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 |
|
Antagonism of levodopa by papaverine. | 1975 Feb 24 |
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Drug-induced hepatitis associated with anticytoplasmic organelle autoantibodies. | 1985 Sep-Oct |
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Papaverine-induced chronic liver disease. | 1986 Apr |
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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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Papaverine-induced coma. | 1988 |
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Diagnosis of male impotence after intracavernous papaverine test. | 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 |
|
Inhibitory effect of papaverine on HIV replication in vitro. | 1989 Apr |
|
Intracoronary electrocardiogram during torsade des pointes secondary to intracoronary papaverine. | 1989 Dec |
|
[Papaverine-induced priapism. Experiences with a new urologic emergency]. | 1989 Feb 10 |
|
Intracavernous papaverine and glaucoma. | 1990 Aug 1 |
|
[Priapism as a complication of the treatment of impotence by local injections of papaverine]. | 1990 Sep 1-15 |
|
Global and regional ventricular function following intracoronary application of papaverine. | 1991 |
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Torsades de pointes after intracoronary papaverine. | 1991 Feb |
|
The role of intracavernous injection of vasoactive medications for the restoration of erection in spinal cord injured males: a three year follow up. | 1992 Feb |
|
A comparative study with intracavernous injection of prostaglandin E1 versus papaverine for the diagnostic assessment of erectile impotence. | 1992 Nov |
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QT prolongation and possibility of ventricular arrhythmias after intracoronary papaverine. | 1994 |
|
Cloning and characterization of PDE7B, a cAMP-specific phosphodiesterase. | 2000 Jan 4 |
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Transthoracic Doppler echocardiographic assessment of left anterior descending coronary artery and intramyocardial small coronary artery flow in patients with hypertrophic cardiomyopathy. | 2001 |
|
Estimation of cerebral oxygenation and hemodynamics in cerebral vasospasm using indocyaningreen dye dilution and near infrared spectroscopy: a case report. | 2001 Jan |
|
Optimal time for predicting myocardial viability after successful primary angioplasty in acute myocardial infarction: a study using myocardial contrast echocardiography. | 2001 Mar 15 |
|
[Acute ischemia of the hand in a drug addict after accidental intra-arterial injection]. | 2002 |
|
Embolic activity subsequent to injection of the internal mammary artery with papaverine hydrochloride. | 2005 |
|
Intra-arterial papaverine infusions for the treatment of cerebral vasospasm induced by aneurysmal subarachnoid hemorrhage. | 2005 |
|
[Sildenafil citrate in diagnosis of erectile dysfunction]. | 2005 Jul-Aug |
|
Haemodynamic changes after intracisternal papaverine instillation during intracranial aneurysmal surgery. | 2006 Dec |
|
Vasorelaxant effect of iloprost on isolated human internal mammary artery. | 2007 Feb |
|
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 |
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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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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 |
|
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 |
|
Cardiac arrest after intracisternal papaverine instillation during intracranial aneurysm surgery. Case report. | 2010 Oct |
|
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
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 UTC 2023
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Record UNII |
91M28639H5
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Record Status |
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Record Version |
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