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

Details

Stereochemistry ACHIRAL
Molecular Formula C19H21N5O4
Molecular Weight 383.4019
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of PRAZOSIN

SMILES

COc1cc2c(cc1OC)nc([nH]c2=N)N3CCN(CC3)C(=O)c4ccco4

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 383.4019
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
Vasoconstrictive drugs increase carbonic anhydrase I in vascular smooth muscle while vasodilating drugs reduce the activity of this isozyme by a direct mechanism of action.
2001
Accurate mass measurement of synthetic analogues of prazosine by matrix-assisted laser desorption/ionisation time-of-flight mass spectrometry.
2001
Diabetes-induced changes in retinal NAD-redox status: pharmacological modulation and implications for pathogenesis of diabetic retinopathy.
2001
Hypoxic-ischaemic brain damage in immature rats: effects of adrenoceptor modulation.
2001
Lower urinary tract symptoms suggestive of benign prostatic obstruction--Triumph: the role of general practice databases.
2001
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
Expression and functional characterization of the mt1 melatonin receptor from rat brain in Xenopus oocytes: evidence for coupling to the phosphoinositol pathway.
2001 Apr
Hemodynamic effects of a combination of prazosin and terlipressin in patients with viral cirrhosis.
2001 Apr
Effect of alpha-adrenoceptor agents on imipramine-induced antinociception in nerve-ligated mice.
2001 Apr
The short-term effects of terazosin in Japanese men with benign prostatic hyperplasia.
2001 Apr
Effect of the blood substitute diaspirin crosslinked hemoglobin in rat mesenteric and human radial collateral arteries.
2001 Apr
MEK1/2-ERK1/2 mediates alpha1-adrenergic receptor-stimulated hypertrophy in adult rat ventricular myocytes.
2001 Apr
Effect of KMD-3213, an alpha1A-adrenoceptor antagonist, on the prostatic urethral pressure and blood pressure in male decerebrate dogs.
2001 Apr
Determinants of terminal mesenteric artery resistance during the first postnatal month.
2001 Apr
A61603-induced vasoconstriction in porcine carotid vasculature: involvement of a non-adrenergic mechanism.
2001 Apr 13
The noradrenaline-dopamine interaction in the rat medial prefrontal cortex studied by multi-probe microdialysis.
2001 Apr 27
beta-Adrenergic stimulation synchronizes intracellular Ca(2+) release during excitation-contraction coupling in cardiac myocytes.
2001 Apr 27
5-HT1A and 5-HT2 receptors differentially regulate the excitability of 5-HT-containing neurones of the guinea pig dorsal raphe nucleus in vitro.
2001 Apr 27
Call for global snake-bite control and procurement funding.
2001 Apr 7
Cis- and trans-N-benzyl-octahydrobenzo[g]quinolines. Adrenergic and dopaminergic activity studies.
2001 Apr 9
Chronic vasodilation induces matrix metalloproteinase 9 (MMP-9) expression during microvascular remodeling in rat skeletal muscle.
2001 Feb
[A randomized comparative study assessing once versus twice a day treatment of benign prostatic hyperplasia with terazosin].
2001 Feb
Neural mechanisms involved in the delay of gastric emptying and gastrointestinal transit of liquid after thoracic spinal cord transection in awake rats.
2001 Feb 20
Effects of losartan, prazosin and a vasopressin V1-receptor antagonist on renal and femoral blood flow in conscious sheep.
2001 Jan
Enhancer aided in vitro permeation of atenolol and prazosin hydrochloride through mice skin.
2001 Jan
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
alpha-1 and alpha-2 Adrenergic antagonists relieve thermal hyperalgesia in experimental mononeuropathy from chronic constriction injury.
2001 Jun
Vascular actions of MDMA involve alpha1 and alpha2-adrenoceptors in the anaesthetized rat.
2001 Jun
Noradrenaline modulates oyster hemocyte phagocytosis via a beta-adrenergic receptor-cAMP signaling pathway.
2001 Jun
Comparison of prazosin, terazosin and tamsulosin: functional and binding studies in isolated prostatic and vascular human tissues.
2001 Jun 1
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
In the formalin model of tonic nociceptive pain, 8-OH-DPAT produces 5-HT1A receptor-mediated, behaviorally specific analgesia.
2001 Jun 8
Enduring vulnerability to transient reinstatement of hemiplegia by prazosin after traumatic brain injury.
2001 Mar
Characterization of [3H]CGP 12177 binding to beta-adrenergic receptors in intact eel hepatocytes.
2001 Mar
Morphological and functional in vitro and in vivo characterization of the mouse corpus cavernosum.
2001 Mar
The role of several alpha(1)- and alpha(2)-adrenoceptor subtypes mediating vasoconstriction in the canine external carotid circulation.
2001 Mar
Nerve evoked P2X receptor contractions of rat mesenteric arteries; dependence on vessel size and lack of role of L-type calcium channels and calcium induced calcium release.
2001 Mar
Modulation of MK-801-induced behaviour by noradrenergic agents in mice.
2001 Mar 1
Effect of JTH-601, a putative alpha(1L)-adrenoceptor antagonist, on guinea pig nasal mucosa vasculature.
2001 Mar 23
Posttraining infusion of norepinephrine and corticotropin releasing factor into the bed nucleus of the stria terminalis enhanced retention in an inhibitory avoidance task.
2001 Mar 31
Initiation of nonselective alpha1-antagonist therapy and occurrence of hypotension-related adverse events among men with benign prostatic hyperplasia: a retrospective cohort study.
2001 May
Evaluating adverse cardiovascular effects of drug treatment for benign prostatic hyperplasia (BPH): methodological considerations.
2001 May
Identification and localization of three photobinding sites of iodoarylazidoprazosin in hamster P-glycoprotein.
2001 May
Structure-hepatic disposition relationships for cationic drugs in isolated perfused rat livers: transmembrane exchange and cytoplasmic binding process.
2001 May
Noradrenaline modulates hemocyte reactive oxygen species production via beta-adrenergic receptors in the oyster Crassostrea gigas.
2001 May
Interaction of formamidine pesticides with the presynaptic alpha(2)-adrenoceptor regulating.
2001 May 1
Role of G(i)-proteins in norepinephrine-mediated vasoconstriction in rat tail artery smooth muscle.
2001 May 1
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 Sat Jun 26 11:16:35 UTC 2021
Edited
by admin
on Sat Jun 26 11:16:35 UTC 2021
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
TERAZOSIN HYDROCHLORIDE DIHYDRATE SPECIFIED IMPURITY K [EP]
Common Name English
1-(4-AMINO-6,7-DIMETHOXYQUINAZOLIN-2-YL)-4-(FURAN-2-YLCARBONYL)PIPERAZINE
Systematic Name English
PRAZOSIN [WHO-DD]
Common Name English
CP-122991
Code English
PRAZOSIN [VANDF]
Common Name English
PRAZOSIN [MI]
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C29713
Created by admin on Sat Jun 26 11:16:36 UTC 2021 , Edited by admin on Sat Jun 26 11:16:36 UTC 2021
WHO-VATC QC02LE01
Created by admin on Sat Jun 26 11:16:36 UTC 2021 , Edited by admin on Sat Jun 26 11:16:36 UTC 2021
NCI_THESAURUS C270
Created by admin on Sat Jun 26 11:16:36 UTC 2021 , Edited by admin on Sat Jun 26 11:16:36 UTC 2021
WHO-ATC C02CA01
Created by admin on Sat Jun 26 11:16:36 UTC 2021 , Edited by admin on Sat Jun 26 11:16:36 UTC 2021
WHO-ATC C02LE01
Created by admin on Sat Jun 26 11:16:36 UTC 2021 , Edited by admin on Sat Jun 26 11:16:36 UTC 2021
NDF-RT N0000175553
Created by admin on Sat Jun 26 11:16:36 UTC 2021 , Edited by admin on Sat Jun 26 11:16:36 UTC 2021
NDF-RT N0000000099
Created by admin on Sat Jun 26 11:16:36 UTC 2021 , Edited by admin on Sat Jun 26 11:16:36 UTC 2021
WHO-VATC QC02CA01
Created by admin on Sat Jun 26 11:16:36 UTC 2021 , Edited by admin on Sat Jun 26 11:16:36 UTC 2021
LIVERTOX 793
Created by admin on Sat Jun 26 11:16:36 UTC 2021 , Edited by admin on Sat Jun 26 11:16:36 UTC 2021
Code System Code Type Description
CAS
19216-56-9
Created by admin on Sat Jun 26 11:16:36 UTC 2021 , Edited by admin on Sat Jun 26 11:16:36 UTC 2021
PRIMARY
PUBCHEM
4893
Created by admin on Sat Jun 26 11:16:36 UTC 2021 , Edited by admin on Sat Jun 26 11:16:36 UTC 2021
PRIMARY
IUPHAR
503
Created by admin on Sat Jun 26 11:16:36 UTC 2021 , Edited by admin on Sat Jun 26 11:16:36 UTC 2021
PRIMARY
ECHA (EC/EINECS)
242-885-8
Created by admin on Sat Jun 26 11:16:36 UTC 2021 , Edited by admin on Sat Jun 26 11:16:36 UTC 2021
PRIMARY
MESH
D011224
Created by admin on Sat Jun 26 11:16:36 UTC 2021 , Edited by admin on Sat Jun 26 11:16:36 UTC 2021
PRIMARY
FDA UNII
XM03YJ541D
Created by admin on Sat Jun 26 11:16:36 UTC 2021 , Edited by admin on Sat Jun 26 11:16:36 UTC 2021
PRIMARY
WIKIPEDIA
PRAZOSIN
Created by admin on Sat Jun 26 11:16:36 UTC 2021 , Edited by admin on Sat Jun 26 11:16:36 UTC 2021
PRIMARY
NCI_THESAURUS
C767
Created by admin on Sat Jun 26 11:16:36 UTC 2021 , Edited by admin on Sat Jun 26 11:16:36 UTC 2021
PRIMARY
ChEMBL
CHEMBL2
Created by admin on Sat Jun 26 11:16:36 UTC 2021 , Edited by admin on Sat Jun 26 11:16:36 UTC 2021
PRIMARY
RXCUI
8629
Created by admin on Sat Jun 26 11:16:36 UTC 2021 , Edited by admin on Sat Jun 26 11:16:36 UTC 2021
PRIMARY RxNorm
EPA CompTox
19216-56-9
Created by admin on Sat Jun 26 11:16:36 UTC 2021 , Edited by admin on Sat Jun 26 11:16:36 UTC 2021
PRIMARY
MERCK INDEX
M9108
Created by admin on Sat Jun 26 11:16:36 UTC 2021 , Edited by admin on Sat Jun 26 11:16:36 UTC 2021
PRIMARY Merck Index
DRUG BANK
DB00457
Created by admin on Sat Jun 26 11:16:36 UTC 2021 , Edited by admin on Sat Jun 26 11:16:36 UTC 2021
PRIMARY
INN
2593
Created by admin on Sat Jun 26 11:16:36 UTC 2021 , Edited by admin on Sat Jun 26 11:16:36 UTC 2021
PRIMARY
LACTMED
Prazosin
Created by admin on Sat Jun 26 11:16:36 UTC 2021 , Edited by admin on Sat Jun 26 11:16:36 UTC 2021
PRIMARY
DRUG CENTRAL
4209
Created by admin on Sat Jun 26 11:16:36 UTC 2021 , Edited by admin on Sat Jun 26 11:16:36 UTC 2021
PRIMARY
EVMPD
SUB10011MIG
Created by admin on Sat Jun 26 11:16:36 UTC 2021 , Edited by admin on Sat Jun 26 11:16:36 UTC 2021
PRIMARY
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Name Property Type Amount Referenced Substance Defining Parameters References
Volume of Distribution PHARMACOKINETIC
Tmax PHARMACOKINETIC ORAL ADMINISTRATION

Biological Half-life PHARMACOKINETIC