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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[1]
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).

Contents 1 Uses 2 Side effects 3 Formulations and Tradenames 4 References 5 External links

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]}

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, hyperbilirubinemia, 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]

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]

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.

• Links to external chemical sources

v • d • e Urologicals (G04)
Acidifiers	Ammonium chloride, Calcium chloride
Urinary antispasmodics	Darifenacin, Emepronium, Flavoxate, Meladrazine, Oxybutynin, Propiverine, Solifenacin, Terodiline, Tolterodine, Trospium
For erectile dysfunction	Alprostadil, Apomorphine, Avanafil, Moxisylyte, Papaverine, Phentolamine, Sildenafil, Tadalafil, Udenafil, Vardenafil, Vendafidel, Yohimbine
Other urologicals	Acetohydroxamic acid, Collagen, Dimethyl sulfoxide, Magnesium hydroxide, Phenazopyridine, Phenyl salicylate, Succinimide
For benign prostatic hypertrophy	5α-reductase inhibitors: Dutasteride, Finasteride Alpha blockers: Alfuzosin, Doxazosin, Tamsulosin, Terazosin Herbals: Pygeum africanum, Serenoa repens