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Papaverine chemical structure
| 1-[(3,4-dimethoxyphenyl)methyl]- 6,7-dimethoxy-isoquinoline|
| CAS number |
| ATC code |
| PubChem |
| DrugBank |
|Molecular weight||339.385 g/mol|
|Elimination half-life||1.5–2 hours|
|Pregnancy category||USA: C|
|Routes of administration||Oral, intravenous, intramuscular, rectal, intracavernosal|
Papaverine (pronounced /pəˈpævəriːn/) 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. While it is found in the opium poppy, papaverine differs in both structure and pharmacological action from the other 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 Papaverine remains available despite the committee's recommendation that it be withdrawn from the market.
Papaverine is approved to treat spasms of the gastrointestinal tract, bile ducts and ureter and for use as a cerebral and coronary vasodilator in subarachnoid hemorrhage (combined with balloon angioplasty) and coronary artery bypass surgery. 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. Functions as a vasodilator during cryopreservation when used in conjunction with verapamil, phentolamine, nifedipine, tolazolines, or nitroprusside.
Papaverine is also being investigated as a topical growth factor in tissue expansion with some success.
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.
Impotence is a long-term complication of diabetes. It is due to dysfunction of the autonomic nerves that mediate the erection. An erection is produced when the parasympathetic nerves that innervate the penile arterioles release acetylcholine, vasoactive intestinal peptide (VIP), and nitric oxide (NO). These neurotransmitters produce vasodilation with increased blood flow into the erectile tissues of the penis. As the penis becomes engorged with blood, the penile veins become compressed, so that outflow is blocked. Diabetes can be complicated by autonomic neuropathy. The exact cause of the neuropathy is unknown, but may include direct toxic effects of high extracellular glucose, accumulation of sorbitol within the nerves, or poor blood supply to the nerves because of decreased NO release by blood vessel endothelial cells.
Side effects Edit
Frequent side effects of papaverine treatment include polymorphic ventricular tachycardia, constipation, interference with sulphobromophthalein retention test (used to determine hepatic function), increased transaminase levels, increased alkaline phosphatase levels, somnolence, and vertigo.
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, and paradoxical aggravation of cerebral vasospasm.
Formulations and trade namesEdit
Papaverine is available as a conjugate of hydrochloride, codecarboxylate, adenylate, and teprosylate. 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. 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, the adenylate as Dicertan, 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), Cardiospan, Papaversan, Cepaverin, Cerespan, Drapavel, Forpaven, Papalease, Pavatest, Paverolan, Therapav (France), 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.
- ↑ Papaverine - EverydayHealth.com
- ↑ 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 the medecine 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.
- a b c SID 544606 -- PubChem Substance Summary. National Center for Biotechnology Information.
- a Papaverine Material Safety Data Sheet.
- a b c d e f g h Unknown (2000). PAPAVERINE. Molécule(s) de base: PAPAVERINE. Biam. (French)
- a Unknown (2004). Who should not take papaverine?. papaverine Consumer Drug Information. Cerner Multum, Inc.
- a b c Unknown (1999). PAPAVERINE CHLORHYDRATE. Molécule(s) de base: PAPAVERINE. Biam. (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. 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. Fulltext options List of Library Holdings
- a SID 149219 -- PubChem Substance Summary. 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. PMID 8613866
- a Molécule de base: PAPAVERINE. Biam.
- a Unknown (1999). PAPAVERINE TEPROSILATE. Molécule(s) de base: PAPAVERINE. Biam. (French)
- a Unknown (1998). PAPAVERINE CODECARBOXYLATE. Molécule(s) de base: PAPAVERINE. Biam. (French)
- a Unknown (1998). PAPAVERINE ADENYLATE. Molécule(s) de base: PAPAVERINE. Biam. (French)
- a SID 660773 PubChem Substance Summary. National Center for Biotechnology Information.
- a SID 660767 -- PubChem Substance Summary. National Center for Biotechnology Information.
- a THERAPAV (PRODUIT PUR) - Détail. CSST - Service du répertoire toxicologique. (French)
- a SID 660767 -- PubChem Substance Summary - Depositor-Supplied Synonyms: All. National Center for Biotechnology Information.
|Urinary antispasmodics (primarily antimuscarinics)|
|For erectile dysfunction|
|For benign prostatic hypertrophy|
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