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Encyclopedia > Tadalafil
Tadalafil
Systematic (IUPAC) name
(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
Identifiers
CAS number 171596-29-5
ATC code G04BE08
PubChem 110635
DrugBank APRD00071
Chemical data
Formula C22H19N3O4 
Mol. mass 389.404 g/mol
SMILES search in eMolecules, PubChem
Pharmacokinetic data
Bioavailability  ?
Protein binding 94%
Metabolism  ?
Half life 17.5 hours
Excretion  ?
Therapeutic considerations
Pregnancy cat.

? Image File history File links Broom_icon. ... drawn in bkchem postprocessing in GIMP This image has been released into the public domain by the copyright holder, its copyright has expired, or it is ineligible for copyright. ... IUPAC nomenclature is a system of naming chemical compounds and of describing the science of chemistry in general. ... CAS registry numbers are unique numerical identifiers for chemical compounds, polymers, biological sequences, mixtures and alloys. ... The Anatomical Therapeutic Chemical Classification System is used for the classification of drugs. ... A section of the Anatomical Therapeutic Chemical Classification System. ... PubChem is a database of chemical molecules. ... The DrugBank database available at the University of Alberta is a unique bioinformatics and cheminformatics resource that combines detailed drug (i. ... A chemical formula is a concise way of expressing information about the atoms that constitute a particular chemical compound. ... For other uses, see Carbon (disambiguation). ... This article is about the chemistry of hydrogen. ... General Name, symbol, number nitrogen, N, 7 Chemical series nonmetals Group, period, block 15, 2, p Appearance colorless gas Standard atomic weight 14. ... General Name, symbol, number oxygen, O, 8 Chemical series nonmetals, chalcogens Group, period, block 16, 2, p Appearance colorless (gas) pale blue (liquid) Standard atomic weight 15. ... The molecular mass (abbreviated Mr) of a substance, formerly also called molecular weight and abbreviated as MW, is the mass of one molecule of that substance, relative to the unified atomic mass unit u (equal to 1/12 the mass of one atom of carbon-12). ... The simplified molecular input line entry specification or SMILES is a specification for unambiguously describing the structure of chemical molecules using short ASCII strings. ... In pharmacology, bioavailability is used to describe the fraction of an administered dose of unchanged drug that reaches the systemic circulation, one of the principal pharmacokinetic properties of drugs. ... A drugs efficacy may be affected by the degree to which it binds to the proteins within blood plasma. ... Drug metabolism is the metabolism of drugs, their biochemical modification or degradation, usually through specialized enzymatic systems. ... The biological half-life of a substance is the time required for half of that substance to be removed from an organism by either a physical or a chemical process. ... The kidneys are important excretory organs in vertebrates. ... The pregnancy category of a pharmaceutical agent is an assessment of the risk of fetal injury due to the pharmaceutical, if it is used as directed by the mother during pregnancy. ...

Legal status
Routes  ?

Tadalafil is an orally administered drug used to treat male erectile dysfunction (impotence). It was initially developed by the biotechnology firm ICOS and subsequently developed and marketed worldwide by a joint venture of ICOS Corporation and Eli Lilly and Company (Lilly ICOS LLC) under the brand name Cialis. The regulation of therapeutic goods, that is drugs and therapeutic devices, varies by jurisdiction. ... In pharmacology and toxicology, a route of administration is the path by which a drug, fluid, poison or other substance is brought into contact with the body. ... This article does not cite any references or sources. ... Erectile dysfunction (ED) or impotence is a sexual dysfunction characterized by the inability to develop or maintain an erection of the penis. ... Impotence or, more clinically, erectile dysfunction is the inability to develop or maintain an erection of the penis for satisfactory sexual intercourse regardless of the capability of ejaculation. ... The structure of insulin Biotechnology is technology based on biology, especially when used in agriculture, food science, and medicine. ... ICOS is a Bothell, Washington-based biotech company that began operations in 1990. ... Eli Lilly and Company (NYSE: LLY) is a global pharmaceutical company and one of the worlds largest corporations. ...


In the United States, tadalafil has Food and Drug Administration approval and became available in December, 2003 as the third impotence pill after sildenafil (Viagra) and vardenafil (Levitra). Due to its 36-hour effect it is also known as the weekend pill. As with sildenafil and vardenafil, it is recommended that tadalafil be used no more than once daily. Tadalafil is also currently undergoing Phase 3 clinical trials for the treatment of pulmonary arterial hypertension. “FDA” redirects here. ... Year 2003 (MMIII) was a common year starting on Wednesday of the Gregorian calendar. ... Sildenafil citrate, sold under the names Viagra, Revatio and generically under various other names, is a drug used to treat male erectile dysfunction (impotence) and pulmonary arterial hypertension (PAH), developed by the pharmaceutical company Pfizer. ... Vardenafil (INN) is a PDE5 inhibitor used in the treatment of erectile dysfunction. ... In health care, including medicine, a clinical trial (synonyms: clinical studies, research protocols, medical research) is a process in which a medicine or other medical treatment is tested for its safety and effectiveness, often in comparison to existing treatments. ... In medicine, pulmonary hypertension (PH) is an increase in blood pressure in the pulmonary artery, pulmonary vein, or pulmonary capillaries, together known as the lung vasculature, leading to shortness of breath, dizziness, fainting, and other symptoms, all of which are exacerbated by exertion. ...

Contents

History

The history of Cialis cannot be discussed without mentioning Pfizer's drug, Viagra (sildenafil). The FDA's approval of Viagra on March 27, 1998, was a groundbreaking event for the treatment of erectile dysfunction and sales eventually reached over a billion dollars. The FDA subsequently approved Levitra (vardenafil) on August 19, 2003, and Cialis (tadalafil) on November 21, 2003. is the 86th day of the year (87th in leap years) in the Gregorian calendar. ... Year 1998 (MCMXCVIII) was a common year starting on Thursday (link will display full 1998 Gregorian calendar). ... is the 231st day of the year (232nd in leap years) in the Gregorian calendar. ... Year 2003 (MMIII) was a common year starting on Wednesday of the Gregorian calendar. ... is the 325th day of the year (326th in leap years) in the Gregorian calendar. ... Year 2003 (MMIII) was a common year starting on Wednesday of the Gregorian calendar. ...


In 1993, the Bothell, Washington-based biotechnology company Icos began studying IC351, which is a phosphodiesterase type 5 (PDE5) enzyme inhibitor. In 1994, Pfizer scientists discovered that sildenafil citrate, which also inhibits the PDE5 enzyme, caused patients that were participating in a clinical study of a heart medicine to have erections. Although the ICOS scientists were not testing the chemical compound IC351 for erectile dysfunction, it was recognized that the compound could have potential usefulness for the treatment of this disorder. Soon Icos received a patent in 1994 for IC351, which is structurally different from sildenafil (and vardenafil), and Phase 1 clinical trials began in 1995. In 1997, Phase 2 clinical studies were initiated in patients with erectile dysfunction and led to pivotal Phase 3 trials that supported approval. Sildenafil citrate, sold under the names Viagra, Revatio and generically under various other names, is a drug used to treat male erectile dysfunction (impotence) and pulmonary arterial hypertension (PAH), developed by the pharmaceutical company Pfizer. ...


In 1998, ICOS Corporation and Eli Lilly and Company formed a joint venture (Lilly ICOS LLC) to further develop and commercialize the drug for erectile dysfunction, and two years later they filed a New Drug Application with the U.S. Food and Drug Administration for IC351 (under the generic name tadalafil and the brand name Cialis). In May of 2002, Lilly ICOS reported to the American Urological Association that clinical trial testing in men with erectile dysfunction showed that tadalafil works for up to 36 hours, and one year later tadalafil was approved. One advantage that Cialis has over Viagra and Levitra is that tadalafil has a half-life of 17.5 hours[1] (and thus Cialis is advertised to work for up to 36 hours, after which time there is still about one quarter of the absorbed dose in the body) as compared to 4 hours half-life for sildenafil (Viagra).[2][3] Half-Life For a quantity subject to exponential decay, the half-life is the time required for the quantity to fall to half of its initial value. ...


Eli Lilly purchased ICOS Corporation for $2.1 billion dollars in 2006.


Chemistry

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. Tadalafil tablets are yellow, film-coated, and almond-shaped, and are produced in 5, 10, or 20 mg doses. In chemistry, the empirical formula of a chemical compound is a simple expression of the relative number of each type of atom (called a chemical element) in it. ... IUPAC nomenclature is a system of naming chemical compounds and of describing the science of chemistry in general. ... The molecular mass of a substance (less accurately called molecular weight and abbreviated as MW) is the mass of one molecule of that substance, relative to the unified atomic mass unit u (equal to 1/12 the mass of one atom of carbon-12). ...


Mechanism of action

Although Viagra, Levitra, and Cialis all work by inhibition of PDE5, tadalafil's distinguishing pharmacologic feature is its longer half-life (17.5 hours) compared with Viagra and Levitra (4-5 hours). This longer half-life results in a longer duration of action and is, in part, responsible for the Cialis nickname of the "weekend pill." This longer half-life also is the basis of current investigation for tadalafil's use in pulmonary arterial hypertension as a once-daily therapy. At present, sildenafil (trade name Revatio) is approved in various regions worldwide as a 3-times daily therapy for pulmonary arterial hypertension.


Penile erection during sexual stimulation is caused by increased penile blood flow resulting from the relaxation of penile arteries and corpus cavernosal smooth muscle. This response is mediated by the release of nitric oxide (NO) from nerve terminals and endothelial cells, which stimulates the synthesis of cGMP in smooth muscle cells. Cyclic GMP causes smooth muscle relaxation and increased blood flow into the corpus cavernosum. The inhibition of phosphodiesterase type 5 (PDE5) enhances erectile function by increasing the amount of cGMP. Tadalafil (as well as sildenafil and vardenafil) inhibits PDE5. Because sexual stimulation is required to initiate the local release of nitric oxide, the inhibition of PDE5 by tadalafil has no effect in the absence of sexual stimulation. A 20 mg dose of tadalafil is comparable to a 100 mg dose of sildenafil (Viagra).[citation needed] However, the recommended starting dose of Cialis in most patients is 10 mg, taken prior to anticipated sexual activity. The dose may be increased to 20 mg or decreased to 5 mg, based on individual efficacy and tolerability Sildenafil citrate, sold under the names Viagra, Revatio and generically under various other names, is a drug used to treat male erectile dysfunction (impotence) and pulmonary arterial hypertension (PAH), developed by the pharmaceutical company Pfizer. ...


Tadalafil is currently undergoing clinical trials for the treatment of pulmonary arterial hypertension. In patients with pulmonary arterial hypertension, it is believed that there is an imablance of the PDE5/NO system in the pulmonary vasculature that favors selective vasoconstriction of the pulmonary artery. Investigation of tadalafil in this disease assumes that PDE5 inhibition will result in pulmonary artery vasodilation, thus lowering pulmonary artery pressure and pulmonary vascular resistance. These physiologic changes may then reduce the workload of the right ventricle of the heart. Right heart failure is the main consequence of pulmonary arterial hypertension. In health care, including medicine, a clinical trial (synonyms: clinical studies, research protocols, medical research) is a process in which a medicine or other medical treatment is tested for its safety and effectiveness, often in comparison to existing treatments. ... In medicine, pulmonary hypertension (PH) is an increase in blood pressure in the pulmonary artery, pulmonary vein, or pulmonary capillaries, together known as the lung vasculature, leading to shortness of breath, dizziness, fainting, and other symptoms, all of which are exacerbated by exertion. ... In the heart, a ventricle is a heart chamber which collects blood from an atrium (another heart chamber that is smaller than a ventricle) and pumps it out of the heart. ...


Side effects

Tadalafil has been used in approximately 15,000 men participating in clinical trials, and over 8 million men wordwide (primarily in the post-approval/post-marketing setting). The most common side effects when using tadalafil are headache, indigestion, back pain, muscle aches, flushing, and stuffy or runny nose. These side effects reflect the ability of PDE5 inhibition to vasodilate (cause blood vessels to widen) and usually go away after a few hours. Back pain and muscle aches can occur 12 to 24 hours after taking the drug, and the symptom usually disappears after 48 hours. Adverse effect, in medicine, is an abnormal, harmful, undesired and/or unintended side-effect, although not necessarily unexpected, which is obtained as the result of a therapy or other medical intervention, such as drug/chemotherapy, physical therapy, surgery, medical procedure, use of a medical device, etc. ... A headache (cephalgia in medical terminology) is a condition of pain in the head; sometimes neck or upper back pain may also be interpreted as a headache. ... Indigestion is a condition that is frequently caused by eating too fast, especially by eating high-fat foods quickly. ...


In May 2005, the U.S. Food and Drug Administration found that tadalafil (along with other PDE5 inhibitors) was associated with vision impairment related to NAION (non-arteritic anterior ischemic optic neuropathy) in certain patients taking these drugs in the post-marketing (outside of clinical trials) setting. Most, but not all, of these patients had underlying anatomic or vascular risk factors for development of NAION unrelated to PDE5 use, including: low cup to disc ratio (“crowded disc”), age over 50, diabetes, hypertension, coronary artery disease, hyperlipidemia and smoking. Given the small number of NAION events with PDE5 use (less than 1 in 1 million), the large number of users of PDE5 inhibitors (millions) and the fact that this event occurs in a similar population to those who do not take these medicines, the FDA concluded that they were not able to draw a cause and effect relationship, given these patients underlying vascular risk factors or anatomical defects. However, the label of all three PDE5 inhibitors was changed to highlight clinicians to a possible association. “FDA” redirects here. ...


Drug interactions

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 (such as the sex drug amyl nitrite) within this timeframe may increase the risk of life-threatening hypotension. In physiology and medicine, hypotension refers to an abnormally low blood pressure. ... Nitrates are the salts of nitric acid. ... Amyl nitrite is the chemical compound with the formula C5H11ONO. A variety of isomers are known, but they all feature an amyl group attached to the nitrito functional group. ...


Since people who have taken tadalafil within the past 48 hours cannot take organic nitrates to relieve angina (such as glyceryl trinitrate spray), these patients should seek immediate medical attention if they experience anginal chest pain.[4] In the event of a medical emergency, paramedics and medical personnel should be notified of any recent doses of tadalafil. Glyceryl trinitrate (GTN) has been used to treat angina and heart failure since at least 1880. ... angina tonsillaris see tonsillitis. ... The Star of Life, a globally recognised symbol for emergency medical services A paramedic is a medical professional, usually a member of the emergency medical service, who responds to medical and trauma emergencies in the pre-hospital environment, provides emergency treatment and, when appropriate, transports a patient to definitive care...


Marketing

In the United States, Eli Lilly has a multiyear agreement to promote tadalafil (Cialis) with professional golf's PGA Tour. Eli Lilly and Company (NYSE: LLY) is a global pharmaceutical company and one of the worlds largest corporations. ... This article is about the sport. ... The PGA Tour is an organization that operates the USAs main professional golf tours. ...


Cialis is one of the most frequent offerings of spam. E-mail spam, also known as bulk e-mail or junk e-mail is a subset of spam that involves sending nearly identical messages to numerous recipients by e-mail. ...


Trivia

Some individuals with the surname of "Cialis" objected to Lilly's naming of the drug, but the company insists that the drug's trade name has nothing to do with the surname.[5]

20 mg Cialis tablet
20 mg Cialis tablet

Image File history File links No higher resolution available. ... Image File history File links No higher resolution available. ...

References

  1. ^ Cialis - Safety Monitoring(s). Epocrates Rx software, produced by Epocrates, Inc.. Information also available online. Retrieved on 2007-04-06.
  2. ^ Viagra - Safety Monitoring(s). Epocrates Rx software, produced by Epocrates, Inc.. Information also available online. Retrieved on 2007-04-06.
  3. ^ (French) Sildenafil: Pharmaco-Cinétique. BIAM (April 20, 2001). Retrieved on 2007-04-06.
  4. ^ Cialis: Warnings, Precautions, Pregnancy, Nursing, Abuse. RxList (2007). Retrieved on 2007-04-06.
  5. ^ Revill, Jo. "Drugs giant says its new pill will pack more punch than rival Viagra", The Observer, February 2, 2003. Retrieved on 2007-04-06. 

Year 2007 (MMVII) is the current year, a common year starting on Monday of the Gregorian calendar and the AD/CE era in the 21st century. ... is the 96th day of the year (97th in leap years) in the Gregorian calendar. ... Year 2007 (MMVII) is the current year, a common year starting on Monday of the Gregorian calendar and the AD/CE era in the 21st century. ... is the 96th day of the year (97th in leap years) in the Gregorian calendar. ... Year 2007 (MMVII) is the current year, a common year starting on Monday of the Gregorian calendar and the AD/CE era in the 21st century. ... is the 96th day of the year (97th in leap years) in the Gregorian calendar. ... Year 2007 (MMVII) is the current year, a common year starting on Monday of the Gregorian calendar and the AD/CE era in the 21st century. ... is the 96th day of the year (97th in leap years) in the Gregorian calendar. ... Wikipedia does not yet have an article with this exact name. ... Year 2007 (MMVII) is the current year, a common year starting on Monday of the Gregorian calendar and the AD/CE era in the 21st century. ... is the 96th day of the year (97th in leap years) in the Gregorian calendar. ...

External links

  • Official site
  • National Institutes of Health
  • RxList - Tadalafil
  • Medical safety data sheet

  Results from FactBites:
 
Tadalafil - Wikipedia, the free encyclopedia (0 words)
Tadalafil is a drug used to treat male erectile dysfunction (impotence).
The most common side effects when using tadalafil are headache, indigestion, back pain, muscle aches, flushing, and stuffy or runny nose.
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.
tadalafil - cialis (0 words)
Tadalafil is a new oral treatment for erectile dysfunction being developed by Lilly ICOS LLC.
Tadalafil was well tolerated, with generally mild-to-moderate side effects that diminished in frequency with continued treatment.
Tadalafil has previously been shown to be both safe and effective in non-diabetic men.
  More results at FactBites »

 
 

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