U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

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=NC(=NC(N)=C2C=C1OC)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
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

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.

Approval Year

Targets

Targets

Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
MINIPRESS

Approved Use

Prazosin hydrochloride capsules are indicated in the treatment of hypertension. They can be used alone or in combination with other antihypertensive drugs such as diuretics or beta-adrenergic blocking agents.

Launch Date

2.04336005E11
Primary
MINIPRESS

Approved Use

Prazosin hydrochloride capsules are indicated in the treatment of hypertension. They can be used alone or in combination with other antihypertensive drugs such as diuretics or beta-adrenergic blocking agents.

Launch Date

2.04336005E11
Primary
MINIPRESS

Approved Use

Prazosin hydrochloride capsules are indicated in the treatment of hypertension. They can be used alone or in combination with other antihypertensive drugs such as diuretics or beta-adrenergic blocking agents.

Launch Date

2.04336005E11
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
40 ng/mL
20 mg single, oral
dose: 20 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
PRAZOSIN plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
281 ng × h/mL
20 mg single, oral
dose: 20 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
PRAZOSIN plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
5.8 h
20 mg single, oral
dose: 20 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
PRAZOSIN plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
Funbound

Funbound

ValueDoseCo-administeredAnalytePopulation
7.5%
20 mg single, oral
dose: 20 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
PRAZOSIN plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG

OverviewOther

Other InhibitorOther SubstrateOther Inducer



Drug as perpetrator​

Drug as perpetrator​

TargetModalityActivityMetaboliteClinical evidence
yes [IC50 1.56 uM]
yes [IC50 12.6 uM]
yes [IC50 80.4 uM]
Tox targets

Tox targets

TargetModalityActivityMetaboliteClinical evidence
PubMed

PubMed

TitleDatePubMed
Haemodynamic effects of prazosin.
1976 Dec
Effect of midodrine on chlorpromazine-induced orthostatic hypotension in rabbits: comparison with amezinium, etilefrine and droxidopa.
2000 Dec
Are alpha-blockers involved in lower urinary tract dysfunction in multiple system atrophy? A comparison of prazosin and moxisylyte.
2000 Mar 15
Role of the alpha(1)- and alpha(2)-adrenoceptors of the paraventricular nucleus on the water and salt intake, renal excretion, and arterial pressure induced by angiotensin II injection into the medial septal area.
2001 Apr
Hemodynamic effects of a combination of prazosin and terlipressin in patients with viral cirrhosis.
2001 Apr
Determinants of terminal mesenteric artery resistance during the first postnatal month.
2001 Apr
[A randomized comparative study assessing once versus twice a day treatment of benign prostatic hyperplasia with terazosin].
2001 Feb
Magnetic resonance imaging and morphometric histologic analysis of prostate tissue composition in predicting the clinical outcome of terazosin therapy in benign prostatic hyperplasia.
2001 Feb
Overstimulation of the alpha1B-adrenergic receptor causes a "seizure plus" syndrome.
2001 Feb
Traceless solid-phase synthesis of 2,4-diaminoquinazolines.
2001 Feb 22
Noradrenaline modulates GABA-mediated synaptic transmission in neurones of the mediolateral part of the guinea pig lateral septum via local circuits.
2001 Jan
Targeted transurethral microwave thermotherapy versus alpha-blockade in benign prostatic hyperplasia: outcomes at 18 months.
2001 Jan
Sarcomere length-induced alterations of capillary hemodynamics in rat spinotrapezius muscle: vasoactive vs passive control.
2001 Jan
Reversal of Haemorrhagic Shock in Rats by Tetrahydroaminoacridine.
2001 Jan
Catecholamine responses to alpha-adrenergic blockade during exercise in women acutely exposed to altitude.
2001 Jan
Catecholaminergic regulation of Na-K-Cl cotransport in pigmented ciliary epithelium: differences between PE and NPE.
2001 Jan
alpha-Blockade improves symptoms suggestive of bladder outlet obstruction but fails to relieve it.
2001 Jan
In vivo demonstration of alpha(1A)-adrenoceptor subtype selectivity of KMD-3213 in rat tissues.
2001 Jan
Increased alpha(1)- and alpha(2)-adrenoceptor-mediated contractile responses of human skeletal muscle resistance arteries in chronic limb ischemia.
2001 Jan
Combined effect of terazosin and finasteride on apoptosis, cell proliferation, and transforming growth factor-beta expression in benign prostatic hyperplasia.
2001 Jan 1
Amantadine-induced cortical myoclonus.
2001 Jan 23
[The adrenoreceptor blocker prazosin does not prevent synchronization of the protein biosynthesis rhythm by exogenous gangliosides in the hepatocyte culture].
2001 Jan-Feb
Hemorrhage-induced alpha-adrenergic signaling results in myocardial TNF-alpha expression and contractile dysfunction.
2001 Jul
Phe-308 and Phe-312 in transmembrane domain 7 are major sites of alpha 1-adrenergic receptor antagonist binding. Imidazoline agonists bind like antagonists.
2001 Jul 6
Noradrenaline modulates oyster hemocyte phagocytosis via a beta-adrenergic receptor-cAMP signaling pathway.
2001 Jun
Synthesis, biological evaluation, and pharmacophore generation of new pyridazinone derivatives with affinity toward alpha(1)- and alpha(2)-adrenoceptors.
2001 Jun 21
A functional assay for detection of the mitoxantrone resistance protein, MXR (ABCG2).
2001 Jun 6
Structure-activity studies for a novel series of bicyclic substituted hexahydrobenz[e]isoindole alpha1A adrenoceptor antagonists as potential agents for the symptomatic treatment of benign prostatic hyperplasia.
2001 Jun 7
The role of several alpha(1)- and alpha(2)-adrenoceptor subtypes mediating vasoconstriction in the canine external carotid circulation.
2001 Mar
Effect of JTH-601, a putative alpha(1L)-adrenoceptor antagonist, on guinea pig nasal mucosa vasculature.
2001 Mar 23
Structure-hepatic disposition relationships for cationic drugs in isolated perfused rat livers: transmembrane exchange and cytoplasmic binding process.
2001 May
Patents

Sample Use Guides

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
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
Created
by admin
on Fri Dec 15 15:15:36 UTC 2023
Edited
by admin
on Fri Dec 15 15:15:36 UTC 2023
Record UNII
XM03YJ541D
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
PRAZOSIN
INN   MI   VANDF   WHO-DD  
INN  
Official Name English
prazosin [INN]
Common Name English
1-(4-AMINO-6,7-DIMETHOXYQUINAZOLIN-2-YL)-4-(FURAN-2-YLCARBONYL)PIPERAZINE
Systematic Name English
CP-122991
Code English
TERAZOSIN HYDROCHLORIDE DIHYDRATE IMPURITY K [EP IMPURITY]
Common Name English
PRAZOSIN [VANDF]
Common Name English
PRAZOSIN [MI]
Common Name English
Prazosin [WHO-DD]
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C29713
Created by admin on Fri Dec 15 15:15:36 UTC 2023 , Edited by admin on Fri Dec 15 15:15:36 UTC 2023
WHO-VATC QC02LE01
Created by admin on Fri Dec 15 15:15:36 UTC 2023 , Edited by admin on Fri Dec 15 15:15:36 UTC 2023
NCI_THESAURUS C270
Created by admin on Fri Dec 15 15:15:36 UTC 2023 , Edited by admin on Fri Dec 15 15:15:36 UTC 2023
WHO-ATC C02CA01
Created by admin on Fri Dec 15 15:15:36 UTC 2023 , Edited by admin on Fri Dec 15 15:15:36 UTC 2023
WHO-ATC C02LE01
Created by admin on Fri Dec 15 15:15:36 UTC 2023 , Edited by admin on Fri Dec 15 15:15:36 UTC 2023
NDF-RT N0000175553
Created by admin on Fri Dec 15 15:15:36 UTC 2023 , Edited by admin on Fri Dec 15 15:15:36 UTC 2023
NDF-RT N0000000099
Created by admin on Fri Dec 15 15:15:36 UTC 2023 , Edited by admin on Fri Dec 15 15:15:36 UTC 2023
WHO-VATC QC02CA01
Created by admin on Fri Dec 15 15:15:36 UTC 2023 , Edited by admin on Fri Dec 15 15:15:36 UTC 2023
LIVERTOX NBK548699
Created by admin on Fri Dec 15 15:15:36 UTC 2023 , Edited by admin on Fri Dec 15 15:15:36 UTC 2023
Code System Code Type Description
CAS
19216-56-9
Created by admin on Fri Dec 15 15:15:36 UTC 2023 , Edited by admin on Fri Dec 15 15:15:36 UTC 2023
PRIMARY
CHEBI
8364
Created by admin on Fri Dec 15 15:15:36 UTC 2023 , Edited by admin on Fri Dec 15 15:15:36 UTC 2023
PRIMARY
PUBCHEM
4893
Created by admin on Fri Dec 15 15:15:36 UTC 2023 , Edited by admin on Fri Dec 15 15:15:36 UTC 2023
PRIMARY
IUPHAR
503
Created by admin on Fri Dec 15 15:15:36 UTC 2023 , Edited by admin on Fri Dec 15 15:15:36 UTC 2023
PRIMARY
ECHA (EC/EINECS)
242-885-8
Created by admin on Fri Dec 15 15:15:36 UTC 2023 , Edited by admin on Fri Dec 15 15:15:36 UTC 2023
PRIMARY
MESH
D011224
Created by admin on Fri Dec 15 15:15:36 UTC 2023 , Edited by admin on Fri Dec 15 15:15:36 UTC 2023
PRIMARY
SMS_ID
100000081402
Created by admin on Fri Dec 15 15:15:36 UTC 2023 , Edited by admin on Fri Dec 15 15:15:36 UTC 2023
PRIMARY
FDA UNII
XM03YJ541D
Created by admin on Fri Dec 15 15:15:36 UTC 2023 , Edited by admin on Fri Dec 15 15:15:36 UTC 2023
PRIMARY
DAILYMED
XM03YJ541D
Created by admin on Fri Dec 15 15:15:36 UTC 2023 , Edited by admin on Fri Dec 15 15:15:36 UTC 2023
PRIMARY
WIKIPEDIA
PRAZOSIN
Created by admin on Fri Dec 15 15:15:36 UTC 2023 , Edited by admin on Fri Dec 15 15:15:36 UTC 2023
PRIMARY
NCI_THESAURUS
C767
Created by admin on Fri Dec 15 15:15:36 UTC 2023 , Edited by admin on Fri Dec 15 15:15:36 UTC 2023
PRIMARY
ChEMBL
CHEMBL2
Created by admin on Fri Dec 15 15:15:36 UTC 2023 , Edited by admin on Fri Dec 15 15:15:36 UTC 2023
PRIMARY
RXCUI
8629
Created by admin on Fri Dec 15 15:15:36 UTC 2023 , Edited by admin on Fri Dec 15 15:15:36 UTC 2023
PRIMARY RxNorm
EPA CompTox
DTXSID4049082
Created by admin on Fri Dec 15 15:15:36 UTC 2023 , Edited by admin on Fri Dec 15 15:15:36 UTC 2023
PRIMARY
MERCK INDEX
m9108
Created by admin on Fri Dec 15 15:15:36 UTC 2023 , Edited by admin on Fri Dec 15 15:15:36 UTC 2023
PRIMARY Merck Index
DRUG BANK
DB00457
Created by admin on Fri Dec 15 15:15:36 UTC 2023 , Edited by admin on Fri Dec 15 15:15:36 UTC 2023
PRIMARY
INN
2593
Created by admin on Fri Dec 15 15:15:36 UTC 2023 , Edited by admin on Fri Dec 15 15:15:36 UTC 2023
PRIMARY
LACTMED
Prazosin
Created by admin on Fri Dec 15 15:15:36 UTC 2023 , Edited by admin on Fri Dec 15 15:15:36 UTC 2023
PRIMARY
DRUG CENTRAL
4209
Created by admin on Fri Dec 15 15:15:36 UTC 2023 , Edited by admin on Fri Dec 15 15:15:36 UTC 2023
PRIMARY
EVMPD
SUB10011MIG
Created by admin on Fri Dec 15 15:15:36 UTC 2023 , Edited by admin on Fri Dec 15 15:15:36 UTC 2023
PRIMARY
Related Record Type Details
TARGET -> INHIBITOR
BINDING
IC50
TRANSPORTER -> INHIBITOR
TARGET -> INHIBITOR
Binding Assay
IC50
LABELED -> NON-LABELED
BINDER->LIGAND
BINDING
TARGET -> INHIBITOR
Binding Assay
IC50
TARGET -> INHIBITOR
TRANSPORTER -> INHIBITOR
TARGET -> INHIBITOR
IC50
TARGET -> INHIBITOR
SALT/SOLVATE -> PARENT
Related Record Type Details
METABOLITE -> PARENT
IN VITRO
METABOLITE -> PARENT
IN VIVO
METABOLITE -> PARENT
IN VITRO
METABOLITE -> PARENT
IN VITRO
METABOLITE -> PARENT
IN VITRO
METABOLITE TOXIC -> PARENT
IN VITRO
METABOLITE -> PARENT
IN VITRO
METABOLITE -> PARENT
IN VITRO
METABOLITE -> PARENT
IN VITRO
METABOLITE -> PARENT
IN VITRO
METABOLITE -> PARENT
IN VITRO
Related Record Type Details
PARENT -> IMPURITY
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
Related Record Type Details
ACTIVE MOIETY
Name Property Type Amount Referenced Substance Defining Parameters References
Volume of Distribution PHARMACOKINETIC
Tmax PHARMACOKINETIC ORAL ADMINISTRATION

Biological Half-life PHARMACOKINETIC