| Revision as of 11:09, 24 October 2011 editBeetstra (talk | contribs)Edit filter managers, Administrators172,071 edits Script assisted update of identifiers for the Chem/Drugbox validation project (updated: 'DrugBank').← Previous edit |
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{{Short description|Chemical compound}} |
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{{Unreferenced stub|auto=yes|date=December 2009}} |
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{{Refimprove|date=December 2009}} |
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{{Drugbox |
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{{Drugbox |
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| verifiedrevid = 457129255 |
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| Verifiedfields = changed |
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| verifiedrevid = 401597182 |
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| IUPAC_name = (3''S'')-oxolan-3-yl ''N''--1-phenylbutan-2-yl]carbamate |
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| IUPAC_name = (3''S'')-oxolan-3-yl ''N''--1-phenylbutan-2-yl]carbamate |
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| image = Amprenavir skeletal.svg |
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| image = Amprenavir structure.svg |
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| image_class = skin-invert-image |
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<!--Clinical data--> |
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<!--Clinical data--> |
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| Drugs.com = {{drugs.com|monograph|amprenavir}} |
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| Drugs.com = {{drugs.com|monograph|amprenavir}} |
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| MedlinePlus = a699051 |
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| MedlinePlus = a699051 |
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| licence_EU = Agenerase |
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| licence_EU = yes |
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| licence_US = Amprenavir |
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| licence_US = Amprenavir |
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| pregnancy_US = C |
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| pregnancy_US = C |
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| pregnancy_category = |
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| pregnancy_category = |
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| legal_status = |
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| legal_status = Rx-only |
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| routes_of_administration = oral |
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| routes_of_administration = Oral (]) |
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<!--Pharmacokinetic data--> |
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<!--Pharmacokinetic data--> |
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| bioavailability = |
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| bioavailability = |
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| protein_bound = 90% |
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| protein_bound = 90% |
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| metabolism = hepatic |
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| metabolism = ] |
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| elimination_half-life = 7.1-10.6 hours |
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| elimination_half-life = 7.1–10.6 hours |
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| excretion = <3% renal |
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| excretion = <3% renal |
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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 = 161814-49-9 |
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| CAS_number = 161814-49-9 |
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| ATC_prefix = J05 |
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| ATC_prefix = J05 |
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| ATC_suffix = AE05 |
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| ATC_suffix = AE05 |
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| ATC_supplemental = |
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| ATC_supplemental = |
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| PubChem = 65016 |
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| PubChem = 65016 |
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| DrugBank_Ref = {{drugbankcite|correct|drugbank}} |
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| DrugBank_Ref = {{drugbankcite|correct|drugbank}} |
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| KEGG_Ref = {{keggcite|correct|kegg}} |
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| KEGG_Ref = {{keggcite|correct|kegg}} |
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| KEGG = D00894 |
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| KEGG = D00894 |
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| ChEBI_Ref = {{ebicite|changed|EBI}} |
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| ChEBI_Ref = {{ebicite|correct|EBI}} |
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| ChEBI = 40050 |
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| ChEBI = 40050 |
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| ChEMBL_Ref = {{ebicite|changed|EBI}} |
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| ChEMBL_Ref = {{ebicite|correct|EBI}} |
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| ChEMBL = 116 |
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| ChEMBL = 116 |
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| NIAID_ChemDB = 006080 |
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<!--Chemical data--> |
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<!--Chemical data--> |
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| C=25 | H=35 | N=3 | O=6 | S=1 |
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| C=25 | H=35 |
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| N=3 | O=6 |
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| S=1 |
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| molecular_weight = 505.628 g/mol |
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| smiles = O=C(O1CCOC1)N(Cc2ccccc2)(O)CN(CC(C)C)S(=O)(=O)c3ccc(N)cc3 |
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| smiles = O=C(O1CCOC1)N(Cc2ccccc2)(O)CN(CC(C)C)S(=O)(=O)c3ccc(N)cc3 |
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| InChI = 1/C25H35N3O6S/c1-18(2)15-28(35(31,32)22-10-8-20(26)9-11-22)16-24(29)23(14-19-6-4-3-5-7-19)27-25(30)34-21-12-13-33-17-21/h3-11,18,21,23-24,29H,12-17,26H2,1-2H3,(H,27,30)/t21-,23-,24+/m0/s1 |
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| InChIKey = YMARZQAQMVYCKC-OEMFJLHTBO |
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| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChI = 1S/C25H35N3O6S/c1-18(2)15-28(35(31,32)22-10-8-20(26)9-11-22)16-24(29)23(14-19-6-4-3-5-7-19)27-25(30)34-21-12-13-33-17-21/h3-11,18,21,23-24,29H,12-17,26H2,1-2H3,(H,27,30)/t21-,23-,24+/m0/s1 |
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| StdInChI = 1S/C25H35N3O6S/c1-18(2)15-28(35(31,32)22-10-8-20(26)9-11-22)16-24(29)23(14-19-6-4-3-5-7-19)27-25(30)34-21-12-13-33-17-21/h3-11,18,21,23-24,29H,12-17,26H2,1-2H3,(H,27,30)/t21-,23-,24+/m0/s1 |
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| StdInChIKey = YMARZQAQMVYCKC-OEMFJLHTSA-N |
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| StdInChIKey = YMARZQAQMVYCKC-OEMFJLHTSA-N |
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}} |
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'''Amprenavir''' ('''Agenerase''', ]) is a ] used to treat ] infection. It was approved by the ] on April 15, 1999, for twice-a-day dosing instead of needing to be taken every eight hours. The convenient dosing came at a price, as the dose required is 1,200 mg, delivered in eight very large gel capsules. |
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'''Amprenavir''' (original brand name '''Agenerase''', ]) is a ] used to treat ]. It was approved by the ] on April 15, 1999, for twice-a-day dosing instead of needing to be taken every eight hours. The convenient dosing came at a price, as the dose required is 1,200 mg, delivered in 8 (eight) very large 150 mg gel capsules or 24 (twenty-four) 50 mg gel capsules twice daily.<ref name = "PI">{{cite web|title=Agenerase (amprenavir) Capsules. Full Prescribing Information. Section Dosage and Administration|url=http://www.accessdata.fda.gov/drugsatfda_docs/label/2002/21007s11,21039s10lbl.pdf|website=US Food and Drug Administration|publisher=GlaxoSmithKline and Vertex Pharmaceuticals Inc.|access-date=29 November 2015}}</ref> |
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Production of amprenavir was discontinued by the manufacturer December 31, 2004; a ] version (]) is available. |
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<!-- Society and culture --> |
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==See also== |
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It was patented in 1992 and approved for medical use in 1999.<ref name=Fis2006>{{cite book | vauthors = Fischer J, Ganellin CR |title=Analogue-based Drug Discovery |date=2006 |publisher=John Wiley & Sons |isbn=9783527607495 |page=509 |url=https://books.google.com/books?id=FjKfqkaKkAAC&pg=PA509 |language=en}}</ref> Production of amprenavir was discontinued by the manufacturer on December 31, 2004; a ] version (]), is available. |
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* ], a prodrug of amprenavir |
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==Background== |
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<br style="clear: both;" /> |
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] dimer with amprenavir (sticks) bound in the active site. PDB entry {{PDBe|3nu3}}<ref>{{cite journal | vauthors = Shen CH, Wang YF, Kovalevsky AY, Harrison RW, Weber IT | title = Amprenavir complexes with HIV-1 protease and its drug-resistant mutants altering hydrophobic clusters | journal = The FEBS Journal | volume = 277 | issue = 18 | pages = 3699–714 | date = September 2010 | pmid = 20695887 | pmc = 2975871 | doi = 10.1111/j.1742-4658.2010.07771.x }}</ref>]] |
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Research aimed at development of ] as potential ] had led to the discovery of compounds that blocked the action of this peptide cleaving enzyme. The amino acid sequence cleaved by ] was found to be fortuitously the same as that required to produce the HIV peptide coat. Structure–activity studies on renin inhibitors proved to be of great value for developing ]. Incorporation of an ] moiety proved crucial to inhibitory activity for many of these agents. This unit is closely related to the one found in the ], an unusual amino acid that forms part of the ], a fermentation product that inhibits protease enzymes.{{cn|date=November 2022}} |
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== References == |
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{{reflist}} |
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== External links == |
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* in the ] |
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{{HIVpharm}} |
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{{HIVpharm}} |
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{{Antimicrobial-stub}} |
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{{Antimicrobial-stub}} |
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