Details
Stereochemistry | ACHIRAL |
Molecular Formula | C20H21NO4.H2O4S |
Molecular Weight | 437.464 |
Optical Activity | NONE |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
OS(O)(=O)=O.COC1=C(OC)C=C(CC2=NC=CC3=CC(OC)=C(OC)C=C23)C=C1
InChI
InChIKey=KYFCEOITJFJQGT-UHFFFAOYSA-N
InChI=1S/C20H21NO4.H2O4S/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;1-5(2,3)4/h5-8,10-12H,9H2,1-4H3;(H2,1,2,3,4)
Molecular Formula | H2O4S |
Molecular Weight | 98.078 |
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 |
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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 |
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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 |
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[Efficacy of intracisternal papaverine on symptomatic vasospasm]. | 1986 Jun |
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[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 |
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Pressor inhibition of angiotensin-induced ACTH secretion. | 1987 Nov |
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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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Serious ventricular dysrhythmias after intracoronary papaverine. | 1988 Dec 1 |
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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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Inhibitory effect of papaverine on HIV replication in vitro. | 1989 Apr |
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Papaverine-induced chest pain due to coronary vascular steal: demonstration with angiographic and intracoronary flow velocity measurements. | 1989 Aug |
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Intracoronary electrocardiogram during torsade des pointes secondary to intracoronary papaverine. | 1989 Dec |
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Comparison of the anti-respiratory syncytial virus activity and toxicity of papaverine hydrochloride and pyrazofurin in vitro and in vivo. | 1989 Feb |
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[Papaverine-induced priapism. Experiences with a new urologic emergency]. | 1989 Feb 10 |
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Papaverine-induced fibrosis of the corpus cavernosum. | 1989 Jan |
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[Epilepsy and hypertensive crisis after intracavernous injection of metaraminol in the treatment of priapism secondary to a papaverine test]. | 1989 May 20 |
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[The intracavernosal administration of papaverine in the diagnosis and treatment of sexual disorders in men]. | 1989 Oct |
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Intracavernous papaverine in the management of psychogenic impotence. | 1990 |
|
Intracavernous papaverine and glaucoma. | 1990 Aug 1 |
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Polymorphous ventricular tachycardia: a side effect of intracoronary papaverine. | 1990 Feb |
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Global and regional ventricular function following intracoronary application of papaverine. | 1991 |
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An improved vasoactive drug combination for a pharmacological erection program. | 1991 Dec |
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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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Double-blind, cross-over study comparing prostaglandin E1 and papaverine in patients with vasculogenic impotence. | 1991 Jun |
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QT prolongation and possibility of ventricular arrhythmias after intracoronary papaverine. | 1994 |
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Activation of the extraneuronal monoamine transporter (EMT) from rat expressed in 293 cells. | 2002 Nov |
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Papaverine blocks hKv1.5 channel current and human atrial ultrarapid delayed rectifier K+ currents. | 2003 Feb |
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Adenosine receptors and phosphodiesterase inhibitors stimulate Cl- secretion in Calu-3 cells. | 2003 Sep |
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Oral terbutaline in the management of pharmacologically induced prolonged erection. | 2004 Oct |
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[Sildenafil citrate in diagnosis of erectile dysfunction]. | 2005 Jul-Aug |
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Development of an indirect competitive ELISA for the determination of papaverine. | 2005 May 15 |
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Contractile responses of rabbit bladder neck to adrenaline, acetylcholine and papaverine after doxazosin treatment. | 2007 |
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Inhibitory effects of coronary vasodilator papaverine on heterologously-expressed HERG currents in Xenopus oocytes. | 2007 Apr |
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Vasorelaxant effect of iloprost on isolated human internal mammary artery. | 2007 Feb |
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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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[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 |
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Intracisternal irrigation of papaverine leading to choroidal infarction. | 2009 Nov |
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Phosphodiesterase 10A inhibitor activity in preclinical models of the positive, cognitive, and negative symptoms of schizophrenia. | 2009 Nov |
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Resolution of peripheral artery catheter-induced ischemic injury in infants -Two case reports-. | 2010 Aug |
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Carbon-11 labeled papaverine as a PET tracer for imaging PDE10A: radiosynthesis, in vitro and in vivo evaluation. | 2010 May |
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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 |
|
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
Fri Dec 15 17:35:14 GMT 2023
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Record UNII |
7A476JZB2T
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Record Status |
Validated (UNII)
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Record Version |
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C744
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C29707
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