Details
| Stereochemistry | ACHIRAL |
| Molecular Formula | C20H21NO4.BrH |
| Molecular Weight | 420.297 |
| Optical Activity | NONE |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
Br.COC1=C(OC)C=C(CC2=NC=CC3=CC(OC)=C(OC)C=C23)C=C1
InChI
InChIKey=ZOTOKALDLZHMJP-UHFFFAOYSA-N
InChI=1S/C20H21NO4.BrH/c1-22-17-6-5-13(10-18(17)23-2)9-16-15-12-20(25-4)19(24-3)11-14(15)7-8-21-16;/h5-8,10-12H,9H2,1-4H3;1H
| Molecular Formula | BrH |
| Molecular Weight | 80.912 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ACHIRAL |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Optical Activity | NONE |
| Molecular Formula | C20H21NO4 |
| Molecular Weight | 339.385 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ACHIRAL |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Optical Activity | NONE |
An alkaloid found in opium but not closely related to the other opium alkaloids in its structure or pharmacological actions. Papaverine is a vasodilating agent. Papaverine is used for the treating certain conditions that are accompanied by smooth muscle spasms (eg, blood vessel, urinary, gallbladder, or intestinal spasm). Papaverine is a nonxanthine phosphodiesterase inhibitor for the relief of cerebral and peripheral ischemia associated with arterial spasm and myocardial ischemia complicated by arrhythmias. The main actions of Papaverine are exerted on cardiac and smooth muscle. Like qathidine, Papaverine acts directly on the heart muscle to depress conduction and prolong the refractory period. Papaverine relaxes various smooth muscles. This relaxation may be prominent if spasm exists. The muscle cell is not paralyzed by Papaverine and still responds to drugs and other stimuli causing contraction. The antispasmodic effect is a direct one, and unrelated to muscle innervation. Papaverine is practically devoid of effects on the central nervous system. Papaverine relaxes the smooth musculature of the larger blood vessels, especially coronary, systemic peripheral, and pulmonary arteries. Papaverine is a potent, specific inhibitor of PDE10A. Papaverine for treatment of erectile dysfunction (ED) is excluded from coverage.
CNS Activity
Approval Year
Targets
| Primary Target | Pharmacology | Condition | Potency |
|---|---|---|---|
| 36.0 nM [IC50] | |||
Target ID: CHEMBL613758 |
|||
Target ID: CHEMBL2916 |
60.0 µM [IC50] | ||
Target ID: CHEMBL240 |
0.58 µM [IC50] |
Conditions
| Condition | Modality | Targets | Highest Phase | Product |
|---|---|---|---|---|
| Primary | Papaverine Approved UsePapaverine is recommended in various conditions accompanied by spasm of smooth muscle, such as vascular spasm associated with acute myocardial infarction (coronary occlusion), angina pectoris, peripheral and pulmonary embolism, peripheral vascular disease in which there is a vasospastic element, or certain cerebral angiospastic states; and visceral spasm, as in ureteral, biliary, or gastrointestinal colic. |
PubMed
| Title | Date | PubMed |
|---|---|---|
| Spasmolytic constituents of Cedrus deodara (Roxb.) Loud: pharmacological evaluation of himachalol. | 1975 Feb |
|
| Intraoperative assessment of aortoiliac stenosis: role of papaverine-induced hyperemia. | 1984 Dec |
|
| Validation in dogs of a rapid digital angiographic technique to measure relative coronary blood flow during routine cardiac catheterization. | 1985 Jan 1 |
|
| Drug-induced hepatitis associated with anticytoplasmic organelle autoantibodies. | 1985 Sep-Oct |
|
| Papaverine-induced chronic liver disease. | 1986 Apr |
|
| Maintenance treatment of erectile impotence by cavernosal unstriated muscle relaxant injection. | 1986 Aug |
|
| [Efficacy of intracisternal papaverine on symptomatic vasospasm]. | 1986 Jun |
|
| [Intracavernous injection of papaverine hydrochloride for impotence in patients with spinal cord injury]. | 1987 Jul |
|
| Incompatibility of Hexabrix and papaverine in peripheral arteriography. | 1987 Mar |
|
| Pressor inhibition of angiotensin-induced ACTH secretion. | 1987 Nov |
|
| Papaverine-induced coma. | 1988 |
|
| Diagnosis of male impotence after intracavernous papaverine test. | 1988 |
|
| Serious ventricular dysrhythmias after intracoronary papaverine. | 1988 Dec 1 |
|
| [Long-term experiences with autoinjection therapy of papaverine in erectile dysfunction]. | 1988 Jan |
|
| [Therapy of erectile dysfunction using papaverine--2 1/2 years' experience]. | 1988 Jul 30 |
|
| Inhibitory effect of papaverine on HIV replication in vitro. | 1989 Apr |
|
| Papaverine-induced chest pain due to coronary vascular steal: demonstration with angiographic and intracoronary flow velocity measurements. | 1989 Aug |
|
| Intracoronary electrocardiogram during torsade des pointes secondary to intracoronary papaverine. | 1989 Dec |
|
| Comparison of the anti-respiratory syncytial virus activity and toxicity of papaverine hydrochloride and pyrazofurin in vitro and in vivo. | 1989 Feb |
|
| [Papaverine-induced priapism. Experiences with a new urologic emergency]. | 1989 Feb 10 |
|
| Papaverine-induced fibrosis of the corpus cavernosum. | 1989 Jan |
|
| [Epilepsy and hypertensive crisis after intracavernous injection of metaraminol in the treatment of priapism secondary to a papaverine test]. | 1989 May 20 |
|
| [The intracavernosal administration of papaverine in the diagnosis and treatment of sexual disorders in men]. | 1989 Oct |
|
| Intracavernous papaverine in the management of psychogenic impotence. | 1990 |
|
| Ventricular arrhythmia due to intracoronary papaverine: analysis of QT intervals and coronary vasodilatory reserve. | 1990 Apr |
|
| Intracavernous papaverine and glaucoma. | 1990 Aug 1 |
|
| Polymorphous ventricular tachycardia: a side effect of intracoronary papaverine. | 1990 Feb |
|
| Determination of coronary flow reserve by digital angiography: validation of a practical method not requiring power injection or electrocardiographic gating. | 1990 Jul |
|
| [Priapism as a complication of the treatment of impotence by local injections of papaverine]. | 1990 Sep 1-15 |
|
| Torsades de pointes after intracoronary papaverine. | 1991 Feb |
|
| Intracavernous injection of prostaglandin E1 in combination with papaverine: enhanced effectiveness in comparison with papaverine plus phentolamine and prostaglandin E1 alone. | 1991 Jan |
|
| A lethal complication of papaverine-induced priapism. | 1991 Jan |
|
| Double-blind, cross-over study comparing prostaglandin E1 and papaverine in patients with vasculogenic impotence. | 1991 Jun |
|
| QT prolongation and possibility of ventricular arrhythmias after intracoronary papaverine. | 1994 |
|
| Peyronie's reconstruction for maximum length and girth gain: geometrical principles. | 2008 |
|
| [Acute embolization into the veins in the splanchnic bed--an overview of current methods of diagnosis and therapies]. | 2008 Nov |
|
| Severe hypotension with intracisternal application of papaverine after clipping of an intracranial aneurysm. | 2009 Dec |
|
| Intracisternal irrigation of papaverine leading to choroidal infarction. | 2009 Nov |
|
| Phosphodiesterase 10A inhibitor activity in preclinical models of the positive, cognitive, and negative symptoms of schizophrenia. | 2009 Nov |
|
| Resolution of peripheral artery catheter-induced ischemic injury in infants -Two case reports-. | 2010 Aug |
|
| Vascular smooth muscle contraction/relaxation of rat carotid artery is not altered by bone grafting substitutes in vitro. | 2010 Jun |
|
| Intravascular ultrasound study and evidence of pathological coronary flow reserve in patients with isolated coronary artery aneurysms. | 2010 Mar |
|
| Micro computed tomography for vascular exploration. | 2010 Mar 5 |
|
| Carbon-11 labeled papaverine as a PET tracer for imaging PDE10A: radiosynthesis, in vitro and in vivo evaluation. | 2010 May |
|
| Antibodies against gonadotropin-releasing hormone (GnRH) and destruction of enteric neurons in 3 patients suffering from gastrointestinal dysfunction. | 2010 May 20 |
|
| New endovascular method for transvascular exit of arteries and veins: developed in simulator, in rat and in rabbit with full clinical integration. | 2010 May 3 |
|
| The modulation of protein kinase A and heat shock protein 70 is involved in the reversible increase of blood-brain tumor barrier permeability induced by papaverine. | 2010 Nov 20 |
|
| Cardiac arrest after intracisternal papaverine instillation during intracranial aneurysm surgery. Case report. | 2010 Oct |
|
| Synthesis, in vivo occupancy, and radiolabeling of potent phosphodiesterase subtype-10 inhibitors as candidates for positron emission tomography imaging. | 2011 Aug 25 |
|
| A HAMP promoter bioassay system for identifying chemical compounds that modulate hepcidin expression. | 2015 May |
Patents
Sample Use Guides
Papaverine Hydrochloride may be administered intravenously or intramuscularly. The intravenous route is recommended when an immediate effect is desired, but the drug must be injected slowly over the course of 1 or 2 minutes to avoid uncomfortable or alarming side effects.
Parenteral administration of papaverine hydrochloride in doses of 1 to 4 mL is repeated every 3 hours as indicated. In the treatment of cardiac extrasystoles, 2 doses may be given 10 minutes apart.
Route of Administration:
Parenteral
| Substance Class |
Chemical
Created
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admin
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Edited
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| Record UNII |
91M28639H5
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| Record Status |
Validated (UNII)
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| Record Version |
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