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
Originator
Sources: https://www.ncbi.nlm.nih.gov/pubmed/20494383
Curator's Comment: Papaverine is a benzylisoquinoline alkaloid that was discovered by Merck (1848) as a minor (ca. 1%) component in the latex of the opium poppy (Papaver somniferum L.). # Merck
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
36.0 nM [IC50] | |||
Target ID: CHEMBL613758 |
|||
Target ID: CHEMBL2916 Sources: https://www.ncbi.nlm.nih.gov/pubmed/25111025 |
60.0 µM [IC50] | ||
Target ID: CHEMBL240 Sources: https://www.ncbi.nlm.nih.gov/pubmed/19034039 |
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 |
---|---|---|
The anti-fibrillation action of papaverine and its value in cardiac resuscitation after chloroform-adrenaline ventricular fibrillation in dogs. | 1948 Apr |
|
Spasmolytic constituents of Cedrus deodara (Roxb.) Loud: pharmacological evaluation of himachalol. | 1975 Feb |
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Validation in dogs of a rapid digital angiographic technique to measure relative coronary blood flow during routine cardiac catheterization. | 1985 Jan 1 |
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Drug-induced hepatitis associated with anticytoplasmic organelle autoantibodies. | 1985 Sep-Oct |
|
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 |
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Incompatibility of Hexabrix and papaverine in peripheral arteriography. | 1987 Mar |
|
Pressor inhibition of angiotensin-induced ACTH secretion. | 1987 Nov |
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Papaverine-induced coma. | 1988 |
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[Long-term experiences with autoinjection therapy of papaverine in erectile dysfunction]. | 1988 Jan |
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[Therapy of erectile dysfunction using papaverine--2 1/2 years' experience]. | 1988 Jul 30 |
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Papaverine-induced chest pain due to coronary vascular steal: demonstration with angiographic and intracoronary flow velocity measurements. | 1989 Aug |
|
[Papaverine-induced priapism. Experiences with a new urologic emergency]. | 1989 Feb 10 |
|
[Epilepsy and hypertensive crisis after intracavernous injection of metaraminol in the treatment of priapism secondary to a papaverine test]. | 1989 May 20 |
|
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 |
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Global and regional ventricular function following intracoronary application of papaverine. | 1991 |
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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 |
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A lethal complication of papaverine-induced priapism. | 1991 Jan |
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Double-blind, cross-over study comparing prostaglandin E1 and papaverine in patients with vasculogenic impotence. | 1991 Jun |
|
Non-invasive management of impotence with transcutaneous nitroglycerin. | 1992 Jan |
|
QT prolongation and possibility of ventricular arrhythmias after intracoronary papaverine. | 1994 |
|
Development of an indirect competitive ELISA for the determination of papaverine. | 2005 May 15 |
|
Inhibitory effects of coronary vasodilator papaverine on heterologously-expressed HERG currents in Xenopus oocytes. | 2007 Apr |
|
Predicting blood pressure improvement in hypertensive patients after renal artery stent placement: renal fractional flow reserve. | 2007 Apr 1 |
|
Vasorelaxant effect of iloprost on isolated human internal mammary artery. | 2007 Feb |
|
Extraction and determination of papaverin in pericarpium papaveris using aqueous two-phase system of poly(ethylene glycol)-(NH4)2SO4 coupled with high-performance liquid chromatography. | 2007 May 8 |
|
Transient facial nerve palsy after topical papaverine application during vestibular schwannoma surgery. Case report. | 2007 Nov |
|
Peyronie's reconstruction for maximum length and girth gain: geometrical principles. | 2008 |
|
[X-ray densitometric measurement of myocardial perfusion reserve in symptomatic patients without angiographically detectable coronary stenoses]. | 2008 Apr |
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Treatment of cerebral vasospasm with biocompatible controlled-release systems for intracranial drug delivery. | 2008 Dec |
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Pharmacologic profiling of human and rat cytochrome P450 1A1 and 1A2 induction and competition. | 2008 Dec |
|
Unrecognized hand ischemia after intraarterial drug injection: successful management of a "near miss" event. | 2008 Dec 9 |
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Insulin resistance functionally limits endothelium-dependent coronary vasodilation in nondiabetic patients. | 2008 Jan |
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[Acute embolization into the veins in the splanchnic bed--an overview of current methods of diagnosis and therapies]. | 2008 Nov |
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Adverse effects of topical papaverine on auditory nerve function. | 2008 Sep |
|
Severe hypotension with intracisternal application of papaverine after clipping of an intracranial aneurysm. | 2009 Dec |
|
Abnormal responses of the human cerebral microcirculation to papaverin during aneurysm surgery. | 2009 Jan |
|
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 |
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Micro computed tomography for vascular exploration. | 2010 Mar 5 |
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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 |
|
Cardiac arrest after intracisternal papaverine instillation during intracranial aneurysm surgery. Case report. | 2010 Oct |
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
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/27860455
In bovine cauda epididymal and ejaculated spermatozoa, the major cAMP-PDE activity was papaverine-sensitive (44.5% and 57.5%, respectively, at 400 nm of papaverine).
Substance Class |
Chemical
Created
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admin
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Edited
Sat Dec 16 02:01:12 GMT 2023
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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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