Terazosin

Names

[ Name ]:
Terazosin

[Synonym ]:
Terazosin Hydrochloride
[4-(4-amino-6,7-dimethoxyquinazolin-2-yl)piperazin-1-yl]-(oxolan-2-yl)methanone
MFCD00467965

Biological Activity

[Description]:

Terazosin is a selective alpha1-antagonist used for treatment of symptoms of benign prostatic hyperplasia (BPH).Target: Alpha-1 Adrenergic ReceptorTerazosin is selective for alpha 1A-adrenoceptors which appear to dominate in the human prostate; the therapeutic relevance of this selectivity remains to be assessed in clinical studies [1]. Administration of terazosin 1 mg orally for 28 d. Terazosin initially shifted the dose-response curve of phenylephrine to the right, with a significant increase in ED50 for phenylephrine from a control value of 102 to 759 ng/min on day 1 of terazosin (P < 0.001). The mean Kd of terazosin was estimated as 11 +/- 15 nM in the first few days of treatment. This study demonstrates that pharmacological tolerance to the alpha 1-adrenoceptor blocking action of terazosin occurs in man and may be responsible for loss in efficacy with chronic therapy [2].

[Related Catalog]:

Signaling Pathways >> GPCR/G Protein >> Adrenergic Receptor

Natural Products >> Alkaloid

Research Areas >> Metabolic Disease

[References]

[1]. Michel, M.C., et al., Drugs for treatment of benign prostatic hyperplasia: affinity comparison at cloned alpha 1-adrenoceptor subtypes and in human prostate. J Auton Pharmacol, 1996. 16(1): p. 21-8.

[2]. Vincent, J., et al., Pharmacological tolerance to alpha 1-adrenergic receptor antagonism mediated by terazosin in humans. J Clin Invest, 1992. 90(5): p. 1763-8.

[Related Small Molecules]

Chemical & Physical Properties

[ Density]:
1.332 g/cm3

[ Boiling Point ]:
664.5ºC at 760 mmHg

[ Melting Point ]:
281-283°C

[ Molecular Formula ]:
C₁₉H₂₅N₅O₄

[ Molecular Weight ]:
387.43300

[ Flash Point ]:
355.7ºC

[ Exact Mass ]:
387.19100

[ PSA ]:
103.04000

[ LogP ]:
1.64090

[ Storage condition ]:
-20°C Freezer

[ Water Solubility ]:
H2O: 25 mg/mL

MSDS

Click to get detail MSDS

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: TK8044925

CHEMICAL NAME :: Piperazine, 1-(4-amino-6,7-dimethoxy-2-quinazolinyl)-4-((tetrahyd ro-2-furanyl)carbonyl )-

CAS REGISTRY NUMBER :: 63590-64-7

LAST UPDATED :: 199806

DATA ITEMS CITED :: 1

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: LDLo - Lowest published lethal dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 3 gm/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: USXXAM United States Patent Document. (U.S. Patent Office, Box 9, Washington, DC 20231) Volume(issue)/page/year: #4734418

Safety Information

[ Symbol ]:

GHS07

[ Signal Word ]:
Warning

[ Hazard Statements ]:
H302

[ Personal Protective Equipment ]:
dust mask type N95 (US);Eyeshields;Gloves

[ Hazard Codes ]:
Xn: Harmful;

[ Risk Phrases ]:
R22

[ Safety Phrases ]:
S26

[ RIDADR ]:
NONH for all modes of transport

[ WGK Germany ]:
3

[ RTECS ]:
TK8044925

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

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