Details
Stereochemistry | ACHIRAL |
Molecular Formula | C20H21NO4 |
Molecular Weight | 339.385 |
Optical Activity | NONE |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
COC1=C(OC)C=C(CC2=NC=CC3=CC(OC)=C(OC)C=C23)C=C1
InChI
InChIKey=XQYZDYMELSJDRZ-UHFFFAOYSA-N
InChI=1S/C20H21NO4/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
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
Originator
Sources: https://www.ncbi.nlm.nih.gov/pubmed/20494383
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
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
36.0 nM [IC50] | |||
Target ID: CHEMBL613758 |
|||
Target ID: CHEMBL2916 Sources: https://www.ncbi.nlm.nih.gov/pubmed/25111025 |
60.0 µM [IC50] | ||
Target ID: CHEMBL240 Sources: https://www.ncbi.nlm.nih.gov/pubmed/19034039 |
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. |
Cmax
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
54.7 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/24217241/ |
3 mg single, intravascular dose: 3 mg route of administration: Intravascular experiment type: SINGLE co-administered: |
PAPAVERINE plasma | Homo sapiens population: UNHEALTHY age: UNKNOWN sex: UNKNOWN food status: UNKNOWN |
|
583 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/489763/ |
150 mg single, oral dose: 150 mg route of administration: Oral experiment type: SINGLE co-administered: |
PAPAVERINE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
|
117 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/489763/ |
150 mg single, oral dose: 150 mg route of administration: Oral experiment type: SINGLE co-administered: |
PAPAVERINE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
|
536 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/489763/ |
150 mg single, oral dose: 150 mg route of administration: Oral experiment type: SINGLE co-administered: |
PAPAVERINE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
|
218 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/489763/ |
200 mg single, oral dose: 200 mg route of administration: Oral experiment type: SINGLE co-administered: |
PAPAVERINE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
AUC
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
1760 mg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/3413033/ |
80 mg single, intravenous dose: 80 mg route of administration: Intravenous experiment type: SINGLE co-administered: |
PAPAVERINE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN |
|
375 mg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/3413033/ |
80 mg single, oral dose: 80 mg route of administration: Oral experiment type: SINGLE co-administered: |
PAPAVERINE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN |
|
1965 mg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/3413033/ |
80 mg single, intravenous dose: 80 mg route of administration: Intravenous experiment type: SINGLE co-administered: |
PAPAVERINE plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
|
855 mg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/3413033/ |
80 mg single, oral dose: 80 mg route of administration: Oral experiment type: SINGLE co-administered: |
PAPAVERINE plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
|
1308 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/489763/ |
150 mg single, oral dose: 150 mg route of administration: Oral experiment type: SINGLE co-administered: |
PAPAVERINE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
|
409 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/489763/ |
150 mg single, oral dose: 150 mg route of administration: Oral experiment type: SINGLE co-administered: |
PAPAVERINE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
|
1247 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/489763/ |
150 mg single, oral dose: 150 mg route of administration: Oral experiment type: SINGLE co-administered: |
PAPAVERINE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
|
800 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/489763/ |
200 mg single, oral dose: 200 mg route of administration: Oral experiment type: SINGLE co-administered: |
PAPAVERINE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
T1/2
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
1.9 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/3413033/ |
80 mg single, intravenous dose: 80 mg route of administration: Intravenous experiment type: SINGLE co-administered: |
PAPAVERINE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN |
|
3.4 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/3413033/ |
80 mg single, intravenous dose: 80 mg route of administration: Intravenous experiment type: SINGLE co-administered: |
PAPAVERINE plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
Doses
Dose | Population | Adverse events |
---|---|---|
500 mg 3 times / day multiple, oral Higher than recommended Dose: 500 mg, 3 times / day Route: oral Route: multiple Dose: 500 mg, 3 times / day Sources: |
unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: |
Disc. AE: Alkaline phosphatase increased, SGOT increased... AEs leading to discontinuation/dose reduction: Alkaline phosphatase increased (4%) Sources: SGOT increased (4%) Eosinophilia (4%) |
15 g single, oral Overdose |
unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: F Food Status: UNKNOWN Sources: |
Disc. AE: Consciousness decreased, Respiration abnormal... AEs leading to discontinuation/dose reduction: Consciousness decreased Sources: Respiration abnormal Metabolic acidosis Respiratory alkalosis Sinus tachycardia Hypokalemia (grade 2) Hyperglycemia (grade 1) Pyruvate increased |
8 g single, oral Overdose |
healthy, ADULT Health Status: healthy Age Group: ADULT Sex: M Food Status: UNKNOWN Sources: |
Disc. AE: Lactic acidosis, Hypokalemia... AEs leading to discontinuation/dose reduction: Lactic acidosis (grade 3) Sources: Hypokalemia Coma (grade 5) Convulsions (grade 3) Vomiting (grade 3) Respiratory alkalosis (grade 5) |
AEs
AE | Significance | Dose | Population |
---|---|---|---|
Alkaline phosphatase increased | 4% Disc. AE |
500 mg 3 times / day multiple, oral Higher than recommended Dose: 500 mg, 3 times / day Route: oral Route: multiple Dose: 500 mg, 3 times / day Sources: |
unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: |
Eosinophilia | 4% Disc. AE |
500 mg 3 times / day multiple, oral Higher than recommended Dose: 500 mg, 3 times / day Route: oral Route: multiple Dose: 500 mg, 3 times / day Sources: |
unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: |
SGOT increased | 4% Disc. AE |
500 mg 3 times / day multiple, oral Higher than recommended Dose: 500 mg, 3 times / day Route: oral Route: multiple Dose: 500 mg, 3 times / day Sources: |
unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: |
Consciousness decreased | Disc. AE | 15 g single, oral Overdose |
unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: F Food Status: UNKNOWN Sources: |
Metabolic acidosis | Disc. AE | 15 g single, oral Overdose |
unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: F Food Status: UNKNOWN Sources: |
Pyruvate increased | Disc. AE | 15 g single, oral Overdose |
unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: F Food Status: UNKNOWN Sources: |
Respiration abnormal | Disc. AE | 15 g single, oral Overdose |
unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: F Food Status: UNKNOWN Sources: |
Respiratory alkalosis | Disc. AE | 15 g single, oral Overdose |
unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: F Food Status: UNKNOWN Sources: |
Sinus tachycardia | Disc. AE | 15 g single, oral Overdose |
unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: F Food Status: UNKNOWN Sources: |
Hyperglycemia | grade 1 Disc. AE |
15 g single, oral Overdose |
unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: F Food Status: UNKNOWN Sources: |
Hypokalemia | grade 2 Disc. AE |
15 g single, oral Overdose |
unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: F Food Status: UNKNOWN Sources: |
Hypokalemia | Disc. AE | 8 g single, oral Overdose |
healthy, ADULT Health Status: healthy Age Group: ADULT Sex: M Food Status: UNKNOWN Sources: |
Convulsions | grade 3 Disc. AE |
8 g single, oral Overdose |
healthy, ADULT Health Status: healthy Age Group: ADULT Sex: M Food Status: UNKNOWN Sources: |
Lactic acidosis | grade 3 Disc. AE |
8 g single, oral Overdose |
healthy, ADULT Health Status: healthy Age Group: ADULT Sex: M Food Status: UNKNOWN Sources: |
Vomiting | grade 3 Disc. AE |
8 g single, oral Overdose |
healthy, ADULT Health Status: healthy Age Group: ADULT Sex: M Food Status: UNKNOWN Sources: |
Coma | grade 5 Disc. AE |
8 g single, oral Overdose |
healthy, ADULT Health Status: healthy Age Group: ADULT Sex: M Food Status: UNKNOWN Sources: |
Respiratory alkalosis | grade 5 Disc. AE |
8 g single, oral Overdose |
healthy, ADULT Health Status: healthy Age Group: ADULT Sex: M Food Status: UNKNOWN Sources: |
Overview
CYP3A4 | CYP2C9 | CYP2D6 | hERG |
---|---|---|---|
OverviewOther
Other Inhibitor | Other Substrate | Other Inducer |
---|---|---|
Drug as perpetrator
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
inconclusive [IC50 >10 uM] | ||||
inconclusive [IC50 >10 uM] | ||||
no [IC50 >10 uM] | ||||
no [IC50 >10 uM] | ||||
no [IC50 >133 uM] | ||||
no [IC50 >133 uM] | ||||
weak [Inhibition 100 uM] | ||||
yes [IC50 0.762 uM] | ||||
yes [IC50 1.9953 uM] | ||||
yes [IC50 12.5893 uM] | ||||
yes [IC50 23.13 uM] | ||||
yes [IC50 <10 uM] | ||||
yes [Inhibition 10 uM] | ||||
yes [Inhibition 10 uM] |
Drug as victim
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
Page: 575 | 580 |
no |
Tox targets
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
PubMed
Title | Date | PubMed |
---|---|---|
Papaverine-induced chronic liver disease. | 1986 Apr |
|
Maintenance treatment of erectile impotence by cavernosal unstriated muscle relaxant injection. | 1986 Aug |
|
Incompatibility of Hexabrix and papaverine in peripheral arteriography. | 1987 Mar |
|
Pressor inhibition of angiotensin-induced ACTH secretion. | 1987 Nov |
|
Diagnosis of male impotence after intracavernous papaverine test. | 1988 |
|
[Efficacy of vascular therapy in complex of treatment of purulent necrotic foot ulcers in patients with diabetes mellitus]. | 2001 Feb |
|
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 |
|
[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 |
|
Abnormal responses of the human cerebral microcirculation to papaverin during aneurysm surgery. | 2009 Jan |
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 Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/27860455
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).
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WHO-VATC |
QG04BE02
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WHO-ATC |
G04BE52
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FDA ORPHAN DRUG |
64991
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NCI_THESAURUS |
C29707
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FDA ORPHAN DRUG |
581417
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WHO-ATC |
G04BE02
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WHO-VATC |
QA03AD01
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WHO-VATC |
QG04BE52
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LIVERTOX |
739
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WHO-ATC |
A03AD01
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NCI_THESAURUS |
C744
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7895
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PAPAVERINE
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C726
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58-74-2
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DAA13NKG2Q
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D010208
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m8392
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136630
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ACTIVE MOIETY
PARENT (SALT/SOLVATE)
SALT/SOLVATE (PARENT)
SALT/SOLVATE (PARENT)