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
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)
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
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
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Target ID: CHEMBL2094251 Sources: https://www.ncbi.nlm.nih.gov/pubmed/9135028 |
2.0 nM [Kd] | ||
Target ID: CHEMBL229 Sources: https://www.ncbi.nlm.nih.gov/pubmed/25557493 |
0.04 nM [Ki] | ||
Target ID: CHEMBL232 Sources: https://www.ncbi.nlm.nih.gov/pubmed/9888842 |
0.28 nM [Ki] | ||
Target ID: CHEMBL223 Sources: https://www.ncbi.nlm.nih.gov/pubmed/24365159 |
0.42 nM [Ki] |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
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Primary | MINIPRESS Approved UsePrazosin 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 Date1976 |
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Primary | MINIPRESS Approved UsePrazosin 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 Date1976 |
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Primary | MINIPRESS Approved UsePrazosin 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 Date1976 |
Cmax
Value | Dose | Co-administered | Analyte | Population |
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40 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/7379445/ |
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
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
281 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/7379445/ |
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
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
5.8 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/7379445/ |
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
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
7.5% EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/7379445/ |
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 |
PubMed
Title | Date | PubMed |
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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 |
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Accurate mass measurement of synthetic analogues of prazosine by matrix-assisted laser desorption/ionisation time-of-flight mass spectrometry. | 2001 |
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Diabetes-induced changes in retinal NAD-redox status: pharmacological modulation and implications for pathogenesis of diabetic retinopathy. | 2001 |
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Hypoxic-ischaemic brain damage in immature rats: effects of adrenoceptor modulation. | 2001 |
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Lower urinary tract symptoms suggestive of benign prostatic obstruction--Triumph: the role of general practice databases. | 2001 |
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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 |
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Expression and functional characterization of the mt1 melatonin receptor from rat brain in Xenopus oocytes: evidence for coupling to the phosphoinositol pathway. | 2001 Apr |
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Hemodynamic effects of a combination of prazosin and terlipressin in patients with viral cirrhosis. | 2001 Apr |
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Effect of alpha-adrenoceptor agents on imipramine-induced antinociception in nerve-ligated mice. | 2001 Apr |
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The short-term effects of terazosin in Japanese men with benign prostatic hyperplasia. | 2001 Apr |
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Effect of the blood substitute diaspirin crosslinked hemoglobin in rat mesenteric and human radial collateral arteries. | 2001 Apr |
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MEK1/2-ERK1/2 mediates alpha1-adrenergic receptor-stimulated hypertrophy in adult rat ventricular myocytes. | 2001 Apr |
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Effect of KMD-3213, an alpha1A-adrenoceptor antagonist, on the prostatic urethral pressure and blood pressure in male decerebrate dogs. | 2001 Apr |
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Determinants of terminal mesenteric artery resistance during the first postnatal month. | 2001 Apr |
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A61603-induced vasoconstriction in porcine carotid vasculature: involvement of a non-adrenergic mechanism. | 2001 Apr 13 |
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The noradrenaline-dopamine interaction in the rat medial prefrontal cortex studied by multi-probe microdialysis. | 2001 Apr 27 |
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beta-Adrenergic stimulation synchronizes intracellular Ca(2+) release during excitation-contraction coupling in cardiac myocytes. | 2001 Apr 27 |
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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 |
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Call for global snake-bite control and procurement funding. | 2001 Apr 7 |
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Cis- and trans-N-benzyl-octahydrobenzo[g]quinolines. Adrenergic and dopaminergic activity studies. | 2001 Apr 9 |
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Chronic vasodilation induces matrix metalloproteinase 9 (MMP-9) expression during microvascular remodeling in rat skeletal muscle. | 2001 Feb |
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[A randomized comparative study assessing once versus twice a day treatment of benign prostatic hyperplasia with terazosin]. | 2001 Feb |
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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 |
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Effects of losartan, prazosin and a vasopressin V1-receptor antagonist on renal and femoral blood flow in conscious sheep. | 2001 Jan |
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Enhancer aided in vitro permeation of atenolol and prazosin hydrochloride through mice skin. | 2001 Jan |
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Hemorrhage-induced alpha-adrenergic signaling results in myocardial TNF-alpha expression and contractile dysfunction. | 2001 Jul |
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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 |
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alpha-1 and alpha-2 Adrenergic antagonists relieve thermal hyperalgesia in experimental mononeuropathy from chronic constriction injury. | 2001 Jun |
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Vascular actions of MDMA involve alpha1 and alpha2-adrenoceptors in the anaesthetized rat. | 2001 Jun |
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Noradrenaline modulates oyster hemocyte phagocytosis via a beta-adrenergic receptor-cAMP signaling pathway. | 2001 Jun |
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Comparison of prazosin, terazosin and tamsulosin: functional and binding studies in isolated prostatic and vascular human tissues. | 2001 Jun 1 |
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Synthesis, biological evaluation, and pharmacophore generation of new pyridazinone derivatives with affinity toward alpha(1)- and alpha(2)-adrenoceptors. | 2001 Jun 21 |
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A functional assay for detection of the mitoxantrone resistance protein, MXR (ABCG2). | 2001 Jun 6 |
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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 |
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In the formalin model of tonic nociceptive pain, 8-OH-DPAT produces 5-HT1A receptor-mediated, behaviorally specific analgesia. | 2001 Jun 8 |
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Enduring vulnerability to transient reinstatement of hemiplegia by prazosin after traumatic brain injury. | 2001 Mar |
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Characterization of [3H]CGP 12177 binding to beta-adrenergic receptors in intact eel hepatocytes. | 2001 Mar |
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Morphological and functional in vitro and in vivo characterization of the mouse corpus cavernosum. | 2001 Mar |
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The role of several alpha(1)- and alpha(2)-adrenoceptor subtypes mediating vasoconstriction in the canine external carotid circulation. | 2001 Mar |
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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 |
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Modulation of MK-801-induced behaviour by noradrenergic agents in mice. | 2001 Mar 1 |
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Effect of JTH-601, a putative alpha(1L)-adrenoceptor antagonist, on guinea pig nasal mucosa vasculature. | 2001 Mar 23 |
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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 |
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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 |
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Evaluating adverse cardiovascular effects of drug treatment for benign prostatic hyperplasia (BPH): methodological considerations. | 2001 May |
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Identification and localization of three photobinding sites of iodoarylazidoprazosin in hamster P-glycoprotein. | 2001 May |
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Structure-hepatic disposition relationships for cationic drugs in isolated perfused rat livers: transmembrane exchange and cytoplasmic binding process. | 2001 May |
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Noradrenaline modulates hemocyte reactive oxygen species production via beta-adrenergic receptors in the oyster Crassostrea gigas. | 2001 May |
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Interaction of formamidine pesticides with the presynaptic alpha(2)-adrenoceptor regulating. | 2001 May 1 |
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Role of G(i)-proteins in norepinephrine-mediated vasoconstriction in rat tail artery smooth muscle. | 2001 May 1 |
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
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/19241077
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).
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C29713
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QC02LE01
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C270
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C02CA01
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C02LE01
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N0000175553
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N0000000099
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QC02CA01
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LIVERTOX |
NBK548699
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DB00457
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Prazosin
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ACTIVE MOIETY
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