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
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
| 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
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 |
|---|---|---|
| A HAMP promoter bioassay system for identifying chemical compounds that modulate hepcidin expression. | 2015-05 |
|
| Synthesis, in vivo occupancy, and radiolabeling of potent phosphodiesterase subtype-10 inhibitors as candidates for positron emission tomography imaging. | 2011-08-25 |
|
| 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. | 2010-11-20 |
|
| Cardiac arrest after intracisternal papaverine instillation during intracranial aneurysm surgery. Case report. | 2010-10 |
|
| Resolution of peripheral artery catheter-induced ischemic injury in infants -Two case reports-. | 2010-08 |
|
| Vascular smooth muscle contraction/relaxation of rat carotid artery is not altered by bone grafting substitutes in vitro. | 2010-06 |
|
| Antibodies against gonadotropin-releasing hormone (GnRH) and destruction of enteric neurons in 3 patients suffering from gastrointestinal dysfunction. | 2010-05-20 |
|
| New endovascular method for transvascular exit of arteries and veins: developed in simulator, in rat and in rabbit with full clinical integration. | 2010-05-03 |
|
| Carbon-11 labeled papaverine as a PET tracer for imaging PDE10A: radiosynthesis, in vitro and in vivo evaluation. | 2010-05 |
|
| Micro computed tomography for vascular exploration. | 2010-03-05 |
|
| Intravascular ultrasound study and evidence of pathological coronary flow reserve in patients with isolated coronary artery aneurysms. | 2010-03 |
|
| Severe hypotension with intracisternal application of papaverine after clipping of an intracranial aneurysm. | 2009-12 |
|
| Intracisternal irrigation of papaverine leading to choroidal infarction. | 2009-11 |
|
| Phosphodiesterase 10A inhibitor activity in preclinical models of the positive, cognitive, and negative symptoms of schizophrenia. | 2009-11 |
|
| [Acute embolization into the veins in the splanchnic bed--an overview of current methods of diagnosis and therapies]. | 2008-11 |
|
| Peyronie's reconstruction for maximum length and girth gain: geometrical principles. | 2008 |
|
| QT prolongation and possibility of ventricular arrhythmias after intracoronary papaverine. | 1994 |
|
| Double-blind, cross-over study comparing prostaglandin E1 and papaverine in patients with vasculogenic impotence. | 1991-06 |
|
| Torsades de pointes after intracoronary papaverine. | 1991-02 |
|
| Intracavernous injection of prostaglandin E1 in combination with papaverine: enhanced effectiveness in comparison with papaverine plus phentolamine and prostaglandin E1 alone. | 1991-01 |
|
| A lethal complication of papaverine-induced priapism. | 1991-01 |
|
| [Priapism as a complication of the treatment of impotence by local injections of papaverine]. | 1990-09-01 |
|
| Intracavernous papaverine and glaucoma. | 1990-08-01 |
|
| Determination of coronary flow reserve by digital angiography: validation of a practical method not requiring power injection or electrocardiographic gating. | 1990-07 |
|
| Ventricular arrhythmia due to intracoronary papaverine: analysis of QT intervals and coronary vasodilatory reserve. | 1990-04 |
|
| Polymorphous ventricular tachycardia: a side effect of intracoronary papaverine. | 1990-02 |
|
| Intracavernous papaverine in the management of psychogenic impotence. | 1990 |
|
| Intracoronary electrocardiogram during torsade des pointes secondary to intracoronary papaverine. | 1989-12 |
|
| [The intracavernosal administration of papaverine in the diagnosis and treatment of sexual disorders in men]. | 1989-10 |
|
| Papaverine-induced chest pain due to coronary vascular steal: demonstration with angiographic and intracoronary flow velocity measurements. | 1989-08 |
|
| [Epilepsy and hypertensive crisis after intracavernous injection of metaraminol in the treatment of priapism secondary to a papaverine test]. | 1989-05-20 |
|
| Inhibitory effect of papaverine on HIV replication in vitro. | 1989-04 |
|
| [Papaverine-induced priapism. Experiences with a new urologic emergency]. | 1989-02-10 |
|
| Comparison of the anti-respiratory syncytial virus activity and toxicity of papaverine hydrochloride and pyrazofurin in vitro and in vivo. | 1989-02 |
|
| Papaverine-induced fibrosis of the corpus cavernosum. | 1989-01 |
|
| Serious ventricular dysrhythmias after intracoronary papaverine. | 1988-12-01 |
|
| [Therapy of erectile dysfunction using papaverine--2 1/2 years' experience]. | 1988-07-30 |
|
| [Long-term experiences with autoinjection therapy of papaverine in erectile dysfunction]. | 1988-01 |
|
| Papaverine-induced coma. | 1988 |
|
| Diagnosis of male impotence after intracavernous papaverine test. | 1988 |
|
| Pressor inhibition of angiotensin-induced ACTH secretion. | 1987-11 |
|
| [Intracavernous injection of papaverine hydrochloride for impotence in patients with spinal cord injury]. | 1987-07 |
|
| Incompatibility of Hexabrix and papaverine in peripheral arteriography. | 1987-03 |
|
| Maintenance treatment of erectile impotence by cavernosal unstriated muscle relaxant injection. | 1986-08 |
|
| [Efficacy of intracisternal papaverine on symptomatic vasospasm]. | 1986-06 |
|
| Papaverine-induced chronic liver disease. | 1986-04 |
|
| Drug-induced hepatitis associated with anticytoplasmic organelle autoantibodies. | 1985-09-01 |
|
| Validation in dogs of a rapid digital angiographic technique to measure relative coronary blood flow during routine cardiac catheterization. | 1985-01-01 |
|
| Intraoperative assessment of aortoiliac stenosis: role of papaverine-induced hyperemia. | 1984-12 |
|
| Spasmolytic constituents of Cedrus deodara (Roxb.) Loud: pharmacological evaluation of himachalol. | 1975-02 |
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).
| Substance Class |
Chemical
Created
by
admin
on
Edited
Mon Mar 31 17:45:02 GMT 2025
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on
Mon Mar 31 17:45:02 GMT 2025
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| Record UNII |
23473EC6BQ
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Validated (UNII)
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NCI_THESAURUS |
C29707
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NCI_THESAURUS |
C744
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| Code System | Code | Type | Description | ||
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SUB14763MIG
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35443
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6084
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200-502-1
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23473EC6BQ
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203132
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CHEMBL19224
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C80006
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61-25-6
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100000091716
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1496008
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PAPAVERINE HYDROCHLORIDE
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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. | ||
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23473EC6BQ
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DBSALT000412
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DTXSID9025825
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m8392
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61-25-6
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ACTIVE MOIETY |