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Terazosin

From Wikipedia, the free encyclopedia
Antihypertensive drug

Pharmaceutical compound
Terazosin
Clinical data
Trade namesHytrin, Zayasel, others
AHFS/Drugs.comMonograph
MedlinePlusa693046
License data
Routes of
administration
By mouth
Drug classα1 blocker
ATC code
Legal status
Legal status
Pharmacokinetic data
Protein binding90–94%
Eliminationhalf-life12 hours
Identifiers
  • (RS)-6,7-Dimethoxy-2-[4-(tetrahydrofuran-2-ylcarbonyl)piperazin-1-yl]quinazolin-4-amine
CAS Number
PubChemCID
IUPHAR/BPS
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard(EPA)
ECHA InfoCard100.118.191Edit this at Wikidata
Chemical and physical data
FormulaC19H25N5O4
Molar mass387.440 g·mol−1
3D model (JSmol)
  • O=C(N3CCN(c2nc1cc(OC)c(OC)cc1c(n2)N)CC3)C4OCCC4
  • InChI=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) checkY
  • Key:VCKUSRYTPJJLNI-UHFFFAOYSA-N checkY
  (verify)

Terazosin, sold under the brand nameHytrin among others, is a medication used to treat symptoms of anenlarged prostate andhigh blood pressure.[1] For high blood pressure, it is a less preferred option.[1] It is taken by mouth.[1]

Common side effects includedizziness,headache, feeling tired, swelling,nausea, andlow blood pressure with standing.[1] Severe side effects may includepriapism andlow blood pressure.[1]Prostate cancer should be ruled out before starting treatment.[1] It is analpha-1 blocker and works by relaxingblood vessels and the opening of thebladder.[1]

Terazosin was patented in 1975 and came into medical use in 1985.[2] It is available as ageneric medication.[3] In 2023, it was the 217th most commonly prescribed medication in the United States, with more than 1 million prescriptions.[4][5]

Synthesis

[edit]
Terazosin synthesis:[6]

Reaction ofpiperazine with2-furoyl chloride followed bycatalytic hydrogenation of thefuran ring leads to2. 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

[edit]

A 2022 study suggests that terazosin may have the potential to confer neuroprotection uponmotor neurons inmotor neuron disease, as a result of its ability to activatePGK1.[7]

References

[edit]
  1. ^abcdefg"Terazosin Hydrochloride Monograph for Professionals".Drugs.com. American Society of Health-System Pharmacists. Retrieved17 March 2019.
  2. ^Fischer J, Ganellin CR (2006).Analogue-based Drug Discovery. John Wiley & Sons. p. 455.ISBN 978-3-527-60749-5.
  3. ^British national formulary: BNF 76 (76 ed.). Pharmaceutical Press. 2018. p. 768.ISBN 978-0-85711-338-2.
  4. ^"The Top 300 of 2023".ClinCalc.Archived from the original on 12 August 2025. Retrieved12 August 2025.
  5. ^"Terazosin - Drug Usage Statistics".ClinCalc. Retrieved20 August 2024.
  6. ^US 4026894, Winn M, Kyncl J, Dunnigan DA, Jones PH, issued 31 May 1977, assigned to Abbott 
  7. ^Chaytow H, Carroll E, Gordon D, Huang YT, van der Hoorn D, Smith HL, et al. (September 2022)."Targeting phosphoglycerate kinase 1 with terazosin improves motor neuron phenotypes in multiple models of amyotrophic lateral sclerosis".eBioMedicine.83 104202.doi:10.1016/j.ebiom.2022.104202.PMC 9482929.PMID 35963713.
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