Terazosin

Last updated

Terazosin
Terazosin.svg
Clinical data
Trade names Hytrin, Zayasel, others
AHFS/Drugs.com Monograph
MedlinePlus a693046
License data
Routes of
administration 		By mouth
Drug class α1 blocker
ATC code
Legal status
Legal status
Pharmacokinetic data
Protein binding 90–94%
Elimination half-life 12 hours
Identifiers
  • (RS)-6,7-Dimethoxy-2-[4-(tetrahydrofuran-2-ylcarbonyl)piperazin-1-yl]quinazolin-4-amine
CAS Number
PubChem CID
IUPHAR/BPS
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard 100.118.191 OOjs UI icon edit-ltr-progressive.svg
Chemical and physical data
Formula C19H25N5O4
Molar mass 387.440 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) Yes check.svgY
  • Key:VCKUSRYTPJJLNI-UHFFFAOYSA-N Yes check.svgY
   (verify)

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

Contents

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

Terazosin was patented in 1975 and came into medical use in 1985. [2] It is available as a generic 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

Terazosin synthesis: Terazocin synthesis.svg
Terazosin 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. [7]

References

  1. 1 2 3 4 5 6 7 "Terazosin Hydrochloride Monograph for Professionals". Drugs.com. American Society of Health-System Pharmacists. Retrieved 17 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. Retrieved 12 August 2025.
  5. ↑ "Terazosin - Drug Usage Statistics". ClinCalc. Retrieved 20 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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