Terazosin

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%
Elimination half-life12 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 InfoCard100.118.191 Edit 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 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]

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 2021, it was the 234th most commonly prescribed medication in the United States, with more than 1 million prescriptions.[4][5]

Synthesis

Terazosin synthesis:[6]

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. ^ a b c d e f g "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.