) |
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| excretion = ] (86%) and fecal (14%) |
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| excretion = ] (86%) and fecal (14%) |
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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 = 143491-57-0 |
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| CAS_number = 143491-57-0 |
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| ATC_prefix = J05 |
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| ATC_suffix = AF09 |
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| PubChem = 60877 |
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| PubChem = 60877 |
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| DrugBank_Ref = {{drugbankcite|correct|drugbank}} |
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| DrugBank_Ref = {{drugbankcite|correct|drugbank}} |
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| ChEMBL_Ref = {{ebicite|correct|EBI}} |
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| ChEMBL_Ref = {{ebicite|correct|EBI}} |
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| ChEMBL = 885 |
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| ChEMBL = 885 |
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| NIAID_ChemDB = 004782 |
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| PDB_ligand = |
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| synonyms = FTC |
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<!--Chemical data--> |
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<!-- Chemical and physical data --> |
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| IUPAC_name = 4-Amino-5-fluoro-1-pyrimidin-2-one |
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| C=8 | H=10 | F=1 | N=3 | O=3 | S=1 |
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| C=8 | H=10 | F=1 | N=3 | O=3 | S=1 |
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| molecular_weight = 247.248 g/mol |
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| smiles = FC=1\C(=N/C(=O)N(C=1)2O(SC2)CO)\N |
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| SMILES = FC=1\C(=N/C(=O)N(C=1)2O(SC2)CO)\N |
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| InChI = 1/C8H10FN3O3S/c9-4-1-12(8(14)11-7(4)10)5-3-16-6(2-13)15-5/h1,5-6,13H,2-3H2,(H2,10,11,14)/t5-,6+/m0/s1 |
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| InChIKey = XQSPYNMVSIKCOC-NTSWFWBYBU |
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| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChI = 1S/C8H10FN3O3S/c9-4-1-12(8(14)11-7(4)10)5-3-16-6(2-13)15-5/h1,5-6,13H,2-3H2,(H2,10,11,14)/t5-,6+/m0/s1 |
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| StdInChI = 1S/C8H10FN3O3S/c9-4-1-12(8(14)11-7(4)10)5-3-16-6(2-13)15-5/h1,5-6,13H,2-3H2,(H2,10,11,14)/t5-,6+/m0/s1 |
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| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChIKey = XQSPYNMVSIKCOC-NTSWFWBYSA-N |
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| StdInChIKey = XQSPYNMVSIKCOC-NTSWFWBYSA-N| density = |
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| density_notes = |
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| melting_point = |
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| solubility = |
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| specific_rotation = |
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}} |
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}} |
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'''Emtricitabine''' (commonly called '''FTC''', systematic name 2',3'-dideoxy-5-fluoro-3'-thiacytidine<ref>{{cite patent | url = https://patents.google.com/patent/US5814639A/en | country = US | number = 5814639 | title = Method for the synthesis, compositions and use of 2'-deoxy-5-fluoro-3'-thiacytidine and related compounds | inventor = Liotta DC, Schinazi RF, Choi WB | assign1 = Emory University | gdate = 29 September 1998 }} {{Webarchive|url=https://web.archive.org/web/20210531100040/https://patents.google.com/patent/US5814639A/en |date=31 May 2021 }}</ref>), with trade name '''Emtriva''' (formerly '''Coviracil'''), is a ] ] (NRTI) for the prevention and treatment of ] infection in adults and children. In 2019, it was the 494th most commonly prescribed medication in the United States, with more than 3{{nbsp}}thousand prescriptions.<ref>{{cite web | title = Emtricitabine - Drug Usage Statistics | website = ClinCalc | url = https://clincalc.com/DrugStats/Drugs/Emtricitabine | access-date = 7 October 2022 | archive-date = 8 July 2020 | archive-url = https://web.archive.org/web/20200708065700/https://clincalc.com/DrugStats/Drugs/Emtricitabine | url-status = live }}</ref> |
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Emtricitabine makes up one fourth of the ] (brand names: Stribild and Genvoya). It is also marketed in a fixed-dose combination with ] (Viread) under the brand name ], and with ] (Vemlidy) under the brand name Descovy. In fixed-dose combinations with tenofovir or with efavirenz and tenofovir it is on the ].<ref name="WHO21st">{{cite book | vauthors = ((World Health Organization)) | title = World Health Organization model list of essential medicines: 21st list 2019 | year = 2019 | hdl = 10665/325771 | author-link = World Health Organization | publisher = World Health Organization | location = Geneva | id = WHO/MVP/EMP/IAU/2019.06. License: CC BY-NC-SA 3.0 IGO | hdl-access=free }}</ref> A fixed-dose triple combination of emtricitabine, tenofovir and ] (Sustiva, marketed by ]) was approved by the ] on July 12, 2006, under the brand name ]. |
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==Medical uses== |
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===HIV infection=== |
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Emtricitabine is indicated in combination with other ] agents for the prevention and treatment of HIV-1 infection.<ref name="Emtriva FDA label">{{cite web | title=Emtriva- emtricitabine capsule Emtriva- emtricitabine solution | website=DailyMed | date=14 December 2018 | url=https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=d6599395-3944-44f9-97f2-e0424c6b6a1f | access-date=24 July 2020 | archive-date=24 July 2020 | archive-url=https://web.archive.org/web/20200724025300/https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=d6599395-3944-44f9-97f2-e0424c6b6a1f | url-status=live }}</ref><ref>{{cite web | title=Emtriva EPAR | website=European Medicines Agency | date=17 September 2018 | url=https://www.ema.europa.eu/en/medicines/human/EPAR/emtriva | access-date=24 July 2020 | archive-date=24 July 2020 | archive-url=https://web.archive.org/web/20200724055926/https://www.ema.europa.eu/en/medicines/human/EPAR/emtriva | url-status=live }}</ref> |
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===HBV infection=== |
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Emtricitabine exhibits clinical activity against the ] (HBV), but is not approved by the U.S. ] (FDA) for the treatment of HBV infection.<ref name="Emtriva FDA label" /> Among individuals with chronic HBV infection, emtricitabine treatment results in significant histologic, virologic, and biochemical improvement. The safety profile of emtricitabine during treatment is similar to that of a placebo. Emtricitabine, like all other FDA approved drugs, cures neither HIV nor HBV infection. In a study involving individuals with HBV infection, symptoms of infection returned in 23% of emtricitabine-treated individuals who were taken off therapy.<ref name="pmid16401810"/> In studies involving individuals with ''chronic'' HIV infection, viral replication also resumes when study subjects are taken off therapy.<ref name="pmid12370434"/> As with drugs used to treat HIV infection, drugs used to treat HBV infection may have to be used in combination to prevent the evolution of drug resistant strains. The effectiveness of emtricitabine in combination with other anti-HBV drugs has not been established. |
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==Side effects== |
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{{unreferenced section|date=July 2020}} |
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In clinical practice, ] with emtricitabine is unusual. The most common treatment-related adverse events are ], ], ], and ]. These symptoms are generally mild to moderate in severity, but they caused 1% of clinical trial patients to give up treatment. Skin discoloration, which is typically reported as ] and usually affects either the palms of the hands or the ] of the feet, is reported in less than 2% of individuals and is almost exclusive to patients of ]. |
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Among the more severe side effects patients may experience are a ] or a ]. |
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==Mechanism of action== |
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{{unreferenced section|date=July 2020}} |
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Emtricitabine is an ] of ]. The drug works by inhibiting ], the enzyme that copies HIV RNA into new viral DNA. By interfering with this process, which is central to the replication of HIV, emtricitabine can help to lower the amount of HIV, or "]", in a patient's body and can indirectly increase the number of ] cells (namely ]s/]s). Both of these changes are associated with healthier immune systems and decreased likelihood of serious illness. |
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==History== |
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Emtricitabine was discovered by ], ], and ] of ] and licensed to ] by Emory in 1996.<ref>{{cite news | url=https://money.cnn.com/magazines/fortune/fortune_archive/2005/09/19/8272884/index.htm | work=CNN | first=Clifton | last=Leaf | name-list-style=vanc | title=The Law of Unintended Consequences | date=September 19, 2005 | access-date=August 3, 2020 | archive-date=November 6, 2020 | archive-url=https://web.archive.org/web/20201106232521/https://money.cnn.com/magazines/fortune/fortune_archive/2005/09/19/8272884/index.htm | url-status=live }}</ref> Triangle Pharmaceuticals was acquired in 2003 by ], which completed development and now markets the product with the brand name Emtriva. |
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It was approved by the FDA July 2, 2003.<ref> {{Webarchive|url=https://web.archive.org/web/20230605085318/https://books.google.com/books?id=cJ0ODtsjbj0C&q=Emtricitabine+was+approved+FDA+July+2003 |date=2023-06-05 }}. Standard & Poor's, McGraw-Hill, (2004), p. 83.</ref> It is very similar to ] (3TC) and cross-resistance between the two is near-universal.{{Medical citation needed|date=October 2010}} |
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== References == |
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{{reflist | refs = |
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<ref name="pmid12370434">{{cite journal | vauthors = Oxenius A, Price DA, Günthard HF, Dawson SJ, Fagard C, Perrin L, Fischer M, Weber R, Plana M, García F, Hirschel B, McLean A, Phillips RE | display-authors = 6 | title = Stimulation of HIV-specific cellular immunity by structured treatment interruption fails to enhance viral control in chronic HIV infection | journal = Proceedings of the National Academy of Sciences of the United States of America | volume = 99 | issue = 21 | pages = 13747–52 | date = October 2002 | pmid = 12370434 | pmc = 129766 | doi = 10.1073/pnas.202372199 | bibcode = 2002PNAS...9913747O | doi-access = free }}</ref> |
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<ref name="pmid16401810">{{cite journal | vauthors = Lim SG, Ng TM, Kung N, Krastev Z, Volfova M, Husa P, Lee SS, Chan S, Shiffman ML, Washington MK, Rigney A, Anderson J, Mondou E, Snow A, Sorbel J, Guan R, Rousseau F | display-authors = 6 | title = A double-blind placebo-controlled study of emtricitabine in chronic hepatitis B | journal = Archives of Internal Medicine | volume = 166 | issue = 1 | pages = 49–56 | date = January 2006 | pmid = 16401810 | doi = 10.1001/archinte.166.1.49 | doi-access = }}</ref> |
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== External links == |
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* {{cite web | url = https://druginfo.nlm.nih.gov/drugportal/name/emtricitabine | publisher = U.S. National Library of Medicine | work = Drug Information Portal | title = Emtricitabine }} |
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{{Antiretroviral drug}} |
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{{Portal bar | Medicine | Viruses }} |
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