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Details

Stereochemistry ACHIRAL
Molecular Formula C19H21N5O4.ClH
Molecular Weight 419.862
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of PRAZOSIN HYDROCHLORIDE

SMILES

Cl.COC1=CC2=NC(=NC(N)=C2C=C1OC)N3CCN(CC3)C(=O)C4=CC=CO4

InChI

InChIKey=WFXFYZULCQKPIP-UHFFFAOYSA-N
InChI=1S/C19H21N5O4.ClH/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);1H

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

Molecular Formula ClH
Molecular Weight 36.461
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

1976
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

1976
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

1976
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
Effect of midodrine on chlorpromazine-induced orthostatic hypotension in rabbits: comparison with amezinium, etilefrine and droxidopa.
2000 Dec
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
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
The short-term effects of terazosin in Japanese men with benign prostatic hyperplasia.
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
Effect of dexmedetomidine on the release of [3H]-noradrenaline from rat kidney cortex slices: characterization of alpha2-adrenoceptor.
2001 Apr
A61603-induced vasoconstriction in porcine carotid vasculature: involvement of a non-adrenergic mechanism.
2001 Apr 13
Characterization of the catalytic cycle of ATP hydrolysis by human P-glycoprotein. The two ATP hydrolysis events in a single catalytic cycle are kinetically similar but affect different functional outcomes.
2001 Apr 13
Left ventricle and arteries: structure, function, hormones, and disease.
2001 Feb
Origins of heart rate variability: autonomic blockade of large magnitude, transient bradycardia in conscious rabbits.
2001 Feb
Lack of involvement of pertussis toxin-sensitive G-proteins in norepinephrine-induced vasoconstriction of rat aorta smooth muscle.
2001 Feb 15
Postjunctional alpha(2C)-adrenoceptor contractility in human saphenous vein.
2001 Feb 16
Sympathetic control of nasal blood flow in the rat mediated by alpha(1)-adrenoceptors.
2001 Feb 16
Unorthodox angiogenesis in skeletal muscle.
2001 Feb 16
Effects of losartan, prazosin and a vasopressin V1-receptor antagonist on renal and femoral blood flow in conscious sheep.
2001 Jan
[The efficacy and safety of terazosin and tamsulosin in patients with urinary disturbance accompanying prostatic hypertrophy].
2001 Jan
A quantitative analysis of antagonism and inverse agonism at wild-type and constitutively active hamster alpha1B-adrenoceptors.
2001 Jan
Alpha2-adrenoceptor-mediated inhibition of cultured sympathetic neurons: changes in alpha2A/D-adrenoceptor-deficient mice.
2001 Jan
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
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
Combined effect of terazosin and finasteride on apoptosis, cell proliferation, and transforming growth factor-beta expression in benign prostatic hyperplasia.
2001 Jan 1
Alpha1A- and alpha1B-adrenoceptors are the major subtypes in human saphenous vein.
2001 Jan 26
Effect of carvedilol on atrioventricular conduction in the ischemic heart.
2001 Jan 26
Hemorrhage-induced alpha-adrenergic signaling results in myocardial TNF-alpha expression and contractile dysfunction.
2001 Jul
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
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
Extracellular matrix proteins in cardiac fibroblasts derived from rat hearts with chronic pressure overload: effects of beta-receptor blockade.
2001 Mar
Enhancement of ATP release in hindlimb sympathetic perivascular nerve of the golden hamster during hibernation.
2001 Mar 1
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
Structure-hepatic disposition relationships for cationic drugs in isolated perfused rat livers: transmembrane exchange and cytoplasmic binding process.
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 Fri Dec 15 15:02:21 GMT 2023
Edited
by admin
on Fri Dec 15 15:02:21 GMT 2023
Record UNII
X0Z7454B90
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
PRAZOSIN HYDROCHLORIDE
EP   HSDB   JAN   MART.   MI   ORANGE BOOK   USAN   USP   USP-RS   VANDF   WHO-DD  
USAN  
Official Name English
MINIPRESS
Brand Name English
1-(4-Amino-6,7-dimethoxy-2-quinazolinyl)-4-(2-furoyl)piperazine monohydrochloride
Systematic Name English
MINIPRESS XL
Brand Name English
PRAZOSIN HCL
Common Name English
Prazosin hydrochloride [WHO-DD]
Common Name English
PRAZOSIN HYDROCHLORIDE [MI]
Common Name English
PRAZOSIN HYDROCHLORIDE [HSDB]
Common Name English
PRAZOSIN HYDROCHLORIDE COMPONENT OF MINIZIDE
Common Name English
PRAZOSIN HYDROCHLORIDE [USP MONOGRAPH]
Common Name English
PRAZOSIN HYDROCHLORIDE [USP-RS]
Common Name English
PRAZOSIN HYDROCHLORIDE [MART.]
Common Name English
PIPERAZINE, 1-(4-AMINO-6,7-DIMETHOXY-2-QUINAZOLINYL)-4-(2-FURANYLCARBONYL)-, MONOHYDROCHLORIDE
Common Name English
PRAZOSIN HYDROCHLORIDE [JAN]
Common Name English
MINIZIDE COMPONENT PRAZOSIN HYDROCHLORIDE
Common Name English
PRAZOSIN HYDROCHLORIDE [EP IMPURITY]
Common Name English
PRAZOSIN HYDROCHLORIDE [ORANGE BOOK]
Common Name English
PRAZOSIN HYDROCHLORIDE [EP MONOGRAPH]
Common Name English
PRAZOSIN HYDROCHLORIDE [USAN]
Common Name English
PRAZOSIN HYDROCHLORIDE [VANDF]
Common Name English
CP-12299-1
Code English
CP-12,299-1
Code English
Classification Tree Code System Code
NCI_THESAURUS C29713
Created by admin on Fri Dec 15 15:02:21 GMT 2023 , Edited by admin on Fri Dec 15 15:02:21 GMT 2023
NCI_THESAURUS C270
Created by admin on Fri Dec 15 15:02:21 GMT 2023 , Edited by admin on Fri Dec 15 15:02:21 GMT 2023
Code System Code Type Description
SMS_ID
100000091039
Created by admin on Fri Dec 15 15:02:21 GMT 2023 , Edited by admin on Fri Dec 15 15:02:21 GMT 2023
PRIMARY
ECHA (EC/EINECS)
242-903-4
Created by admin on Fri Dec 15 15:02:21 GMT 2023 , Edited by admin on Fri Dec 15 15:02:21 GMT 2023
PRIMARY
EPA CompTox
DTXSID50172822
Created by admin on Fri Dec 15 15:02:21 GMT 2023 , Edited by admin on Fri Dec 15 15:02:21 GMT 2023
PRIMARY
FDA UNII
X0Z7454B90
Created by admin on Fri Dec 15 15:02:21 GMT 2023 , Edited by admin on Fri Dec 15 15:02:21 GMT 2023
PRIMARY
MERCK INDEX
m9108
Created by admin on Fri Dec 15 15:02:21 GMT 2023 , Edited by admin on Fri Dec 15 15:02:21 GMT 2023
PRIMARY Merck Index
ChEMBL
CHEMBL2
Created by admin on Fri Dec 15 15:02:21 GMT 2023 , Edited by admin on Fri Dec 15 15:02:21 GMT 2023
PRIMARY
EVMPD
SUB04013MIG
Created by admin on Fri Dec 15 15:02:21 GMT 2023 , Edited by admin on Fri Dec 15 15:02:21 GMT 2023
PRIMARY
NCI_THESAURUS
C1507
Created by admin on Fri Dec 15 15:02:21 GMT 2023 , Edited by admin on Fri Dec 15 15:02:21 GMT 2023
PRIMARY
CAS
19237-84-4
Created by admin on Fri Dec 15 15:02:21 GMT 2023 , Edited by admin on Fri Dec 15 15:02:21 GMT 2023
PRIMARY
DAILYMED
X0Z7454B90
Created by admin on Fri Dec 15 15:02:21 GMT 2023 , Edited by admin on Fri Dec 15 15:02:21 GMT 2023
PRIMARY
RS_ITEM_NUM
1554705
Created by admin on Fri Dec 15 15:02:21 GMT 2023 , Edited by admin on Fri Dec 15 15:02:21 GMT 2023
PRIMARY
HSDB
3298
Created by admin on Fri Dec 15 15:02:21 GMT 2023 , Edited by admin on Fri Dec 15 15:02:21 GMT 2023
PRIMARY
RXCUI
203210
Created by admin on Fri Dec 15 15:02:21 GMT 2023 , Edited by admin on Fri Dec 15 15:02:21 GMT 2023
PRIMARY RxNorm
PUBCHEM
68546
Created by admin on Fri Dec 15 15:02:21 GMT 2023 , Edited by admin on Fri Dec 15 15:02:21 GMT 2023
PRIMARY
DRUG BANK
DBSALT000329
Created by admin on Fri Dec 15 15:02:21 GMT 2023 , Edited by admin on Fri Dec 15 15:02:21 GMT 2023
PRIMARY
CHEBI
8365
Created by admin on Fri Dec 15 15:02:21 GMT 2023 , Edited by admin on Fri Dec 15 15:02:21 GMT 2023
PRIMARY
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