Terazosin

Structural formula
	1: 1 mixture of ( R ) -form (top) and ( S ) -form (bottom)
General
Non-proprietary name	Terazosin
other names	( RS ) -1- (4-Amino-6,7-dimethoxyquinazolin-2-yl) -4- (tetrahydrofuran-2-carbonyl) piperazine ( IUPAC ) ; (±) -1- (4-Amino-6,7-dimethoxyquinazolin-2-yl) -4- (tetrahydrofuran-2-carbonyl) piperazine; rac -1- (4-amino-6,7-dimethoxyquinazolin-2-yl) -4- (tetrahydrofuran-2-carbonyl) piperazine; Terazosinum ( Latin ) ;
Molecular formula	C 19 H 25 N 5 O 4 ; C 19 H 25 N 5 O 4 HCl ( hydrochloride ) ; C 19 H 25 N 5 O 4 HCl 2 H 2 O (hydrochloride dihydrate) ;
External identifiers / databases
EC number	613-265-8
ECHA InfoCard	100.118.191
PubChem	5401
ChemSpider	5208
DrugBank	DB01162
Wikidata	Q280786
Drug information
ATC code	G04 CA03
Drug class	Antihypertensive drugs
Mechanism of action	α 1 -adrenoceptor - antagonist
properties
Molar mass	387.43 g · mol -1 ; 459.92 g · mol -1 (hydrochloride dihydrate) ;
Melting point	272.6-274 ° C ; 267.3 ° C (hydrochloride, morphological form 1) ; 271.0 ° C (hydrochloride, morphological form 2) ; 268.5 ° C (hydrochloride, morphological form 3) ; 270.4 ° C (hydrochloride, morphological form 4) ;
pK s value	7.1
safety instructions
	Please note the exemption from the labeling requirement for drugs, medical devices, cosmetics, food and animal feed
GHS labeling of hazardous substances Hydrochloride; Caution
H and P phrases	H: 302
	P: no P-phrases
Toxicological data	277 mg kg −1 ( LD 50 , rat, male , iv , hydrochloride dihydrate) ; 293 mg kg −1 ( LD 50 , rat, female , iv , hydrochloride dihydrate) ;
	As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Terazosin is a drug from the group of alpha blockers that is used to treat clinical symptoms and urination disorders in benign prostatic hyperplasia (BPH) and - as a reserve drug - to treat arterial hypertension . Terazosin was patented by Abbott ( trade name Hytrin ^® ) in 1977 and is commercially available as a generic .

Together with doxazosin and indoramine, it belongs to the prazosin derivatives, but in contrast to prazosin it has a higher bioavailability (90%) and a longer half-life (10-18 hours).

Via competitive antagonism at the postsynaptic α ₁ -adrenoceptor , it inhibits the action of noradrenaline and thus has a sympatholytic effect. The increased binding of norepinephrine to the presynaptic α ₂ -adrenoceptors also leads to an increased effect. The lowering of blood pressure achieved in this way (with lowering of pre- and afterload) is used in the therapy of arterial hypertension .

Trade names

Monopreparations : Flotrin (D), Heitrin (D), Hytrin (CH), Tera TAD (D), Terablock (D), Teranar (D), Terazid (D), Urocard (A), Uroflo (A), Urozosin ( D), Vicard (A)

Individual evidence

↑ ^a ^b entry on terazosin. In: Römpp Online . Georg Thieme Verlag, accessed on November 10, 2014.
↑ ^a ^b ^c ^d J. Bauer, J. Morley, S. Spanton, FJJ Leusen, R. Henry, S. Hollis, W. Heitmann, A. Mannino, J. Quick, W. Dziki: Identification, preparation, and characterization of several polymorphs and solvates of terazosin hydrochloride. In: Journal of Pharmaceutical Sciences. 95, 2006, pp. 917-928, doi: 10.1002 / jps.20425 .
↑ ^a ^b Datasheet Terazosin hydrochloride from Sigma-Aldrich , accessed on April 23, 2011 ( PDF ).
^ ^A ^b The Merck Index: An Encyclopedia of Chemicals, Drugs, and Biologicals. 14th Edition, Merck & Co., Inc., Whitehouse Station, NJ, USA 2006, ISBN 978-0-911910-00-1 , p. 1574.
↑ Roehrborn CG: Efficacy of alpha-Adrenergic Receptor Blockers in the Treatment of Male lower urinary tract symptoms . In: Reviews in Urology . 11, No. Suppl 1, 2009, pp. S1-8. PMID 20126606 . PMC 2812889 (free full text).
↑ Lepor H: Alpha blockers for the treatment of benign prostatic hyperplasia . In: Reviews in Urology . 9, No. 4, 2007, pp. 181-190. PMID 18231614 . PMC 2213889 (free full text).

Web links

Wikibooks: Pharmacology and Toxicology: Sympathetic-Selective α1-Blockers - Learning and Teaching Materials

Entries in the NIH study registry

[RÖMPP_Online-1] try on terazosin. In: Römpp Online . Georg Thieme Verlag, accessed on November 10, 2014.

[Bauer-2] J. Bauer, J. Morley, S. Spanton, FJJ Leusen, R. Henry, S. Hollis, W. Heitmann, A. Mannino, J. Quick, W. Dziki: Identification, preparation, and characterization of several polymorphs and solvates of terazosin hydrochloride. In: Journal of Pharmaceutical Sciences. 95, 2006, pp. 917-928, doi: 10.1002 / jps.20425 .

[Sigma-3] Datasheet Terazosin hydrochloride from Sigma-Aldrich , accessed on April 23, 2011 ( PDF ).

[MERCK_Index-4] A ^b The Merck Index: An Encyclopedia of Chemicals, Drugs, and Biologicals. 14th Edition, Merck & Co., Inc., Whitehouse Station, NJ, USA 2006, ISBN 978-0-911910-00-1 , p. 1574.

[pmid20126606-5] Roehrborn CG: Efficacy of alpha-Adrenergic Receptor Blockers in the Treatment of Male lower urinary tract symptoms . In: Reviews in Urology . 11, No. Suppl 1, 2009, pp. S1-8. PMID 20126606 . PMC 2812889 (free full text).

[pmid18231614-6] Lepor H: Alpha blockers for the treatment of benign prostatic hyperplasia . In: Reviews in Urology . 9, No. 4, 2007, pp. 181-190. PMID 18231614 . PMC 2213889 (free full text).