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Details

Stereochemistry ACHIRAL
Molecular Formula C19H21N5O4
Molecular Weight 383.4011
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of PRAZOSIN

SMILES

COC1=CC2=C(C=C1OC)C(N)=NC(=N2)N3CCN(CC3)C(=O)C4=CC=CO4

InChI

InChIKey=IENZQIKPVFGBNW-UHFFFAOYSA-N
InChI=1S/C19H21N5O4/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/h3-4,9-11H,5-8H2,1-2H3,(H2,20,21,22)

HIDE SMILES / InChI

Molecular Formula C19H21N5O4
Molecular Weight 383.4011
Charge 0
Count
MOL RATIO 1 MOL RATIO (average)
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description

Prazosin (trade names Minipress, Vasoflex, Lentopres, and Hypovase) is a selective α-1-adrenergic receptor antagonist used to treat hypertension. Prazosin acts by inhibiting the postsynaptic alpha-1-adrenoceptors on vascular smooth muscle. This inhibits the vasoconstrictor effect of circulating and locally released catecholamines (epinephrine and norepinephrine), resulting in peripheral vasodilation. Prazosin is orally active and has a minimal effect on cardiac function due to its alpha-1 receptor selectivity. However, when prazosin is started, heart rate and contractility go up in order to maintain the pre-treatment blood pressures because the body has reached homeostasis at its abnormally high blood pressure. The blood pressure lowering effect becomes apparent when prazosin is taken for longer periods of time. The heart rate and contractility go back down over time and blood pressure decreases. The antihypertensive characteristics of prazosin make it a second-line choice for the treatment of high blood pressure. Prazosin is also useful in treating urinary hesitancy associated with prostatic hyperplasia, blocking alpha-1 receptors, which control constriction of both the prostate and urethra. Although not a first line choice for either hypertension or prostatic hyperplasia, it is a choice for patients who present with both problems concomitantly. Common (4–10% frequency) side effects of prazosin include dizziness, headache, drowsiness, lack of energy, weakness, palpitations, and nausea. Less frequent (1–4%) side effects include vomiting, diarrhea, constipation, edema, orthostatic hypotension, dyspnea, syncope, vertigo, depression, nervousness, and rash.

CNS Activity

Originator

Approval Year

Targets

Primary TargetPharmacologyConditionPotency
2.0 nM [Kd]
0.04 nM [Ki]
0.28 nM [Ki]
0.42 nM [Ki]

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
MINIPRESS
Primary
MINIPRESS
Primary
MINIPRESS

Cmax

ValueDoseCo-administeredAnalytePopulation
40 ng/mL
20 mg single, oral
PRAZOSIN plasma
Homo sapiens

AUC

ValueDoseCo-administeredAnalytePopulation
281 ng × h/mL
20 mg single, oral
PRAZOSIN plasma
Homo sapiens

T1/2

ValueDoseCo-administeredAnalytePopulation
5.8 h
20 mg single, oral
PRAZOSIN plasma
Homo sapiens

Funbound

ValueDoseCo-administeredAnalytePopulation
7.5%
20 mg single, oral
PRAZOSIN plasma
Homo sapiens

Overview

CYP3A4CYP2C9CYP2D6hERG

OverviewOther

Other InhibitorOther SubstrateOther Inducer



Drug as perpetrator​

Tox targets

PubMed

Sample Use Guides

In Vivo Use Guide
Initial: 1 mg PO q8-12hr Maintenance: 6-15 mg/day divided 2 or 3 times daily; alternatively, 1-5 mg PO BID; may increase dose to 20 mg/day in divided doses; some patients may benefit from up to 40 mg/day in divided doses
Route of Administration: Oral
In Vitro Use Guide
Both HEL and K562 cells, with a start cell number of 1×E4 cells/ml, were incubated in 24-well plates 2 or 3 days with different concentrations of the receptor subtype-specific adrenergic antagonists, prazosin in triplicates. All antagonists were obtained from Sigma Austria and were added to the culture medium dissolved in Aqua bidest. After the incubation period, proliferation and viability of the cells were measured with a CASY-1® Cell Counter and Analyzer (Schaerfe, Reutlingen, Germany).
Substance Class Chemical
Record UNII
XM03YJ541D
Record Status Validated (UNII)
Record Version