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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
Structure of PAPAVERINE HYDROCHLORIDE

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

HIDE SMILES / InChI

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

Molecular Formula ClH
Molecular Weight 36.461
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
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
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
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
Papaverine-induced chest pain due to coronary vascular steal: demonstration with angiographic and intracoronary flow velocity measurements.
1989 Aug
Intracoronary electrocardiogram during torsade des pointes secondary to intracoronary papaverine.
1989 Dec
Comparison of the anti-respiratory syncytial virus activity and toxicity of papaverine hydrochloride and pyrazofurin in vitro and in vivo.
1989 Feb
[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
Intracavernous papaverine in the management of psychogenic impotence.
1990
Ventricular arrhythmia due to intracoronary papaverine: analysis of QT intervals and coronary vasodilatory reserve.
1990 Apr
Intracavernous papaverine and glaucoma.
1990 Aug 1
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
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
QT prolongation and possibility of ventricular arrhythmias after intracoronary papaverine.
1994
Transient facial nerve palsy after topical papaverine application during vestibular schwannoma surgery. Case report.
2007 Nov
[X-ray densitometric measurement of myocardial perfusion reserve in symptomatic patients without angiographically detectable coronary stenoses].
2008 Apr
Pharmacologic profiling of human and rat cytochrome P450 1A1 and 1A2 induction and competition.
2008 Dec
Insulin resistance functionally limits endothelium-dependent coronary vasodilation in nondiabetic patients.
2008 Jan
Adverse effects of topical papaverine on auditory nerve function.
2008 Sep
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
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
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 15:03:40 GMT 2023
Edited
by admin
on Fri Dec 15 15:03:40 GMT 2023
Record UNII
23473EC6BQ
Record Status Validated (UNII)
Record Version
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Name Type Language
PAPAVERINE HYDROCHLORIDE
EP   HSDB   MART.   MI   USP   USP-RS   VANDF   WHO-DD   WHO-IP  
Common Name English
Papaverine hydrochloride [WHO-DD]
Common Name English
PAPAVERINE HYDROCHLORIDE [MI]
Common Name English
PAPAVERINE HYDROCHLORIDE [HSDB]
Common Name English
6,7-Dimethoxy-1-veratrylisoquinoline hydrochloride
Systematic Name English
NSC-35443
Code English
PAPAVERINE HCL
Common Name English
PAPAVERINE HYDROCHLORIDE [WHO-IP]
Common Name English
VASORIN
Common Name English
ISOQUINOLINE, 1-((3,4-DIMETHOXYPHENYL)METHYL)-6,7-DIMETHOXY-, HYDROCHLORIDE
Systematic Name English
PAPAVERINE HYDROCHLORIDE [USP-RS]
Common Name English
PAPAVERINE HYDROCHLORIDE [MART.]
Common Name English
ARTEGODAN
Common Name English
CARDOVERINA
Common Name English
PAPAVERINE HYDROCHLORIDE [VANDF]
Common Name English
PAPAVERINE HYDROCHLORIDE [EP MONOGRAPH]
Common Name English
PAPAVERINE HYDROCHLORIDE [JAN]
Common Name English
PAPAVERINI HYDROCHLORIDUM [WHO-IP LATIN]
Common Name English
PAPAVERINE HYDROCHLORIDE [USP MONOGRAPH]
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
EVMPD
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
NSC
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
PUBCHEM
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
ECHA (EC/EINECS)
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
DAILYMED
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
RXCUI
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
ChEMBL
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
NCI_THESAURUS
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
CAS
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
SMS_ID
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
RS_ITEM_NUM
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
WHO INTERNATIONAL PHARMACOPEIA
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.
FDA UNII
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
DRUG BANK
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
EPA CompTox
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
MERCK INDEX
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
HSDB
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
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