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Tadalafil |
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Systematic (IUPAC) name |
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(6R-trans)-6-(1,3-benzodioxol-5-yl)-
2,3,6,7,12,12a-hexahydro-2-methyl-pyrazino [1', 2':1,6]
pyrido[3,4-b]indole-1,4-dione |
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Identifiers |
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Chemical data |
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C22H19N3O4 |
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389.404 g/mol |
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Pharmacokinetic data |
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94% |
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17.5 hours |
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Therapeutic considerations |
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Tadalafil is a drug used to treat male erectile dysfunction (impotence). In the United States, tadalafil has Food and Drug Administration approval and became available in December, 2003 as the third pill after Viagra and Levitra. Due to its 36-hour effect it is also known as
the "Weekend Pill".
It was developed by the biotechnology firm ICOS and marketed worldwide by Eli
Lilly and Company
under the brand name Cialis.
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It works by inhibiting an enzyme known as PDE5. A 20mg dose of Tadalafil is comparable to a
100mg dose of sildenafil (Viagra).
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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-pyrazino[1 ,2 :1,6]pyrido[3,4-b]indole-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.
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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, including diabetics. An investigation is currently ongoing.
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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 [1]. In the event of a medical emergency, paramedics and medical personnel should be notified of
any recent doses of tadalafil.
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In the
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