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药品详细

Prazosin(哌唑嗪)

化学结构式图
中文名
哌唑嗪
英文名
Prazosin
分子式
C19H21N5O4
化学名
2-{4-[(furan-2-yl)carbonyl]piperazin-1-yl}-6,7-dimethoxyquinazolin-4-amine
分子量
Average: 383.4011
Monoisotopic: 383.159354185
CAS号
19216-56-9
ATC分类
C02C 未知
药物类型
small molecule
阶段
approved
商品名
Furazosin;Lentopres;Minipress (Pfizer);Minipress Xl (Pfizer);Vasoflex;
同义名
Prazocin;Prazosin HCl;Prazosin Hydrochloride;Prazosina [INN-Spanish];Prazosine [INN-French];Prazosinum [INN-Latin];
基本介绍

Prazosin is a selective α-1-adrenergic receptor antagonist used to treat hypertension. It has also been used to decrease urinary obstruction and relieve symptoms associated with symptomatic benign prostatic hyperplasia. α1-Receptors mediate contraction and hypertrophic growth of smooth muscle cells. Antagonism of these receptors leads to smooth muscle relaxation in the peripheral vasculature and prostate gland. Prazosin has also been used in conjunction with cardiac glycosides and diuretics in the management of severe congestive heart failure. It has also been used alone or in combination with β-blockers in the preoperative management of signs and symptoms of pheochromocytoma.

生产厂家
  • American therapeutics inc
  • Clonmel healthcare ltd
  • Ivax pharmaceuticals inc sub teva pharmaceuticals usa
  • Mylan pharmaceuticals inc
  • Pfizer inc
  • Pfizer laboratories div pfizer inc
  • Purepac pharmaceutical co
  • Sandoz inc
  • Watson laboratories inc
封装厂家
参考
Synthesis Reference Not Available
General Reference
  1. Bawaskar HS, Bawaskar PH: Utility of scorpion antivenin vs prazosin in the management of severe Mesobuthus tamulus (Indian red scorpion) envenoming at rural setting. J Assoc Physicians India. 2007 Jan;55:14-21. Pubmed
  2. Cushman WC, Ford CE, Cutler JA, Margolis KL, Davis BR, Grimm RH, Black HR, Hamilton BP, Holland J, Nwachuku C, Papademetriou V, Probstfield J, Wright JT Jr, Alderman MH, Weiss RJ, Piller L, Bettencourt J, Walsh SM: Success and predictors of blood pressure control in diverse North American settings: the antihypertensive and lipid-lowering treatment to prevent heart attack trial (ALLHAT). J Clin Hypertens (Greenwich). 2002 Nov-Dec;4(6):393-404. Pubmed
  3. Hiraoka Y, Taniguchi T, Tanaka T, Okada K, Kanamaru H, Muramatsu I: Pharmacological characterization of unique prazosin-binding sites in human kidney. Naunyn Schmiedebergs Arch Pharmacol. 2003 Jul;368(1):49-56. Epub 2003 Jun 25. Pubmed
  4. Sigma Aldrich Link
剂型
规格
化合物类型
Type small molecule
Classes
  • Quinazolines
Substructures
  • Quinazolines
  • Phenols and Derivatives
  • Amino Ketones
  • Aliphatic and Aryl Amines
  • Piperazines
  • Ethers
  • Benzene and Derivatives
  • Pyrimidines and Derivatives
  • Catechols
  • Heterocyclic compounds
  • Aromatic compounds
  • Anisoles
  • Carboxamides and Derivatives
  • Furans
  • Cyanamides
  • Phenyl Esters
适应症
ANTIHYPERTENSIVES 降血压;
药理
Indication For treatment of hypertension, symptomatic benign prostatic hyperplasia, and severe congestive heart failure. May also be used alone or in combination with β-blockers in the preoperative management of signs and symptoms of pheochromocytoma.
Pharmacodynamics Prazosin is an alpha-adrenergic blocking agent used to treat hypertension and benign prostatic hyperplasia. Accordingly, Prazosin is a selective inhibitor of the alpha1 subtype of alpha adrenergic receptors. In the human prostate, Prazosin antagonizes phenylephrine (alpha1 agonist)-induced contractions, in vitro, and binds with high affinity to the alpha1c adrenoceptor, which is thought to be the predominant functional type in the prostate. Studies in normal human subjects have shown that Prazosin competitively antagonized the pressor effects of phenylephrine (an alpha1 agonist) and the systolic pressor effect of norepinephrine. The antihypertensive effect of Prazosin results from a decrease in systemic vascular resistance and the parent compound Prazosin is primarily responsible for the antihypertensive activity.
Mechanism of action 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.
Absorption Well-absorbed from gastrointestinal tract; bioavailability is variable (50 to 85%).
Volume of distribution Not Available
Protein binding 97%
Metabolism
Primarily hepatic. Several metabolites have been identified in humans and animals (6- O -demethyl, 7- O -demethyl, 2-[1-piperazinyl]-4-amino-6, 7-dimethoxyquinazoline, 2,4-diamino-6,7-dimethoxyquinazoline).

Important The metabolism module of DrugBank is currently in beta. Questions or suggestions? Please contact us.

Substrate Enzymes Product
Prazosin
    		2,4-diamino-6,7-dimethoxyquinazoline Details
    Prazosin
      		6-O-demethyl,7-O-demethyl,2-[1-piperazinyl]-4-amino-6,7-dimethoxyquinazoline Details
      Route of elimination Animal studies indicate that prazosin hydrochloride is extensively metabolized, primarily by demethylation and conjugation, and excreted mainly via bile and feces. Less extensive human studies suggest similar metabolism and excretion in man.
      Half life 2-3 hours
      Clearance Not Available
      Toxicity Not Available
      Affected organisms
      • Humans and other mammals
      Pathways Not Available
      理化性质
      Properties
      State solid
      Experimental Properties
      Property Value Source
      melting point 279 °C PhysProp
      water solubility 0.5 mg/mL (HCl salt) Sigma Aldrich
      logP 1.3 Not Available
      Caco2 permeability -4.36 ADME Research, USCD
      Predicted Properties
      Property Value Source
      water solubility 6.93e-01 g/l ALOGPS
      logP 1.93 ALOGPS
      logP 1.65 ChemAxon
      logS -2.7 ALOGPS
      pKa (strongest basic) 7.24 ChemAxon
      physiological charge 1 ChemAxon
      hydrogen acceptor count 7 ChemAxon
      hydrogen donor count 1 ChemAxon
      polar surface area 106.95 ChemAxon
      rotatable bond count 4 ChemAxon
      refractivity 104.5 ChemAxon
      polarizability 40.49 ChemAxon
      药物相互作用
      Drug Interaction
      Acebutolol Risk of hypotension at the beginning of therapy
      Atenolol Risk of hypotension at the beginning of therapy
      Betaxolol Beta-Blockers such as betaxolol may enhance the orthostatic hypotensive effect of Alpha1-Blockers such as prazosin. The risk associated with ophthalmic products is probably less than systemic products. Exercise caution if an alpha1-blocker is added to existing beta-blocker therapy. Monitor for hypotension during first few days of concomitant therapy. A priori reduction in alpha1-blocker (especially systemic) dose may be warranted. Administering the first dose of systemic agents at bedtime may help minimize risk of severe hypotension. The risk associated with the use of ophthalmic products in either interacting group is probably less than that associated with systemic agents. If the alpha1-blocker is being used to treat BPH, consider using tamsulosin since its alpha1-A selectivity is least likely to cause hypotension.
      Bevantolol Risk of hypotension at the beginning of therapy
      Bisoprolol Risk of hypotension at the beginning of therapy
      Carteolol Risk of hypotension at the beginning of therapy
      Carvedilol Risk of hypotension at the beginning of therapy
      Dabigatran etexilate P-Glycoprotein inducers such as prazosin may decrease the serum concentration of dabigatran etexilate. This combination should be avoided.
      Digoxin Prazosin increases the effect of digoxin
      Esmolol Risk of hypotension at the beginning of therapy
      Labetalol Risk of hypotension at the beginning of therapy
      Metoprolol Risk of hypotension at the beginning of therapy
      Nadolol Risk of hypotension at the beginning of therapy
      Oxprenolol Risk of hypotension at the beginning of therapy
      Penbutolol Risk of hypotension at the beginning of therapy
      Pindolol Risk of hypotension at the beginning of therapy
      Practolol Risk of hypotension at the beginning of therapy
      Propranolol Risk of hypotension at the beginning of therapy
      Sotalol Risk of hypotension at the beginning of therapy
      Tadalafil Tadalafil may enhance the hypotensive effect of Prazosin. Monitor for hypotension during concomitant therapy.
      Tamsulosin Concomitant use of alpha1-adrenergic antagonists, Tamsulosin and Prazosin, may result in additive antihypertensive effects. Combination therapy is not recommended.
      Timolol Risk of hypotension at the beginning of therapy
      Treprostinil Additive hypotensive effect. Monitor antihypertensive therapy during concomitant use.
      Vardenafil Additive hypotensive effects of the PDE5 inhibitor, Vardenafil, and alpha1-blocker, Prazosin, may occur. Monitor for hypotension during concomitant therapy.
      Verapamil Risk of hypotension at the beginning of therapy
      食物相互作用
      • Avoid alcohol.
      • Avoid natural licorice.
      • Take without regard to meals.

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