From Wikipedia, the free encyclopedia
Antihypertensive medication used to treat hypertension
Terazosin
Trade names Hytrin, Zayasel, others
AHFS /
Drugs.com
Monograph
MedlinePlus
a693046
License data
Routes of administration
By mouth
ATC code
Legal status
Protein binding 90–94%
Elimination half-life 12 hours
(RS )-6,7-Dimethoxy-2-[4-(tetrahydrofuran-2-ylcarbonyl)piperazin-1-yl]quinazolin-4-amine
CAS Number
PubChem
CID
IUPHAR/BPS
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (
EPA )
ECHA InfoCard
100.118.191
Formula C 19 H 25 N 5 O 4
Molar mass 387.440 g·mol−1 3D model (
JSmol )
O=C(N3CCN(c2nc1cc(OC)c(OC)cc1c(n2)N)CC3)C4OCCC4
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)
Y Key:VCKUSRYTPJJLNI-UHFFFAOYSA-N
Y
(verify)
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] In 2021, it was the 234th most commonly prescribed medication in the United States, with more than 1 million prescriptions.
[4]
[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 ).
Research
A 2022 study suggests that terazosin may have the potential to confer neuroprotection upon motor neurons in motor neuron disease, as a result of its ability to activate PGK1.
[7]
References
^
a
b
c
d
e
f
g
"Terazosin Hydrochloride Monograph for Professionals" . Drugs.com . American Society of Health-System Pharmacists. Retrieved 17 March 2019 .
^ Fischer J, Ganellin CR (2006).
Analogue-based Drug Discovery . John Wiley & Sons. p. 455.
ISBN
9783527607495 .
^ British national formulary : BNF 76 (76 ed.). Pharmaceutical Press. 2018. p. 768.
ISBN
9780857113382 .
^
"The Top 300 of 2021" . ClinCalc .
Archived from the original on 15 January 2024. Retrieved 14 January 2024 .
^
"Terazosin - Drug Usage Statistics" . ClinCalc . Retrieved 14 January 2024 .
^
US 4026894 , Winn M, Kyncl J, Dunnigan DA, Jones PH, issued 31 May 1977, assigned to Abbott
^ Chaytow H, Carroll E, Gordon D, Huang YT, van der Hoorn D, Smith HL, et al. (September 2022).
"Targeting phosphoglycerate kinase 1 with terazosin improves motor neuron phenotypes in multiple models of amyotrophic lateral sclerosis" . eBioMedicine . 83 : 104202.
doi :
10.1016/j.ebiom.2022.104202 .
PMC
9482929 .
PMID
35963713 .
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