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Details

Stereochemistry RACEMIC
Molecular Formula C19H25N5O4
Molecular Weight 387.4329
Optical Activity ( + / - )
Defined Stereocenters 0 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of TERAZOSIN

SMILES

COC1=CC2=C(C=C1OC)C(N)=NC(=N2)N3CCN(CC3)C(=O)C4CCCO4

InChI

InChIKey=VCKUSRYTPJJLNI-UHFFFAOYSA-N
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)

HIDE SMILES / InChI

Molecular Formula C19H25N5O4
Molecular Weight 387.4329
Charge 0
Count
MOL RATIO 1 MOL RATIO (average)
Stereochemistry RACEMIC
Additional Stereochemistry No
Defined Stereocenters 0 / 1
E/Z Centers 0
Optical Activity ( + / - )

Description

Terazosin (marketed as Hytrin or Zayasel) is a selective alpha1-antagonist used for treatment of symptoms of benign prostatic hyperplasia (BPH). It also acts to lower blood pressure, so it is a drug of choice for men with hypertension and prostate enlargement. All three receptor subtypes appear to be involved in maintaining vascular tone. The α1A-receptor maintains basal vascular tone while the α1B-receptor mediates the vasocontrictory effects of exogenous α1-agonists. Activation of α1-receptors activates Gq-proteins, which results in intracellular stimulation of phospholipases C, A2, and D. This results in mobilization of Ca2+ from intracellular stores, activation of mitogen-activated kinase and PI3 kinase pathways and subsequent vasoconstriction.

CNS Activity

Originator

Approval Year

Targets

Primary TargetPharmacologyConditionPotency

Conditions

ConditionModalityTargetsHighest PhaseProduct
Curative
TERAZOSIN HYDROCHLORIDE
Primary
TERAZOSIN HYDROCHLORIDE

Cmax

ValueDoseCo-administeredAnalytePopulation
48 ng/mL
2 mg single, oral
TERAZOSIN plasma
Homo sapiens
37 ng/mL
2 mg single, oral
TERAZOSIN plasma
Homo sapiens

AUC

ValueDoseCo-administeredAnalytePopulation
408 ng × h/mL
2 mg single, oral
TERAZOSIN plasma
Homo sapiens
418 ng × h/mL
2 mg single, oral
TERAZOSIN plasma
Homo sapiens

T1/2

ValueDoseCo-administeredAnalytePopulation
8.4 h
2 mg single, oral
TERAZOSIN plasma
Homo sapiens
9.5 h
2 mg single, oral
TERAZOSIN plasma
Homo sapiens

Funbound

ValueDoseCo-administeredAnalytePopulation
8%
TERAZOSIN plasma
Homo sapiens

Doses

AEs

Overview

CYP3A4CYP2C9CYP2D6hERG

OverviewOther

Other InhibitorOther SubstrateOther Inducer


Drug as perpetrator​

Drug as victim

Tox targets

PubMed

Sample Use Guides

In Vivo Use Guide
for Hypertension: Initial dose: 1 mg orally once a day at bedtime; Maintenance dose: 1-5 mg orally once a day. Maximum dose: 20 mg per day. Usual Adult Dose for Benign Prostatic Hyperplasia: Initial dose: 1 mg orally once a day at bedtime. Maintenance dose: Increased in a stepwise fashion to 2 mg, 5 mg, or 10 mg once a day to achieve desired improvement of symptoms.
Route of Administration: Oral
In Vitro Use Guide
Unknown
Substance Class Chemical
Record UNII
8L5014XET7
Record Status Validated (UNII)
Record Version