Terazosin

Terazosin
Names
Trade namesHytrin, Zayasel, others
Other names[4-(4-amino-6,7-dimethoxy-quinazolin-2-yl)piperazin-1-yl]-tetrahydrofuran-2-yl-methanone
IUPAC name
  • (RS)-6,7-Dimethoxy-2-[4-(tetrahydrofuran-2-ylcarbonyl)piperazin-1-yl]quinazolin-4-amine
Clinical data
WHO AWaReUnlinkedWikibase error: ⧼unlinkedwikibase-error-statements-entity-not-set⧽
Defined daily dose5 mg[1]
External links
AHFS/Drugs.comMonograph
MedlinePlusa693046
Legal
Legal status
Pharmacokinetics
Protein binding90-94%
Elimination half-life12 hours
Chemical and physical data
FormulaC19H25N5O4
Molar mass387.440 g·mol−1
3D model (JSmol)
SMILES
  • O=C(N3CCN(c2nc1cc(OC)c(OC)cc1c(n2)N)CC3)C4OCCC4
InChI
  • 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

Terazosin, sold under the brand name Hytrin among others, is a medication used to treat symptoms of an enlarged prostate and high blood pressure.[2] For high blood pressure, it is a less preferred option.[2] It is taken by mouth.[2]

Common side effects include dizziness, headache, tiredness, swelling, nausea, and low blood pressure with standing.[2] Severe side effects may include priapism and low blood pressure.[2] Prostate cancer should be ruled out before starting treatment.[2] It is an alpha-1 blocker and works by relaxing blood vessels and the opening of the bladder.[2]

Terazosin was patented in 1975 and came into medical use in 1985.[3] It is available as a generic medication.[4] A month supply in the United Kingdom costs the NHS around £5 as of 2021.[4] In the United States the wholesale cost of this amount is about US$4.50.[5] In 2017, it was the 194th most commonly prescribed medication in the United States, with more than two million prescriptions.[6][7]

Medical use

Dosage

The defined daily dose is 5 mg by mouth.[1]

It is available in 1 mg, 2 mg, 5 mg or 10 mg doses.[8]

Synthesis

Terazosin synthesis:[9]

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).

Society and culture

Cost

A month supply in the United Kingdom costs the NHS around £5 as of 2021.[4] In the United States the wholesale cost of this amount is about US$4.50.[5] In 2017, it was the 194th most commonly prescribed medication in the United States, with more than two million prescriptions.[6][7]

  • Terazosin costs (US)
    Terazosin costs (US)
  • Terazosin prescriptions (US)
    Terazosin prescriptions (US)

References

  1. 1 2 "WHOCC - ATC/DDD Index". www.whocc.no. Archived from the original on 1 July 2020. Retrieved 7 September 2020.
  2. 1 2 3 4 5 6 7 "Terazosin Hydrochloride Monograph for Professionals". Drugs.com. American Society of Health-System Pharmacists. Archived from the original on 7 August 2020. Retrieved 17 March 2019.
  3. ↑ Fischer, Jnos; Ganellin, C. Robin (2006). Analogue-based Drug Discovery. John Wiley & Sons. p. 455. ISBN 9783527607495. Archived from the original on 2019-12-22. Retrieved 2019-02-28.
  4. 1 2 3 "7. Genito-urinary system". British National Formulary (BNF) (82 ed.). London: BMJ Group and the Pharmaceutical Press. September 2021 – March 2022. p. 833. ISBN 978-0-85711-413-6.{{cite book}}: CS1 maint: date format (link)
  5. 1 2 "NADAC". Centers for Medicare and Medicaid Services. 27 February 2019. Archived from the original on 2019-03-06. Retrieved 2019-03-17.
  6. 1 2 "The Top 300 of 2020". ClinCalc. Archived from the original on 18 March 2020. Retrieved 11 April 2020.
  7. 1 2 "Terazosin - Drug Usage Statistics". ClinCalc. Archived from the original on 8 October 2020. Retrieved 11 April 2020.
  8. ↑ "Terazosin Hydrochloride Capsule". DailyMed. National Library of Medicine, National Institutes of Health. Archived from the original on 2019-08-20. Retrieved 2015-10-16.
  9. ↑ US 4026894, Winn M, Kyncl J, Dunnigan DA, Jones PH, issued 31 May 1977, assigned to Abbott 
Identifiers:
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