Terazosin

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Terazosin
Terazosin.svg
Clinical data
Trade names Hytrin
Synonyms [4-(4-amino-6,7-dimethoxy-quinazolin-2-yl)piperazin-1-yl]-tetrahydrofuran-2-yl-methanone
AHFS/Drugs.com Monograph
MedlinePlus a693046
ATC code
Legal status
Legal status
Pharmacokinetic data
Protein binding 90-94%
Elimination half-life 12 hours
Identifiers
CAS Number
PubChem CID
IUPHAR/BPS
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
ECHA InfoCard 100.118.191 Edit this at Wikidata
Chemical and physical data
Formula C19H25N5O4
Molar mass 387.433 g/mol
3D model (JSmol)
  (verify)

Terazosin (marketed as Hytrin or Zayasel) is a selective alpha-1 antagonist used for treatment of symptoms of an enlarged prostate (BPH). It also acts to lower the blood pressure, and is therefore a drug of choice for men with hypertension and prostate enlargement. It is available in 1 mg, 2 mg, 5 mg or 10 mg doses.[1]

It works by blocking the action of adrenaline on smooth muscle of the bladder and the blood vessel walls.

Most common side effects include dizziness, drowsiness, headache, constipation, loss of appetite, fatigue, nasal congestion or dry eyes, but they generally go away after only a few days of use. Therapy should always be started with a low dose to avoid first dose phenomenon.[2] Sexual side effects are rare, but may include priapism or erectile dysfunction.


Synthesis[edit]

Terazosin synthesis:[3]

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).

See also[edit]

References[edit]