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Identification
Name Papaverine
Accession Number DB01113 (APRD00628, DB07725)
Type small molecule
Groups approved
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
Download: MOL | SDF | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms
  • Chlorhydrate de Papaverine
  • Papavarine Chlorhydrate
  • Papaverin
  • Papaverine Chlorohydrate
  • Papaverine Hcl
  • Papaverine Hydrochloride
  • Papaverine Monohydrochloride
  • Papaverinium Chloride
Synonyms
Chlorhydrate de Papaverine
Papavarine Chlorhydrate
Papaverin
Papaverine Chlorohydrate
Papaverine Hcl
Papaverine Hydrochloride
Papaverine Monohydrochloride
Papaverinium Chloride
Salts Not Available
Brand names
Name Company
Alapav
Artegodan
Cardiospan
Cardoverina
Cepaverin
Cerebid
Cerespan
Delapav
Dilaves
Dispamil
Drapavel
Durapav
Dynovas
Forpavin
Genabid
Myobid
Optenyl
Pameion
Pamelon
Panergon
Pap H
Papacon
Papalease
Papanerin
Papanerin-Hcl
Papanerine
Papaversan
Papital T.R.
Paptial T.R.
Pavabid
Pavabid Hp
Pavacap
Pavacels
Pavacen
Pavacot
Pavadel
Pavagen
Pavakey
Pavarine
Pavased
Pavatest
Pavatine
Pavatym
Paverolan
Paveron
Pavnell
Qua Bid
Ro-Papav
Robaxapap
Spasmo-Nit
Therapav
Vasal
Vaso-Pav
First Prev Next Last
Brand mixtures Not Available
Categories
  • Vasodilator Agents
  • Phosphodiesterase Inhibitors
CAS number 61-25-6
Weight Average: 339.385
Monoisotopic: 339.147058165
Chemical Formula C20H21NO4
InChI Key InChIKey=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
Plain Text
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
Plain Text
Mass Spec Not Available
Taxonomy
Kingdom Organic
Classes
  • Benzylisoquinolines
Substructures
  • Phenols and Derivatives
  • Benzylisoquinolines
  • Pyridines and Derivatives
  • Ethers
  • Benzene and Derivatives
  • Catechols
  • Heterocyclic compounds
  • Aromatic compounds
  • Anisoles
  • Imines
  • (Iso)quinolines and Derivatives
  • Phenyl Esters
Pharmacology
Indication For the treatment of impotence and vasospasms.
Pharmacodynamics 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.
Mechanism of action Perhaps 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.
Absorption Not Available
Volume of distribution Not Available
Protein binding ~90%
Metabolism Not Available
Route of elimination Not Available
Half life 0.5-2 hours
Clearance Not Available
Toxicity Not Available
Affected organisms
  • Humans and other mammals
Pathways Not Available
Pharmacoeconomics
Manufacturers Not Available
Packagers
Dosage forms
Form Route Strength
Liquid Intravenous
Prices
Unit description Cost Unit
Papaverine 150 mg capsule sa 1.86 USD capsule
Papaverine 60 mg/2 ml vial 1.68 USD ml
Papaverine hcl powder 0.76 USD g
Para-time 150 mg capsule sa 0.23 USD capsule
Patents Not Available
Properties
State solid
Melting point Not Available
Experimental Properties
Property Value Source
logP 3 PhysProp
Predicted Properties
Property Value Source
water solubility 1.29e-02 g/l ALOGPS
logP 4.19 ALOGPS
logP 3.08 ChemAxon Molconvert
logS -4.4 ALOGPS
pKa 0 ChemAxon Molconvert
hydrogen acceptor count 5 ChemAxon Molconvert
hydrogen donor count 0 ChemAxon Molconvert
polar surface area 49.81 ChemAxon Molconvert
rotatable bond count 6 ChemAxon Molconvert
refractivity 95.52 ChemAxon Molconvert
polarizability 36.57 ChemAxon Molconvert
References
Synthesis Reference Not Available
General Reference
  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
  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
  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
External Links
Resource Link
KEGG Compound C06533 Link_out
PubChem Compound 4680 Link_out
PubChem Substance 46508003 Link_out
ChemSpider 4518 Link_out
BindingDB 14754 Link_out
Therapeutic Targets Database DAP000959 Link_out
PharmGKB PA450779 Link_out
HET EV1 Link_out
Drug Product Database 9881 Link_out
RxList http://www.rxlist.com/cgi/generic/papaverine.htm Link_out
Drugs.com http://www.drugs.com/cdi/papaverine.html Link_out
Wikipedia http://en.wikipedia.org/wiki/Papaverine Link_out
ATC Codes
  • A03AD01
  • G04BE02
AHFS Codes
  • 24:12.92
PDB Entries Not Available
FDA label Not Available
MSDS show (74.4 KB)
Interactions
Drug Interactions
Drug Interaction
Treprostinil Additive hypotensive effect. Monitor antihypertensive therapy during concomitant use.
Food Interactions Not Available
Targets

1. cAMP-specific 3',5'-cyclic phosphodiesterase 4B

Pharmacological action: yes
Actions: inhibitor

May be involved in mediating central nervous system effects of therapeutic agents ranging from antidepressants to antiasthmatic and anti-inflammatory agents

Organism class: human
UniProt ID: Q07343 Link_out
Gene: PDE4B Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

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
  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
  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
  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. Epub 2009 Jan 22. Pubmed

2. cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A

Pharmacological action: unknown
Actions: inhibitor

Plays a role in signal transduction by regulating the intracellular concentration of cyclic nucleotides. This enzyme can hydrolyze both cAMP and cGMP, having a higher affinity for cAMP

Organism class: human
UniProt ID: Q9Y233 Link_out
Gene: PDE10A Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

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. Epub 2008 Dec 9. Pubmed
Comments
Drug created on June 13, 2005 07:24 / Updated on February 14, 2012 11:45