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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
Spasmolytic constituents of Cedrus deodara (Roxb.) Loud: pharmacological evaluation of himachalol.
1975 Feb
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
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
Incompatibility of Hexabrix and papaverine in peripheral arteriography.
1987 Mar
Pressor inhibition of angiotensin-induced ACTH secretion.
1987 Nov
Papaverine-induced coma.
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
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
[Epilepsy and hypertensive crisis after intracavernous injection of metaraminol in the treatment of priapism secondary to a papaverine test].
1989 May 20
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
Global and regional ventricular function following intracoronary application of papaverine.
1991
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
Double-blind, cross-over study comparing prostaglandin E1 and papaverine in patients with vasculogenic impotence.
1991 Jun
Non-invasive management of impotence with transcutaneous nitroglycerin.
1992 Jan
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
Inhibitory effects of coronary vasodilator papaverine on heterologously-expressed HERG currents in Xenopus oocytes.
2007 Apr
Predicting blood pressure improvement in hypertensive patients after renal artery stent placement: renal fractional flow reserve.
2007 Apr 1
Vasorelaxant effect of iloprost on isolated human internal mammary artery.
2007 Feb
Extraction and determination of papaverin in pericarpium papaveris using aqueous two-phase system of poly(ethylene glycol)-(NH4)2SO4 coupled with high-performance liquid chromatography.
2007 May 8
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
[X-ray densitometric measurement of myocardial perfusion reserve in symptomatic patients without angiographically detectable coronary stenoses].
2008 Apr
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
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
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
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
Cardiac arrest after intracisternal papaverine instillation during intracranial aneurysm surgery. Case report.
2010 Oct
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 GMT 2023
Edited
by admin
on Sat Dec 16 02:01:12 GMT 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 GMT 2023 , Edited by admin on Sat Dec 16 02:01:13 GMT 2023
PRIMARY
FDA UNII
91M28639H5
Created by admin on Sat Dec 16 02:01:13 GMT 2023 , Edited by admin on Sat Dec 16 02:01:13 GMT 2023
PRIMARY
EPA CompTox
DTXSID90210515
Created by admin on Sat Dec 16 02:01:13 GMT 2023 , Edited by admin on Sat Dec 16 02:01:13 GMT 2023
PRIMARY
PUBCHEM
3083940
Created by admin on Sat Dec 16 02:01:13 GMT 2023 , Edited by admin on Sat Dec 16 02:01:13 GMT 2023
PRIMARY
CAS
6152-78-9
Created by admin on Sat Dec 16 02:01:13 GMT 2023 , Edited by admin on Sat Dec 16 02:01:13 GMT 2023
PRIMARY
ECHA (EC/EINECS)
228-166-1
Created by admin on Sat Dec 16 02:01:13 GMT 2023 , Edited by admin on Sat Dec 16 02:01:13 GMT 2023
PRIMARY
EVMPD
SUB14762MIG
Created by admin on Sat Dec 16 02:01:13 GMT 2023 , Edited by admin on Sat Dec 16 02:01:13 GMT 2023
PRIMARY
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