Wikipedia:WikiProject Chemicals/Chembox validation/VerifiedDataSandbox and Terazosin: Difference between pages

{{Short description|Antihypertensive medication used to treat hypertension}}

{{Use dmy dates|date=August 2021}}

{{cs1 config |name-list-style=vanc |display-authors=6}}

| Watchedfields = changed

| class = [[Alpha-1 blocker|α₁ blocker]]

| verifiedrevid = 470602141

| width = 250

<!--Clinical data-->| tradename = Hytrin, Zayasel, others

| DailyMedID = Terazosin

| pregnancy_category =

| routes_of_administration = [[Oral administration|By mouth]]

| ATC_prefix = G04

| ATC_suffix = CA03

| ATC_supplemental =

| legal_US = Rx-only

<!--Pharmacokinetic data-->| bioavailability =

| protein_bound = 90–94%

| metabolism =

| excretion = <!--Identifiers-->

| IUPHAR_ligand = 7302

| ChEBI_Ref = {{ebicite|correct|EBI}}

| synonyms = <!--Chemical data-->

| IUPAC_name = (''RS'')-6,7-Dimethoxy-2-[4-(tetrahydrofuran-2-ylcarbonyl)piperazin-1-yl]quinazolin-4-amine

| C = 19

| H = 25

| N = 5

| O = 4

| SMILES = O=C(N3CCN(c2nc1cc(OC)c(OC)cc1c(n2)N)CC3)C4OCCC4

<!-- Definition and medical uses -->

'''Terazosin''', sold under the brand name '''Hytrin''' among others, is a medication used to treat symptoms of an [[benign prostatic hyperplasia|enlarged prostate]] and [[high blood pressure]].<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/>

<!-- Side effects and mechanisms -->

Common side effects include [[dizziness]], [[headache]], feeling tired, swelling, [[nausea]], and [[low blood pressure with standing]].<ref name=AHFS2019/> Severe side effects may include [[priapism]] and [[low blood pressure]].<ref name=AHFS2019/> [[Prostate cancer]] should be ruled out before starting treatment.<ref name=AHFS2019/> It is an [[alpha-1 blocker]] and works by relaxing [[blood vessels]] and the opening of the [[bladder]].<ref name=AHFS2019/>

<!-- Society and culture -->

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 [[generic medication]].<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>

==Synthesis==

[[File:Terazocin synthesis.svg|thumb|center|500px|Terazosin synthesis:<ref>{{cite patent | inventor = Winn M, Kyncl J, Dunnigan DA, Jones PH | assign1 = Abbott | country = US | number = 4026894 | gdate = 31 May 1977 }}</ref>]]

Reaction of [[piperazine]] with [[2-furoyl chloride]] followed by [[catalytic hydrogenation]] of the [[furan]] 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''').

==Research on neuroprotective effects ==

A 2022 study suggests that terazosin may have the potential to confer neuroprotection upon [[motor neuron]]s in [[motor neuron disease]], as a result of its ability to activate [[PGK1]].<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>

==References==

{{Reflist}}

{{Drugs used in benign prostatic hypertrophy}}

{{Adrenergic receptor modulators}}

{{Portal bar | Medicine}}

{{Authority control}}

[[Category:Alpha-1 blockers]]

[[Category:Carboxamides]]

[[Category:Phenol ethers]]

[[Category:Piperazines]]

[[Category:Quinazolines]]

[[Category:Tetrahydrofurans]]

[[Category:Wikipedia medicine articles ready to translate]]