Doxazosin

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Structural formula
Structural formula of doxazosin
1: 1 mixture of ( R ) -form (top) and ( S ) -form (bottom)
General
Non-proprietary name Doxazosin
other names
  • ( RS ) -1- (4-Amino-6,7-dimethoxyquinazolin-2-yl) -4- (2,3-dihydro-1,4-benzodioxin-2-ylcarbonyl) piperazine
  • DL -1- (4-Amino-6,7-dimethoxy-2-quinazolinyl) -4 - [(2,3-dihydro-1,4-benzodioxin-2-yl) carbonyl] piperazine
Molecular formula C 23 H 25 N 5 O 5
External identifiers / databases
CAS number
  • 74191-85-8 (doxazosin)
  • 77883-43-3 (doxazosin mesilate )
EC number 616-059-6
ECHA InfoCard 100.128.642
PubChem 3157
ChemSpider 3045
DrugBank DB00590
Wikidata Q419939
Drug information
ATC code

C02 CA04

Drug class

Alpha blockers

Mechanism of action

α 1 -adrenoceptor - antagonist

properties
Molar mass 451.48 g · mol -1
Physical state

firmly

Melting point

289–290 ° C (doxazosin hydrochloride )

solubility

Slightly soluble in water, sparingly soluble in methanol, practically insoluble in acetone

safety instructions
Please note the exemption from the labeling requirement for drugs, medical devices, cosmetics, food and animal feed
GHS labeling of hazardous substances
no GHS pictograms
H and P phrases H: no H-phrases
P: no P-phrases
Toxicological data
As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Doxazosin is a drug from the group of alpha blockers that is used to treat benign prostatic hyperplasia and arterial hypertension .

Clinical information

Doxazosin selectively blocks α 1 receptors , causing peripheral expansion of blood vessels and thus lowering blood pressure .

Further, it causes a lowering of the serum - cholesterol .

Pharmacological properties

side effect

Among other things, at the beginning of treatment with doxazosin, there may be a sharp drop in blood pressure with dizziness and headaches (“first-dose effect”). The orthostatic hypotension is characteristic of alpha blockers. Side effects such as priapism are rather rare.

Other information

Doxazosin was patented by Pfizer as an α 1 sympatholytic in 1979/1980 and introduced in Germany in 1989 as Cardular . There are now generics on the market. Of doxazosin, only the mesilate is used because of its better solubility compared to the hydrochloride . Like the structurally related prazosin hydrochloride, doxazosin mesilate exists in several polymorphic forms. The specific synthesis of some polymorphs takes place from solvates of doxazosin mesilate in solvents that do not form solvates with this salt. X-ray diffraction and thermal analysis are suitable for characterizing the polymorphism in doxazosin mesilate . The polymorphic forms of doxazosin mesilate differ markedly in the storage stability, because they tend more or less quickly to hydration .

Trade names

Monopreparations

Adoxa (A), Ascalan (A), Cardular PP (D), Cardura (CH), Diblocin PP (D), Doxacor (D), Hibadren (A), Jutalar (D), Prostadilat (A), Supressin (A ), Uriduct (D), numerous generics (D, A, CH)

Individual evidence

  1. ^ The Merck Index : An Encyclopedia of Chemicals, Drugs, and Biologicals , 14th Edition (Merck & Co., Inc.), Whitehouse Station, NJ, USA, 2006; P. 581, ISBN 978-0-911910-00-1 .
  2. ↑ European Pharmacopoeia, 8th edition, Grundwerk 2014, p. 3133 f. Deutscher Apotheker Verlag, Stuttgart.
  3. ↑ a b Data sheet Doxazosin mesylate, ≥97% (HPLC), powder from Sigma-Aldrich , accessed on February 13, 2013 ( PDF ).
  4. ↑ a b entry on doxazosin. In: Römpp Online . Georg Thieme Verlag, accessed on November 11, 2014.
  5. ↑ HPT Ammon (Ed.): Hunnius Pharmaceutical Dictionary . 9th edition. Walter de Gruyter, Berlin a. New York 2004, p. 475.
  6. ↑ MU Avisror, IA Fernandez et al. Journal of Urology 163, 238 (2000)
  7. ↑ Young-Taek son, Lee Yoon-Hee; Archives of Pharmacal Research 28 (6), 730 (2005), doi: 10.1007 / BF02969365 ; Chem. Abstr. 143, 465 795.
  8. ↑ M. Grčman, F. Vrečer, A. Meden; Journal of Thermal Analysis and Calorimetry 68, 373 (2002), doi: 10.1023 / A: 1016019214704 ; Chem. Abstr. 138, 243 003.
  9. ↑ EP 849 264 (1996) [1] ; I. Grafe, P. Moersdorf (Heumann Pharma GmbH); New polymorphic form of doxazosin mesylate (Form I).
  10. ↑ EP 849 265 (1996) [2] ; I. Grafe, P. Moersdorf (Heumann Pharma GmbH); New polymorphic form of doxazosin mesylate (Form II).
  11. ↑ EP 849 266 (1996) [3] ; I. Grafe, P. Moersdorf (Heumann Pharma GmbH); New polymorphic form of doxazosin mesylate (Form III).
  12. ^ VV Chernyshev, D. Machon et al .; Acta Cryst. B59, 787 (2003); Chem. Abstr. 140, 243 792.