Doxazosin

Doxazosin, sold under the brand names Cardura among others, is a medication used to treat symptoms of benign prostatic hyperplasia (enlarged prostate) and hypertension (high blood pressure). For high blood pressure, it is a less preferred option. It is taken by mouth.

Doxazosin
Clinical data
Pronunciation/dɒkˈseɪzəsɪn/
dok-SAY-zə-sin OR
/ˌdɒksəˈzoʊsɪn/
DOK-sə-ZOH-sin
Trade namesCardura, Carduran, others
AHFS/Drugs.comMonograph
MedlinePlusa693045
License data
Routes of
administration		By mouth
ATC code
Legal status
Legal status
  • US: ℞-only
Pharmacokinetic data
Bioavailability65%
Protein binding98%
MetabolismLiver
Elimination half-life22 hours
Identifiers
  • (RS)-2-[4-(2,3-Dihydro-1,4-benzodioxine-2-carbonyl)piperazin-1-yl]-6,7-dimethoxyquinazolin-4-amine
CAS Number
PubChem CID
IUPHAR/BPS
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.128.642
Chemical and physical data
FormulaC23H25N5O5
Molar mass451.483 g·mol−1
3D model (JSmol)
ChiralityRacemic mixture
SMILES
  • O=C(N3CCN(c2nc1cc(OC)c(OC)cc1c(n2)N)CC3)C4Oc5c(OC4)cccc5
  • InChI=1S/C23H25N5O5/c1-30-18-11-14-15(12-19(18)31-2)25-23(26-21(14)24)28-9-7-27(8-10-28)22(29)20-13-32-16-5-3-4-6-17(16)33-20/h3-6,11-12,20H,7-10,13H2,1-2H3,(H2,24,25,26) Y
  • Key:RUZYUOTYCVRMRZ-UHFFFAOYSA-N Y
  (verify)

Common side effects include dizziness, sleepiness, swelling, nausea, shortness of breath, and abdominal pain. Severe side effects may include low blood pressure with standing, an irregular heart beat, and priapism. It is a α1-selective adrenergic blocker in the quinazoline class of compounds.

Doxazosin was patented in 1977 and came into medical use in 1988. It is available as a generic medication. In 2021, it was the 195th most commonly prescribed medication in the United States, with more than 2 million prescriptions.

A 2021 study associated doxazosin with decelerated biological aging in humans and confirmed its causal role in longevity in C. elegans.

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