Papaverine

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Image:Papaverin - Papaverine.svg
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 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][1] Functions as a vasodilator during cryopreservation when used in conjunction with verapamil, phentolamine, nifedipine, tolazolines, or nitroprusside.[1][1]

Papaverine is also being investigated as a topical growth factor in tissue expansion with some success.[1]

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

  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. 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. 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
Drugs for functional gastrointestinal disorders (A03)
Drugs for functional bowel disordersantimuscarinics: 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
Propulsivesprimarily dopamine antagonists (Metoclopramide/Bromopride, Domperidone, Alizapride) - serotonin agonists (Cisapride) - Clebopride
v • d • e
Urologicals (G04)
AcidifiersAmmonium chloride, Calcium chloride
Urinary antispasmodics (primarily antimuscarinics)Darifenacin, Emepronium, Fesoterodine, Flavoxate, Meladrazine, Oxybutynin, Propiverine, Solifenacin, Terodiline, Tolterodine, Trospium
For erectile dysfunctionprostaglandins: Alprostadil

PDE5 inhibitors: Avanafil - Sildenafil - Tadalafil - Udenafil - Vardenafil

alpha blockers: Moxisylyte - Phentolamine - Yohimbine

others: Apomorphine - Papaverine
Other urologicalsAcetohydroxamic acid, Collagen, Dimethyl sulfoxide, Magnesium hydroxide, Pentosan polysulfate, Phenazopyridine, Phenyl salicylate, Succinimide
For benign prostatic hypertrophy5α-reductase inhibitors: Dutasteride, Finasteride

Alpha blockers: Alfuzosin, Doxazosin, Silodosin, Tamsulosin, Terazosin

Herbals: Pygeum africanum, Serenoa repens

de:Papaverin eo:Papaverino fr:Papavérine ja:パパベリンsk:Papaverín sv:Papaverin

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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 .

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