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Revision as of 11:32, 5 December 2011 editBeetstra (talk | contribs)Edit filter managers, Administrators172,031 edits Saving copy of the {{drugbox}} taken from revid 452187380 of page Papaverine for the Chem/Drugbox validation project (updated: 'DrugBank').		Latest revision as of 10:07, 2 June 2024 edit Kku (talk | contribs)Extended confirmed users115,409 editsm link glycosaminoglycan
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			{{Short description|Chemical compound}}
	{{ambox | text = This page contains a copy of the infobox ({{tl|drugbox}}) taken from revid of page ] with values updated to verified values.}}
	{{Drugbox		{{Drugbox
			| Verifiedfields = changed
⚫	| verifiedrevid = 420028570
			| Watchedfields = changed
⚫	| IUPAC_name = 1-(3,4-dimethoxybenzyl)-6,7-dimethoxyisoquinoline
		⚫	| verifiedrevid = 464197236
⚫	| image = Papaverin - Papaverine.svg
		⚫	| IUPAC_name = 1--6,7-dimethoxyisoquinoline
	| width = 200px
		⚫	| image = Papaverine.svg
	| image2 = Papaverine-from-xtal-3D-balls-B.png		| image2 = Papaverine-from-xtal-3D-balls-B.png
	| width2 = 200px
	<!--Clinical data-->		<!--Clinical data-->
			| pronounce = {{IPAc-en|p|ə|ˈ|p|æ|v|ər|iː|n}}
	| tradename = Pavabid		| tradename = Pavabid, others
	| Drugs.com = {{drugs.com|monograph|papaverine-hydrochloride}}		| Drugs.com = {{drugs.com|monograph|papaverine-hydrochloride}}
	| MedlinePlus = a682707		| MedlinePlus = a682707
			| pregnancy_AU = A
	| pregnancy_category = ]: C{{Ref_label|4|4|a}}
			| pregnancy_US = C
⚫	| routes_of_administration = Oral, ], ], rectal,{{Ref_label|5|5|a}} ]
			| legal_AU = S4
			| legal_US = Rx-only
		⚫	| routes_of_administration = Oral, ], ], rectal, ]
	<!--Pharmacokinetic data-->		<!--Pharmacokinetic data-->
	| bioavailability = 80%{{Ref_label|3|3|a}}		| bioavailability = 80%
	| protein_bound = ~90%		| protein_bound = ~90%
	| metabolism = ]{{Ref_label|3|3|b}}		| metabolism = ]
	| elimination_half-life = 1.5–2 hours{{Ref_label|3|3|c}}		| elimination_half-life = 1.5–2 hours
	| excretion = ]{{Ref_label|3|3|d}}		| excretion = ]
	<!--Identifiers-->		<!--Identifiers-->
	| CASNo_Ref = {{cascite|correct|CAS}}		| CAS_number_Ref = {{cascite|correct|??}}
	| CAS_number = 58-74-2		| CAS_number = 58-74-2
	| CAS_supplemental = <br/>61-25-6 (hydrochloride) <!-- Also CAS verified -->		| CAS_supplemental = <br/>61-25-6 (hydrochloride) <!-- Also CAS verified -->
	| ATC_prefix = A03		| ATC_prefix = A03
	| ATC_suffix = AD01		| ATC_suffix = AD01
	| ATC_supplemental = {{ATC|G04|BE02}}		| ATC_supplemental = {{ATC|G04|BE02}}
	| PubChem = 4680		| PubChem = 4680
	| DrugBank_Ref = {{drugbankcite|correct|drugbank}}		| DrugBank_Ref = {{drugbankcite|correct|drugbank}}
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	| KEGG_Ref = {{keggcite|correct|kegg}}		| KEGG_Ref = {{keggcite|correct|kegg}}
	| KEGG = D07425		| KEGG = D07425
			| ChEBI_Ref = {{ebicite|changed|EBI}}
			| ChEBI = 28241
	| ChEMBL_Ref = {{ebicite|correct|EBI}}		| ChEMBL_Ref = {{ebicite|correct|EBI}}
	| ChEMBL = 19224		| ChEMBL = 19224
	<!--Chemical data-->		<!--Chemical data-->
	| C=20 | H=21 | N=1 | O=4		| C=20 | H=21 | N=1 | O=4
	| molecular_weight = 339.385 g/mol{{Ref_label|1|1|c}}
	| smiles = COc1ccc(cc1OC)Cc2c3cc(c(cc3ccn2)OC)OC		| smiles = COc1ccc(cc1OC)Cc2c3cc(c(cc3ccn2)OC)OC
	| 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,9H2,1-4H3
	| InChIKey = XQYZDYMELSJDRZ-UHFFFAOYAJ
	| StdInChI_Ref = {{stdinchicite|correct|chemspider}}		| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
	| StdInChI = 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		| StdInChI = 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
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	| StdInChIKey = XQYZDYMELSJDRZ-UHFFFAOYSA-N		| StdInChIKey = XQYZDYMELSJDRZ-UHFFFAOYSA-N
	}}		}}
			'''Papaverine''' (] '']'', "poppy") is an ] ] ] drug, used primarily in the treatment of visceral ]s and ]s (especially those involving the intestines, heart, or brain), occasionally in the treatment of ] and ]. While it is found in the ], papaverine differs in both structure and pharmacological action from the analgesic ] and its derivatives (such as ]).
			In addition to opium, papaverine is purported to be present in high concentrations in ].<ref name="99mTc-DTPA">{{cite journal |doi=10.1159/000029336 |author=Kao CH |author2=Ho YJ |author3=Wu CL |author4=ChangLai SP |year=1999 |title=Using 99mTc-DTPA Radioaerosol Inhalation Lung Scintigraphies to Detect the Lung Injury Induced by Consuming Sauropus androgynus Vegetable and Comparison with Conventional Pulmonary Function Tests |journal=Respiration |publisher=Karger AG |volume=66 |issue=1 |pages=46–51 |pmid=9973690|s2cid=38378580 }}</ref>
			== History ==
			]
			Papaverine was discovered in 1848 by Georg Merck (1825–1873).<ref>{{cite journal | vauthors = Merck G | year = 1848 | title = Vorläufige Notiz über eine neue organische Base im Opium |trans-title=Preliminary notice of a new organic base in opium | url = https://books.google.com/books?id=nDY9AAAAcAAJ&pg=PA125| journal = Annalen der Chemie und Pharmacie | volume = 66 | pages = 125–128 | doi=10.1002/jlac.18480660121}}</ref> Merck was a student of the German chemists ] and ], and he was the son of ] (1794–1855), founder of the ] corporation, a major German chemical and pharmaceutical company.<ref>{{Cite book | vauthors = Brock WH |url= https://books.google.com/books?id=VugoemP2th0C&pg=PA120 |title=Justus Von Liebig: The Chemical Gatekeeper |date=2002-06-20 |publisher=Cambridge University Press |isbn=978-0-521-52473-5 |page=120 |language=en}}</ref>
			== Uses ==
			Papaverine is approved to treat spasms of the gastrointestinal tract, ]s and ] and for use as a ] and ] ] in ] (combined with ])<ref>{{cite journal | vauthors = Liu JK, Couldwell WT | title = Intra-arterial papaverine infusions for the treatment of cerebral vasospasm induced by aneurysmal subarachnoid hemorrhage | journal = Neurocritical Care | volume = 2 | issue = 2 | pages = 124–132 | year = 2005 | pmid = 16159054 | doi = 10.1385/NCC:2:2:124 | author-link2 = William T. Couldwell | s2cid = 35400205 }}</ref> and ].<ref>{{cite journal | vauthors = Takeuchi K, Sakamoto S, Nagayoshi Y, Nishizawa H, Matsubara J | title = Reactivity of the human internal thoracic artery to vasodilators in coronary artery bypass grafting | journal = European Journal of Cardio-Thoracic Surgery | volume = 26 | issue = 5 | pages = 956–959 | date = November 2004 | pmid = 15519189 | doi = 10.1016/j.ejcts.2004.07.047 | doi-access = free }}</ref> Papaverine may also be used as a smooth muscle relaxant in ] where it is applied directly to blood vessels.
			Papaverine is used as an ] drug, alone or sometimes in combination.<ref>{{cite journal | vauthors = Desvaux P | title = | journal = Presse Médicale | volume = 34 | issue = 13 Suppl | pages = 5–7 | date = July 2005 | pmid = 16158020 }}</ref><ref>{{cite journal | vauthors = Bella AJ, Brock GB | title = Intracavernous pharmacotherapy for erectile dysfunction | journal = Endocrine | volume = 23 | issue = 2–3 | pages = 149–155 | year = 2004 | pmid = 15146094 | doi = 10.1385/ENDO:23:2-3:149 | s2cid = 13056029 }}</ref> Papaverine, when injected in penile tissue, causes direct ] relaxation and consequent filling of the ] with blood resulting in ]. A ] is also available for ED treatment.<ref>{{cite journal | vauthors = Kim ED, el-Rashidy R, McVary KT | title = Papaverine topical gel for treatment of erectile dysfunction | journal = The Journal of Urology | volume = 153 | issue = 2 | pages = 361–365 | date = February 1995 | pmid = 7815584 | doi = 10.1097/00005392-199502000-00019 }}</ref>
			It is also commonly used in ] of ] along with the other ]s and protein suspensions.<ref>{{cite journal | vauthors = Müller-Schweinitzer E, Ellis P | title = Sucrose promotes the functional activity of blood vessels after cryopreservation in DMSO-containing fetal calf serum | journal = Naunyn-Schmiedeberg's Archives of Pharmacology | volume = 345 | issue = 5 | pages = 594–597 | date = May 1992 | pmid = 1528275 | doi = 10.1007/bf00168954 | s2cid = 10441842 }}</ref><ref>{{cite journal | vauthors = Müller-Schweinitzer E, Hasse J, Swoboda L | title = Cryopreservation of human bronchi | journal = The Journal of Asthma | volume = 30 | issue = 6 | pages = 451–457 | year = 1993 | pmid = 8244915 | doi = 10.3109/02770909309056754 }}
			</ref> Functions as a ] during cryopreservation when used in conjunction with ], ], ], ] or ].<ref>{{cite journal | vauthors = Brockbank KG | title = Effects of cryopreservation upon vein function in vivo | journal = Cryobiology | volume = 31 | issue = 1 | pages = 71–81 | date = February 1994 | pmid = 8156802 | doi = 10.1006/cryo.1994.1009 }}</ref><ref>{{cite journal | vauthors = Giglia JS, Ollerenshaw JD, Dawson PE, Black KS, Abbott WM | title = Cryopreservation prevents arterial allograft dilation | journal = Annals of Vascular Surgery | volume = 16 | issue = 6 | pages = 762–767 | date = November 2002 | pmid = 12391500 | doi = 10.1007/s10016-001-0072-1 | s2cid = 24777062 }}</ref>
			Papaverine is also being investigated as a topical growth factor in ] with some success.<ref>{{cite journal | vauthors = Tang Y, Luan J, Zhang X | title = Accelerating tissue expansion by application of topical papaverine cream | journal = Plastic and Reconstructive Surgery | volume = 114 | issue = 5 | pages = 1166–1169 | date = October 2004 | pmid = 15457029 | doi = 10.1097/01.PRS.0000135854.48570.76 }}</ref>
			Papaverine is used as an ] ] (preventative) of ].<ref>{{cite journal | vauthors = Sillanpää M, Koponen M | title = Papaverine in the prophylaxis of migraine and other vascular headache in children | journal = Acta Paediatrica Scandinavica | volume = 67 | issue = 2 | pages = 209–212 | date = March 1978 | pmid = 343489 | doi = 10.1111/j.1651-2227.1978.tb16304.x | s2cid = 28817628 }}</ref><ref>{{cite journal | vauthors = Vijayan N | title = Brief therapeutic report: papaverine prophylaxis of complicated migraine | journal = Headache | volume = 17 | issue = 4 | pages = 159–162 | date = September 1977 | pmid = 893088 | doi = 10.1111/j.1526-4610.1977.hed1704159.x | s2cid = 36626189 }}</ref><ref>{{cite journal | vauthors = Poser CM | title = Letter: Papaverine in prophylactic treatment of migraine | journal = Lancet | volume = 1 | issue = 7869 | pages = 1290 | date = June 1974 | pmid = 4134173 | doi = 10.1016/S0140-6736(74)90045-2 }}</ref> It is not a first line drug such as a few ], ], ], and some ] such as ], but rather when these first line drugs and secondary drugs such as ], ]s, etc. fail in the prophylaxis of migraines, have intolerable side effects or are contraindicated.
			Papaverine is also present in combinations of opium alkaloid salts such as ] (], ]) and others, along with ], ], and in some cases ] and others in a percentage similar to that in opium, or modified for a given application.
			Papaverine is found as a contaminant in some ]<ref>{{cite journal | vauthors = Paterson S, Cordero R | title = Comparison of the various opiate alkaloid contaminants and their metabolites found in illicit heroin with 6-monoacetyl morphine as indicators of heroin ingestion | journal = Journal of Analytical Toxicology | volume = 30 | issue = 4 | pages = 267–273 | date = May 2006 | pmid = 16803666 | doi = 10.1093/jat/30.4.267 | quote = In addition to morphine, street heroin contains various alkaloids extracted from the opium poppy, Papaversomniferum, including codeine, thebaine, noscapine, and papaverine | doi-access = free }}</ref> and can be used by forensic laboratories in heroin profiling to identify its source.<ref>{{cite journal | vauthors = Seetohul LN, Maskell PD, De Paoli G, Pounder DJ | title = Biomarkers for illicit heroin: a previously unrecognized origin of papaverine | journal = Journal of Analytical Toxicology | volume = 37 | issue = 2 | pages = 133 | date = March 2013 | pmid = 23316026 | doi = 10.1093/jat/bks099 | doi-access = free }}</ref> The metabolites can also be found in the urine of heroin users, allowing street heroin to be distinguished from pharmaceutical ].<ref>{{cite journal | vauthors = Strang J, Metrebian N, Lintzeris N, Potts L, Carnwath T, Mayet S, Williams H, Zador D, Evers R, Groshkova T, Charles V, Martin A, Forzisi L | display-authors = 6 | title = Supervised injectable heroin or injectable methadone versus optimised oral methadone as treatment for chronic heroin addicts in England after persistent failure in orthodox treatment (RIOTT): a randomised trial | journal = Lancet | volume = 375 | issue = 9729 | pages = 1885–1895 | date = May 2010 | pmid = 20511018 | doi = 10.1016/s0140-6736(10)60349-2 | s2cid = 205958031 }}</ref>
			==Mechanism==
			The ''in vivo'' mechanism of action is not entirely clear, but an inhibition of the ] phosphodiesterase causing elevation of cyclic AMP and cyclic GMP{{Clarify|date=November 2017}} levels is significant. It may also alter ]l ].
			Papaverine has also been demonstrated to be a selective ] for the ] subtype found mainly in the ] of the brain. When administered chronically to mice, it produced motor and cognitive deficits and ], but conversely may produce an ] effect,<ref>{{cite journal | vauthors = Siuciak JA, Chapin DS, Harms JF, Lebel LA, McCarthy SA, Chambers L, Shrikhande A, Wong S, Menniti FS, Schmidt CJ | display-authors = 6 | title = Inhibition of the striatum-enriched phosphodiesterase PDE10A: a novel approach to the treatment of psychosis | journal = Neuropharmacology | volume = 51 | issue = 2 | pages = 386–396 | date = August 2006 | pmid = 16780899 | doi = 10.1016/j.neuropharm.2006.04.013 | s2cid = 13447370 }}</ref><ref>{{cite journal | vauthors = Hebb AL, Robertson HA, Denovan-Wright EM | title = Phosphodiesterase 10A inhibition is associated with locomotor and cognitive deficits and increased anxiety in mice | journal = European Neuropsychopharmacology | volume = 18 | issue = 5 | pages = 339–363 | date = May 2008 | pmid = 17913473 | doi = 10.1016/j.euroneuro.2007.08.002 | s2cid = 9621541 }}</ref> although not all studies support this view.<ref name="Weber_2009_papaverine_PPI">{{cite journal | vauthors = Weber M, Breier M, Ko D, Thangaraj N, Marzan DE, Swerdlow NR | title = Evaluating the antipsychotic profile of the preferential PDE10A inhibitor, papaverine | journal = Psychopharmacology | volume = 203 | issue = 4 | pages = 723–735 | date = May 2009 | pmid = 19066855 | pmc = 2748940 | doi = 10.1007/s00213-008-1419-x }}</ref>
			== Side effects ==
			Frequent side effects of papaverine treatment include polymorphic ], constipation, interference with ]{{cn|date=June 2023}} retention test (used to determine hepatic function), increased ] levels, increased ] levels, ], and ].
			Rare side effects include flushing of the face, ] (excessive sweating), ], arterial ], ], loss of appetite, ], ], ], mixed ], headache, allergic reaction, chronic active hepatitis, and paradoxical aggravation of cerebral vasospasm.<ref>{{cite journal | vauthors = Clyde BL, Firlik AD, Kaufmann AM, Spearman MP, Yonas H | title = Paradoxical aggravation of vasospasm with papaverine infusion following aneurysmal subarachnoid hemorrhage. Case report | journal = Journal of Neurosurgery | volume = 84 | issue = 4 | pages = 690–695 | date = April 1996 | pmid = 8613866 | doi = 10.3171/jns.1996.84.4.0690 | s2cid = 1172874 }}</ref>
			Papaverine in the plant ] is linked to ].<ref name="pmid26413127">{{cite journal | vauthors = Bunawan H, Bunawan SN, Baharum SN, Noor NM | title = Sauropus androgynus (L.) Merr. Induced Bronchiolitis Obliterans: From Botanical Studies to Toxicology | journal = Evidence-Based Complementary and Alternative Medicine | volume = 2015 | pages = 714158 | year = 2015 | pmid = 26413127 | pmc = 4564651 | doi = 10.1155/2015/714158 | doi-access = free }}</ref>
			== Formulations and trade names==
			Papaverine is available in its salt form as the ], ], ], and teprosylate. It was also once available as a salt of ], ], cromesilate, ], and ]. The hydrochloride salt is available for intramuscular, intravenous, rectal and oral administration. The teprosylate is available in intravenous, intramuscular, and orally administered formulations. The codecarboxylate is available in oral form, only, as is the adenylate.
			The codecarboxylate is sold under the name Albatran,{{cn|date=June 2023}} the adenylate as Dicertan,{{cn|date=June 2023}} and the hydrochloride salt is sold variously as Artegodan (Germany), Cardioverina (countries outside Europe and the United States), Dispamil (countries outside Europe and the United States), Opdensit (Germany), Panergon (Germany), Paverina Houde (Italy, Belgium), Pavacap (United States), Pavadyl (United States), Papaverine (Israel), Papaverin-Hamelin (Germany), Paveron (Germany), Spasmo-Nit (Germany), Cardiospan, Papaversan, Cepaverin, Cerespan, Drapavel, Forpaven, Papalease, Pavatest, Paverolan, Therapav (Canada<ref>{{cite web | url=http://www.reptox.csst.qc.ca/Produit.asp?no_produit=108688&nom=THERAPAV+(PRODUIT+PUR)&incr=0 | title=THERAPAV (PRODUIT PUR) - Détail | access-date=26 September 2005 }} CSST - Service du répertoire toxicologique. (French)</ref>), Vasospan, Cerebid, Delapav, Dilaves, Durapav, Dynovas, Optenyl, Pameion, Papacon, Pavabid, Pavacen, Pavakey, Pavased, Pavnell, Alapav, Myobid, Vasal, Pamelon, Pavadel, Pavagen, Ro-Papav, Vaso-Pav, Papanerin-hcl, Qua bid, Papital T.R., Paptial T.R., Pap-Kaps-150.{{cn|date=June 2023}} In ], papaverine and ] are used in mild drugs that help "flush" the ].<ref>{{cite web|url=http://www.ogyi.hu/drug_database/index.php?action=show_details&item=21736|title=Országos Gyógyszerészeti és Élelmezés-egészségügyi Intézet|website=www.ogyi.hu|access-date=2008-10-14|archive-url=https://web.archive.org/web/20150123100209/http://www.ogyi.hu/drug_database/index.php?action=show_details&item=21736|archive-date=2015-01-23|url-status=dead}}</ref>
			== References ==
			{{Reflist|2}}
			{{Components of Opium}}
			{{Drugs for functional gastrointestinal disorders}}
			{{Drugs for erectile dysfunction and PE}}
			{{Phosphodiesterase inhibitors}}
			]
			]
			]
			]
			]
			]
			]