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Doxazosin

Names

[ CAS No. ]:
74191-85-8

[ Name ]:
Doxazosin

[Synonym ]:
Doxazosine [French]
1-(4-amino-6,7-dimethoxy-2-quinazolinyl)-4-[(2,3-dihydro-1,4-benzodioxin-2-yl)carbonyl]piperazine
Doxazosinum
Normothen
Cardura
Doxazosina
Doxazosine
Cardura-1
Cardura-2
Cardura-4
MFCD00800482
4-amino-2-[4-(1,4-benzodioxan-2-carbonyl)piperazin-1-yl]-6,7-dimethoxyquinazoline
[4-(4-amino-6,7-dimethoxyquinazolin-2-yl)piperazin-1-yl]-(2,3-dihydro-1,4-benzodioxin-3-yl)methanone

Biological Activity

[Description]:

Doxazosin(UK 33274) is a quinazoline-derivative that selectively antagonizes postsynaptic α1-adrenergic receptors.Target: Adrenergic ReceptorDoxazosin is a long-lasting inhibitor of α1-adrenoceptors that is widely used to treat benign prostatic hyperplasia and lower urinary tract symptoms [1]. doxazosin may have a direct inhibitory effect on cholesterol synthesis independent of the LDL receptor. The inhibition of cholesterol synthesis by doxazosin may cause cells to compensate by upregulating the LDL receptor, thereby increasing the importation of lipoprotein cholesterol and reducing LDL cholesterol in the medium [2]. Doxazosin monotherapy was effective in eight of 12 patients (66.7%), and combined therapy with a beta-blocker was effective in 11 of 12 patients (91.7%). The mean pulse rate remained constant throughout therapy. Adverse reactions were minor and transient and occurred in only three patients. Urinary and plasma catecholamine levels tended to decrease or remained unchanged during doxazosin therapy [3].Clinical indications: Hypertension; Prostate hyperplasiaFDA Approved Date: February 22, 2005Toxicity: Symptoms of overdose include hypotension

[Related Catalog]:

Signaling Pathways >> GPCR/G Protein >> Adrenergic Receptor
Natural Products >> Alkaloid
Research Areas >> Cardiovascular Disease

[References]

[1]. Sun, J.A., et al., Stereoselective binding of doxazosin enantiomers to plasma proteins from rats, dogs and humans in vitro. Acta Pharmacol Sin, 2013. 34(12): p. 1568-74.

[2]. D'Eletto, R.D. and N.B. Javitt, Effect of doxazosin on cholesterol synthesis in cell culture. J Cardiovasc Pharmacol, 1989. 13 Suppl 2: p. S1-4; discussion S4.

[3]. Miura, Y. and K. Yoshinaga, Doxazosin: a newly developed, selective alpha 1-inhibitor in the management of patients with pheochromocytoma. Am Heart J, 1988. 116(6 Pt 2): p. 1785-9.


[Related Small Molecules]

Isoprenaline hydrochloride | ICI 118,551 (hydrochloride) | Phenylephrine hydrochloride | Yohimbine hydrochloride | Adrenaline | Ivabradine hydrochloride | Prazosin hydrochloride | Clenbuterol hydrochloride | Phentolamine mesilate | guanfacine hydrochloride | pimozide | Sotalol hydrochloride | Carvedilol | Atenolol | Metroprolol succinate

Chemical & Physical Properties

[ Density]:
1.371 g/cm3

[ Boiling Point ]:
718ºC at 760 mmHg

[ Melting Point ]:
289-290°C

[ Molecular Formula ]:
C23H25N5O5

[ Molecular Weight ]:
451.48

[ Flash Point ]:
388ºC

[ PSA ]:
175.02000

[ LogP ]:
2.88670

[ Storage condition ]:
-20℃

Safety Information

[ Hazard Codes ]:
T,Xi

[ Risk Phrases ]:
R23/24/25:Toxic by inhalation, in contact with skin and if swallowed . R34:Causes burns. R40:Limited evidence of a carcinogenic effect. R43:May cause sensitization by skin contact. R36/37/38:Irritating to eyes, respiratory system and skin . R38:Irritating

[ Safety Phrases ]:
S36/37-S37/39-S26-S36

[ RIDADR ]:
UN 1198 3/PG 3

[ WGK Germany ]:
2

[ RTECS ]:
LP8925000

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

Related Compounds