papaverine
American Heritage Dictionary:
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pa·pav·er·ine
(pə-păv'ə-rēn', -ər-ĭn) 
n.
A nonaddictive opium derivative, C20H21NO4, used medicinally to relieve spasms of smooth muscle.
n.
A nonaddictive opium derivative, C20H21NO4, used medicinally to relieve spasms of smooth muscle.
[Latin papāver, poppy + -INE2.]
Drug Info:
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Papaverine
Brand names: Para-Time™
Chemical formula:
- Drug Forms:
- Papaverine extended-release capsules (below)
- Papaverine injection
- Papaverine Hydrochloride Solution for injection
- Papaverine Hydrochloride Oral capsule, extended-release
- Espa�ol:
- Cápsulas de liberación prolongada de papaverina
- Inyección de papaverina
- Clorhidrato de papaverina, Solución para inyección
- Clorhidrato de papaverina, Cápsula oral de liberación prolongada
Papaverine extended-release capsules
What are papaverine extended-release capsules?
PAPAVERINE (PAVABID®, PAVACOT®) is a vasodilator that relaxes blood vessels and makes them wider and allows the blood to pass through them more easily. Generic papaverine extended-release capsules are available.What should I tell my health care provider before I take this medicine?
They need to know if you have, or have had, any of these conditions:• an alcohol problem
• heart disease or irregular heartbeats
• liver disease
• glaucoma
• Parkinson's disease
• an unusual or allergic reaction to papaverine, other medicines, foods, dyes, or preservatives
• pregnant or trying to get pregnant
• breast-feeding
How should I use this medicine?
Take papaverine by mouth. Follow the directions on the prescription label. Swallow the capsules with a drink of water. Do not chew, open, break or crush the capsules. The capsules are formulated to release the drug slowly in your body. Take your doses at regular intervals. Do not take your medicine more often than directed.What if I miss a dose?
If you miss a dose, take it as soon as you can. If it is almost time for your next dose, take only that dose. Do not take double or extra doses.What drug(s) may interact with papaverine?
• alcohol• barbiturate medicines for inducing sleep or treating seizures (convulsions)
• medicines for anxiety or sleeping problems, such as diazepam or temazepam
• medicines for Parkinson's disease
• some medicines for pain (narcotic analgesics such as morphine, tramadol)
Tell your prescriber or health care professional about all other medicines you are taking, including non-prescription medicines, nutritional supplements, or herbal products. Also tell your prescriber or health care professional if you are a frequent user of drinks with caffeine or alcohol, if you smoke, or if you use illegal drugs. These may affect the way your medicine works. Check with your health care professional before stopping or starting any of your medicines.
What should I watch for while taking papaverine?
If you experience dizziness or feel faint, this may be due to the lowering of your blood pressure. Lie down immediately and raise your legs. If symptoms persist, call your prescriber or health care professional. Do not drive, use machinery, or do anything that requires mental alertness until you know how papaverine affects you.What side effects may I notice from using papaverine?
Side effects that you should report to your prescriber or health care professional as soon as possible:• fainting or falling spells
• fast or irregular heartbeat
• stomach pain
• yellowing or the eyes or skin
Side effects that usually do not require medical attention report to your prescriber or health care professional if they continue or are bothersome):
• nausea or vomiting, decreased appetite, diarrhea, constipation
• dizziness
• drowsiness
• headache
• sweating or flushing
Where can I keep my medicine?
Keep out of the reach of children in a container that small children cannot open.Store the bottle at room temperature at 15—30 degrees C (59—86 degrees F).
Last updated: 7/1/2002
Important Disclaimer: The drug information provided here is for educational purposes only. It is intended to supplement, not substitute for, the diagnosis, treatment and advice of a medical professional. This drug information does not cover all possible uses, precautions, side effects and interactions. It should not be construed to indicate that this or any drug is safe for you. Consult your medical professional for guidance before using any prescription or over the counter drugs.
Oxford A-Z of Medicinal Drugs:
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papaverine
An alkaloid, derived from opium, that relaxes smooth muscle. It is an ingredient of papaveretum. Alone, papaverine is used in the treatment of impotence, being injected directly into the penis to achieve an erection, although it does not have a licence for this purpose. Papaverine is available as a solution for injection on prescription only.
Side effects and precautions:
there may be a burning pain and bruising at the injection site. An erection that lasts for longer than four hours is a medical emergency and requires prompt treatment (by withdrawing blood from the penis followed, if necessary, by injections of phenylephrine or adrenaline).
| papaveretum, pantoprazole, panitumumab | |
| paracetamol, paraldehyde, parasympathetic nervous system |
Columbia Encyclopedia:
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papaverine
papaverine (pəpăv'ərēn), alkaloid found in opium that acts as a muscle relaxant and vasodilator. The drug relaxes the smooth muscle of the larger blood vessels and is used to increase the blood supply to the brain or to the heart, as in the treatment of angina pectoris. It is also used in the treatment of some types of blood clot formation and in the treatment of impotence when the condition is caused by a lack of blood flow.
Oxford Dictionary of Biochemistry:
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papaverine
1-[(3,4-dimethoxyphenyl)methyl]-6,7-dimethoxyisoquinoline; a constituent of opium that acts as a smooth muscle relaxant; this action is thought to be due to phosphodiesterase inhibitory activity and blockade of membrane calcium channels. Like codeine and morphine it is a metabolic derivative of (S)-reticuline.
| papain, pantoyl, pantothenyl | |
| paper chromatogram, paper chromatography, paper electrophoresis |
Saunders Veterinary Dictionary:
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papaverine
An alkaloid obtained from opium and prepared synthetically; the hydrochloride salt is used as a smooth muscle relaxant.
Wikipedia on Answers.com:
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Papaverine
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| Systematic (IUPAC) name | |
| 1-(3,4-dimethoxybenzyl)-6,7-dimethoxyisoquinoline | |
| Clinical data | |
| Trade names | Pavabid |
| AHFS/Drugs.com | monograph |
| MedlinePlus | a682707 |
| Pregnancy cat. | USA: C[4] |
| Legal status | ? |
| Routes | Oral, intravenous, intramuscular, rectal,[5] intracavernosal |
| Pharmacokinetic data | |
| Bioavailability | 80%[3] |
| Protein binding | ~90% |
| Metabolism | Hepatic[3] |
| Half-life | 1.5–2 hours[3] |
| Excretion | Renal[3] |
| Identifiers | |
| CAS number | 58-74-2  61-25-6 (hydrochloride) |
| ATC code | A03AD01 G04BE02 |
| PubChem | CID 4680 |
| DrugBank | DB01113 |
| ChemSpider | 4518 |
| UNII | DAA13NKG2Q |
| KEGG | D07425 |
| ChEMBL | CHEMBL19224 |
| Chemical data | |
| Formula | C20H21NO4 |
| Mol. mass | 339.385 g/mol[1] |
| SMILES | eMolecules & PubChem |
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Papaverine (
/pəˈpævəriːn/)[1] is an opium alkaloid antispasmodic drug, 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 analgesic (morphine-related) opium alkaloids (opioids).
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Contents
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History
Papaverine was discovered in 1848 by Georg Merck (1825-1873).[2] Merck was a student of the German chemists Justus von Liebig and August Hofmann, and he was the son of Emanuel Merck (1794-1855), founder of the Merck corporation, a major German chemical and pharmaceutical company.[3]
Merck explained the origin of the name of "papaverine":
Original : " ... es ist mir gelungen, in einer in dem chemischen Laboratorium zu Giessen angestellten Untersuchung einiger in der Fabrik meines Vaters angehäuften Rückstände von Morphium-präparaten, eine neue Basis aufzufinden, welche ich mit dem Namen Papaverin bezeichnen werde."[4]
Translation : " ... while I was engaged at the Giessen chemical laboratory [of Justus von Liebig] in an investigation of some residues from morphine preparations, which had accumulated at my father's factory, I succeeded in discovering a new base, which I will designate with the name 'papaverin'."[5]
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.
Papaverine is used as an erectile dysfunction drug, alone or sometimes in combination.[6][7] Papaverine, when injected in penile tissue causes direct smooth muscle relaxation and consequent filling of the corpus cavernosum with blood resulting in erection. A topical gel is also available for ED treatment.[8]
It is also commonly used in cryopreservation of blood vessels along with the other glycosaminoglycans and protein suspensions.[9][10] Functions as a vasodilator during cryopreservation when used in conjunction with verapamil, phentolamine, nifedipine, tolazoline or nitroprusside.[11][12]
Papaverine is also being investigated as a topical growth factor in tissue expansion with some success.[13]
Papaverine is used as an off label prophylaxis (preventative) of migraine headaches.[14][15][16] It is not a first line drug such as a few beta blockers, calcium channel blockers, tricyclic antidepressants, and some anticonvulsants such as divalproex, but rather when these first line drugs and secondary drugs such as SSRIs, angiotensin II receptor antagonists, etc. fail in the prophylaxis of migraines, have intolerable side effects or are contraindicated.
Papaverine is also present in combinations of opium alkaloid salts such as papaveretum (Omnopon, Pantopon) and others, along with morphine, codeine, and in some cases noscapine and others in a percentage similar to that in opium, or modified for a given application.
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.
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.,[17][18] even though not all studies support this view.[19]
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), Papaverine (Israel), Papaverin-Hamelin (Germany), Paveron (Germany), Spasmo-Nit (Germany),[5] Cardiospan, Papaversan, Cepaverin, Cerespan, Drapavel, Forpaven, Papalease, Pavatest, Paverolan, Therapav (Québec[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]. In Hungary, papaverine and homatropine methylbromide are used in mild drugs that help "flush" the bile (e.g. Neo-Bilagit).
References
- ^ Papaverine - EverydayHealth.com
- ^ Georg Merck (1848) "Vorläufige Notiz über eine neue organische Base im Opium" (Preliminary notice of a new organic base in opium), Annalen der Chemie und Pharmacie, vol. 66, pages 125-128.
- ^ William H. Brock, Justus von Liebig: The Chemical Gatekeeper (Cambridge, England: Cambridge University Press, 1997). page 120.
- ^ Merck (1848), page 126.
- ^ "Papaverin" is thus a combination of the words "papa" (dad) and "Verein" (association (company)), so "papaverin" = dad's company, the original source of the compound.
- ^ Desvaux, P (2005). "An overview of the management of erectile disorders". Presse medicale (Paris, France : 1983) 34 (13 Suppl): 5–7. PMID 16158020.
- ^ Bella, A. J.; Brock, G. B. (2004). "Intracavernous Pharmacotherapy for Erectile Dysfunction". Endocrine 23 (2–3): 149–155. doi:10.1385/ENDO:23:2-3:149. PMID 15146094.
- ^ Kim, E.; Elrashidy, R.; McVary, K. (1995). "Papaverine Topical Gel for Treatment of Erectile Dysfunction". The Journal of Urology 153 (2): 361. doi:10.1097/00005392-199502000-00019. PMID 7815584.
- ^ Müller-Schweinitzer E, Ellis P (May 1992). "Sucrose promotes the functional activity of blood vessels after cryopreservation in DMSO-containing fetal calf serum". Naunyn Schmiedebergs Arch. Pharmacol. 345 (5): 594–7. PMID 1528275.
- ^ Müller-Schweinitzer E, Hasse J, Swoboda L (1993). "Cryopreservation of human bronchi". J Asthma 30 (6): 451–7. doi:10.3109/02770909309056754. PMID 8244915.
- ^ Brockbank KG (February 1994). "Effects of cryopreservation upon vein function in vivo". Cryobiology 31 (1): 71–81. doi:10.1006/cryo.1994.1009. PMID 8156802. http://linkinghub.elsevier.com/retrieve/pii/S0011-2240(84)71009-1.
- ^ Giglia JS, Ollerenshaw JD, Dawson PE, Black KS, Abbott WM (November 2002). "Cryopreservation prevents arterial allograft dilation". Ann Vasc Surg 16 (6): 762–7. doi:10.1007/s10016-001-0072-1. PMID 12391500.
- ^ 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.
- ^ Sillanpää, M; Koponen, M (1978). "Papaverine in the prophylaxis of migraine and other vascular headache in children". Acta paediatrica Scandinavica 67 (2): 209–12. doi:10.1111/j.1651-2227.1978.tb16304.x. PMID 343489.
- ^ Vijayan, N. (1977). "Brief therapeutic report: papaverine prophylaxis of complicated migraine". Headache 17 (4): 159–162. doi:10.1111/j.1526-4610.1977.hed1704159.x. PMID 893088.
- ^ Poser, C. M. (1974). "Letter: Papaverine in prophylactic treatment of migraine". Lancet 1 (7869): 1290–1222. doi:10.1016/S0140-6736(74)90045-2. PMID 4134173.
- ^ Siuciak JA, Chapin DS, Harms JF, et al. (August 2006). "Inhibition of the striatum-enriched phosphodiesterase PDE10A: a novel approach to the treatment of psychosis". Neuropharmacology 51 (2): 386–96. doi:10.1016/j.neuropharm.2006.04.013. PMID 16780899. http://linkinghub.elsevier.com/retrieve/pii/S0028-3908(06)00106-7.
- ^ Hebb AL, Robertson HA, Denovan-Wright EM (May 2008). "Phosphodiesterase 10A inhibition is associated with locomotor and cognitive deficits and increased anxiety in mice". Eur Neuropsychopharmacol 18 (5): 339–63. doi:10.1016/j.euroneuro.2007.08.002. PMID 17913473. http://linkinghub.elsevier.com/retrieve/pii/S0924-977X(07)00172-1.
- ^ Weber M, Breier M, Ko D, Thangaraj N, Marzan DE, Swerdlow NR (May 2009). "Evaluating the antipsychotic profile of the preferential PDE10A inhibitor, papaverine". Psychopharmacology (Berl.) 203 (4): 723–35. doi:10.1007/s00213-008-1419-x. . PMID 19066855. http://www.pubmedcentral.nih.gov/articlerender.fcgi?tool=pmcentrez&artid=2748940.
- a b c "SID 544606 — PubChem Substance Summary". http://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?sid=544606.
- a "Papaverine Material Safety Data Sheet". http://bulkpharm.mallinckrodt.com/_attachments/msds/PAPVN.htm. Retrieved 25 September 2005.
- a b c d e f g h Unknown (2000). "PAPAVERINE". Molécule(s) de base: PAPAVERINE. Biam. http://www.biam2.org/www/Sub3015.html. Retrieved 25 September 2005. (French)
- a Unknown (2004). "Who should not take papaverine?". papaverine Consumer Drug Information. Cerner Multum, Inc. http://www.drugs.com/MTM/papaverine.html. Retrieved 26 September 2005.
- a b c Unknown (1999). "PAPAVERINE CHLORHYDRATE". Molécule(s) de base: PAPAVERINE. Biam. http://www.biam2.org/www/Sub65.html. Retrieved 25 September 2005. (French)
- a Liu JK, Couldwell WT (2005). "Intra-arterial papaverine infusions for the treatment of cerebral vasospasm induced by aneurysmal subarachnoid hemorrhage". Neurocrit Care 2 (2): 124–32. doi:10.1385/NCC:2:2:124. PMID 16159054.
- a Takeuchi K, Sakamoto S, Nagayoshi Y, Nishizawa H, Matsubara J (November 2004). "Reactivity of the human internal thoracic artery to vasodilators in coronary artery bypass grafting". Eur J Cardiothorac Surg 26 (5): 956–9. doi:10.1016/j.ejcts.2004.07.047. PMID 15519189. http://linkinghub.elsevier.com/retrieve/pii/S1010-7940(04)00621-9.
- a "SID 149219 — PubChem Substance Summary". http://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?sid=149219.
- a Clyde BL, Firlik AD, Kaufmann AM, Spearman MP, Yonas H (April 1996). "Paradoxical aggravation of vasospasm with papaverine infusion following aneurysmal subarachnoid hemorrhage. Case report". J. Neurosurg. 84 (4): 690–5. doi:10.3171/jns.1996.84.4.0690. PMID 8613866. http://thejns.org/doi/abs/10.3171/jns.1996.84.4.0690?url_ver=Z39.88-2003&rfr_id=ori:rid:crossref.org&rfr_dat=cr_pub%3dncbi.nlm.nih.gov.
- a "Molécule de base: PAPAVERINE". http://www.biam2.org/www/Gsu1575.html. Retrieved 26 September 2005. Biam.
- a Unknown (1999). "PAPAVERINE TEPROSILATE". Molécule(s) de base: PAPAVERINE. Biam. http://www.biam2.org/www/Sub70.html. Retrieved 26 September 2005. (French)
- a Unknown (1998). "PAPAVERINE CODECARBOXYLATE". Molécule(s) de base: PAPAVERINE. Biam. http://www.biam2.org/www/Sub1293.html. Retrieved 26 September 2005. (French)
- a Unknown (1998). "PAPAVERINE ADENYLATE". Molécule(s) de base: PAPAVERINE. Biam. http://www.biam2.org/www/Sub1295.html. Retrieved 26 September 2005. (French)
- a "SID 660773 — PubChem Substance Summary". http://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?sid=660773.
- a "SID 660767 — PubChem Substance Summary". http://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?sid=660767.
- a "THERAPAV (PRODUIT PUR) - Détail". http://www.reptox.csst.qc.ca/Produit.asp?no_produit=108688&nom=THERAPAV+(PRODUIT+PUR)&incr=0. Retrieved 26 September 2005. CSST - Service du répertoire toxicologique. (French)
- a "SID 660767 — PubChem Substance Summary — Depositor-Supplied Synonyms: All". http://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?sid=40460&ncount=61#Synonyms.
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Copyrights:
American Heritage Dictionary
The American Heritage® Dictionary of the English Language, Fourth Edition Copyright © 2007, 2000 by Houghton Mifflin Company. Updated in 2009. Published by Houghton Mifflin Company. All rights reserved.
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Oxford A-Z of Medicinal Drugs
Market University Press. © 2000, 2003, 2010 An A-Z of Medicinal Drugs. All rights reserved.
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Columbia Encyclopedia
The Columbia Electronic Encyclopedia, Sixth Edition Copyright © 2012, Columbia University Press. Licensed from Columbia University Press. All rights reserved. www.cc.columbia.edu/cu/cup/.
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Oxford Dictionary of Biochemistry
Oxford University Press. Oxford Dictionary of Biochemistry and Molecular Biology © 1997, 2000, 2006 All rights reserved.
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Saunders Veterinary Dictionary
Saunders Comprehensive Veterinary Dictionary 3rd Edition. Copyright © 2007 by D.C. Blood, V.P. Studdert and C.C. Gay, Elsevier. All rights reserved.
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