terazosin
{{Short description|Antihypertensive medication used to treat hypertension}}
{{Use dmy dates|date=August 2021}}
{{cs1 config |name-list-style=vanc |display-authors=6}}
{{Drugbox
| Watchedfields = changed
| class = α1 blocker
| verifiedrevid = 470602141
| image = Terazosin.svg
| width = 250
| tradename = Hytrin, Zayasel, others
| Drugs.com = {{drugs.com|monograph|terazosin-hydrochloride}}
| DailyMedID = Terazosin
| MedlinePlus = a693046
| pregnancy_category =
| routes_of_administration = By mouth
| ATC_prefix = G04
| ATC_suffix = CA03
| ATC_supplemental =
| legal_US = Rx-only
| bioavailability =
| protein_bound = 90–94%
| metabolism =
| elimination_half-life = 12 hours
| excretion =
| IUPHAR_ligand = 7302
| CAS_number_Ref = {{cascite|correct|??}}
| CAS_number = 63590-64-7
| PubChem = 5401
| DrugBank_Ref = {{drugbankcite|correct|drugbank}}
| DrugBank = DB01162
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 5208
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = 8L5014XET7
| KEGG_Ref = {{keggcite|correct|kegg}}
| KEGG = D08569
| ChEBI_Ref = {{ebicite|correct|EBI}}
| ChEBI = 9445
| ChEMBL_Ref = {{ebicite|correct|EBI}}
| ChEMBL = 611
| synonyms =
| 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
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| 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)
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = VCKUSRYTPJJLNI-UHFFFAOYSA-N
}}
Terazosin, sold under the brand name Hytrin among others, is a medication used to treat symptoms of an enlarged prostate and high blood pressure.{{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}} For high blood pressure, it is a less preferred option. It is taken by mouth.
Common side effects include dizziness, headache, feeling tired, swelling, nausea, and low blood pressure with standing. Severe side effects may include priapism and low blood pressure. Prostate cancer should be ruled out before starting treatment. It is an alpha-1 blocker and works by relaxing blood vessels and the opening of the bladder.
Terazosin was patented in 1975 and came into medical use in 1985.{{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}} It is available as a generic medication.{{cite book|title=British national formulary : BNF 76 |date=2018 |publisher=Pharmaceutical Press |isbn=9780857113382 |pages=768 |edition=76 }} In 2021, it was the 234th most commonly prescribed medication in the United States, with more than 1{{nbsp}}million prescriptions.{{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 }}{{cite web | title = Terazosin - Drug Usage Statistics | website = ClinCalc | url = https://clincalc.com/DrugStats/Drugs/Terazosin | access-date = 14 January 2024}}
Synthesis
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 neurons in motor neuron disease, as a result of its ability to activate PGK1.{{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 }}
References
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{{Drugs used in benign prostatic hypertrophy}}
{{Adrenergic receptor modulators}}
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