Papaverine
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| Image:Papaverin - Papaverine.svg | |
| Papaverine
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| Systematic (IUPAC) name | |
| 1-[(3,4-dimethoxyphenyl)methyl]-6,7-dimethoxy-isoquinoline | |
| Identifiers | |
| CAS number | |
| ATC code | A03 G04BE02 |
| PubChem | |
| DrugBank | |
| Chemical data | |
| Formula | C20H21NO4 |
| Mol. mass | 339.385 g/mol[1] |
| Pharmacokinetic data | |
| Bioavailability | 80%[3] |
| Protein binding | ~90% |
| Metabolism | Hepatic[3] |
| Half life | 1.5–2 hours[3] |
| Excretion | Renal[3] |
| Therapeutic considerations | |
| Pregnancy cat. | |
| Legal status | |
| Routes | Oral, intravenous, intramuscular, rectal,[5] intracavernosal |
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Papaverine is an 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.[3] While it is found in the opium poppy, papaverine differs in both structure and pharmacological action from the other opium alkaloids (opiates).
Uses
Papaverine is approved to treat spasms of the gastointestinal tract, bile ducts and ureter and for use as a cerebral and coronary vasodilator[3] in subarachnoid hemorrhage (combined with balloon angioplasty)[6] and coronary artery bypass surgery.[7] Papaverine may also be used as a smooth muscle relaxant in microsurgery where it is applied directly to blood vessels.
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 mitochondrial respiration.
It is also commonly used in cryopreservation of blood vessels along with other glycosaminoglycans and protein suspensions.[1][2] Functions as a vasodilator during cryopreservation when used in conjunction with verapamil, phentolamine, nifedipine, tolazolines, or nitroprusside.[3][4]
Papaverine is also being investigated as a topical growth factor in tissue expansion with some success.[5]
Side effects
Frequent side effects of papaverine treatment include polymorphic ventricular tachycardia, constipation, interference with sulphobromophthalein[8] retention test (used to determine hepatic function), increased transaminase levels, increased alkaline phosphatase levels, somnolence, and vertigo.[3]
Rare side effects include flushing of the face, hyperhidrosis (excessive sweating), cutaneous eruption, arterial hypotension, tachycardia, lack of appetite, jaundice, eosinophilia, thrombopenia, mixed hepatitis, headache, allergic reaction, chronic active hepatitis,[3] and paradoxical aggravation of cerebral vasospasm.[9]
Formulations and trade names
Papaverine is available as a conjugate of hydrochloride, codecarboxylate, adenylate, and teprosylate.[10] It was also once available as a salt of hydrobromide, camsylate, cromesilate, nicotinate, and phenylglycolate. The hydrochloride salt is available for intramuscular, intravenous, rectal and oral administration.[5] The teprosylate is available in intravenous, intramuscular, and orally administered formulations.[11] The codecarboxylate is available in oral form, only,[12] as is the adenylate.[13]
The codecarboxylate is sold under the name Albatran®,[14] the adenylate as Dicertan®,[15] 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),[5] Cardiospan®, Papaversan®, Cepaverin®, Cerespan®, Drapavel®, Forpaven®, Papalease®, Pavatest®, Paverolan®, Therapav® (France[16]), 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®.[17]
References
- ↑ 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
- ↑ Muller-Schweinitzer E, Hasse J, Swoboda L. : "Cryopreservation of human bronchi.". J Asthma. 1993;30(6):451-7. Links
- ↑ Brockbank KG.: "Effects of cryopreservation upon vein function in vivo". Cryobiology. 1994 Feb;31(1):71-81
- ↑ 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
- ↑ Tang Y, Luan J, Zhang X (2004). "Accelerating tissue expansion by application of topical papaverine cream". Plast. Reconstr. Surg. 114 (5): 1166–9. PMID 15457029.
- a b c SID 544606 -- PubChem Substance Summary. Retrieved on 25 September, 2005. National Center for Biotechnology Information.
- a Papaverine Material Safety Data Sheet. Retrieved on 25 September, 2005.
- a b c d e f g h Unknown (2000). PAPAVERINE. Molécule(s) de base : PAPAVERINE. Biam. Retrieved on 25 September, 2005. (French)
- a Unknown (2004). Who should not take papaverine?. papaverine Consumer Drug Information. Cerner Multum, Inc. Retrieved on 26 September, 2005.
- a b c Unknown (1999). PAPAVERINE CHLORHYDRATE. Molécule(s) de base : PAPAVERINE. Biam. Retrieved on 25 September, 2005. (French)
- a Liu, James K.; Couldwell, William T (2005). "Intra-arterial papaverine infusions for the treatment of cerebral vasospasm induced by aneurysmal subarachnoid hemorrhage". Neurocritical Care 2 (2): 124-32. PMID 16159054. Fulltext options List of Library Holdings
- a Takeuchi K, Sakamoto S, Nagayoshi Y, Nishizawa H, Matsubara J (2004). "Reactivity of the human internal thoracic artery to vasodilators in coronary artery bypass grafting". European Journal of Cardio-Thoracic Surgery 26 (5): 956-9. PMID 15519189. Fulltext options List of Library Holdings
- a SID 149219 -- PubChem Substance Summary. Retrieved on 26 September, 2005. National Center for Biotechnology Information.
- a Clyde BL, Firlik AD, Kaufmann AM, Spearman MP, Yonas H (1996). "Paradoxical aggravation of vasospasm with papaverine infusion following aneurysmal subarachnoid hemorrhage. Case report". Journal of Neurosurgery 84 (4): 690-5. PubMed
- a Molécule de base : PAPAVERINE. Retrieved on 26 September, 2005. Biam.
- a Unknown (1999). PAPAVERINE TEPROSILATE. Molécule(s) de base : PAPAVERINE. Biam. Retrieved on 26 September, 2005. (French)
- a Unknown (1998). PAPAVERINE CODECARBOXYLATE. Molécule(s) de base : PAPAVERINE. Biam. Retrieved on 26 September, 2005. (French)
- a Unknown (1998). PAPAVERINE ADENYLATE. Molécule(s) de base : PAPAVERINE. Biam. Retrieved on 26 September, 2005. (French)
- a SID 660773 PubChem Substance Summary. Retrieved on 25 September, 2005. National Center for Biotechnology Information.
- a SID 660767 -- PubChem Substance Summary. Retrieved on 25 September, 2005. National Center for Biotechnology Information.
- a THERAPAV (PRODUIT PUR) - Détail. Retrieved on 26 September, 2005. CSST - Service du répertoire toxicologique. (French)
- a SID 660767 -- PubChem Substance Summary - Depositor-Supplied Synonyms: All. Retrieved on 26 September, 2005. National Center for Biotechnology Information.
Drugs for functional gastrointestinal disorders (A03) | |
|---|---|
| Drugs for functional bowel disorders | antimuscarinics: Mebeverine - Dicycloverine - Propantheline
papaverine and derivatives: Papaverine - Drotaverine - Moxaverine acting on serotonin receptors: 5-HT3 antagonists (Alosetron, Cilansetron) - 5HT4 agonists (Mosapride, Tegaserod) other: Diisopromine - Isometheptene - Phloroglucinol - Proglumide - Tridihexethyl |
| Belladonna and derivatives (antimuscarinics) | Atropine - Hyoscyamine - Butylscopolamine - Methylscopolamine |
| Propulsives | primarily dopamine antagonists (Metoclopramide/Bromopride, Domperidone, Alizapride) - serotonin agonists (Cisapride) - Clebopride |
eo:Papaverinosk:Papaverín sv:Papaverin
Acknowledgement and Attribution Regarding Sources of Content
Some of the initial content on this page may be incorporated in part from copyleft sources in the public domain including wikis such as Wikipedia and AskDrWiki. Drug information for patients came from the The National Library of Medicine. Infectious disease information may have come from the Centers for Disease Control (CDC). Differential Diagnoses are drawn from clinicians as well as an amalgamation of 3 sources: 1.The Disease Database; 2. Kahan, Scott, Smith, Ellen G. In A Page: Signs and Symptoms. Malden, Massachusetts: Blackwell Publishing, 2004:3; 3. Sailer, Christian, Wasner, Susanne. Differential Diagnosis Pocket. Hermosa Beach, CA: Borm Bruckmeir Publishing LLC, 2002:7 .
