Terazosin
Names | |
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Trade names | Hytrin, Zayasel, others |
Other names | [4-(4-amino-6,7-dimethoxy-quinazolin-2-yl)piperazin-1-yl]-tetrahydrofuran-2-yl-methanone |
IUPAC name
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Clinical data | |
Defined daily dose | 5 mg[1] |
External links | |
AHFS/Drugs.com | Monograph |
US NLM | Terazosin |
MedlinePlus | a693046 |
Legal | |
Legal status |
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Pharmacokinetics | |
Protein binding | 90-94% |
Elimination half-life | 12 hours |
Chemical and physical data | |
Formula | C19H25N5O4 |
Molar mass | 387.440 g·mol−1 |
3D model (JSmol) | |
SMILES
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InChI
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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
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 prescriptions (US)
References
- 1 2 "WHOCC - ATC/DDD Index". www.whocc.no. Archived from the original on 1 July 2020. Retrieved 7 September 2020.
- 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.
- ↑ 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.
- 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) - 1 2 "NADAC". Centers for Medicare and Medicaid Services. 27 February 2019. Archived from the original on 2019-03-06. Retrieved 2019-03-17.
- 1 2 "The Top 300 of 2020". ClinCalc. Archived from the original on 18 March 2020. Retrieved 11 April 2020.
- 1 2 "Terazosin - Drug Usage Statistics". ClinCalc. Archived from the original on 8 October 2020. Retrieved 11 April 2020.
- ↑ "Terazosin Hydrochloride Capsule". DailyMed. National Library of Medicine, National Institutes of Health. Archived from the original on 2019-08-20. Retrieved 2015-10-16.
- ↑ US 4026894, Winn M, Kyncl J, Dunnigan DA, Jones PH, issued 31 May 1977, assigned to Abbott
External links
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