| Revision as of 12:21, 10 January 2012 editBeetstra (talk | contribs)Edit filter managers, Administrators172,031 edits Saving copy of the {{drugbox}} taken from revid 466211044 of page Terazosin for the Chem/Drugbox validation project (updated: 'DrugBank'). |
Latest revision as of 20:10, 6 October 2024 edit Slothwizard (talk | contribs)Extended confirmed users1,358 edits Added drug class and linksTags: Visual edit Mobile edit Mobile web edit |
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{{Short description|Antihypertensive medication used to treat hypertension}} |
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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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{{Use dmy dates|date=August 2021}} |
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{{cs1 config |name-list-style=vanc |display-authors=6}} |
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{{Drugbox |
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{{Drugbox |
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| Verifiedfields = changed |
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| Watchedfields = changed |
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| class = ] |
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| verifiedrevid = 409978319 |
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| verifiedrevid = 470602141 |
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| IUPAC_name = 6,7-dimethoxy-2-quinazolin-4-amine |
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| image = Terazosin.svg |
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| image = Terazosin.svg |
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| width = 250 |
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<!--Clinical data--> |
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<!--Clinical data-->| tradename = Hytrin, Zayasel, others |
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| tradename = Hytrin |
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| Drugs.com = {{drugs.com|monograph|terazosin-hydrochloride}} |
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| Drugs.com = {{drugs.com|monograph|terazosin-hydrochloride}} |
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| DailyMedID = Terazosin |
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| MedlinePlus = a693046 |
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| MedlinePlus = a693046 |
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| pregnancy_category = |
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| pregnancy_category = |
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| routes_of_administration = ] |
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| legal_status = |
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| ATC_prefix = G04 |
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| routes_of_administration = |
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| ATC_suffix = CA03 |
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| ATC_supplemental = |
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| legal_US = Rx-only |
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<!--Pharmacokinetic data--> |
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<!--Pharmacokinetic data-->| bioavailability = |
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| protein_bound = 90–94% |
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| bioavailability = |
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| protein_bound = 90-94% |
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| metabolism = |
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| metabolism = |
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| elimination_half-life = 12 hours |
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| elimination_half-life = 12 hours |
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| excretion = <!--Identifiers--> |
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| IUPHAR_ligand = 7302 |
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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 = 63590-64-7 |
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| CAS_number = 63590-64-7 |
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| ATC_prefix = G04 |
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| ATC_suffix = CA03 |
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| ATC_supplemental = |
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| PubChem = 5401 |
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| PubChem = 5401 |
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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 = D08569 |
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| KEGG = D08569 |
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| ChEBI_Ref = {{ebicite|changed|EBI}} |
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| ChEBI_Ref = {{ebicite|correct|EBI}} |
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| ChEBI = 9445 |
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| ChEBI = 9445 |
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| ChEMBL_Ref = {{ebicite|correct|EBI}} |
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| ChEMBL_Ref = {{ebicite|correct|EBI}} |
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| ChEMBL = 611 |
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| ChEMBL = 611 |
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| synonyms = <!--Chemical data--> |
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| IUPAC_name = (''RS'')-6,7-Dimethoxy-2-quinazolin-4-amine |
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<!--Chemical data--> |
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| C=19 | H=25 | N=5 | O=4 |
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| C = 19 |
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| H = 25 |
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| molecular_weight = 387.433 g/mol |
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| N = 5 |
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| smiles = O=C(N3CCN(c2nc1cc(OC)c(OC)cc1c(n2)N)CC3)C4OCCC4 |
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| O = 4 |
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| InChI = 1/C19H25N5O4/c1-26-15-10-12-13(11-16(15)27-2)21-19(22-17(12)20)24-7-5-23(6-8-24)18(25)14-4-3-9-28-14/h10-11,14H,3-9H2,1-2H3,(H2,20,21,22) |
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| SMILES = O=C(N3CCN(c2nc1cc(OC)c(OC)cc1c(n2)N)CC3)C4OCCC4 |
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| InChIKey = VCKUSRYTPJJLNI-UHFFFAOYAV |
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| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChI = 1S/C19H25N5O4/c1-26-15-10-12-13(11-16(15)27-2)21-19(22-17(12)20)24-7-5-23(6-8-24)18(25)14-4-3-9-28-14/h10-11,14H,3-9H2,1-2H3,(H2,20,21,22) |
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| StdInChI = 1S/C19H25N5O4/c1-26-15-10-12-13(11-16(15)27-2)21-19(22-17(12)20)24-7-5-23(6-8-24)18(25)14-4-3-9-28-14/h10-11,14H,3-9H2,1-2H3,(H2,20,21,22) |
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| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChIKey = VCKUSRYTPJJLNI-UHFFFAOYSA-N |
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| StdInChIKey = VCKUSRYTPJJLNI-UHFFFAOYSA-N |
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| synonyms = <small>-tetrahydrofuran-2-yl-methanone</small> |
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}} |
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}} |
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<!-- Definition and medical uses --> |
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'''Terazosin''', sold under the brand name '''Hytrin''' among others, is a medication used to treat symptoms of an ] and ].<ref name=AHFS2019>{{cite web |title=Terazosin Hydrochloride Monograph for Professionals |url=https://www.drugs.com/monograph/terazosin-hydrochloride.html |website=Drugs.com |publisher=American Society of Health-System Pharmacists |access-date=17 March 2019 |language=en}}</ref> For high blood pressure, it is a less preferred option.<ref name=AHFS2019/> It is taken by mouth.<ref name=AHFS2019/> |
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<!-- Side effects and mechanisms --> |
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Common side effects include ], ], feeling tired, swelling, ], and ].<ref name=AHFS2019/> Severe side effects may include ] and ].<ref name=AHFS2019/> ] should be ruled out before starting treatment.<ref name=AHFS2019/> It is an ] and works by relaxing ] and the opening of the ].<ref name=AHFS2019/> |
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<!-- Society and culture --> |
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Terazosin was patented in 1975 and came into medical use in 1985.<ref>{{cite book | vauthors = Fischer J, Ganellin CR |title=Analogue-based Drug Discovery |date=2006 |publisher=John Wiley & Sons |isbn=9783527607495 |page=455 |url=https://books.google.com/books?id=FjKfqkaKkAAC&pg=PA455 |language=en}}</ref> It is available as a ].<ref name=BNF76>{{cite book|title=British national formulary : BNF 76 |date=2018 |publisher=Pharmaceutical Press |isbn=9780857113382 |pages=768 |edition=76 }}</ref> In 2021, it was the 234th most commonly prescribed medication in the United States, with more than 1{{nbsp}}million prescriptions.<ref>{{cite web | title=The Top 300 of 2021 | url=https://clincalc.com/DrugStats/Top300Drugs.aspx | website=ClinCalc | access-date=14 January 2024 | archive-date=15 January 2024 | archive-url=https://web.archive.org/web/20240115223848/https://clincalc.com/DrugStats/Top300Drugs.aspx | url-status=live }}</ref><ref>{{cite web | title = Terazosin - Drug Usage Statistics | website = ClinCalc | url = https://clincalc.com/DrugStats/Drugs/Terazosin | access-date = 14 January 2024}}</ref> |
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==Synthesis== |
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] |
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Reaction of ] with ] followed by ] of the ] ring leads to '''2'''. This, when heated in the presence of 2-chloro-6,7-dimethoxyquinazolin-4-amine ('''1''') undergoes direct alkylation to terazosin ('''3'''). |
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==Research on neuroprotective effects == |
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A 2022 study suggests that terazosin may have the potential to confer neuroprotection upon ]s in ], as a result of its ability to activate ].<ref>{{cite journal | vauthors = Chaytow H, Carroll E, Gordon D, Huang YT, van der Hoorn D, Smith HL, Becker T, Becker CG, Faller KM, Talbot K, Gillingwater TH | title = Targeting phosphoglycerate kinase 1 with terazosin improves motor neuron phenotypes in multiple models of amyotrophic lateral sclerosis | journal = eBioMedicine | volume = 83 | pages = 104202 | date = September 2022 | pmid = 35963713 | pmc = 9482929 | doi = 10.1016/j.ebiom.2022.104202 }}</ref> |
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==References== |
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{{Reflist}} |
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{{Drugs used in benign prostatic hypertrophy}} |
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{{Adrenergic receptor modulators}} |
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{{Portal bar | Medicine}} |
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{{Authority control}} |
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