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Terazosin

Terazosin
Terazosin.svg
Clinical data
Trade namesHytrin, Zayasel, others
Synonyms[4-(4-amino-6,7-dimethoxy-quinazolin-2-yl)piperazin-1-yl]-tetrahydrofuran-2-yl-methanone
AHFS/Drugs.comMonograph
MedlinePlusa693046
ATC code
Legal status
Legal status
Pharmacokinetic data
Protein binding90-94%
Elimination half-life12 hours
Identifiers
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 mass387.433 g/mol g·mol−1
3D model (JSmol)
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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.[1] For high blood pressure, it is a less preferred option.[1] It is taken by mouth.[1]

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] A month supply in the United Kingdom costs the NHS less than 2 £ as of 2019.[3] In the United States the wholesale cost of this amount is about US$4.50.[4]

Formulations

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

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, Jnos; Ganellin, C. Robin (2006). Analogue-based Drug Discovery. John Wiley & Sons. p. 455. ISBN 9783527607495.
  3. ^ a b British national formulary : BNF 76 (76 ed.). Pharmaceutical Press. 2018. p. 768. ISBN 9780857113382.
  4. ^ "NADAC as of 2019-02-27". Centers for Medicare and Medicaid Services. Retrieved 3 March 2019.
  5. ^ Terazosin Hydrochloride Capsule, DailyMed, National Library of Medicine, National Institutes of Health
  6. ^ M. Winn, J. Kyncl, D. A. Dunnigan, and P. H. Jones, {{US Patent|4,026,894}} (1977); Chem. Abstr., 87; 68411m (1977).