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20-September-2008 09:55:50 - Sildenafil Semi-protected Viagra redirects here. For the Russian/Ukrainian girl group also known as Via Gra, see Nu Virgos Sildenafil Systematic IUPAC name 1-4-ethoxy-3-6,7-dihydro-1-methyl- 7-oxo-3-propyl-1H-pyrazolo4,3-dpyrimidin-5-yl phenylsulfonyl-4-methylpiperazine citrate Identifiers CAS number 139755-83-2 ATC code G04BE03 PubChem 5281023 DrugBank APRD00556 Chemical data Formula C22H30N6O4S Mol. mass base: 474.6 g/mol SMILES eMolecules PubChem Pharmacokinetic data Bioavailability 40% Metabolism Hepatic Half life 3-4h Excretion CYP3A4 Therapeutic considerations Pregnancy cat. BUS Legal status â„ž Prescription only Routes Oral Sildenafil citrate, sold as Viagra, Revatio and under various other trade names, is a drug used to treat erectile dysfunction male impotence and pulmonary arterial hypertension PAH. It was developed and is being marketed by the pharmaceutical company Pfizer. It acts by inhibiting cGMP specific phosphodiesterase type 5, an enzyme that regulates blood flow in the penis. Since becoming available in 1998, sildenafil has been the prime treatment for erectile dysfunction; its primary competitors on the market are tadalafil Cialis and vardenafil Levitra. Contents 1 History 2 Mechanism of action 3 Uses 3.1 Sexual dysfunction 3.2 Pulmonary hypertension 3.3 Altitude sickness 3.4 Use in sports 4 Non-medical use 4.1 Recreational use 4.2 Prevention of plant wilting 4.3 Jet lag research 5 Dosage 6 Contraindications 7 Side effects 8 Chemical synthesis 9 See also 10 References 11 External links History Sildenafil compound UK-92,480 was synthesized by a group of pharmaceutical chemists working at Pfizer's Sandwich, Kent research facility in England. It was initially studied for use in hypertension high blood pressure and angina pectoris a symptom of ischaemic heart disease. The first clinical trials were conducted in Morriston Hospital in Swansea.1 Phase I clinical trials under the direction of Ian Osterloh suggested that the drug had little effect on angina, but that it could induce marked penile erections.23 Pfizer therefore decided to market it for erectile dysfunction, rather than for angina. The drug was patented in 1996, approved for use in erectile dysfunction by the Food and Drug Administration on March 27, 1998, becoming the first oral treatment approved to treat erectile dysfunction in the United States, and offered for sale in the United States later that year.4 It soon became a great success: annual sales of Viagra in the period 1999-2001 exceeded $1 billion.citation needed The British press portrayed Peter Dunn and Albert Wood as the inventors of the drug, a claim which Pfizer disputes.5 Their names are on the manufacturing patent application drug, but Pfizer claims this is only for convenience.citation needed Even though sildenafil is available only by prescription from a doctor, it was advertised directly to consumers on U.S. TV famously being endorsed by former United States Senator Bob Dole and soccer star Pelé. Numerous sites on the Internet offer Viagra for sale after an online consultation, often a simple web questionnaire.citation needed The Viagra name has become so well known that many fake aphrodisiacs now call themselves herbal Viagra or are presented as blue tablets imitating the shape and colour of Pfizer's product. Viagra is also informally known as Vitamin V, the Blue Pill, as well as various other nicknames.citation needed In 2000, Viagra sales accounted for 92 percent of the global market for prescribed erectile dysfunction pills.6 By 2007, Viagra's global share had plunged to about 50 percent7 due to several factors, including the entry of Cialis and Levitra, along with several other counterfeits and clones, and reports of vision loss in people taking PDE5 inhibitors.89 In February 2007, it was announced that Boots the Chemist would trial over the counter sales of Viagra in stores in Manchester, England. Men aged between 30 and 65 would be eligible to buy four tablets after a consultation with a pharmacist.10 Pfizer's worldwide patents on sildenafil citrate will expire in 2011-2013. The UK patent held by Pfizer on the use of PDE5 inhibitors see below as treatment of impotence was invalidated in 2000 because of obviousness; this decision was upheld on appeal in 2002.citation needed Mechanism of action The mechanism of action of Sildenafil citrate involves the release of nitric oxide NO in the corpus cavernosum of the penis. NO binds to the receptors of the enzyme guanylate cyclase which results in increased levels of cyclic guanosine monophosphate cGMP, leading to smooth muscle relaxation vasodilation of the intimal cushions of the helicine arteries, resulting in increased inflow of blood and an erection.11 Sildenafil is a potent and selective inhibitor of cGMP specific phosphodiesterase type 5 PDE5 which is responsible for degradation of cGMP in the corpus cavernosum. The molecular structure of sildenafil is similar to that of cGMP and acts as a competitive binding agent of PDE5 in the corpus cavernosum, resulting in more cGMP and better erections.11 Without sexual stimulation, and therefore lack of activation of the NO/cGMP system, sildenafil should not cause an erection. Other drugs that operate by the same mechanism include tadalafil Cialis and vardenafil Levitra.citation needed Sildenafil is metabolised by liver enzymes and excreted by both the liver and kidneys. If taken with a high-fat meal, absorption is reduced; the time taken to reach the maximum plasma concentration increases by around one hour, and the maximum concentration itself is decreased by nearly one-third.12 Uses Sexual dysfunction Sildenafil is used primarily in the treatment of erectile dysfunction inability to sustain a satisfactory erection to complete intercourse.citation needed It use is now standard treatment for erectile dysfunction in all settings, including diabetes.13 People on antidepressants may experience sexual dysfunction, either as a result of their illness or as a result of their treatment. A 2003 study showed that sildenafil improved sexual function in men in this situation.14 Following up to earlier reports from 1999,15 the same researchers found that sildenafil was able to improve sexual function in female patients on antidepressants as well.16 Pulmonary hypertension As well as erectile dysfunction, sildenafil citrate is also effective in the rare disease pulmonary arterial hypertension PAH. It relaxes the arterial wall, leading to decreased pulmonary arterial resistance and pressure. This in turn reduces the workload of the right ventricle of the heart and improves symptoms of right-sided heart failure. Because PDE-5 is primarily distributed within the arterial wall smooth muscle of the lungs and penis, sildenafil acts selectively in both these areas without inducing vasodilation in other areas of the body. Pfizer submitted an additional registration for sildenafil to the FDA, and sildenafil was approved for this indication in June 2005. The preparation is named Revatio, to avoid confusion with Viagra, and the 20 milligram tablets are white and round. Sildenafil joins bosentan and prostacyclin-based therapies for this condition.17 Altitude sickness Sildenafil has been shown to be useful for the prevention and treatment of High altitude pulmonary edema associated with altitude sickness such as that suffered by mountain climbers.1819 While this effect has only recently been discovered, sildenafil is already becoming an accepted treatment for this condition, particularly in situations where the standard treatment of rapid descent has been delayed for some reason.20 Use in sports Professional sports players have been using drugs such as Viagra thinking that the opening of their blood vessels will enrich their muscles, therefore enhancing their performance.21 Non-medical use Recreational use Viagra's popularity with young adults has increased over the years.22 It is sometimes used recreationally, though this use is somewhat pointless in young, healthy men, as they receive no benefit from the drug.22 Some users mix Viagra with methylenedioxymethamphetamine MDMA, ecstasy or other stimulants in an attempt to compensate for the side effect common to many amphetamines of erectile dysfunction, a combination known as sextasy, rockin' and rollin', or 'trail mix'. Mixing with amyl nitrite is particularly dangerous, and is potentially fatal.22 Prevention of plant wilting A low-concentration solution of sildenafil in water significantly prolongs the time before cut flowers wilt; one experiment showed a doubling in time from one week to two weeks. The mechanism of action is similar to that in humans: nitric oxide leads to the production of cGMP whose degradation by PDE5 is inhibited by sildenafil.23 Jet lag research The 2007 Ig Nobel Prize in Aviation went to Patricia V. Agostino, Santiago A. Plano and Diego A. Golombek of Universidad Nacional de Quilmes, Argentina, for their discovery that Viagra aids jet lag recovery in hamsters.24 Their research was published in the Proceedings of the National Academy of Sciences.25 Dosage Viagra Viagra Viagra pills are blue and diamond-shaped with the words Pfizer engraved on one side, and VGR xx where xx stands for 25, 50 or 100, the dose of that pill in milligrams engraved on the other. The dose of sildenafil for erectile dysfunction is 25 mg to 100 mg taken not more than once per day between 30 minutes and 4 hours prior to sexual intercourse. It is usually recommended to start with a dosage of 50 mg or even 25 mg and then lower or raise the dosage as appropriate.citation needed The dosage for pulmonary arterial hypertension Revatio is one 20 mg tablet three times a day. Revatio pills are white, round, film-coated tablets imprinted with RVT 20 on one side and Pfizer on the other.citation needed Contraindications Contraindications include:citation needed When taking nitric oxide donors, organic nitrites and nitrates, such as glyceryl trinitrate nitroglycerin, sodium nitroprusside, amyl nitrite poppers26 In men for whom sexual intercourse is inadvisable due to cardiovascular risk factors Severe hepatic impairment decreased liver function Severe impairment in renal function Hypotension low blood pressure Recent stroke or heart attack Herary degenerative retinal disorders including genetic disorders of retinal phosphodiesterases Side effects Amongst sildenafil's rare but serious adverse effects are: priapism, severe hypotension, myocardial infarction, ventricular arrhythmias, stroke and increased intraocular pressure.citation needed Common side effects include sneezing, headache, flushing, dyspepsia, palpitations and photophobia.citation needed Care should be exercised by patients who are also taking Protease inhibitors for the treatment of HIV. Protease inhibitors inhibit the metabolism of sildenafil, effectively multiplying the plasma levels of sildenafil, increasing the incidence and severity of side-effects. It is recommended that patients using protease inhibitors limit their use of sildenafil to no more than one 25-mg dose every 48 hours.citation needed Some sildenafil users have complained of seeing everything tinted blue cyanopsia. 27. Some complained of blurriness and loss of peripheral vision. In May of 2005, the U.S. Food and Drug Administration found that sildenafil could lead to vision impairment28 and a number of studies have linked sildenafil use with nonarteritic anterior ischemic optic neuropathy.293031323334 In October 2007, the FDA announced that the labeling for all PDE5 inhibitors, including sildenafil, requires a more prominent warning of the potential risk of sudden hearing loss as the result of postmarketing reports of deafness associated with use of PDE5 inhibitors.35 When used with an alpha blocker, hypotension low blood pressure may occur, but this effect does not occur if they are taken at least four hours apart.36 Chemical synthesis The preparation steps for synthesis of Viagra sildenafil citrate are as follows:37 Methylation of 3-propylpyrazole-5-carboxylic acid ethyl ester with hot dimethyl sulfate. Hydrolysis with aqueous NaOH to free acid. Nitration with oleum/fuming nitric acid. Carboxamide formation with refluxing thionyl chloride/NH4OH. Reduction of nitro group to amino. Acylation with 2-ethoxybenzoyl chloride. Cyclization. Sulfonation to the chlorosulfonyl derivative. Condensation with 1-methylpiperazine. See also Pharmacy and Pharmacology portal Tadalafil Cialis Vardenafil Levitra References ^ Aubetawe Bro Morgannwg University NHS Trust 2008-07-04. Research at ABM. Retrieved on 2008-08-06. ^ Boolell M, Allen MJ, Ballard SA, Gepi-Attee S, Muirhead GJ, Naylor AM, Osterloh IH, Gingell C 1996. Sildenafil: an orally active type 5 cyclic GMP-specific phosphodiesterase inhibitor for the treatment of penile erectile dysfunction. Int J Impot Res 8 2: 47-52. PMID 8858389. ^ Terrett NK et al 1996. Sildenafil Viagra, a potent and selective inhibitor of Type 5 cGMP phosphodiesterase with utility for the treatment of male erectile dysfunction. Bioorg Med Chem Lett 6: 1819-1824. doi:10.1016/0960-894X9600323-X. ^ Kling J 1998. From hypertension to angina to Viagra. Mod Drug Discov 1: 31-38. ^ Bellis M. Viagra, the patenting of an aphrodisiac. About.com. ^ Keith A 2000. The economics of Viagra PDF. Health Aff Millwood 19 2: 147-57. PMID 10718028. ^ McGuire, Stephen January 1, 2007. Cialis gaining market share worldwide, Medical Marketing Media. Retrieved on August 20, 2008 through AllBusiness.com. ^ Mullin, Rick June 20, 2005. Viagra. Chemical Engineering News 83 25. Retrieved on 2008-08-20. ^ Berenson, Alex December 4, 2005. Sales of Impotence Drugs Fall, Defying Expectations, The New York Times. Retrieved on 2008-08-20. ^ Over-the-counter Viagra piloted. British Broadcasting Corporation 2007-02-11. ^ a b Webb, D.J.; Freestone, S.; Allen, M.J.; Muirhead, G.J. March 4, 1999. Sildenafil citrate and blood-pressure-lowering drugs: results of drug interaction studies with an organic nitrate and a calcium antagonist. Am. J. Cardiol. 83 5A: 21C-28C. doi:10.1016/S0002-91499900044-2. PMID 10078539. ^ Viagra Clinical Pharmacology. RxList.com 2008. Retrieved on 2008-08-20. ^ Vardi M, Nini A 2007. Phosphodiesterase inhibitors for erectile dysfunction in patients with diabetes mellitus. Cochrane Database Syst Rev 1: CD002187. doi:10.1002/14651858.CD002187.pub3. PMID 17253475. ^ Nurnberg HG, Hensley PL, Gelenberg AJ, Fava M, Lauriello J, Paine S January 2003. Treatment of antidepressant-associated sexual dysfunction with sildenafil: a randomized controlled trial. JAMA 289 1: 56-64. PMID 12503977. ^ Nurnberg HG, Hensley PL, Lauriello J, Parker LM, Keith SJ August 1999. Sildenafil for women patients with antidepressant-induced sexual dysfunction. Psychiatr Serv 50 8: 1076-8. PMID 10445658. ^ Nurnberg HG, Hensley PL, Heiman JR, Croft HA, Debattista C, Paine S 2008. Sildenafil Treatment of Women With Antidepressant-Associated Sexual Dysfunction. JAMA 300 4: 395-404. doi:10.1001/jama.300.4.395. PMID 18647982. ^ Pfizer, Inc. June 6, 2005. FDA Approves Pfizer's Revatio as Treatment for Pulmonary Arterial Hypertension. 2005 News Releases. Pfizer. Retrieved on December 27, 2005. ^ Richalet JP, Gratadour P, Robach P, et al 2005. Sildenafil inhibits altitude-induced hypoxemia and pulmonary hypertension. Am. J. Respir. Crit. Care Med. 171 3: 275-81. doi:10.1164/rccm.200406-804OC. PMID 15516532. ^ Perimenis P 2005. Sildenafil for the treatment of altitude-induced hypoxaemia. Expert Opin Pharmacother 6 5: 835-7. doi:10.1517/14656566.6.5.835. PMID 15934909. ^ Fagenholz PJ, Gutman JA, Murray AF, Harris NS 2007. Treatment of high altitude pulmonary edema at 4240 m in Nepal. High Alt. Med. Biol. 8 2: 139-46. doi:10.1089/ham.2007.1055. PMID 17584008. ^ Source: Roger Clemens, host of athletes pop Viagra to help onfield performance. New York Daily News 2008-06-10. ^ a b c Peterson K 2001-03-21. Young men add Viagra to their drug arsenal, USAToday. ^ Siegel-Itzkovich J 1999. Viagra makes flowers stand up straight. Student BMJ 9. ^ 1 ^ Agostino PV, Plano SA, Golombek DA 2007. Sildenafil accelerates reentrainment of circadian rhythms after advancing light schedules. Proc. Natl. Acad. Sci. U.S.A. 104 23: 9834-9. doi:10.1073/pnas.0703388104. PMID 17519328. ^ Cheitlin MD, Hutter AM Jr, Brindis RG, Ganz P, Kaul S, Russell RO Jr, Zusman RM 1999. ACC/AHA expert consensus document. Use of sildenafil Viagra in patients with cardiovascular disease. American College of Cardiology/American Heart Association. Journal of the American College of Cardiology 33 1: 273-82. doi:10.1016/S0735-10979800656-1. PMID 9935041. ^ Viagra and vision. visionweb n.d.. ^ Alert for Healthcare Professionals: Sildenafil citrate marketed as Viagra. United States Food and Drug Administration July 2005. ^ Pomeranz HD and Bhavsar AR 2005. Nonarteritic ischemic optic neuropathy developing soon after use of sildenafil viagra: a report of seven new cases. J Neuroophthalmol 25 1: 9-13. PMID 15756125. ^ Egan R and Pomeranz H 2000. Sildenafil Viagra associated anterior ischemic optic neuropathy. Arch Ophthalmol 118 2: 291-2. PMID 10676804. ^ Pomeranz HD, Smith KH, Hart WM, Egan RA 2002. Sildenafil-associated nonarteritic anterior ischemic optic neuropathy. Ophthalmology 109 3: 584-7. doi:10.1016/S0161-64200100976-9. PMID 11874765. ^ Cunningham AV and Smith KH 2001. Anterior ischemic optic neuropathy associated with viagra. J Neuroophthalmol 21 1: 22-5. PMID 11315976. ^ Boshier A, Pambakian N, Shakir SA 2002. A case of nonarteritic ischemic optic neuropathy NAION in a male patient taking sildenafil. Int J Clin Pharmacol Ther 40 9: 422-3. PMID 12358159. ^ Akash R, Hrishikesh D, Amith P, Sabah S 2005. Case report: association of combined nonarteritic anterior ischemic optic neuropathy NAION and obstruction of cilioretinal artery with overdose of Viagra. J Ocul Pharmacol Ther 24 4: 315-7. doi:10.1089/jop.2005.21.315. PMID 16117695. ^ FDA Announces Revisions to Labels for Cialis, Levitra and Viagra. Food and Drug Administration 2007-10-18. Retrieved on 2007-12-08. ^ Kloner RA 2005. Pharmacology and drug interaction effects of the phosphodiesterase 5 inhibitors: focus on alpha-blocker interactions. Am J Cardiol 96 12B: 42M-46M. doi:10.1016/j.amjcard.2005.07.011. PMID 16387566. ^ Dunn PJ 2005. Synthesis of Commercial PhosphodiesteraseV Inhibitors. Org Process Res Dev 2005 1: 88-97. doi:10.1021/op040019c. External links Find more about Viagra on 's sister projects: Dictionary definitions Textbooks Quotations Source texts Images and media News stories Learning resources Official Viagra Website Official Revatio Website Official Pfizer Website - manufacturer of Viagra; prescribing information for Viagra and prescribing information for Revatio FDA Consumer Information MedlinePLUS Information on Side Effects v d e Urologicals G04 Acidifiers Ammonium chloride, Calcium chloride Urinary antispasmodics primarily antimuscarinics Darifenacin, Emepronium, Fesoterodine, Flavoxate, Imidafenacin, Meladrazine, Oxybutynin, Propiverine, Solifenacin, Terodiline, Tolterodine, Trospium For erectile dysfunction Prostaglandins E Alprostadil PDE5 inhibitors Avanafil - Sildenafil - Tadalafil - Udenafil - Vardenafil Alpha blockers Moxisylyte - Phentolamine - Yohimbine Others Apomorphine - Papaverine Other urologicals Acetohydroxamic acid, Collagen, Dimethyl sulfoxide, Magnesium hydroxide, Pentosan polysulfate, Phenazopyridine, Phenyl salicylate, Succinimide For BPH 5α-reductase inhibitors Dutasteride, Finasteride Alpha blockers α1 Alfuzosin, Doxazosin, Silodosin, Tamsulosin, Terazosin Herbals Pygeum africanum, Serenoa repens v d e Medications used in the management of pulmonary arterial hypertension B01, C02 Prostacyclin analogues Beraprost, Epoprostenol, Iloprost, Treprostinil Endothelin receptor antagonists Ambrisentan, Bosentan, Sitaxsentan PDE5 inhibitors Sildenafil, Tadalafil Adjunctive therapy Calcium channel blockers, Diuretics, Digoxin, Oxygen therapy, Warfarin v d e Selective Phosphodiesterase inhibitors C01CE, G04BE PDE1 Vinpocetine PDE2 EHNA PDE3 Amrinone, Bucladesine, Enoximone, Milrinone PDE4 Cilomilast, Etazolate, Glaucine, HT-0712, Ibudilast, Mesembrine, Rolipram PDE5 Acetildenafil, Avanafil, Sildenafil, Tadalafil, Thiomethisosildenafil, Udenafil, Vardenafil Retrieved from http://en..org/wiki/Sildenafil Categories: PDE5 inhibitors | CitratesHidden categories: Semi-protected | All articles with statements | Articles with statements since August 2008 | Articles with statements since July 2008 | Articles with statements since December 2007 Views Article Discussion View source History Personal tools Log in / create account Navigation Main page Contents Featured content Current events Random article Search Go Search Interaction Community portal Recent changes Contact Donate to Help Toolbox What links here Related changes Upload file Special pages Printable version Permanent link Cite this page Languages العربية Català Česky Dansk Deutsch Español Français Bahasa Indonesia Italiano עברית Magyar Nederlands 日本語 ‪Norsk bokmÃ¥l‬ Polski Português РуÑ?Ñ?кий Shqip Simple English SlovenÅ¡Ä?ina Suomi Svenska ไทย Tiếng Việt Türkçe УкраїнÑ?ька ŽemaitÄ—Å¡ka ä¸æ–‡ This page was last modified on 21 August 2008, at 02:3
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