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Identification
NamePapaverine
Accession NumberDB01113  (APRD00628, DB07725)
TypeSmall Molecule
GroupsApproved
Description

An alkaloid found in opium but not closely related to the other opium alkaloids in its structure or pharmacological actions. It is a direct-acting smooth muscle relaxant used in the treatment of impotence and as a vasodilator, especially for cerebral vasodilation. The mechanism of its pharmacological actions is not clear, but it apparently can inhibit phosphodiesterases and it may have direct actions on calcium channels. [PubChem]

Structure
Thumb
Synonyms
Mesotina
External Identifiers Not Available
Approved Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Papaverine Hydrochloride Injection USPliquid65 mgintramuscular; intravenous; subcutaneousSandoz Canada Incorporated1951-12-31Not applicableCanada
Approved Generic Prescription ProductsNot Available
Approved Over the Counter ProductsNot Available
Unapproved/Other Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Papaverine Hydrochlorideinjection, solution30 mg/mLintravenousAmerican Regent, Inc.1995-09-01Not applicableUs
Papaverine Hydrochlorideinjection, solution30 mg/mLintravenousAmerican Regent, Inc.1995-09-01Not applicableUs
International Brands
NameCompany
AlapavNot Available
AlbatranNot Available
ArtegodanNot Available
CardioverinaNot Available
CerebidNot Available
CerespanNot Available
DelapavNot Available
DilavesNot Available
DispamilNot Available
DrapavelNot Available
DurapavNot Available
DynovasNot Available
MesotinaNot Available
MyobidNot Available
OptenylNot Available
PameionNot Available
PamelonNot Available
PanergonNot Available
PapaconNot Available
PapaleaseNot Available
PapaversanNot Available
Papital T.R.Not Available
Paptial T.R.Not Available
PavabidNot Available
PavacapNot Available
PavacenNot Available
PavadelNot Available
PavagenNot Available
PavakeyNot Available
PavasedNot Available
PavatestNot Available
PaverolanNot Available
PaveronNot Available
PavnellNot Available
Qua BidNot Available
Ro-PapavNot Available
TherapavNot Available
VasalNot Available
Vaso-PavNot Available
Brand mixturesNot Available
Salts
Name/CASStructureProperties
Papaverine Codecarboxylate
56896-69-6
Thumb
  • InChI Key: VTJFMXLVZKZSGE-UHFFFAOYSA-N
  • Monoisotopic Mass: 586.171631734
  • Average Mass: 586.5269
DBSALT000784
Papaverine Hydrochloride
61-25-6
Thumb
  • InChI Key: UOTMYNBWXDUBNX-UHFFFAOYSA-N
  • Monoisotopic Mass: 375.123735904
  • Average Mass: 375.846
DBSALT000412
Categories
UNIIDAA13NKG2Q
CAS number58-74-2
WeightAverage: 339.385
Monoisotopic: 339.147058165
Chemical FormulaC20H21NO4
InChI KeyInChIKey=XQYZDYMELSJDRZ-UHFFFAOYSA-N
InChI
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
IUPAC Name
1-[(3,4-dimethoxyphenyl)methyl]-6,7-dimethoxyisoquinoline
SMILES
COC1=C(OC)C=C(CC2=NC=CC3=CC(OC)=C(OC)C=C23)C=C1
Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as benzylisoquinolines. These are organic compounds containing an isoquinoline to which a benzyl group is attached.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassIsoquinolines and derivatives
Sub ClassBenzylisoquinolines
Direct ParentBenzylisoquinolines
Alternative Parents
Substituents
  • Benzylisoquinoline
  • O-dimethoxybenzene
  • Dimethoxybenzene
  • Methoxybenzene
  • Phenol ether
  • Anisole
  • Alkyl aryl ether
  • Benzenoid
  • Pyridine
  • Monocyclic benzene moiety
  • Heteroaromatic compound
  • Azacycle
  • Ether
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Pharmacology
IndicationFor the treatment of impotence and vasospasms.
PharmacodynamicsPapaverine 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.
Mechanism of actionPerhaps by its direct vasodilating action on cerebral blood vessels, Papaverine increases cerebral blood flow and decreases cerebral vascular resistance in normal subjects; oxygen consumption is unaltered. These effects may explain the benefit reported from the drug in cerebral vascular encephalopathy.
Related Articles
AbsorptionNot Available
Volume of distributionNot Available
Protein binding~90%
MetabolismNot Available
Route of eliminationNot Available
Half life0.5-2 hours
ClearanceNot Available
ToxicityNot Available
Affected organisms
  • Humans and other mammals
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9911
Blood Brain Barrier+0.9633
Caco-2 permeable+0.8866
P-glycoprotein substrateNon-substrate0.5389
P-glycoprotein inhibitor INon-inhibitor0.6485
P-glycoprotein inhibitor IINon-inhibitor0.8005
Renal organic cation transporterNon-inhibitor0.7229
CYP450 2C9 substrateNon-substrate0.796
CYP450 2D6 substrateSubstrate0.8918
CYP450 3A4 substrateSubstrate0.6263
CYP450 1A2 substrateInhibitor0.9107
CYP450 2C9 inhibitorNon-inhibitor0.9071
CYP450 2D6 inhibitorInhibitor0.8448
CYP450 2C19 inhibitorInhibitor0.778
CYP450 3A4 inhibitorInhibitor0.7959
CYP450 inhibitory promiscuityHigh CYP Inhibitory Promiscuity0.8558
Ames testNon AMES toxic0.689
CarcinogenicityNon-carcinogens0.9503
BiodegradationNot ready biodegradable0.9262
Rat acute toxicity2.9877 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9329
hERG inhibition (predictor II)Non-inhibitor0.7274
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397 )
Pharmacoeconomics
ManufacturersNot Available
Packagers
Dosage forms
FormRouteStrength
Injection, solutionintravenous30 mg/mL
Liquidintramuscular; intravenous; subcutaneous65 mg
Prices
Unit descriptionCostUnit
Papaverine 150 mg capsule sa1.86USD capsule
Papaverine 60 mg/2 ml vial1.68USD ml
Papaverine hcl powder0.76USD g
Para-time 150 mg capsule sa0.23USD capsule
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
PatentsNot Available
Properties
StateSolid
Experimental Properties
PropertyValueSource
melting point226 (dec) °CPhysProp
logP3Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.0129 mg/mLALOGPS
logP4.19ALOGPS
logP3.08ChemAxon
logS-4.4ALOGPS
pKa (Strongest Basic)6.03ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area49.81 Å2ChemAxon
Rotatable Bond Count6ChemAxon
Refractivity95.52 m3·mol-1ChemAxon
Polarizability36.57 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Not Available
Spectra
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot Available
References
Synthesis ReferenceNot Available
General References
  1. Tang Y, Luan J, Zhang X: Accelerating tissue expansion by application of topical papaverine cream. Plast Reconstr Surg. 2004 Oct;114(5):1166-9. [PubMed:15457029 ]
  2. Liu JK, Couldwell WT: Intra-arterial papaverine infusions for the treatment of cerebral vasospasm induced by aneurysmal subarachnoid hemorrhage. Neurocrit Care. 2005;2(2):124-32. [PubMed:16159054 ]
  3. Takeuchi K, Sakamoto S, Nagayoshi Y, Nishizawa H, Matsubara J: Reactivity of the human internal thoracic artery to vasodilators in coronary artery bypass grafting. Eur J Cardiothorac Surg. 2004 Nov;26(5):956-9. [PubMed:15519189 ]
External Links
ATC CodesG04BE02G04BE52A03AD01
AHFS Codes
  • 24:12.92
PDB EntriesNot Available
FDA labelNot Available
MSDSDownload (74.4 KB)
Interactions
Drug Interactions
Drug
AldesleukinThe risk or severity of adverse effects can be increased when Aldesleukin is combined with Papaverine.
ButabarbitalButabarbital may increase the hypotensive activities of Papaverine.
ButethalButethal may increase the hypotensive activities of Papaverine.
DuloxetinePapaverine may increase the orthostatic hypotensive activities of Duloxetine.
HeptabarbitalHeptabarbital may increase the hypotensive activities of Papaverine.
HexobarbitalHexobarbital may increase the hypotensive activities of Papaverine.
LevodopaPapaverine may increase the hypotensive activities of Levodopa.
MethohexitalMethohexital may increase the hypotensive activities of Papaverine.
NicorandilNicorandil may increase the hypotensive activities of Papaverine.
PentobarbitalPentobarbital may increase the hypotensive activities of Papaverine.
PrimidonePrimidone may increase the hypotensive activities of Papaverine.
RisperidonePapaverine may increase the hypotensive activities of Risperidone.
SecobarbitalSecobarbital may increase the hypotensive activities of Papaverine.
ValsartanThe risk or severity of adverse effects can be increased when Valsartan is combined with Papaverine.
Food InteractionsNot Available

Targets

Kind
Protein
Organism
Human
Pharmacological action
yes
Actions
inhibitor
General Function:
Metal ion binding
Specific Function:
Hydrolyzes the second messenger cAMP, which is a key regulator of many important physiological processes. May be involved in mediating central nervous system effects of therapeutic agents ranging from antidepressants to antiasthmatic and anti-inflammatory agents.
Gene Name:
PDE4B
Uniprot ID:
Q07343
Molecular Weight:
83342.695 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284 ]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423 ]
  3. Xin ZC, Kim EK, Lin CS, Liu WJ, Tian L, Yuan YM, Fu J: Effects of icariin on cGMP-specific PDE5 and cAMP-specific PDE4 activities. Asian J Androl. 2003 Mar;5(1):15-8. [PubMed:12646997 ]
  4. Zhu S, Gan Z, Li Z, Liu Y, Yang X, Deng P, Xie Y, Yu M, Liao H, Zhao Y, Zhao L, Liao F: The measurement of cyclic nucleotide phosphodiesterase 4 activities via the quantification of inorganic phosphate with malachite green. Anal Chim Acta. 2009 Mar 16;636(1):105-10. doi: 10.1016/j.aca.2009.01.035. Epub 2009 Jan 22. [PubMed:19231363 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
inhibitor
General Function:
Metal ion binding
Specific Function:
Plays a role in signal transduction by regulating the intracellular concentration of cyclic nucleotides. Can hydrolyze both cAMP and cGMP, but has higher affinity for cAMP and is more efficient with cAMP as substrate.
Gene Name:
PDE10A
Uniprot ID:
Q9Y233
Molecular Weight:
88411.71 Da
References
  1. Weber M, Breier M, Ko D, Thangaraj N, Marzan DE, Swerdlow NR: Evaluating the antipsychotic profile of the preferential PDE10A inhibitor, papaverine. Psychopharmacology (Berl). 2009 May;203(4):723-35. doi: 10.1007/s00213-008-1419-x. Epub 2008 Dec 9. [PubMed:19066855 ]
Comments
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Drug created on June 13, 2005 07:24 / Updated on August 17, 2016 12:23