Papaverin: Razlika med redakcijama
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Vrstica 1:
{{drugbox
| IUPAC_name = 1-(3,4-dimetoksibenzil)-6,7-dimetoxiizokinolin
| image = Papaverin - Papaverine.svg
| image2 = Papaverine-from-xtal-3D-balls-B.png
| width = 300px
| width2 = 200px
| CAS_number = 58-74-2
| CASNo_Ref = {{cascite}}
| CAS_supplemental = <br/>61-25-6 (hidroklorid) <!-- Also CAS verified -->
| ATC_prefix = A03
| ATC_suffix = AD01
| ATC_supplemental = {{ATC|G04|BE02}}
| PubChem = 4680
| DrugBank = APRD00628
| C=20 | H=21 | N=1 | O=4
| molecular_weight = 339.385 g/mol{{ref_label|1|1|c}}
| bioavailability = 80%{{ref_label|3|3|a}}
| protein_bound = ~90%
| metabolism = [[Hepatic]]{{ref_label|3|3|b}}
| elimination_half-life = 1.5–2 uri{{ref_label|3|3|c}}
| pregnancy_category = [[United States|USA]]: C{{ref_label|4|4|a}}
| legal_status =
| routes_of_administration = Oralno, [[intravenozno]], [[intramuskularno]], rektalno,{{ref_label|5|5|a}} [[intracavernosal]]
| excretion = [[Renal]]{{ref_label|3|3|d}}
}}
'''Papaverin''' <ref>Papaverine - EverydayHealth.com[http://www.everydayhealth.com/DrugsAZ/Papaverine.aspx]</ref> je [[opium]] [[alkaloid]] used primarily in the treatment of visceral [[spasm]], [[vasospasm]] (especially those involving the [[heart]] and the [[brain]]), and occasionally in the treatment of [[erectile dysfunction]].{{ref_label|3|3|e}} While it is found in the [[opium poppy]], papaverine differs in both structure and pharmacological action from the analgetic (morphine-related) opium alkaloids ([[opiates]]). In 1979, a Food and Drug Administration Advisory Committee evaluated studies on papaverine and concluded that there was a lack of objective data to support the therapeutic use of papaverine for these conditions. Papaverine remains available despite the committee's recommendation that it be withdrawn from the market.
== Uses ==
Papaverine is approved to treat spasms of the gastrointestinal tract, [[bile duct]]s and [[ureter]] and for use as a [[cerebral]] and [[coronary]] [[vasodilator]]{{ref_label|3|3|f}} in [[subarachnoid hemorrhage]] (combined with [[balloon angioplasty]]){{ref_label|6|6|a}} and [[coronary artery bypass surgery]].{{ref_label|7|7|a}} Papaverine may also be used as a smooth muscle relaxant in [[microsurgery]] where it is applied directly to blood vessels.
It is also commonly used in [[cryopreservation]] of [[blood vessels]] along with the other glycosaminoglycans and protein suspensions.<ref>E. Müller-Schweinitzer and P. Ellis: "Sucrose promotes the functional activity of blood vessels after cryopreservation in DMSO-containing fetal calf serum". Naunyn-Schmiedeberg's Archives of Pharmacology, Volume 345, Number 5 / May, 1992</ref><ref>Muller-Schweinitzer E, Hasse J, Swoboda L. : "Cryopreservation of human bronchi.". J Asthma. 1993;30(6):451-7. Links
</ref> Functions as a [[vasodilator]] during cryopreservation when used in conjunction with [[verapamil]], [[phentolamine]], [[nifedipine]], [[tolazoline]] or [[nitroprusside]].<ref>Brockbank KG.: "Effects of the medecine upon vein function in vivo". Cryobiology. 1994 Feb;31(1):71-81</ref><ref>Joseph S. Giglia, Jeremy D. Ollerenshaw, Patti E. Dawson, Kirby S. Black, William M. Abbott: "Cryopreservation Prevents Arterial Allograft Dilation ". Annals of Vascular Surgery Volume 16, Number 6 / December, 2002</ref>
Papaverine is also being investigated as a topical growth factor in tissue expansion with some success.<ref>{{cite journal |author=Tang Y, Luan J, Zhang X |title=Accelerating tissue expansion by application of topical papaverine cream |journal=Plast. Reconstr. Surg. |volume=114 |issue=5 |pages=1166–9 |year=2004 |pmid=15457029 |doi=10.1097/01.PRS.0000135854.48570.76}}</ref>
Papaverine is also present in combinations of opium alkaloid salts such as [[Omnopon]], [[Pantopon]], [[Papaveretum]], and others along with [[morphine]], [[codeine]], and in some cases [[noscapine]] and others in a percentage similar to that in opium or modified for a given application.
==Mechanism==
The in vivo mechanism of action is not entirely clear, but an inhibition of the [[enzyme]] phosphodiesterase causing elevation of cyclic AMP levels is significant. It may also alter [[mitochondria]]l [[Cellular respiration|respiration]].
Papaverine has also been demonstrated to be a selective [[phosphodiesterase inhibitor]] for the PDE<sub>10A</sub> subtype found mainly in the [[striatum]] of the brain. When administered chronically to mice it produced motor and cognitive deficits and [[anxiogenic|increased anxiety]], but conversely may produce an [[antipsychotic]] effect.<ref>Siuciak JA, Chapin DS, Harms JF, Lebel LA, McCarthy SA, Chambers L, Shrikhande A, Wong S, Menniti FS, Schmidt CJ. Inhibition of the striatum-enriched phosphodiesterase PDE10A: a novel approach to the treatment of psychosis. ''Neuropharmacology''. 2006 Aug;51(2):386-96. PMID 16780899</ref><ref>Hebb AL, Robertson HA, Denovan-Wright EM. Phosphodiesterase 10A inhibition is associated with locomotor and cognitive deficits and increased anxiety in mice. ''European Neuropsychopharmacology''. 2008 May;18(5):339-63. PMID 17913473</ref>
== Side effects ==
Frequent side effects of papaverine treatment include polymorphic [[ventricular tachycardia]], constipation, interference with [[sulphobromophthalein]]{{ref_label|8|8|a}} [[retention test]] (used to determine hepatic function), increased [[transaminase]] levels, increased [[alkaline phosphatase]] levels, [[somnolence]], and [[Vertigo (medical)|vertigo]].{{ref_label|3|3|g}}
Rare side effects include flushing of the face, [[hyperhidrosis]] (excessive sweating), [[cutaneous eruption]], arterial [[hypotension]], tachycardia, loss of appetite, [[jaundice]], [[eosinophilia]], [[thrombopenia]], mixed [[hepatitis]], headache, allergic reaction, chronic active hepatitis,{{ref_label|3|3|h}} and paradoxical aggravation of cerebral vasospasm.{{ref_label|9|9|a}}
== Formulations and trade names==
Papaverine is available as a [[Conjugated system|conjugate]] of [[hydrochloride]], [[pyridoxal phosphate|codecarboxylate]], [[adenosine monophosphate|adenylate]], and [[teprosylate]].{{ref_label|10|10|a}} It was also once available as a salt of [[hydrobromide]], [[camphorsulfonic acid|camsylate]], [[cromesilate]], [[nicotinic acid|nicotinate]], and [[amygdalic acid|phenylglycolate]]. The hydrochloride salt is available for intramuscular, intravenous, rectal and oral administration.{{ref_label|5|5|b}} The teprosylate is available in intravenous, intramuscular, and orally administered formulations.{{ref_label|11|11|a}} The codecarboxylate is available in oral form, only,{{ref_label|12|12|a}} as is the adenylate.{{ref_label|13|13|a}}
The codecarboxylate is sold under the name Albatran,{{ref_label|14|14|a}} the adenylate as Dicertan,{{ref_label|15|15|a}} 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), Papaverin-Hamelin (Germany), Paveron (Germany), Spasmo-Nit (Germany),{{ref_label|5|5|c}} Cardiospan, Papaversan, Cepaverin, Cerespan, Drapavel, Forpaven, Papalease, Pavatest, Paverolan, Therapav (France{{ref_label|16|16|a}}), 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.{{ref_label|17|17|a}}. In [[Hungary]] papaverine and [[homatropine]]-[[methylbromide]] are used in mild drugs that help "flush" the [[bile]] (e.g. [http://www.ogyi.hu/drug_database/index.php?action=show_details&item=21736 Neo-Bilagit]).
==References==
{{Reflist}}
<div class="references-small">
# {{note_label|1|1|a}} {{note_label|1|1|b}} {{note_label|1|1|c}} {{cite web | url=http://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?sid=544606 | title=SID 544606 -- PubChem Substance Summary | accessdate=25 September 2005 | dateformat=dmy }} National Center for Biotechnology Information.
# {{note_label|2|2|a}} {{cite web | url=http://bulkpharm.mallinckrodt.com/_attachments/msds/PAPVN.htm | title=Papaverine Material Safety Data Sheet | accessdate=25 September 2005 | dateformat=dmy }}
# {{note_label|3|3|a}} {{note_label|3|3|b}} {{note_label|3|3|c}} {{note_label|3|3|d}} {{note_label|3|3|e}} {{note_label|3|3|f}} {{note_label|3|3|g}} {{note_label|3|3|h}} {{cite web | | author=Unknown |
year=2000 | title=PAPAVERINE | work=Molécule(s) de base: PAPAVERINE | publisher=Biam | url=http://www.biam2.org/www/Sub3015.html | accessdate=25 September 2005 | dateformat=dmy}} (French)
# {{note_label|4|4|a}} {{cite web | author=Unknown | year=2004 | title=Who should not take papaverine? | work=papaverine Consumer Drug Information | publisher=Cerner Multum, Inc | url=http://www.drugs.com/MTM/papaverine.html | accessdate=26 September 2005 | dateformat=dmy}}
# {{note_label|5|5|a}} {{note_label|5|5|b}} {{note_label|5|5|c}} {{cite web | author=Unknown |
year=1999 | title=PAPAVERINE CHLORHYDRATE | work=Molécule(s) de base: PAPAVERINE | publisher=Biam | url=http://www.biam2.org/www/Sub65.html | accessdate=25 September 2005 | dateformat=dmy}} (French)
# {{note_label|6|6|a}} {{cite journal | author=Liu, James K.; Couldwell, William T | title=Intra-arterial papaverine infusions for the treatment of cerebral vasospasm induced by aneurysmal subarachnoid hemorrhage | journal=Neurocritical Care | volume=2 | issue=2 | year=2005 | pages=124–32 | pmid=16159054 | doi=10.1385/NCC:2:2:124}} [http://www.ncbi.nlm.nih.gov/entrez/query.fcgi?cmd=Retrieve&db=pubmed&list_uids=16159054&dopt=ExternalLink Fulltext options] [http://www.ncbi.nlm.nih.gov/entrez/query.fcgi?cmd=Retrieve&db=pubmed&list_uids=16159054&dopt=ExternalLink&ExternalLink=libs List of Library Holdings]
# {{note_label|7|7|a}} {{cite journal | author=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 | year=2004 | pages=956–9 | pmid=15519189 | doi=10.1016/j.ejcts.2004.07.047}} [http://www.ncbi.nlm.nih.gov/entrez/query.fcgi?cmd=Retrieve&db=pubmed&list_uids=15519189&dopt=ExternalLink Fulltext options] [http://www.ncbi.nlm.nih.gov/entrez/query.fcgi?cmd=Retrieve&db=pubmed&list_uids=15519189&dopt=ExternalLink&ExternalLink=libs List of Library Holdings]
# {{note_label|8|8|a}} {{cite web | url=http://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?sid=149219 | title=SID 149219 -- PubChem Substance Summary | accessdate=26 September 2005 | dateformat=dmy }} National Center for Biotechnology Information.
# {{note_label|9|9|a}} {{cite journal | author=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 | year=1996 | pages=690–5}} {{PMID|8613866}}
# {{note_label|10|10|a}} {{cite web | url=http://www.biam2.org/www/Gsu1575.html | title=Molécule de base: PAPAVERINE | accessdate=26 September 2005 | dateformat=dmy }} ''Biam.''
# {{note_label|11|11|a}} {{cite web | author=Unknown |
year=1999 | title=PAPAVERINE TEPROSILATE | work=Molécule(s) de base: PAPAVERINE | publisher=Biam | url=http://www.biam2.org/www/Sub70.html | accessdate=26 September 2005 | dateformat=dmy}} (French)
# {{note_label|12|12|a}} {{cite web | author=Unknown | year=1998 | title=PAPAVERINE CODECARBOXYLATE | work=Molécule(s) de base: PAPAVERINE | publisher=Biam | url=http://www.biam2.org/www/Sub1293.html | accessdate=26 September 2005 | dateformat=dmy}} (French)
# {{note_label|13|13|a}} {{cite web | author=Unknown | year=1998 | title=PAPAVERINE ADENYLATE | work=Molécule(s) de base: PAPAVERINE | publisher=Biam | url=http://www.biam2.org/www/Sub1295.html | accessdate=26 September 2005 | dateformat=dmy}} (French)
# {{note_label|14|14|a}} {{cite web | url=http://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?sid=660773 | title=SID 660773 PubChem Substance Summary | accessdate=25 September 2005 | dateformat=dmy }} National Center for Biotechnology Information.
# {{note_label|15|15|a}} {{cite web | url=http://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?sid=660767 | title=SID 660767 -- PubChem Substance Summary | accessdate=25 September 2005 | dateformat=dmy }} National Center for Biotechnology Information.
# {{note_label|16|16|a}} {{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 | accessdate=26 September 2005 | dateformat=dmy }} CSST - Service du répertoire toxicologique. (French)
# {{note_label|17|17|a}} {{cite web | url=http://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?sid=40460&ncount=61#Synonyms | title=SID 660767 -- PubChem Substance Summary - Depositor-Supplied Synonyms: All | accessdate=26 September 2005 | dateformat=dmy }} National Center for Biotechnology Information.
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{{Components of Opium}}
{{Drugs for functional gastrointestinal disorders}}
{{Urologicals}}
{{Phosphodiesterase inhibitors}}
[[Category:Natural opium alkaloids]]
[[Category:Vasodilators]]
[[Category:Bitter compounds]]
[[Category:Phosphodiesterase inhibitors]]
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