The History and Development of Sildenafil Citrate
This metabolite also has an affinity for the PDE receptors, about 40% of that of sildenafil. Thus, the metabolite is responsible for about 20% of sildenafil's action. Sildenafil is excreted as metabolites predominantly in the feces (about 80% of administered oral dose) and to a lesser extent in the urine (around 13% of the administered oral dose). 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. When taken orally, sildenafil for erectile dysfunction results in an average time to onset of erections of 27 minutes (ranging from 12 to 70 minutes). Sublingual use of sildenafil for erectile dysfunction results in an average onset of action of 15 minutes and lasting for an average of 40 minutes. The preparation steps for synthesis of sildenafil are:[54] Methylation of 3-propylpyrazole-5-carboxylic acid ethyl ester with hot dimethyl sulfate Hydrolysis with aqueous sodium hydroxide (NaOH) to free acid Carboxamide formation with refluxing thionyl chloride/NH4OH Reduction of nitro group to amino group Sildenafil (compound UK-92,480) was synthesized by a group of pharmaceutical chemists led by Simon Campbell[55] 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). [56] The first clinical trials were conducted in Morriston Hospital in Swansea.
Other Uses for Sildenafil
This metabolite also has an affinity for the PDE receptors, about 40% of that of sildenafil. Thus, the metabolite is responsible for about 20% of sildenafil's action. Sildenafil is excreted as metabolites predominantly in the feces (about 80% of administered oral dose) and to a lesser extent in the urine (around 13% of the administered oral dose). 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. When taken orally, sildenafil for erectile dysfunction results in an average time to onset of erections of 27 minutes (ranging from 12 to 70 minutes).
Noms commerciaux
Sublingual use of sildenafil for erectile dysfunction results in an average onset of action of 15 minutes and lasting for an average of 40 minutes. The preparation steps for synthesis of sildenafil are:[54] Methylation of 3-propylpyrazole-5-carboxylic acid ethyl ester with hot dimethyl sulfate Hydrolysis with aqueous sodium hydroxide (NaOH) to free acid Carboxamide formation with refluxing thionyl chloride/NH4OH Reduction of nitro group to amino group Sildenafil (compound UK-92,480) was synthesized by a group of pharmaceutical chemists led by Simon Campbell[55] 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). [56] The first clinical trials were conducted in Morriston Hospital in Swansea. [57] Phase I clinical trials under the direction of Ian Osterloh suggested the drug had little effect on angina, but it could induce marked penile erections.
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[58][59] Pfizer therefore decided to market it for erectile dysfunction, rather than for angina; this decision became an often-cited example of drug repositioning. [60][61] The drug was patented in 1996, approved for use in erectile dysfunction by the FDA on 27 March 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. [62] It soon became a great success: annual sales of Viagra peaked in 2008 at US$1.934 billion. In the US, even though sildenafil is available only by prescription from a doctor, it was advertised directly to consumers on TV (famously being endorsed by former United States Senator Bob Dole and football star Pelé). Numerous sites on the Internet offer Viagra for sale after an "online consultation", often a simple web questionnaire. [57] Phase I clinical trials under the direction of Ian Osterloh suggested the drug had little effect on angina, but it could induce marked penile erections.
| Product | Dosage | Quantity + Bonus | Price | |
|---|---|---|---|---|
| Viagra Generic | 100mg | 120 + 6 Pills | 149.50€ 142.38€ | |
| Viagra Generic | 150mg | 90 + 6 Pills | 147.18€ 140.17€ | |
| Viagra Generic | 25mg | 360 + 10 Pills | 213.68€ 203.50€ | |
| Kamagra Polo | 100mg | 120 + 6 Pills | 327.15€ 311.57€ | |
| Kamagra Soft Tabs | 100mg | 32 Pills | 120.11€ 114.39€ | |
| Kamagra Polo | 100mg | 180 + 8 Pills | 446.52€ 425.26€ | |
| Kamagra | 100mg | 84 + 6 Pills | 264.44€ 251.85€ | |
| Kamagra Polo | 100mg | 20 Pills | 83.56€ 79.58€ | |
| Kamagra Polo | 100mg | 60 + 4 Pills | 189.39€ 180.37€ | |
| Viagra Generic | 25mg | 90 + 6 Pills | 105.03€ 100.03€ |
[58][59] Pfizer therefore decided to market it for erectile dysfunction, rather than for angina; this decision became an often-cited example of drug repositioning.
What should I know about storage and disposal of this medication?
The patent for Pfizer's Viagra sildenafil to treat erectile dysfunction expired in April 2020. In 2026 a chocolate syrup called Boner Bears from Lockout Supplements was recalled through the FDA because of it containing Sildenafil as an undisclosed ingredient. Counterfeit Viagra, despite generally being cheaper,[88] can contain harmful substances or substances that affect how Viagra works, such as blue printer ink, amphetamines, metronidazole, boric acid, and rat poison. Viagra is one of the world's most counterfeited medicines. [90][91] According to a 2012 Pfizer study, around 80% of sites claiming to sell Viagra were selling counterfeits.
More common
An October 2023 release stated that erectile dysfunction medicines were the most seized drugs by the Interpol[92] accounting for 22% of seizures. In 1992, Pfizer filed a patent covering the substance sildenafil and its use to treat cardiovascular diseases. [96] This would be marketed as Revatio. The patent was published in 1993 and expired in 2012. The patent on Revatio (indicated for pulmonary arterial hypertension rather than erectile dysfunction) expired in late 2012.
Who can use Sildenafil Citrate Tablets?
Generic versions of this low-dose form of sildenafil have been available in the US from a number of manufacturers, including Greenstone, Mylan, and Watson, since early 2013. [97] Health care providers may prescribe generic sildenafil for erectile dysfunction. [98] For a time, the generic was not available in the same dosages as branded Viagra, so using dosages typically required for treating ED required patients to take multiple pills. In 1994, Pfizer filed a patent covering the use of sildenafil to treat erectile dysfunction. [99] This would be marketed as Viagra. [60][61] The drug was patented in 1996, approved for use in erectile dysfunction by the FDA on 27 March 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. [62] It soon became a great success: annual sales of Viagra peaked in 2008 at US$1.934 billion. In the US, even though sildenafil is available only by prescription from a doctor, it was advertised directly to consumers on TV (famously being endorsed by former United States Senator Bob Dole and football star Pelé).
- Sildenafil citrate was approved by the FDA in 1998.
- Its discovery revolutionized the treatment of erectile dysfunction.
- The medication requires sexual stimulation to be effective.
- It is not an aphrodisiac; it facilitates natural response.
- Overdose symptoms may include severe hypotension.
- Recreational use of sildenafil without prescription is risky.
- Combining with alcohol can increase side effects.
- It should be stored at room temperature away from moisture.
Numerous sites on the Internet offer Viagra for sale after an "online consultation", often a simple web questionnaire.
More about sildenafil
[112] However, on 9 November 2012, Pfizer filed a motion for a re-hearing of the appeal in the Supreme Court of Canada,[113] on the grounds that the court accidentally exceeded its jurisdiction by voiding the patent. [114] Finally, on 22 April 2013, the Supreme Court of Canada invalidated Pfizer's patent altogether. Manufacture and sale of sildenafil citrate drugs is common in China, where Pfizer's patent claim is not widely enforced. Egypt approved Viagra for sale in 2002, but soon afterwards allowed local companies to produce generic versions of the drug, citing the interests of poor people who would not be able to afford Pfizer's price. In June 2013 Pfizer's patent on sildenafil citrate expired in some member countries of the European Union, including Austria, Denmark, France, Germany, Ireland, Italy, The Netherlands, Spain, Sweden, the United Kingdom, and Switzerland. Viagra and other products for sexual dysfunction, termed sexuopharmaceuticals, proliferated new types of specialised marketing for such products. [66] Viagra and similar prescription pharmaceuticals were promoted by images in media to the extent of becoming a cultural icon, at the time a relatively new phenomenon known to be permitted only in the United States and New Zealand and which is believed to have significantly contributed to norms regarding male sexuality. [67] One author notes that although the effect of Viagra is only limited to penile blood vessels, advertisements routinely use imagery of couples hugging, smiling and dancing, with the author claiming that pharmaceutical companies were deceptive in the use of such advertisements. In 2000, Viagra sales accounted for 92% of the global market for prescribed erectile dysfunction pills. [69] By 2007, Viagra's global share had plunged to about 50%[70] due to several factors, including the entry of Cialis and Levitra, along with several counterfeits and clones, and reports of vision loss in people taking PDE5 inhibitors. [71][72] In 2008, the FDA forced Pfizer to remove Viva Cruiser, an advergame for Viagra, from appearing on Forbes, after the game failed to disclose risk information about the drug. In February 2007, it was announced that Boots, the UK pharmacy chain, would try over-the-counter sales of Viagra in stores in Manchester, England.
Voir aussi
This patent was published in 2002 and expired in 2019. Teva sildenafil 20 mg prescription sued to have the latter patent invalidated, but Pfizer prevailed in an August 2011 federal district court case. [100] An agreement with Pfizer allowed Teva to begin to provide the generic drug in December 2017. In the United States, Pfizer received two patents for sildenafil: one for its indication to treat cardiovascular disease (marketed as Revatio) and another for its indication to treat erectile dysfunction (marketed as Viagra). The substance is the same under both brand names.
Dysfonction érectile
Sildenafil is available as a generic drug in the United States, labeled for pulmonary arterial hypertension,[98] and to treat erectile dysfunction, as the patent expired in April 2020. In the US, Revatio and Viagra are marketed by Viatris after Upjohn was spun off from Pfizer. In Canada, Pfizer's patent 2,324,324 for Revatio (sildenafil used to treat pulmonary hypertension) was found invalid by the Federal Court in June 2010, on an application by Ratiopharm Inc.[106][107] On 8 November 2012, the Supreme Court of Canada ruled that Pfizer's patent 2,163,446 on Viagra was invalid from the beginning because the company did not provide full disclosure in its application. The decision, Teva Canada Ltd. v.
Oral Administration
Pfizer Canada Inc., pointed to section 27(3)(b) of The Patent Act which requires that disclosure must include sufficient information "to enable any person skilled in the art or science to which it pertains" to produce it. It added further: "As a matter of policy and sound statutory interpretation, patentees cannot be allowed to 'game' the system in this way. This, in my view, is the key issue in this appeal. Teva Canada launched Novo-Sildenafil, a generic version of Viagra, on the day the Supreme Court of Canada released its decision. [109][110][111] To remain competitive, Pfizer then reduced the price of Viagra in Canada. Males between the ages of 30 and 65 would be eligible to buy four tablets after a consultation with a pharmacist. [75] In 2017, the Medicines and Healthcare products Regulatory Agency (MHRA) enacted legislation that expanded this nationwide,[76] allowing a particular branded formulation of Sildenafil, Viagra Connect (50 mg), to be sold over the counter and without a prescription throughout the UK from early 2018.
4. Bottom Line
Viagra and other products for sexual dysfunction, termed sexuopharmaceuticals, proliferated new types of specialised marketing for such products. [66] Viagra and similar prescription pharmaceuticals were promoted by images in media to the extent of becoming a cultural icon, at the time a relatively new phenomenon known to be permitted only in the United States and New Zealand and which is believed to have significantly contributed to norms regarding male sexuality. [67] One author notes that although the effect of Viagra is only limited to penile blood vessels, advertisements routinely use imagery of couples hugging, smiling and dancing, with the author claiming that pharmaceutical companies were deceptive in the use of such advertisements. In 2000, Viagra sales accounted for 92% of the global market for prescribed erectile dysfunction pills. [69] By 2007, Viagra's global share had plunged to about 50%[70] due to several factors, including the entry of Cialis and Levitra, along with several counterfeits and clones, and reports of vision loss in people taking PDE5 inhibitors.
What is Sildenafil Citrate used for?
[71][72] In 2008, the FDA forced Pfizer to remove Viva Cruiser, an advergame for Viagra, from appearing on Forbes, after the game failed to disclose risk information about the drug. In February 2007, it was announced that Boots, the UK pharmacy chain, would try over-the-counter sales of Viagra in stores in Manchester, England. Males between the ages of 30 and 65 would be eligible to buy four tablets after a consultation with a pharmacist. [75] In 2017, the Medicines and Healthcare products Regulatory Agency (MHRA) enacted legislation that expanded this nationwide,[76] allowing a particular branded formulation of Sildenafil, Viagra Connect (50 mg), to be sold over the counter and without a prescription throughout the UK from early 2018. While the sale remains subject to a consultation with a pharmacist, the other restrictions from the trial have been removed, allowing customers over the age of 18 to purchase an unlimited number of pills.
What should happen if a dose is missed?
In May 2013, Pfizer, which manufactures Viagra, told the Associated Press they will begin selling the drug directly to people on its website. Pfizer's patents on Viagra expired outside the US in 2012; in the US they were set to expire, but Pfizer settled litigation with each of Mylan and Teva which agreed that both companies could introduce generics in the US in December 2017. [79][80] In December 2017, Pfizer released its own generic version of Viagra. As of 2018[update], the US sildenafil 130mg Food and Drug Administration has approved fifteen drug manufacturers to market generic sildenafil in the United States. Seven of these companies are based in India. While the sale remains subject to a consultation with a pharmacist, the other restrictions from the trial have been removed, allowing customers over the age of 18 to purchase an unlimited number of pills. In May 2013, Pfizer, which manufactures Viagra, told the Associated Press they will begin selling the drug directly to people on its website. Pfizer's patents on Viagra expired outside the US in 2012; in the US they were set to expire, but Pfizer settled litigation with each of Mylan and Teva which agreed that both companies could introduce generics in the US in December 2017. [79][80] In December 2017, Pfizer released its own generic version of Viagra. As of 2018[update], the US sildenafil 130mg Food and Drug Administration has approved fifteen drug manufacturers to market generic sildenafil in the United States. Seven of these companies are based in India. The patent for Pfizer's Viagra sildenafil to treat erectile dysfunction expired in April 2020. In 2026 a chocolate syrup called Boner Bears from Lockout Supplements was recalled through the FDA because of it containing Sildenafil as an undisclosed ingredient. Counterfeit Viagra, despite generally being cheaper,[88] can contain harmful substances or substances that affect how Viagra works, such as blue printer ink, amphetamines, metronidazole, boric acid, and rat poison. Viagra is one of the world's most counterfeited medicines. [90][91] According to a 2012 Pfizer study, around 80% of sites claiming to sell Viagra were selling counterfeits. An October 2023 release stated that erectile dysfunction medicines were the most seized drugs by the Interpol[92] accounting for 22% of seizures. In 1992, Pfizer filed a patent covering the substance sildenafil and its use to treat cardiovascular diseases. [96] This would be marketed as Revatio.
The Key Differences Between Viagra and Sildenafil
[117][118][119] A 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. Manufacture and sale of sildenafil citrate drugs known as "generic Viagra" is common in India, where Pfizer's patent claim does not apply. The patent was published in 1993 and expired in 2012. The patent on Revatio (indicated for pulmonary arterial hypertension rather than erectile dysfunction) expired in late 2012. Generic versions of this low-dose form of sildenafil have been available in the US from a number of manufacturers, including Greenstone, Mylan, and Watson, since early 2013. [97] Health care providers may prescribe generic sildenafil for erectile dysfunction.
| Form | Strengths | Route of Administration | Notes |
|---|---|---|---|
| Tablets | 25 mg, 50 mg, 100 mg | Oral | Most common form |
| Sublingual Tablets | 25 mg, 50 mg | Sublingual | Faster absorption |
| Extended-release Capsules | 100 mg | Oral | Less common |
| Oral Suspension | Customizable doses | Oral | Experimental/clinical use |
[98] For a time, the generic was not available in the same dosages as branded Viagra, so using dosages typically required for treating ED required patients to take multiple pills. In 1994, Pfizer filed a patent covering the use of sildenafil to treat erectile dysfunction.
| Country | Legal Status | Prescription Requirement | Notes |
|---|---|---|---|
| USA | Prescription-only medication | Yes | FDA approved |
| UK | Prescription-only | Yes | MHRA regulated |
| India | Over-the-counter and prescription | Both are possible | Varies by state |
| Australia | Prescription only | Yes | TGA regulated |
[99] This would be marketed as Viagra. This patent was published in 2002 and expired in 2019. Teva sildenafil 20 mg prescription sued to have the latter patent invalidated, but Pfizer prevailed in an August 2011 federal district court case. [100] An agreement with Pfizer allowed Teva to begin to provide the generic drug in December 2017. In the United States, Pfizer received two patents for sildenafil: one for its indication to treat cardiovascular disease (marketed as Revatio) and another for its indication to treat erectile dysfunction (marketed as Viagra). The substance is the same under both brand names. Sildenafil is available as a generic drug in the United States, labeled for pulmonary arterial hypertension,[98] and to treat erectile dysfunction, as the patent expired in April 2020. In the US, Revatio and Viagra are marketed by Viatris after Upjohn was spun off from Pfizer. In Canada, Pfizer's patent 2,324,324 for Revatio (sildenafil used to treat pulmonary hypertension) was found invalid by the Federal Court in June 2010, on an application by Ratiopharm Inc.[106][107] On 8 November 2012, the Supreme Court of Canada ruled that Pfizer's patent 2,163,446 on Viagra was invalid from the beginning because the company did not provide full disclosure in its application. The decision, Teva Canada Ltd.
| Effect | Mechanism | Onset Time | Duration |
|---|---|---|---|
| Vasodilation | Increased cGMP in smooth muscle | 30 mins | 4-6 hours |
| Blood Pressure Reduction | Vasodilation effects | Rapid | Several hours |
| Enhanced Erectile Function | Increased blood flow to penis | 30 mins | Up to 4-6 hours |
v. Pfizer Canada Inc., pointed to section 27(3)(b) of The Patent Act which requires that disclosure must include sufficient information "to enable any person skilled in the art or science to which it pertains" to produce it. It added further: "As a matter of policy and sound statutory interpretation, patentees cannot be allowed to 'game' the system in this way. This, in my view, is the key issue in this appeal. Teva Canada launched Novo-Sildenafil, a generic version of Viagra, on the day the Supreme Court of Canada released its decision. [109][110][111] To remain competitive, Pfizer then reduced the price of Viagra in Canada. [112] However, on 9 November 2012, Pfizer filed a motion for a re-hearing of the appeal in the Supreme Court of Canada,[113] on the grounds that the court accidentally exceeded its jurisdiction by voiding the patent. [114] Finally, on 22 April 2013, the Supreme Court of Canada invalidated Pfizer's patent altogether. Manufacture and sale of sildenafil citrate drugs is common in China, where Pfizer's patent claim is not widely enforced. Egypt approved Viagra for sale in 2002, but soon afterwards allowed local companies to produce generic versions of the drug, citing the interests of poor people who would not be able to afford Pfizer's price. In June 2013 Pfizer's patent on sildenafil citrate expired in some member countries of the European Union, including Austria, Denmark, France, Germany, Ireland, Italy, The Netherlands, Spain, Sweden, the United Kingdom, and Switzerland.
- Sildenafil citrate can be combined with lifestyle changes.
- Exercise and weight management improve erectile function.
- Quitting smoking enhances medication effectiveness.
- Reducing alcohol intake minimizes side effects.
- Psychological therapy may support ED treatment.
- Counseling can address underlying emotional issues.
- Regular medical check-ups are recommended.
- Patient education improves safe and effective use.
[117][118][119] A 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. Manufacture and sale of sildenafil citrate drugs known as "generic Viagra" is common in India, where Pfizer's patent claim does not apply.