{"ATC Code":["A - Alimentary tract and metabolism","A03 - Drugs for functional gastrointestinal disorders","A03A - Drugs for functional gastrointestinal disorders","A03AD - Papaverine and derivatives","A03AD01 - Papaverine","G - Genito urinary system and sex hormones","G04 - Urologicals","G04B - Urologicals","G04BE - Drugs used in erectile dysfunction","G04BE02 - Papaverine","QA - Alimentary tract and metabolism","QA03 - Drugs for functional gastrointestinal disorders","QA03A - Drugs for functional gastrointestinal disorders","QA03AD - Papaverine and derivatives","QA03AD01 - Papaverine","QG - Genito urinary system and sex hormones","QG04 - Urologicals","QG04B - Urologicals","QG04BE - Drugs used in erectile dysfunction","QG04BE02 - Papaverine"],"Absorption, Distribution and Excretion":"It is not known whether this drug is excreted in human milk.","Aliases":["Robaxapap","1-(3,4-Dimethoxybenzyl)-6,7-dimethoxyisoquinoline","6,7-Dimethoxy-1-veratrylisoquinoline","Pavacap","Papaverinum","Isoquinoline, 1-[(3,4-dimethoxyphenyl)methyl]-6,7-dimethoxy-","1-((3,4-Dimethoxyphenyl)methyl)-6,7-dimethoxyisoquinoline","NSC-136630","Isoquinoline, 1-((3,4-dimethoxyphenyl)methyl)-6,7-dimethoxy-","Dtxsid4023418","Pavatym","Chebi:28241","NSC136630","Dtxcid603418","200-397-2","Papaverin","Papanerine","Papanerin","Papaverina","Cerespan","Pavabid","Papaverine free base","NSC 136630","Isoquinoline, 6,7-dimethoxy-1-veratryl-","S-M-R","1-[(3,4-dimethoxyphenyl)methyl]-6,7-dimethoxy-isoquinoline","Chembl19224","4-[(6,7-Dimethoxyisoquinolyl)methyl]-1,2-dimethoxybenzene","HSDB 3147","Pavacot","Ceraspan","Mesotina","EV1","Cas-61-25-6","Ncgc00015810-02","Einecs 200-397-2","Unii-daa13nkg2q","Brn 0312930","Pavadyl","2wey","RS 47","TNP00305","6,7-Dimethoxy-1-(3,4-dimethoxybenzyl)isoquinoline","Noscapine Impurity 4","Spectrum_000071","Prestwick0_000583","Prestwick1_000583","Prestwick2_000583","Prestwick3_000583","Spectrum2_000978","Spectrum3_000537","Spectrum4_000467","Spectrum5_001188","Lopac-P-3510","Isoquinoline, 6,7-dimethoxy-1-veratryl-(8Cl)","Lopac0_000957","Oprea1_387689","Oprea1_810508","Schembl34702","BSPBio_000426","BSPBio_002153","KBioGR_000914","KBioSS_000471","5-21-06-00182","DivK1c_000321","SPBio_001015","SPBio_002645","BPBio1_000470","MEGxp0_001880","Schembl29360983","Schembl29387160","ACon1_000238","ACon1_002094","BDBM14754","GTPL13147","KBio1_000321","KBio2_000471","KBio2_003039","KBio2_005607","KBio3_001653","1-[(3,4-Dimethoxyphenyl)methyl]6,7-dimethoxyisoquinoline","Ninds_000321","HMS3561N11","HMS3746M21","Albb-010475","1-{[3,4-bis(methyloxy)phenyl]methyl}-6,7-bis(methyloxy)isoquinoline","BBL012345","EBC-26648","Mfcd00024138","STK039035","Isoquinoline,7-dimethoxy-1-veratryl-","Akos000277460","CCG-202821","CS-7800","DB01113","KS-5336","Sdccgmls-0003037.p003","Sdccgsbi-0050931.p005","Idi1_000321","Ncgc00015810-01","Ncgc00015810-03","Ncgc00015810-04","Ncgc00015810-05","Ncgc00015810-06","Ncgc00015810-07","Ncgc00015810-08","Ncgc00015810-09","Ncgc00015810-13","Ncgc00015810-24","Ncgc00015810-29","Ncgc00024428-03","Ncgc00024428-04","HY-18077","Nci60_003183","Papaverine 100 microg/mL in Acetonitrile","ST023301","Noscapine impurity a","Sbi-0050931.p004","DB-053252","AB00053515","NS00007287","C06533","D07425","En300-177755","Ab00053515_14","Wln: t66 cnj b1r co1 do1\u0026 ho1 io1","Ag-205/03660043","6,7-dimethoxy-1-veratryl-isoquinoline;hydrochloride","1-(3,4-Dimethoxybenzyl)-6,7-dimethoxyisoquinoline #","Brd-k15567136-001-01-1","Brd-k15567136-003-06-6","Brd-k15567136-003-18-1","Brd-k15567136-003-27-2","Isoquinoline,4-dimethoxyphenyl)methyl]-6,7-dimethoxy-","Sr-01000003098-10","InChI=1/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,9H2,1-4H"],"Biological Half-Life":"0.5-2 hours","Boiling Point":"Sublimes at 135 °C","CAS":"58-74-2","Chemical Classes":"Alkaloids, Natural Products, Plant","ChemicalClasses":["phenol"],"Chirality":"achiral","Color/Form":"White prisms from alcohol-diethyl ether; needles from petroleum ether","Decomposition":"When heated to decomposition it emits toxic fumes of /oxides of nitrogen/.","Density":"1.337 g/cu cm at 20 °C g/cm\u003csup\u003e3\u003c/sup\u003e","Drug Classes":["Breast Feeding","Lactation","Milk, Human","Phosphodiesterase Inhibitors","Vasodilator Agents","Urological Agents"],"Drug Indication":"For the treatment of impotence and vasospasms.","Drug Warnings":"Intra-arterial papaverine (IAP) is used to treat symptomatic cerebral vasospasm following aneurysmal subarachnoid hemorrhage (SAH). IAP, however, can increase intracranial pressure (ICP). In this study, /investigators/ examined whether IAP alters brain oxygen (BtO2). Poor clinical grade (Hunt \u0026 Hess IV or V) SAH patients who underwent continuous ICP and BtO2 monitoring during IAP infusion for symptomatic cerebral vasospasm were evaluated as part of a prospective observational study. ... IAP infusion to treat cerebral vasospasm following SAH can increase ICP and reduce BtO2. The IAP-induced reduction in BtO2 may help explain why IAP, although it reverses arterial narrowing, does not improve patient outcome.","EliminationHalfLife":"1.5 – 2 hours","Erowid Experience Reports":[],"Esters":[],"European Community (EC) Number":"200-397-2","Formating":[],"HMDB ID":"HMDB0015245","HeavyAtomCount":25,"Human Drugs":"Breast Feeding; Lactation; Milk, Human; Phosphodiesterase Inhibitors; Vasodilator Agents; Urological Agents","IUPACName":"1-[(3,4-dimethoxyphenyl)methyl]-6,7-dimethoxyisoquinoline","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","InChIKey":"XQYZDYMELSJDRZ-UHFFFAOYSA-N","Interactions":"The effects of different concentrations of beta-cyclodextrin (beta-CyD), hydroxypropyl-beta-cyclodextrin (HP-beta-CyD) and 2,6-di-O-methyl-beta-cyclodextrin (DM-beta-CyD) on percutaneous absorption of papaverine hydrochloride (PAP) were investigated. Abdominal rat skin mounted in Franz cells was used for in vitro experiments. To evaluate CyD interaction with a bilayer structure model, dipalmitoyl-sn-glycero-3-phosphocholine (DPPC) and DPPC-Chol (8:2 mole ratio) vesicles were used. CyD vesicle interaction was evaluated by differential scanning calorimetry. Permeation through rat skin and calorimetric experiments demonstrated that at low concentrations DM-beta-CyD shows higher enhancer activity as a possible result of a perturbing action on the skin by a complexation of its lipid components, but at higher concentrations HP-beta-CyD is the most effective. By considering that HP-beta-CyD presents a very moderate destabilizing action on the skin, /it was concluded/ that a 10% aqueous solution of this macrocycle appears to be the most suitable transdermal absorption enhancer for PAP.","KEGG Entries":[{"Id":"D02218","Interactions":[],"Synonyms":["Papaverine hydrochloride","Pavabid"]},{"Id":"D07425","Interactions":[],"Synonyms":["Papaverine","Mesotina"]},{"Id":"D07439","Interactions":[],"Synonyms":["Papaverine sulfate"]}],"MeSH Headers":[{"Id":"M0015830","Link":"https://id.nlm.nih.gov/mesh/M0015830.html","Name":"Papaverine","Ref":147},{"Id":"M0353767","Link":"https://id.nlm.nih.gov/mesh/M0353767.html","Name":"Pavatym","Ref":149},{"Id":"DescTree","Link":"https://www.nlm.nih.gov/mesh/meshhome.html","Name":"MeSH Tree","Ref":150},{"Id":"PubMed from MeSH","Link":"https://www.nlm.nih.gov/mesh/meshhome.html","Name":null,"Ref":176},{"Id":"M0016659","Link":"https://id.nlm.nih.gov/mesh/M0016659.html","Name":"Phosphodiesterase Inhibitors","Ref":177},{"Id":"M0022559","Link":"https://id.nlm.nih.gov/mesh/M0022559.html","Name":"Vasodilator Agents","Ref":178},{"Id":"M0584314","Link":"https://id.nlm.nih.gov/mesh/M0584314.html","Name":"Urological Agents","Ref":179}],"MeSH Pharmacological Classification":[{"Id":"M0016659","Link":"https://id.nlm.nih.gov/mesh/M0016659.html","Name":"Phosphodiesterase Inhibitor","Ref":177},{"Id":"M0022559","Link":"https://id.nlm.nih.gov/mesh/M0022559.html","Name":"Vasodilator Agent","Ref":178},{"Id":"M0584314","Link":"https://id.nlm.nih.gov/mesh/M0584314.html","Name":"Urological Agent","Ref":179}],"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.","Melting Point":"147.5 °C","Metabolism/Metabolites":"Papaverine yielded demethylpapaverine in rabbit. Axelrod J, Biochem J (63) 634, 1956. /from table/","MolecularFormula":"C\u003csub\u003e20\u003c/sub\u003eH\u003csub\u003e21\u003c/sub\u003eNO\u003csub\u003e4\u003c/sub\u003e","MolecularWeight":"339.4 g/mol","Non-Human Toxicity Values":"LD50 Mouse intradermal 150 mg/kg","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.","Physical Description":"Solid","PubChemId":4680,"Record Description":["LiverTox|Cardiac|Angina|Phosphodiesterase inhibition"],"Records":{"UNII":{"Impurities":[]}},"RefChem":"56338","RefCount":3,"RefCur":"","References":[{"Name":"Wikipedia","Urls":[{"Link":"https://en.wikipedia.org/wiki/Papaverine","Name":"Papaverine","Sub":false}]},{"Name":"Wikidata","Urls":[{"Link":"https://www.wikidata.org/wiki/Q410374","Name":"Papaverine","Sub":false}]},{"Name":"DrugBank","Urls":[{"Link":"https://go.drugbank.com/DB01113","Name":"Papaverine","Sub":false}]},{"Name":"PubChem","Urls":[{"Link":"https://pubchem.ncbi.nlm.nih.gov/compound/4680","Name":"Papaverine","Sub":false}]},{"Name":"Common Chemistry","Urls":[{"Link":"https://commonchemistry.cas.org/detail?cas_rn=58-74-2","Name":"Papaverine","Sub":false}]},{"Name":"HMDB","Urls":[{"Link":"https://hmdb.ca/metabolites/HMDB0015245","Name":"Papaverine","Sub":false}]},{"Name":"KEGG","Urls":[{"Link":"https://www.kegg.jp/entry/C06533","Name":"Papaverine","Sub":false}]},{"Name":"UNII","Urls":[{"Link":"https://gsrs.ncats.nih.gov/ginas/app/ui/substances/DAA13NKG2Q","Name":"Papaverine","Sub":false}]},{"Name":"EPA DSSTox","Urls":[{"Link":"https://comptox.epa.gov/dashboard/chemical/details/DTXSID4023418","Name":"Papaverine","Sub":false}]}],"Refs":["National Center for Biotechnology Information. PubChem Compound Summary for CID 4680, papaverine. Accessed May 6, 2026. \u003ca href=https://pubchem.ncbi.nlm.nih.gov/compound/4680\u003ehttps://pubchem.ncbi.nlm.nih.gov/compound/4680\u003c/a\u003e","U.S. Food and Drug Administration; National Center for Advancing Translational Sciences. Papaverine. UNII: DAA13NKG2Q. Global Substance Registration System. Accessed May 6, 2026. \u003ca href=https://gsrs.ncats.nih.gov/ginas/app/beta/substances/DAA13NKG2Q\u003ehttps://gsrs.ncats.nih.gov/ginas/app/beta/substances/DAA13NKG2Q\u003c/a\u003e"],"SMILES":"COC1=C(C=C(C=C1)CC2=NC=CC3=CC(=C(C=C32)OC)OC)OC","SaltData":[{"AcidCount":1,"Amine":"Papaverine","AmineCount":1,"Formula":"Cl","Name":"hydrochloride","RName":"hydrochloride","Structure":"\u003csvg xmlns=\"http://www.w3.org/2000/svg\" preserveAspectRatio=\"none\" style=\"display:block\" viewBox=\"0 0 143.779 101.16\"\u003e\u003crect width=\"100%\" height=\"100%\" fill=\"#fff\"/\u003e\u003cdesc\u003eGenerated by the Chemistry Development Kit (http://github.com/cdk)\u003c/desc\u003e\u003cg fill=\"#ff0d0d\" stroke=\"#000\" stroke-linecap=\"round\" stroke-linejoin=\"round\" stroke-width=\".7\"\u003e\u003cpath fill=\"#fff\" stroke=\"none\" d=\"M0 0h144v102H0z\"/\u003e\u003cg class=\"mol\"\u003e\u003cpath d=\"m53.832 1.038-9.919 5.729M40.636 12.582l.002 11.318\" class=\"bond\"/\u003e\u003cg 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0-.929-.387-1.453-.381-.524-1.209-.524-.833 0-1.226.524t-.393 1.453\" class=\"atom\"/\u003e\u003cpath stroke=\"#ff0d0d\" d=\"m43.913 6.767 4.96-2.864M40.636 12.582l.001 5.659\" class=\"hi\"/\u003e\u003cpath stroke=\"#3050f8\" d=\"m56.981 94.324 5.023 2.898\" class=\"hi\"/\u003e\u003cpath stroke=\"#ff0d0d\" d=\"m80.232 35.427.002 5.659M83.509 29.612l4.959-2.866M103.353 48.638l-4.959 2.863M109.909 48.635l4.961 2.864M17.512 25.8l4.962 2.865M10.956 25.803l-4.959 2.863\" class=\"hi\"/\u003e\u003c/g\u003e\u003c/g\u003e\u003c/svg\u003e","Therapeutic Uses":"/EXPERIMENTAL THER:/ The present study evaluates whether intrathecal papaverine induces changes in spinal cord blood flow (SCBF) of injured spinal cord and prevents secondary injury. After laminectomy was performed and contusive spinal cord injuries were induced in adult female Macaca rhesus, three received intrathecal papaverine, and three received saline 0.9% for control. ... Mean arterial blood pressure showed no significant change in both groups. In the papaverine group, SCBF recovered to 81.35+/-7.8% of baseline at 15 min, 75.24+/-6.3% at 30 min, 73.38+/-2.3% at 90 min and 72.57+/-4.1% at 180 min after the completion of infusion. SCBF was significantly higher than the control groups (P\u003c0.01). There was no occlusion of the arteries, but occluded veins were identified at the injured site. The MVD in the spinal cord of the control group was significantly lesser than the papaverine group (P\u003c0.01). Luxol Fast Blue staining showed that intrathecal papaverine reduced myelin loss in the lesion 2 weeks after injury (P\u003c0.05). Intrathecal administration of papaverine increased SCBF in non-human primates. It is likely that the effects of papaverine can reduce secondary injury in spinal cord injured Macaca rhesus.","Title":"Papaverine","UNII":"DAA13NKG2Q","Wikidata":"Q410374","Wikipedia":"Papaverine","XLogP":3.9,"pH":"Optimal pH for storage of papverine solutions: 2.0-2.8"}