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
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, tiredness, 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 2021, it was the 234th 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

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]

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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   9783527607495.
  3. British national formulary : BNF 76 (76 ed.). Pharmaceutical Press. 2018. p. 768. ISBN   9780857113382.
  4. "The Top 300 of 2021". ClinCalc. Archived from the original on 15 January 2024. Retrieved 14 January 2024.
  5. "Terazosin - Drug Usage Statistics". ClinCalc. Retrieved 14 January 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.