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
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 |
|---|---|---|
| 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 |
|
| Papaverine, drug-induced stereotypy and catalepsy and biogenic amines in the brain of the rat. | 1976 Jul |
|
| Intraoperative assessment of aortoiliac stenosis: role of papaverine-induced hyperemia. | 1984 Dec |
|
| Drug-induced hepatitis associated with anticytoplasmic organelle autoantibodies. | 1985 Sep-Oct |
|
| Papaverine-induced chronic liver disease. | 1986 Apr |
|
| 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 |
|
| [Therapy of erectile dysfunction using papaverine--2 1/2 years' experience]. | 1988 Jul 30 |
|
| [Papaverine-induced priapism. Experiences with a new urologic emergency]. | 1989 Feb 10 |
|
| Papaverine-induced fibrosis of the corpus cavernosum. | 1989 Jan |
|
| 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 |
|
| 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 |
|
| Evaluation of natural products as inhibitors of human immunodeficiency virus type 1 (HIV-1) reverse transcriptase. | 1991 Jan-Feb |
|
| Non-invasive management of impotence with transcutaneous nitroglycerin. | 1992 Jan |
|
| QT prolongation and possibility of ventricular arrhythmias after intracoronary papaverine. | 1994 |
|
| Inhibition of adipocyte lipolysis by papaverine: papaverine can inhibit the redistribution of hormone-sensitive lipase. | 2000 |
|
| Transthoracic Doppler echocardiographic assessment of left anterior descending coronary artery and intramyocardial small coronary artery flow in patients with hypertrophic cardiomyopathy. | 2001 |
|
| [Efficacy of vascular therapy in complex of treatment of purulent necrotic foot ulcers in patients with diabetes mellitus]. | 2001 Feb |
|
| 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 |
|
| Inward remodeling follows chronic vasoconstriction in isolated resistance arteries. | 2002 Jan-Feb |
|
| Activation of the extraneuronal monoamine transporter (EMT) from rat expressed in 293 cells. | 2002 Nov |
|
| [The mechanisms underlying the formation of systemic hemodynamic reactions: role of initial vessel tone and arterial pressure]. | 2002 Nov-Dec |
|
| Adenosine receptors and phosphodiesterase inhibitors stimulate Cl- secretion in Calu-3 cells. | 2003 Sep |
|
| Identification, characterization and subcellular localization of TcPDE1, a novel cAMP-specific phosphodiesterase from Trypanosoma cruzi. | 2004 Feb 15 |
|
| Reactivity of the human internal thoracic artery to vasodilators in coronary artery bypass grafting. | 2004 Nov |
|
| Oral terbutaline in the management of pharmacologically induced prolonged erection. | 2004 Oct |
|
| Intra-arterial papaverine infusions for the treatment of cerebral vasospasm induced by aneurysmal subarachnoid hemorrhage. | 2005 |
|
| Development of an indirect competitive ELISA for the determination of papaverine. | 2005 May 15 |
|
| Haemodynamic changes after intracisternal papaverine instillation during intracranial aneurysmal surgery. | 2006 Dec |
|
| Inhibitory effects of coronary vasodilator papaverine on heterologously-expressed HERG currents in Xenopus oocytes. | 2007 Apr |
|
| Peyronie's reconstruction for maximum length and girth gain: geometrical principles. | 2008 |
|
| Unrecognized hand ischemia after intraarterial drug injection: successful management of a "near miss" event. | 2008 Dec 9 |
|
| [Acute embolization into the veins in the splanchnic bed--an overview of current methods of diagnosis and therapies]. | 2008 Nov |
|
| 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 |
|
| 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 |
|
| 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
by
admin
on
Edited
Fri Dec 16 22:32:53 UTC 2022
by
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on
Fri Dec 16 22:32:53 UTC 2022
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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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2053-26-1
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74925
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C97985
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218-149-7
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SUB14767MIG
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PARENT -> SALT/SOLVATE |
