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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
Structure of PAPAVERINE HYDROBROMIDE

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

HIDE SMILES / InChI

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

Curator's Comment: CNS active in animal models, but it is practically devoid of effects on the central nervous system in humans. When administered chronically to mice, Papaverine produced motor and cognitive deficits and increased anxiety, but conversely could produce an antipsychotic effect.

Originator

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

TargetsConditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Papaverine

Approved Use

Papaverine 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

PubMed

TitleDatePubMed
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
Drug-induced hepatitis associated with anticytoplasmic organelle autoantibodies.
1985 Sep-Oct
Papaverine-induced chronic liver disease.
1986 Apr
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
Papaverine-induced coma.
1988
Diagnosis of male impotence after intracavernous papaverine test.
1988
[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
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
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
QT prolongation and possibility of ventricular arrhythmias after intracoronary papaverine.
1994
Cloning and characterization of PDE7B, a cAMP-specific phosphodiesterase.
2000 Jan 4
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
Treatment of cerebral vasospasm with biocompatible controlled-release systems for intracranial drug delivery.
2008 Dec
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
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 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
by admin
on Sat Dec 16 02:01:12 UTC 2023
Edited
by admin
on Sat Dec 16 02:01:12 UTC 2023
Record UNII
91M28639H5
Record Status Validated (UNII)
Record Version
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Name Type Language
PAPAVERINE HYDROBROMIDE
WHO-DD  
Common Name English
Papaverine hydrobromide [WHO-DD]
Common Name English
ISOQUINOLINE, 1-((3,4-DIMETHOXYPHENYL)METHYL)-6,7-DIMETHOXY-, HYDROBROMIDE (1:1)
Systematic Name English
Code System Code Type Description
SMS_ID
100000079722
Created by admin on Sat Dec 16 02:01:13 UTC 2023 , Edited by admin on Sat Dec 16 02:01:13 UTC 2023
PRIMARY
FDA UNII
91M28639H5
Created by admin on Sat Dec 16 02:01:13 UTC 2023 , Edited by admin on Sat Dec 16 02:01:13 UTC 2023
PRIMARY
EPA CompTox
DTXSID90210515
Created by admin on Sat Dec 16 02:01:13 UTC 2023 , Edited by admin on Sat Dec 16 02:01:13 UTC 2023
PRIMARY
PUBCHEM
3083940
Created by admin on Sat Dec 16 02:01:13 UTC 2023 , Edited by admin on Sat Dec 16 02:01:13 UTC 2023
PRIMARY
CAS
6152-78-9
Created by admin on Sat Dec 16 02:01:13 UTC 2023 , Edited by admin on Sat Dec 16 02:01:13 UTC 2023
PRIMARY
ECHA (EC/EINECS)
228-166-1
Created by admin on Sat Dec 16 02:01:13 UTC 2023 , Edited by admin on Sat Dec 16 02:01:13 UTC 2023
PRIMARY
EVMPD
SUB14762MIG
Created by admin on Sat Dec 16 02:01:13 UTC 2023 , Edited by admin on Sat Dec 16 02:01:13 UTC 2023
PRIMARY
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