Tadalafil structure
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Cialis

Tadalafil is a drug used to treat male erectile dysfunction (impotence). It was developed by the biotechnology firm ICOS and marketed worldwide by Eli Lilly and Company under the brand name Cialis. It works by inhibiting an enzyme known as PDE5. Due to its 36-hour effect it is also known as the "Weekend Pill". In the United States, tadalafil has Food and Drug Administration approval and became available in December, 2003. more...

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Chemical information

The empirical formula for tadalafil is C22H19N3O4, and its official organic name is (6R,12aR)-6-(1,3-benzodioxol-5-yl)-2,3,6,7,12,12a- hexahydro-2-methyl-pyrazinopyridoindole-1,4-dione. The molecular weight is 389.41. The tablets are yellow, film-coated, and almond-shaped, and are produced in 5, 10, or 20mg doses. A 20mg dose of Tadalafil is comparable to a 100mg dose of sildenafil (Viagra). The MSDS for this compound can be found here:

Side effects

The most common side effects when using tadalafil are headache, indigestion, back pain, muscle aches, flushing, and stuffy or runny nose. These side effects usually go away after a few hours. Patients who get back pain and muscle aches usually get it 12 to 24 hours after taking the drug, and the symptom usually goes away after 48 hours.

In May 2005, the U.S. Food and Drug Administration found that tadalafil (along with other PDE5 inhibitors) could lead to vision impairment in certain patient groups, e.g. diabetics. An investigation is currently ongoing.

Drug interactions

Organic nitrates

Since PDE5 inhibitors such as tadalafil may cause transiently low blood pressure (hypotension), organic nitrates should not be taken for at least 48 hours after taking the last dose of tadalafil. Using organic nitrates within this timeframe may increase the risk of life-threatening hypotension. Since people who have taken tadalafil within the past 48 hours cannot take organic nitrates to relieve angina, these patients should seek immediate medical attention if they experience anginal chest pain . In the event of a medical emergency, paramedics and medical personnel should be notified of any recent doses of tadalafil.

Marketing

In the United States, Eli Lilly has a multiyear agreement to promote tadalafil (Cialis) with professional golf's PGA TOUR.

Trivia

  • The word "specialist" is frequently caught by primitive spam email blockers because it contains the word "cialis."

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Party hard: with Viagra and its coitus-enabling cousins so easy to score, throngs of young, impotence-free guys are popping pills to become wayward weekend
From Men's Fitness, 11/1/04 by Jonathan Yevin

"A FEW YEARS AGO, I GOT offered a Viagra at a party" says Mike Rodriguez, 26, recalling the first time he took the blue pill. "I was with this girl I met the week before and I was pretty, sure I could take her home. I popped the pill a half-hour before we left the party. We had sex until she literally made me stop."

Rodriguez, a network engineer from New York City, had never suffered from impotence or performance anxiety. Yet he was using Viagra anyway, in this case as an insurance policy against the effects of alcohol.

Xavier Motley, a 27-year-old soldier from Pennsylvania, buys Viagra from an online pharmacy in Mexico. "I take it to enhance my endurance," says Motley, who has never had performance issues, either.

Viagra and its newer rivals, Levitra and Cialis, are erectile-dysfunction drugs, which were developed and intended for old salts who had trouble hoisting their sails. But in the last few years, these pharmaceuticals have caught on as recreational drugs with the under-30 crowd.

A new study published in the International Journal of Impotence Research (yes, it's a real publication) found that, while the largest group of Viagra users are still in the 56-and-older age group, there's been a 300% increase in prescriptions for men under 45 since the drug was launched in 1998. Add to that the untold thousands who buy it online, and it's clear that the country is in for some hard times.

But there's a dark side to this invisible helping hand. The consequences of large numbers of men taking potency pills they don't need are raising eyebrows in the medical community. For one thing, Viagra works for four to six hours, which, when combined with alcohol, can open the door wider to making unwise late-night choices. "Alcohol promotes uninhibited behavior," notes Andrew McCullough, M.D., a Manhattan urologist. "All of a sudden, an inebriated guy might decide, 'I'm not gonna wear a condom tonight.'"

The same goes for men who get all revved up and have no place to go. Desperately searching for release with any matter of partner can also lead to less-than-smart lifestyle decisions. "If I'm out and I pop a pill and I can't get sex," admits Rodriguez, "I usually call an escort service."

These pharmaceuticals are creating another potential set of dilemmas. Scientists have found that, while men don't develop physical dependencies on the drugs or loss of normal function if they stop taking them after extended use, psychological dependence is a different matter altogether. The recreational user might take Viagra to help sell himself as a sexual superman early in a relationship. But once things get serious, he has to perform without the support of his little diamond-shaped friend.

Says Motley, "I worry that not taking it will cause my girlfriends to notice a drop-off in my performance."

All erectile-dysfunction drugs work in the same way. Each blocks an enzyme called phosphodiesterase-5, relaxing smooth-muscle cells to allow increased blood flow to the penis. (All three also have similar possible side effects, the must common being headaches and facial flushing.)

Each of the three drugs has also targeted the same demographic: younger men. Though Viagra is still far and away the industry leader, Cialis and Levitra have made serious inroads in market share, especially in Europe. So tar, Viagra has been prescribed 170 million times to 23 million men worldwide. Since Cialis and Levitra were launched last year, they have claimed 24% and 12%, respectively, of the European marketplace, compared with Viagra's 64%. In France, Cialis has been dubbed "Le Weekender,' as it stays potent for up to 36 hours. Cool. But imagine the problems posed by an almost two-day stiffy.

"I saw a 22-year-old with a prolonged erection," says McCullough. "I saw another with a penile fracture. He had had rodeo sex. She came down on him and it broke" Ouch.

Buckin' broncos aside, there are many young males who have legitimate erectile dysfunction. For them, Viagra and the other drugs may mean the difference between knocking down three pointers from the top of the key and warming the bench. But other than for reproductive sex, what is Viagra for if not recreational use?

"The problem in our society is, if good is good, why not be better than good?" says McCullough. "We haven't studied the effect in men without erectile dysfunction--there may be consequences. Enhancing sex for the sake of enhancing sex should not be condoned."

Jonathan Yevin, a Brooklyn-based writer and photographer, knows every Viagra joke in the book.

COPYRIGHT 2004 Weider Publications
COPYRIGHT 2004 Gale Group

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