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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
Structure of PAPAVERINE SULFATE

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)

HIDE SMILES / InChI

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

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
Maintenance treatment of erectile impotence by cavernosal unstriated muscle relaxant injection.
1986 Aug
Serious ventricular dysrhythmias after intracoronary papaverine.
1988 Dec 1
Intracoronary electrocardiogram during torsade des pointes secondary to intracoronary papaverine.
1989 Dec
[Papaverine-induced priapism. Experiences with a new urologic emergency].
1989 Feb 10
[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
Determination of coronary flow reserve by digital angiography: validation of a practical method not requiring power injection or electrocardiographic gating.
1990 Jul
Intracavernous injection of prostaglandin E1 in combination with papaverine: enhanced effectiveness in comparison with papaverine plus phentolamine and prostaglandin E1 alone.
1991 Jan
Progressive treatment of erectile dysfunction with intracorporeal injections of different combinations of vasoactive agents.
1999 Feb
Inhibition of adipocyte lipolysis by papaverine: papaverine can inhibit the redistribution of hormone-sensitive lipase.
2000
Simple isoquinoline and benzylisoquinoline alkaloids as potential antimicrobial, antimalarial, cytotoxic, and anti-HIV agents.
2001 Nov
Short-term histopathologic effects of different intracavernosal agents on corpus cavernosum and antifibrotic activity of intracavernosal verapamil: an experimental study.
2001 Sep
[Acute ischemia of the hand in a drug addict after accidental intra-arterial injection].
2002
Accelerating tissue expansion by application of topical papaverine cream.
2004 Oct
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
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
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
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
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 Fri Dec 15 17:35:14 GMT 2023
Edited
by admin
on Fri Dec 15 17:35:14 GMT 2023
Record UNII
7A476JZB2T
Record Status Validated (UNII)
Record Version
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Name Type Language
PAPAVERINE SULFATE
WHO-DD  
Common Name English
Papaverine sulfate [WHO-DD]
Common Name English
PAPAVERINE SULPHATE (1:1)
Common Name English
ISOQUINOLINE, 1-((3,4-DIMETHOXYPHENYL)METHYL)-6,7-DIMETHOXY-, SULFATE (1:1)
Systematic Name English
PAPAVERINE SULPHATE
Common Name English
ISOQUINOLINE, 1-((3,4-DIMETHOXYPHENYL)METHYL)-6,7-DIMETHOXY-, SULPHATE (1:1)
Systematic Name English
SYNPAVERINE
Common Name English
PAPAVERINE SULFATE (1:1)
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C744
Created by admin on Fri Dec 15 17:35:14 GMT 2023 , Edited by admin on Fri Dec 15 17:35:14 GMT 2023
NCI_THESAURUS C29707
Created by admin on Fri Dec 15 17:35:14 GMT 2023 , Edited by admin on Fri Dec 15 17:35:14 GMT 2023
Code System Code Type Description
EPA CompTox
DTXSID70942701
Created by admin on Fri Dec 15 17:35:14 GMT 2023 , Edited by admin on Fri Dec 15 17:35:14 GMT 2023
PRIMARY
DRUG BANK
DBSALT002205
Created by admin on Fri Dec 15 17:35:14 GMT 2023 , Edited by admin on Fri Dec 15 17:35:14 GMT 2023
PRIMARY
CAS
2053-26-1
Created by admin on Fri Dec 15 17:35:14 GMT 2023 , Edited by admin on Fri Dec 15 17:35:14 GMT 2023
PRIMARY
PUBCHEM
74925
Created by admin on Fri Dec 15 17:35:14 GMT 2023 , Edited by admin on Fri Dec 15 17:35:14 GMT 2023
PRIMARY
NCI_THESAURUS
C97985
Created by admin on Fri Dec 15 17:35:14 GMT 2023 , Edited by admin on Fri Dec 15 17:35:14 GMT 2023
PRIMARY
SMS_ID
100000079724
Created by admin on Fri Dec 15 17:35:14 GMT 2023 , Edited by admin on Fri Dec 15 17:35:14 GMT 2023
PRIMARY
ECHA (EC/EINECS)
218-149-7
Created by admin on Fri Dec 15 17:35:14 GMT 2023 , Edited by admin on Fri Dec 15 17:35:14 GMT 2023
PRIMARY
EVMPD
SUB14767MIG
Created by admin on Fri Dec 15 17:35:14 GMT 2023 , Edited by admin on Fri Dec 15 17:35:14 GMT 2023
PRIMARY
FDA UNII
7A476JZB2T
Created by admin on Fri Dec 15 17:35:14 GMT 2023 , Edited by admin on Fri Dec 15 17:35:14 GMT 2023
PRIMARY
Related Record Type Details
PARENT -> SALT/SOLVATE