Terazosin

Terazosin
Clinical data
Trade names	Hytrin, Zayasel, others
AHFS/Drugs.com	Monograph
MedlinePlus	a693046
License data	US DailyMed: Terazosin;
Routes of; administration	By mouth
ATC code	G04CA03 (WHO) ;
Legal status
Legal status	US: ℞-only;
Pharmacokinetic data
Protein binding	90–94%
Elimination half-life	12 hours
Identifiers
	IUPAC name (RS)-6,7-Dimethoxy-2-quinazolin-4-amine;
CAS Number	63590-64-7 ;
PubChem CID	5401;
IUPHAR/BPS	7302;
DrugBank	DB01162 ;
ChemSpider	5208 ;
UNII	8L5014XET7;
KEGG	D08569 ;
ChEBI	CHEBI:9445 ;
ChEMBL	ChEMBL611 ;
CompTox Dashboard (EPA)	DTXSID3023639 ;
ECHA InfoCard	100.118.191
Chemical and physical data
Formula	C19H25N5O4
Molar mass	387.440 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES O=C(N3CCN(c2nc1cc(OC)c(OC)cc1c(n2)N)CC3)C4OCCC4;
	InChI 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) ; Key:VCKUSRYTPJJLNI-UHFFFAOYSA-N ;
	(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

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.

Zdroj:https://en.wikipedia.org?pojem=Terazosin
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[AHFS2019-1] ^ ^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 J, Ganellin CR (2006). Analogue-based Drug Discovery. John Wiley & Sons. p. 455. ISBN 9783527607495.

[BNF76-3] British national formulary : BNF 76 (76 ed.). Pharmaceutical Press. 2018. p. 768. ISBN 9780857113382.

[4] "The Top 300 of 2021". ClinCalc. Archived from the original on 15 January 2024. Retrieved 14 January 2024.

[5] "Terazosin - Drug Usage Statistics". ClinCalc. Retrieved 14 January 2024.

[6] US 4026894, Winn M, Kyncl J, Dunnigan DA, Jones PH, issued 31 May 1977, assigned to Abbott

[7] 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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v t e Drugs used in benign prostatic hyperplasia (G04C)
5α-Reductase inhibitors	Dutasteride Epristeride Finasteride (+tadalafil)
Alpha-1 blockers	Alfuzosin Doxazosin Silodosin Tamsulosin Terazosin
Steroidal antiandrogens	Allylestrenol Delmadinone acetate Gestonorone caproate Osaterone acetate Oxendolone
Herbal products	Pygeum africanum Saw palmetto extract
Others	Mepartricin