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 |
|---|---|---|
| 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 |
|
| 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 |
|
| [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 |
|
| Intracoronary electrocardiogram during torsade des pointes secondary to intracoronary papaverine. | 1989 Dec |
|
| [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 |
|
| Ventricular arrhythmia due to intracoronary papaverine: analysis of QT intervals and coronary vasodilatory reserve. | 1990 Apr |
|
| 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 |
|
| 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 |
|
| Development of an indirect competitive ELISA for the determination of papaverine. | 2005 May 15 |
|
| Treatment of cerebral vasospasm with biocompatible controlled-release systems for intracranial drug delivery. | 2008 Dec |
|
| Unrecognized hand ischemia after intraarterial drug injection: successful management of a "near miss" event. | 2008 Dec 9 |
|
| Insulin resistance functionally limits endothelium-dependent coronary vasodilation in nondiabetic patients. | 2008 Jan |
|
| [Acute embolization into the veins in the splanchnic bed--an overview of current methods of diagnosis and therapies]. | 2008 Nov |
|
| 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 |
|
| 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 |
|
| 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
by
admin
on
Edited
Sat Dec 17 13:25:43 UTC 2022
by
admin
on
Sat Dec 17 13:25:43 UTC 2022
|
| Record UNII |
91M28639H5
|
| Record Status |
Validated (UNII)
|
| Record Version |
|
-
Download
| Name | Type | Language | ||
|---|---|---|---|---|
|
Common Name | English | ||
|
Common Name | English | ||
|
Systematic Name | English |
| Code System | Code | Type | Description | ||
|---|---|---|---|---|---|
|
91M28639H5
Created by
admin on Sat Dec 17 13:25:43 UTC 2022 , Edited by admin on Sat Dec 17 13:25:43 UTC 2022
|
PRIMARY | |||
|
91M28639H5
Created by
admin on Sat Dec 17 13:25:43 UTC 2022 , Edited by admin on Sat Dec 17 13:25:43 UTC 2022
|
PRIMARY | |||
|
DTXSID90210515
Created by
admin on Sat Dec 17 13:25:43 UTC 2022 , Edited by admin on Sat Dec 17 13:25:43 UTC 2022
|
PRIMARY | |||
|
3083940
Created by
admin on Sat Dec 17 13:25:43 UTC 2022 , Edited by admin on Sat Dec 17 13:25:43 UTC 2022
|
PRIMARY | |||
|
6152-78-9
Created by
admin on Sat Dec 17 13:25:43 UTC 2022 , Edited by admin on Sat Dec 17 13:25:43 UTC 2022
|
PRIMARY | |||
|
228-166-1
Created by
admin on Sat Dec 17 13:25:43 UTC 2022 , Edited by admin on Sat Dec 17 13:25:43 UTC 2022
|
PRIMARY | |||
|
SUB14762MIG
Created by
admin on Sat Dec 17 13:25:43 UTC 2022 , Edited by admin on Sat Dec 17 13:25:43 UTC 2022
|
PRIMARY |
| Related Record | Type | Details | ||
|---|---|---|---|---|
|
SALT/SOLVATE -> PARENT |
| Related Record | Type | Details | ||
|---|---|---|---|---|
|
ACTIVE MOIETY |