Papaverine

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Papaverine
Systematic (IUPAC) name
1-[(3,4-dimethoxyphenyl)methyl]- 6,7-dimethoxy-isoquinoline
Identifiers
CAS number 61-25-6
ATC code A03AD01 G04BE02
PubChem 4680
DrugBank APRD00628
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.

USA: C[4]
Legal status
Routes Oral, intravenous, intramuscular, rectal,[5] intracavernosal

Papaverine (pronounced /pəˈpævəriːn/[1]) 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).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 Papaverine remains available despite the committee's recommendation that it be withdrawn from the market.

Contents

Uses

Papaverine is approved to treat spasms of the gastrointestinal 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.

It is also commonly used in cryopreservation of blood vessels along with the other glycosaminoglycans and protein suspensions.[2][3] Functions as a vasodilator during cryopreservation when used in conjunction with verapamil, phentolamine, nifedipine, tolazoline or nitroprusside.[4][5]

Papaverine is also being investigated as a topical growth factor in tissue expansion with some success.[6]

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 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.

Papaverine has also been demonstrated to be a selective phosphodiesterase inhibitor for the PDE10A subtype found mainly in the striatum of the brain. When administered chronically to mice it produced motor and cognitive deficits and increased anxiety, but conversely may produce an antipsychotic effect.[7][8]

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, loss 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

  1. ^ Papaverine - EverydayHealth.com[1]
  2. ^ 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
  3. ^ Muller-Schweinitzer E, Hasse J, Swoboda L. : "Cryopreservation of human bronchi.". J Asthma. 1993;30(6):451-7. Links
  4. ^ Brockbank KG.: "Effects of the medecine upon vein function in vivo". Cryobiology. 1994 Feb;31(1):71-81
  5. ^ 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
  6. ^ Tang Y, Luan J, Zhang X (2004). "Accelerating tissue expansion by application of topical papaverine cream". Plast. Reconstr. Surg. 114 (5): 1166–9. doi:10.1097/01.PRS.0000135854.48570.76. PMID 15457029. 
  7. ^ 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
  8. ^ 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
  1. a  b  c  "SID 544606 -- PubChem Substance Summary". Retrieved on 25 September 2005. National Center for Biotechnology Information.
  2. a  "Papaverine Material Safety Data Sheet". Retrieved on 25 September 2005.
  3. a  b  c  d  e  f  g  h  Unknown (2000). "PAPAVERINE". Molécule(s) de base: PAPAVERINE. Biam. Retrieved on 25 September 2005. (French)
  4. a  Unknown (2004). "Who should not take papaverine?". papaverine Consumer Drug Information. Cerner Multum, Inc. Retrieved on 26 September 2005.
  5. a  b  c  Unknown (1999). "PAPAVERINE CHLORHYDRATE". Molécule(s) de base: PAPAVERINE. Biam. Retrieved on 25 September 2005. (French)
  6. 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. doi:10.1385/NCC:2:2:124. PMID 16159054.  Fulltext options List of Library Holdings
  7. 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. doi:10.1016/j.ejcts.2004.07.047. PMID 15519189.  Fulltext options List of Library Holdings
  8. a  "SID 149219 -- PubChem Substance Summary". Retrieved on 26 September 2005. National Center for Biotechnology Information.
  9. 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
  10. a  "Molécule de base: PAPAVERINE". Retrieved on 26 September 2005. Biam.
  11. a  Unknown (1999). "PAPAVERINE TEPROSILATE". Molécule(s) de base: PAPAVERINE. Biam. Retrieved on 26 September 2005. (French)
  12. a  Unknown (1998). "PAPAVERINE CODECARBOXYLATE". Molécule(s) de base: PAPAVERINE. Biam. Retrieved on 26 September 2005. (French)
  13. a  Unknown (1998). "PAPAVERINE ADENYLATE". Molécule(s) de base: PAPAVERINE. Biam. Retrieved on 26 September 2005. (French)
  14. a  "SID 660773 PubChem Substance Summary". Retrieved on 25 September 2005. National Center for Biotechnology Information.
  15. a  "SID 660767 -- PubChem Substance Summary". Retrieved on 25 September 2005. National Center for Biotechnology Information.
  16. a  "THERAPAV (PRODUIT PUR) - Détail". Retrieved on 26 September 2005. CSST - Service du répertoire toxicologique. (French)
  17. a  "SID 660767 -- PubChem Substance Summary - Depositor-Supplied Synonyms: All". Retrieved on 26 September 2005. National Center for Biotechnology Information.
v • d • e
Components of Opium
Morphine group
(Phenanthrenes)
Isoquinolines

Cotarnine • Eupaverine • Hydrocotarnine • Laudanosine • Laudanine • Papaverine • Papaveraldine • Xanthaline
Protopine group
Tetrahydroprotoberberine group
Aporphine group
Phtalide-isoquinolines
Others
v • d • e
Drugs for functional gastrointestinal disorders (A03)
Drugs for
functional bowel disorders
Tertiary
amino group
Papaverine · Drotaverine · Moxaverine
Other
Belladonna and derivatives
(antimuscarinics)
Propulsives
v • d • e
Urologicals (G04)
Acidifiers
Urinary antispasmodics
(primarily antimuscarinics)
For erectile dysfunction
Others
Apomorphine - Papaverine
Other urologicals
For BPH
v • d • e
Selective Phosphodiesterase inhibitors (C01CE, G04BE)
PDE1
PDE2
PDE3
PDE4
PDE5
PDE10A
Papaverine • PF-2545920 • Tofisopam

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