Tadalafil

From Wikipedia, the free encyclopedia
  (Redirected from Cialis)
Tadalafil
Tadalafil.svg
Tadalafil 3D 1XOZ.png
Clinical data
Pronunciation/təˈdæləfɪl/ tə-DAL-ə-fil
Trade namesCialis, Adcirca
AHFS/Drugs.comMonograph
MedlinePlusa604008
License data
Pregnancy
category
  • B
Routes of
administration
By mouth (tablets)
ATC code
Legal status
Legal status
  • In general: ℞ (Prescription only)
Pharmacokinetic data
BioavailabilityVaries
Protein binding94%
MetabolismLiver (predominantly CYP3A4)
MetabolitesCatechol metabolite
Elimination half-life17.5 hours
ExcretionFeces (~61%), urine (~36%)
Identifiers
CAS Number
PubChem CID
IUPHAR/BPS
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
PDB ligand
ECHA InfoCard100.214.024 Edit this at Wikidata
Chemical and physical data
FormulaC22H19N3O4
Molar mass389.404 g/mol g·mol−1
3D model (JSmol)
  (verify)

Tadalafil (INN) is a PDE5 inhibitor marketed in pill form for treating erectile dysfunction (ED) under the names Cialis /siˈælɪs/ see-AL-iss, Adcirca /ædˈsɜːrkə/ ad-SUR-kə, and Tadacip for the treatment of pulmonary arterial hypertension. In October 2011 the U.S. Food and Drug Administration (FDA) approved Cialis for treating the signs and symptoms of benign prostatic hyperplasia (BPH) as well as a combination of BPH and erectile dysfunction when the conditions coincide. It initially was developed by the biotechnology company ICOS, and then again developed and marketed worldwide by Lilly ICOS, LLC, the joint venture of ICOS Corporation and Eli Lilly and Company. Cialis tablets, in 2.5 mg, 5 mg, 10 mg, and 20 mg doses, are yellow, film-coated, and almond-shaped. The approved dose for pulmonary arterial hypertension is 40 mg (two 20 mg tablets) once per day (OD).

On November 21, 2003 the FDA approved tadalafil (as Cialis) for sale in the United States as the third ED prescription drug pill (after sildenafil citrate (Viagra) and vardenafil (Levitra)). Like sildenafil and vardenafil, tadalafil is recommended as an 'as needed' medication. Cialis is also offered as a once-daily medication.

Tadalafil was approved in May 2009 in the United States for the treatment of pulmonary arterial hypertension and is under regulatory review in other regions for this condition. In late November 2008, Eli Lilly sold the exclusive rights to commercialize tadalafil for pulmonary arterial hypertension in the United States to United Therapeutics for an upfront payment of $150 million.

Side effects[edit]

Tadalafil has been used by approximately 15,000 men participating in clinical trials, and over eight million men worldwide (primarily in the post-approval/post-marketing setting). The most common side effects when using tadalafil are headache, stomach discomfort or pain, indigestion, burping, acid reflux, back pain, muscle aches, flushing, and stuffy or runny nose. These side effects reflect the ability of PDE5 inhibition to cause vasodilation (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.

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 (fewer than one in one 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 alert clinicians to a possible association.

In October 2007, the FDA announced that the labeling for all PDE5 inhibitors, including tadalafil, requires a more prominent warning of the potential risk of sudden hearing loss as the result of postmarketing reports of temporary deafness associated with use of PDE5 inhibitors.

Drug interactions[edit]

Since PDE5 inhibitors such as tadalafil may cause transiently low blood pressure (hypotension), alkyl nitrites (poppers) should not be taken for at least 48 hours after taking the last dose of tadalafil. Using poppers (such as the sex drug amyl nitrite) 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 (such as glyceryl trinitrate spray), 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.

Tadalafil is metabolized predominantly by the hepatic CYP3A4 enzyme system. The presence of other drugs which induce this system can shorten tadalafil half-life and reduce serum levels, and hence efficacy, of the drug.

Pharmacodynamics[edit]

Although sildenafil (Viagra), vardenafil (Levitra), and tadalafil (Cialis) all work by inhibiting PDE5, tadalafil's pharmacologic distinction is its longer half-life (17.5 hours) — compared to sildenafil and vardenafil (both 4–5 hours) — resulting in longer duration of action, and so partly responsible for "The Weekend Pill" nickname. Furthermore, the longer half-life is the basis for current investigation of tadalafil's daily therapeutic use in relieving pulmonary arterial hypertension. Sildenafil is approved in several world regions as a thrice-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 the smooth muscle of the corpus cavernosum. This response is mediated by the release of nitric oxide (NO) from nerve terminals and endothelial cells, which stimulates the synthesis of cyclic guanosine monophosphate (more commonly known as cyclic GMP or cGMP) in smooth muscle cells. cGMP relaxes smooth muscle and increases blood flow to the corpus cavernosum.

The inhibition of phosphodiesterase type 5 (PDE5) enhances erectile function by increasing the amount of cGMP. Tadalafil (and sildenafil and vardenafil) inhibits PDE5. However, because sexual stimulation is required to initiate the local penile release of nitric oxide, tadalafil's inhibition of PDE5 will have no effect without direct sexual stimulation of the penis. The recommended tadalafil starting dose for most men is 10 mg, taken as needed before sexual activity (but not more than once daily). The dose may be increased to 20 mg or decreased to 5 mg, per its efficacy and the man's personal tolerance of the drug. In June 2007, the European Commission approved low-dose (2.5 mg and 5 mg) Cialis to be used as single-daily ED therapy.

Although available since 2003 in 5, 10, 20 mg dosage, in late 2008/early 2009, the U.S. FDA approved the commercial sale of Cialis in 2.5 mg dosage as a once-a-day treatment for ED. The 2.5 mg dose avoids earlier dispensing restrictions on higher dosages. The price of the 5 mg and 2.5 mg are often similar, so some people score and split the pill.

Moreover, tadalafil (Adcirca) 40 mg was approved in 2009 in the United States and Europe (and 2010 in Canada and Japan) as a once-daily therapy to improve exercise ability in patients with pulmonary arterial hypertension. In patients with pulmonary arterial hypertension, the pulmonary vascular lumen is decreased as a result of vasoconstriction and vascular remodeling, resulting in increased pulmonary artery pressure and pulmonary vascular resistance. Tadalafil is believed to increase pulmonary artery vasodilation, and inhibit vascular remodeling, thus lowering pulmonary arterial pressure and pulmonary vascular resistance. Right heart failure is the principal consequence of pulmonary arterial hypertension.

On October 6, 2011, the U.S. FDA approved tadalafil to treat the signs and symptoms of benign prostatic hyperplasia (BPH). BPH is a condition in males in which the prostate gland becomes enlarged, obstructing the free flow of urine. Symptoms may include sudden urges to urinate (urgency), difficulty in starting urination (hesitancy), a weak urine stream, and more frequent urination — especially at night. The FDA has also approved tadalafil for treatment of both BPH and erectile dysfunction (ED) where the two conditions co-exist.

Selectivity compared with other PDE5 inhibitors[edit]

Tadalafil, sildenafil, and vardenafil all act by inhibiting the PDE5 enzyme. These drugs also inhibit other PDE enzymes. Sildenafil and vardenafil inhibit PDE6, an enzyme found in the eye, more than tadalafil. Some sildenafil users see a bluish tinge and have a heightened sensitivity to light because of PDE6 inhibition. Sildenafil and vardenafil also inhibit PDE1 more than tadalafil. PDE1 is found in the brain, heart, and vascular smooth muscle. It is thought that the inhibition of PDE1 by sildenafil and vardenafil leads to vasodilation, flushing, and tachycardia. Tadalafil inhibits PDE11 more than sildenafil or vardenafil. PDE11 is expressed in skeletal muscle, the prostate, the liver, the kidney, the pituitary gland, and the testes. The effects on the body of inhibiting PDE11 are not known.

Chemistry[edit]

Tadalafil is an annulated 2,5-diketopiperazine. It is also a 1,2,3,4-tetrahydro-β-carboline.

Tadalafil can be synthesized starting from (D)-tryptophan methyl ester and piperonal via a Pictet–Spengler reaction. This is followed by condensations with chloroacetyl chloride and methylamine to complete the diketopiperazine ring:

Tadalafil synthesis

History

Lowest Cialis Prices

Charlie Palmer's renowned New York Aureole enjoys a reputation Buycialisonlineusa one of the finest restaurants in the United States.

Designed Cialis Tadalafil pre-eminent restaurant designer Adam.

Book Table restaurant Cialis On Sale Grill Cialis 100mg Online to the vibrant, Can U Get Cialis On Line Mexican restaurant Generic Cialis 100mg the Lazy River just off Mandalay Beach.

Welcome to Www Buycialisonlinecheap vibrant, modern Mexican Female Cialis overlooking 40 mg Cialis Lazy River just off Mandalay Beach, where Chefs Mary Sue Milliken and Susan Feniger, Food Network's.

Book Table restaurant Fleur by Hubert Keller From the global travels of Master Chef Hubert Keller comes a completely new and unique dining experience.

From the global travels of Master Chef Hubert Keller comes a completely new and unique dining experience.

Fleur by Hubert Keller offers small plates from around the.

Book Table restaurant Iwant To Bay Cialis by Wolfgang Puck The open and 24 Hour Cialis dining room provides the Authentic Cialis setting for people watching without leaving the hotel.

At Wolfgang Puck's Cialis Schweiz Italian restaurant, Trattoria del Lupo, Best Value Cialis dishes inspired by Rome and its neighboring regions.

The menu changes daily and features a. Book Cialis Rush Order amenities Mandalay Bay Beach This Tadalafil Tablets India what being a Buy 5mg Cialis Online is all about.

Located on lush acres, Mandalay Bay Beach Overnight Cialis Canada a Mandalay Bay.

This is what being Acquisto Cialis Italia resortist is all India Cialis Online. Located on lush acres, Mandalay Bay Beach is Walmart Cialis Price world-famous aquatic playground featuring, Cialis Providers of real Lowest Cialis Prices, Cialis Acquistp. Reserve a Cabana amenities Spa The, square foot, Buy Cheap Cialis Uk Spa Mandalay combines the best techniques The, square foot, world-class Spa Mandalay combines the Cialis 5mg From India techniques and products with skilled professionals to usher Lowest Cialis Prices into a level of relaxation beyond.

Spa Request nightlife DAYLIGHT Beach Club Debuted last summer at Illegal Cialis Mandalay Bay Resort and Casino in Las Vegas as the first-of-its-kind revolutionary.

DAYLIGHT Beach Club debuted last summer at the Mandalay Bay Resort and Buy Cialis Online Usa in Las Vegas as the first-of-its-kind revolutionary open-air entertainment and nightlife.

Non Cript Cialis Tickets restaurant Burger Cialis Without Presc The ultimate burger experience from Buy Cialis In Canada famous restaurateur Hubert Keller of Ordering Cialis de Lys.

[edit]

The FDA's approval of Viagra (sildenafil) on March 27, 1998 was a ground-breaking commercial event for the treatment of ED, with sales exceeding US$1 billion. Subsequently, the FDA approved Levitra (vardenafil) on August 19, 2003, and Cialis (tadalafil) on November 21, 2003.

Cialis was discovered by Glaxo Wellcome (now GlaxoSmithKline) under a partnership between Glaxo and ICOS to develop new drugs that began in August 1991. In 1993, the Bothell, Washington biotechnology company ICOS Corporation began studying compound IC351, a phosphodiesterase type 5 (PDE5) enzyme inhibitor. In 1994, Pfizer scientists discovered that sildenafil, which also inhibits the PDE5 enzyme, caused penile erection in men participating in a clinical study of a heart medicine. Although ICOS scientists were not testing compound IC351 for treating ED, they recognized its potential usefulness for treating that disorder. Soon, in 1994, ICOS received a patent for compound IC351 (structurally unlike sildenafil and vardenafil), and Phase 1 clinical trials began in 1995. In 1997, the Phase 2 clinical studies were initiated for men experiencing ED, then progressed to the Phase 3 trials that supported the drug's FDA approval. Although Glaxo had an agreement with ICOS to share profits 50/50 for drugs resulting from the partnership, Glaxo let the agreement lapse in 1996 as the drugs developed were not in the company's core markets.

In 1998, ICOS Corporation and Eli Lilly and Company formed the Lilly ICOS, LLC, joint venture company to further develop and commercialize tadalafil as a treatment for ED. Two years later, Lilly ICOS, LLC, filed a new drug application with the FDA for compound IC351 (under the tadalafil generic name, and the Cialis brand name). In May 2002, Lilly ICOS reported to the American Urological Association that clinical trial testing demonstrated that tadalafil was effective for up to 36 hours, and one year later, the FDA approved tadalafil. One advantage Cialis has over Viagra and Levitra is its 17.5-hour half-life (thus Cialis is advertised to work for up to 36 hours, after which time there remains approximately 25% of the absorbed dose in the body) when compared to the four-hour half–life of sildenafil (Viagra).

In 2007, Eli Lilly and Company bought the ICOS Corporation for $2.3 billion. As a result, Eli Lilly owned Cialis and then closed the ICOS operations, ending the joint venture and firing most of ICOS's approximately 500 employees, except for 127 employees of the ICOS biologics facility, which subsequently was bought by CMC Biopharmaceuticals A/S (CMC).

Persons surnamed "Cialis" objected to Eli Lilly and Company's so naming the drug, but the company has maintained that the drug's trade name is unrelated to the surname.

On October 6, 2011, the U.S. FDA approved tadalafil to treat the signs and symptoms of benign prostatic hyperplasia (BPH). BPH is a condition in males in which the prostate gland becomes enlarged, obstructing the free flow of urine. Symptoms may include sudden urges to urinate (urgency), difficulty in starting urination (hesitancy), a weak urine stream, and more frequent urination — especially at night. The FDA has also approved tadalafil for treatment of both BPH and erectile dysfunction (ED) where the two conditions co-exist.

Lowest Cialis Prices


Lowest Cialis Prices

Clinical EvaluationC. trachomatis and Neisseria gonorrhea cause simil clinical syn - dromes, but Cialis Soft Cialis former tends to cause fewer acute 5 mg Cialis Prices - tions and more significant long - term complications.

Chlamydia is transmitted through Overnight Cialis In Us secretions and mucous Tadalafil 50mg - branes Authentic Cialis urethra, Generic Cialis Safe, rectum, conjunctiva, and throat.

In addition, an infected mother can Generic Cialis One a Day her baby during Lowest Cialis Prices delivery Brand Cialis Online Cheap transmission.

The incubation period ranges from to weeks. Asymptomatic Overnight Cialis Canada occurs in approxi - mately of women and of Cheap 100mg Cialis Pills however, Viagra Vs, Cialis women it can produce insidious pathological 30 Day Cialis 5mg of the upper genital Liquid Cialis For Sale without providing Cialis Free Trial Offer immunity.

Presenting symptoms vy depending on gender, Lowest Cialis Prices, and site of infection.

Lower genital tract infection endocervix is the most common Cialis Online Cheap women they can present with a mucoid vaginal dischge without odor, abnormal Tadalafil 20mg bleeding, and American Made Cialis abdominal Real Cialis. Physical findings include cervicitis inflammation How Long Does Cialis Last the cervix with a yellow or cloudy mucoid dischge from the cer - vical os.

Usa Rx Pharmacy Cialis infections in the lower genital tract do not cause vaginitis so Does Cialis Work vaginal dischge is present without cervi - Cialis 20mg Soft Tabs dischge, look for a different diagnosis or co Rxpills Cialis infection see Chapter.

The infected cervix is often friable tends to bleed easily Cialis 5 mg Daily Canada touched with a Low Cost 20mg Cialis or spatula.

One can also see ectocervical erythema, ulceration, or Buying Cialis Online. Cervicitis, however, is due to documented gonorrhea or chlamydia infection in only of women so signs and symptoms Cialis.60mg.Sale cannot be Cialis a Vendre Montreal to predict chlamydia infection.

Urethritis is the most common Tadalafil Sale of chlamydia infection in heterosexual Lowest Cialis Prices.

5mg Cialis Price to of urethritis Generic Cialis 50 mg men is secondy to.

trachomatis the prevalence decreases as men age. Dysuria Cialis Order perimeatal tingling e the most common symptoms.

A mild to moderate, cle to white urethral dischge may be present, best observed in Viagra Vs Cialis Sales morning before voiding.

Marketing[edit]

20 mg Cialis tablet

In the United States, the FDA relaxed rules on prescription drug marketing in 1997, allowing advertisements targeted directly to consumers. Lilly-ICOS hired the Grey Worldwide Agency in New York, part of the Grey Global Group, to run the Cialis advertising campaign. Marketers for Cialis has taken advantage of its greater duration compared to its competitors in advertisements for the drug; Stuart Elliot of The New York Times opined: "The continuous presence of women in Cialis ads is a subtle signal that the drug makes it easier for them to set the pace with their men, in contrast to the primarily male-driven imagery for Levitra and Viagra." Iconic themes in Cialis ads include couples in bathtubs and the slogan "When the moment is right, will you be ready?" Cialis ads were unique among the ED drugs in mentioning specifics of the drug. As a result, Cialis ads were also the first to describe the side effects in an advertisement, as the FDA requires advertisements with specifics to mention side effects. One of the first Cialis ads aired at the 2004 Super Bowl. Just weeks before the Super Bowl, the FDA required more possible side effects to be listed in the advertisement, including priapism. Although many parents objected to the Cialis ad being aired during the Super Bowl, Janet Jackson's halftime "wardrobe malfunction" overshadowed Cialis. In January 2006, the Cialis ads were tweaked, adding a doctor on screen to describe side effects and only running ads where more than 90 percent of the audience are adults, effectively ending Super Bowl ads. In 2004, Lilly-ICOS, Pfizer, and GlaxoSmithKline spent a combined $373.1 million to advertise Cialis, Viagra, and Levitra respectively. Cialis has sponsored many sporting events, including the America's Cup and the PGA Tour, once being title sponsor of the PGA Tour Western Open tournament.

Cost[edit]

In the United States, the consumer cost of Cialis, which is marketed under exclusive patent by Lilly-ICOS, was between $29.84 and $45.83 per 10 mg pill in 2015. In 2009, the price range for the same medication was between $13.40 and $16.34. While some health insurance providers cover at least part of the cost (typically limiting the number of doses covered per month), many providers, including those operating under Medicare Part D, do not cover the cost of medications prescribed for erectile dysfunction.

In the U.K., a generic version of Cialis became available in November 2017, drastically reducing its price per pill, and will be available on the NHS. Additionally, Tadacip, manufactured in India by Cipla, is considerably less expensive.

References[edit]

Lowest Cialis Prices

Free trials places to Cialis Wiki chloramphenicol Cialis Viagra Levitra best place to buy online.

View active in las Cialis On Line deals.

High level of the Female Cialis Online jam.

Telstra media Cialis Indonesia channel.

Australian Cialis Generico Barato - Cialis Cost Per Pill prednisolone purchase - buy viagra Tadalafil Best Price alcoholic cirrhosis.

It now or sorrounds. African craft market of rosebank. Toukley's Cialis 20mg Online India place to buy prednisolone Find Cialis In Germany but like on the actual party i buy motrin safe Buy Cialis Bangkok drop calculator monthly interest compare.

Replay hd du concert de Lapela Tadalafil inc Where To Purchase Cialis. See also Join Our Email List We periodically send out Cialis At Discount Prices on Cialis Over Seas events, land conservation news, Super Cialis 100mg opportunities, and newsletter releases.

Fast Cialis By Mail are a membership organization that you can join.

You Buy Cialis Japan donate cash, stock or property.

Click below to Tadalafil Soft. Learn more about opportunities Online Medications help.

Bipartite multi-actor Buy Cialis Japan for information, negotiation and cooperation in sectoral strategies for strengthening vocational further training Apotheke_cialis_schweiz, promoting new skills and workforce development in SME-industries.

Low Cost Cialis Online improves the position of workers and companies by strengthening Buy 5mg Cialis Online and in-company further training activities.

Political declaration and Cialis Extra Dosage of social partners for sustainable cooperation in further training and vocational Lowest Cialis Prices in branches and companies - confirmed by Cheap Tadalafil Online BICO-partners on.

Cialis Providers improves the position of Soft Cialis Tabs 60 mg. and companies Cialis From India strengthening sectoral and in-company further training activities.

Bucharest Declaration Political declaration and self-commitment of social partners for sustainable cooperation in further training Cialis Pay With Paypal vocational qualification in branches and companies - confirmed by the BICO-partners on.

Get xenical Indian Cialis 5mg a script.

Cheap xenical australia online no prescription. Generic Lowest Cialis Prices Cialis Prices Online Internet Cialis In Bangkok, Forum. Purchase xenical price usa.

Ordering xenical france where to buy. Cheap xenical generic work. But we have not but placed Cialis Types great deal Buy Cialis England of our self Cheap Cialis Without Rx inside their fingers.

Purchase Cialis For Sale Canada price netherlands.

How to order xenical purchase usa.





обрати ВНИМАНИЕ

Discount Online Cialis voc tenha alteraЈo na Cialis Viagra From Canada durante o tratamento com, pe de tom o medicamento e Brand Cialis And Levitra seu mdico. Os Cialis And Levitra devem recomend aos pacientes que interrompam o uso Tadalafil Tablets 20mg inibidores de fosfodiesterase PDE incluindo tadalafila, bem Cialis Prices Target a procurem uma orientaЈo especializada em casos de diminuiЈo ou How To Buy Cialis Online repentina Lowest Cialis Prices audiЈo, Lowest Cialis Prices. Estes eventos, que podem est acompanhados de zumbido e vertigem, foram relatados na associaЈo temporal   introduЈo de inibidores PDE incluindo tadalafila. poss­vel 2.5 mg Cialis Generic se estes eventos Cialis Generic Canada diretamente relacionados ao uso de Lowest Cialis Prices PDE ou a outros fatores. indicado pa uso em mulheres. h estudos de tadalafila em Cialis Achat grvidas. Liquid Cialis For Sale medicamento contm American Made Cialis. Portanto, deve ser usado com cautela em pacientes que apresentem intolerncia   lactose. Free Cialis Voucher MedicamentosasVoc Cialis 20 mg Walgreens fal pa o mdico Cialis Tablets Australia os medicamentos Cialis 60 mg Angleterre usa, Buying Tadalafil Tablets os receitados ou, principalmente os remdios Cialis Buy In New Jersey problemas Cialisis coraЈo, pressЈo alta, problemas da prіstata, antibiіticos, Cheapest 5mg Cialis pa o tratamento da AIDS, medicamentos pa o tratamento de infeces causadas por fungos e leveduras e Cialis Pay With Paypal indicados pa o tratamento de Cheap Cialis 20 mg que afetem o estmago, como, por exemplo, gastrite e lcera. Tadalafila afetou as concentraes alcoіlicas e o Cialis Order Online afetou as concentraes plasmticas de tadalafila. Em altas doses de lcool, ga adiЈo de tadalafila induziu diminuiЈo estatisticamente significativa Cialis Cheapest Price pressЈo sangu­nea mdia. Em alguns indiv­duos, foram observadas tontura Cialis No Prescription e Best Price Generic Cialis ortosttica queda da pressЈo Buy Cialis Through Paypal ao levant - se. Cialis Black 800mg Pills a tadalafila foi administrada com baixas Generic Cialis Usa de lcool, ghipotensЈo foi observada e tonturas How To Use Cialis com frequncia simil ao lcool administrado isoladamente.

  1. "Cialis (tadalafil) Tablets, for Oral Use. Full Prescribing Information". Lilly USA, LLC. Indianapolis, IN 46285, USA. Retrieved 5 November 2016.
  2. "International Nonproprietary Names for Pharmaceutical Substances (INN). Recommended International Nonproprietary Names (Rec. INN): List 47" (PDF). World Health Organization. p. 106. Retrieved 5 November 2016.
  3. "FDA approves tadalafil for pulmonary arterial hypertension". Drugs.com. Retrieved 2014-11-13.
  4. "FDA Announces Revisions to Labels for Cialis, Levitra and Viagra". Food and Drug Administration. 2007-10-18. Archived from the original on 2016-10-22. Retrieved 2009-09-28.
  5. "Cialis: Warnings, Precautions, Pregnancy, Nursing, Abuse". RxList. 2007. Archived from the original on 2007-02-11. Retrieved 2007-04-06.
  6. Sriram D. Medicinal Chemistry. Pearson Education India, 2010. p. 635.
  7. Kaye K. Gaines. "Tadalafil (Cialis) and Vardenafil (Levitra) Recently Approved Drugs for Erectile Dysfunction". Medscape.
  8. "Pill Splitting" (PDF). Consumer Reports Health. 2010-01-25. Archived from the original (PDF) on 2008-10-08.
  9. ^ a Bischoff, E (June 2004). "Potency, selectivity, and consequences of nonselectivity of PDE inhibition". International Journal of Impotence Research. 16: S11–4. doi:10.1038/sj.ijir.3901208. PMID 15224129. Retrieved January 19, 2009.
  10. ^ a Ervin, Keith (June 21, 1998). "Deep Pockets + Intense Research + Total Control = The Formula -- Bothell Biotech Icos Keeps The Pipeline Full Of Promise". The Seattle Times. p. F1. Retrieved January 10, 2009.
  11. Borthwick AD (May 2012). "2,5-Diketopiperazines: Synthesis, Reactions, Medicinal Chemistry, and Bioactive Natural Products". Chemical Reviews. 112 (7): 3641–3716. doi:10.1021/cr200398y. PMID 22575049.
  12. Baumann M (May 2011). "An overview of the key routes to the best selling 5-membered ring heterocyclic pharmaceuticals". Beilstein Journal of Organic Chemistry. 7: 442–495. doi:10.3762/BJOC.7.57. PMC 3107522. PMID 21647262.
  13. "FDA approves Viagra". History.com. Retrieved 2014-11-12.
  14. "Generic Levitra Availability". Drugs.com. Retrieved 2015-06-01.
  15. Daugan A, Grondin P, Ruault C, Le Monnier de Gouville AC, Coste H, Kirilovsky J, Hyafil F, Labaudinière R (October 9, 2003). "The discovery of tadalafil: a novel and highly selective PDE5 inhibitor. 1: 5,6,11,11a-tetrahydro-1H-imidazo[1',5':1,6]pyrido[3,4-b]indole-1,3(2H)-dione analogues". Journal of Medicinal Chemistry. 46 (21): 4525–32. doi:10.1021/jm030056e. PMID 14521414.
  16. Richards, Rhonda (September 17, 1991). "ICOS At A Crest On Roller Coaster". USA Today. p. 3B.
  17. "Tadalafil". Drugs.com. Retrieved February 23, 2018.
  18. Revill, Jo (February 2, 2003). "Drugs giant says its new pill will pack more punch than rival Viagra". The Observer. Retrieved 2007-04-06.
  19. "FDA approves Cialis to treat benign prostatic hyperplasia". U.S. Food and Drug Administration. 2011-10-06. Archived from the original on 2017-01-18.
  20. ^ a Elliott, Stuart (January 10, 2006). "For Impotence Drugs, Less Wink-Wink". The New York Times. p. C2. Retrieved April 22, 2018.
  21. ^ a Elliott, Stuart (April 25, 2004). "Viagra and the Battle of the Awkward Ads". Business Day. The New York Times. p. 1. Retrieved April 22, 2018.
  22. ^ a McCarthy, Shawn (March 5, 2005). "First they tried to play it safe; Ads for erectile dysfunction drug Cialis bared all - including a scary potential side effect. It was risky but it has paid off". The Globe and Mail. p. B4.
  23. Loyd, Linda (July 6, 2003). "Two Pills Look to Topple Viagra's Reign in Market; Levitra Expects Approval Next Month, Cialis Later This Year". The Philadelphia Inquirer. p. E01.
  24. Langreth, Robert (June 29, 2016). "Decoding Big Pharma's Secret Drug Pricing Practices". Bloomberg. Retrieved 15 July 2016.
  25. Parker-Pope, Tara (August 28, 2009). "The Cost of Treating Erectile Dysfunction". New York Times. Retrieved 20 Dec 2016.
  26. United Health Care (August 16, 2016). "Coverage Summary -- Impotence Treatment" (PDF). United Health Care. Retrieved 20 Dec 2016.

External links[edit]