Details
| Stereochemistry | ACHIRAL |
| Molecular Formula | C20H21NO4.ClH |
| Molecular Weight | 375.846 |
| Optical Activity | NONE |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
Cl.COC1=C(OC)C=C(CC2=NC=CC3=CC(OC)=C(OC)C=C23)C=C1
InChI
InChIKey=UOTMYNBWXDUBNX-UHFFFAOYSA-N
InChI=1S/C20H21NO4.ClH/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
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 |
|
| 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 |
|
| Serious ventricular dysrhythmias after intracoronary papaverine. | 1988 Dec 1 |
|
| 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 |
|
| 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 |
|
| 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 |
|
| 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 |
|
| 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 |
|
| 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 |
|
| Intracoronary papaverine and complete atrioventricular block. | 1992 Oct 10 |
|
| QT prolongation and possibility of ventricular arrhythmias after intracoronary papaverine. | 1994 |
|
| [Acute ischemia of the hand in a drug addict after accidental intra-arterial injection]. | 2002 |
|
| 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 |
|
| Papaverine blocks hKv1.5 channel current and human atrial ultrarapid delayed rectifier K+ currents. | 2003 Feb |
|
| Adenosine receptors and phosphodiesterase inhibitors stimulate Cl- secretion in Calu-3 cells. | 2003 Sep |
|
| Intra-arterial papaverine infusions for the treatment of cerebral vasospasm induced by aneurysmal subarachnoid hemorrhage. | 2005 |
|
| The surgical treatment of Peyronie's disease: replacement of plaque by free autograft of buccal mucosa. | 2005 Jul |
|
| Haemodynamic changes after intracisternal papaverine instillation during intracranial aneurysmal surgery. | 2006 Dec |
|
| [Short history of erectile dysfunction treatment]. | 2006 Dec 6 |
|
| 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 |
|
| 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 |
|
| 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 |
|
| 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 |
|
| Cardiac arrest after intracisternal papaverine instillation during intracranial aneurysm surgery. Case report. | 2010 Oct |
|
| 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
| Name | Type | Language | ||
|---|---|---|---|---|
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Systematic Name | English | ||
|
Code | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Systematic Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English |
| Classification Tree | Code System | Code | ||
|---|---|---|---|---|
|
NCI_THESAURUS |
C29707
Created by
admin on Fri Dec 15 15:03:40 GMT 2023 , Edited by admin on Fri Dec 15 15:03:40 GMT 2023
|
||
|
NCI_THESAURUS |
C744
Created by
admin on Fri Dec 15 15:03:40 GMT 2023 , Edited by admin on Fri Dec 15 15:03:40 GMT 2023
|
| Code System | Code | Type | Description | ||
|---|---|---|---|---|---|
|
SUB14763MIG
Created by
admin on Fri Dec 15 15:03:40 GMT 2023 , Edited by admin on Fri Dec 15 15:03:40 GMT 2023
|
PRIMARY | |||
|
35443
Created by
admin on Fri Dec 15 15:03:40 GMT 2023 , Edited by admin on Fri Dec 15 15:03:40 GMT 2023
|
PRIMARY | |||
|
6084
Created by
admin on Fri Dec 15 15:03:40 GMT 2023 , Edited by admin on Fri Dec 15 15:03:40 GMT 2023
|
PRIMARY | |||
|
200-502-1
Created by
admin on Fri Dec 15 15:03:40 GMT 2023 , Edited by admin on Fri Dec 15 15:03:40 GMT 2023
|
PRIMARY | |||
|
23473EC6BQ
Created by
admin on Fri Dec 15 15:03:40 GMT 2023 , Edited by admin on Fri Dec 15 15:03:40 GMT 2023
|
PRIMARY | |||
|
203132
Created by
admin on Fri Dec 15 15:03:40 GMT 2023 , Edited by admin on Fri Dec 15 15:03:40 GMT 2023
|
PRIMARY | RxNorm | ||
|
CHEMBL19224
Created by
admin on Fri Dec 15 15:03:40 GMT 2023 , Edited by admin on Fri Dec 15 15:03:40 GMT 2023
|
PRIMARY | |||
|
C80006
Created by
admin on Fri Dec 15 15:03:40 GMT 2023 , Edited by admin on Fri Dec 15 15:03:40 GMT 2023
|
PRIMARY | |||
|
61-25-6
Created by
admin on Fri Dec 15 15:03:40 GMT 2023 , Edited by admin on Fri Dec 15 15:03:40 GMT 2023
|
PRIMARY | |||
|
100000091716
Created by
admin on Fri Dec 15 15:03:40 GMT 2023 , Edited by admin on Fri Dec 15 15:03:40 GMT 2023
|
PRIMARY | |||
|
1496008
Created by
admin on Fri Dec 15 15:03:40 GMT 2023 , Edited by admin on Fri Dec 15 15:03:40 GMT 2023
|
PRIMARY | |||
|
PAPAVERINE HYDROCHLORIDE
Created by
admin on Fri Dec 15 15:03:40 GMT 2023 , Edited by admin on Fri Dec 15 15:03:40 GMT 2023
|
PRIMARY | Description: Colourless crystals or a white, crystalline powder; odourless. Solubility: Sparingly soluble in water; soluble in 120 parts of ethanol (~750 g/l) TS; practically insoluble in ether R. Category: Spasmolytic. Storage: Papaverine hydrochloride should be kept in a well-closed container, protected from light. Definition. Papaverine hydrochloride contains not less than 98.5% and not more than 101.0% of C20H21NO4,HCl, calculated withreference to the dried substance. | ||
|
23473EC6BQ
Created by
admin on Fri Dec 15 15:03:40 GMT 2023 , Edited by admin on Fri Dec 15 15:03:40 GMT 2023
|
PRIMARY | |||
|
DBSALT000412
Created by
admin on Fri Dec 15 15:03:40 GMT 2023 , Edited by admin on Fri Dec 15 15:03:40 GMT 2023
|
PRIMARY | |||
|
DTXSID9025825
Created by
admin on Fri Dec 15 15:03:40 GMT 2023 , Edited by admin on Fri Dec 15 15:03:40 GMT 2023
|
PRIMARY | |||
|
m8392
Created by
admin on Fri Dec 15 15:03:40 GMT 2023 , Edited by admin on Fri Dec 15 15:03:40 GMT 2023
|
PRIMARY | Merck Index | ||
|
61-25-6
Created by
admin on Fri Dec 15 15:03:40 GMT 2023 , Edited by admin on Fri Dec 15 15:03:40 GMT 2023
|
PRIMARY |
ACTIVE MOIETY
SUBSTANCE RECORD
