Detail

Tadalafil

Description

Name: Tadalafil
Type: small molecule
Groups: Array
Indication: Used for the treatment of erectile dysfunction.
Accession Number: DB00820 ( APRD00071)
Description: Tadalafil is an orally adminstered drug used to treat male erectile dysfunction (impotence). It is marketed worldwide under the brand name Cialis. It is a phosphodiesterase 5 (PDE5) inhibitor. 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. [Wikipedia]
Structure:
Prescription Products:
NameDosageStrengthRouteMarketing StartMarketing EndCountry
Adcircatablet20 mg/1oral03-08-2009US
Adcircatablet20 mgoral19-01-2010Canada
Cialistablet, film coated20 mg/1oral26-11-2003US
Cialistablet, film coated5 mg/1oral26-11-2003US
Cialistablet, film coated10 mg/1oral26-11-2003US
Cialistablet, film coated20 mg/1oral26-11-2003US
Cialistablet, film coated2.5 mg/1oral07-01-2008US
Cialistablet2.5 mgoral18-01-2008Canada
Cialistablet5.0 mgoral18-01-2008Canada
Cialistablet, film coated20 mg/1oral11-12-2003US
Cialistablet, film coated20 mg/1oral26-11-2003US
Cialistablet10 mgoral11-12-2003Canada
Cialistablet20 mgoral25-11-2003Canada
Cialistablet, film coated5 mg/1oral23-10-2008US
Cialistablet, film coated20 mg/1oral26-11-2003US
Cialistablet, film coated2.5 mg/1oral07-01-2008US
Cialistablet, film coated5 mg/1oral26-11-2003US
Cialistablet, film coated20 mg/1oral26-11-2003US
Cialistablet, film coated10 mg/1oral26-11-2003US
Cialistablet, film coated20 mg/1oral26-11-2003US
Cialistablet, film coated10 mg/1oral03-12-2003US
Cialistablet, film coated5 mg/1oral26-11-2003US
Cialistablet, film coated10 mg/1oral26-11-2003US

Generic Prescription Products:
NameDosageStrengthRouteMarketing StartMarketing EndCountry
Apo-tadalafil Pahtablet20 mgoral15-10-2015Canada

Over the Counter Products: Not Available
International Brands
  • No Brands

Brand Names
  • No Brands

Brand Mixtures
Brand NameIngredients
CialisTadalafil
CialisTadalafil
CialisTadalafil
CialisTadalafil
CialisTadalafil
CialisTadalafil
CialisTadalafil
CialisTadalafil
CialisTadalafil
CialisTadalafil
CialisTadalafil
CialisTadalafil
CialisTadalafil
CialisTadalafil
CialisTadalafil
CialisTadalafil
AdcircaTadalafil
CialisTadalafil
CialisTadalafil
CialisTadalafil
CialisTadalafil
CialisTadalafil
AdcircaTadalafil
Apo-tadalafil PahTadalafil

Categories
  • Vasodilator Agents
  • Phosphodiesterase 5 Inhibitors

Pharmacology

Indication: Used for the treatment of erectile dysfunction.
Pharmacodynamics: Not Available
Mechanism of action: Tadalafil inhibits the cGMP specific phosphodiesterase type 5 (PDE5) which is responsible for degradation of cGMP in the corpus cavernosum located around the penis. 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) by tadalafil enhances erectile function by increasing the amount of cGMP.
Absorption: After single oral-dose administration, the maximum observed plasma concentration (Cmax) of tadalafil is achieved between 30 minutes and 6 hours (median time of 2 hours). Absolute bioavailability of tadalafil following oral dosing has not been determined.
Volume of distribution:
  • 63 L

Protein binding: 94%
Metabolism: Not Available
Route of elimination: Tadalafil is excreted predominantly as metabolites, mainly in the feces (approximately 61% of the dose) and to a lesser extent in the urine (approximately 36% of the dose).
Half life: 17.5 hours
Clearance: Not Available
Toxicity: Oral, Rat LD50 = 2000 mg/kg, no deaths or toxicity.
Affected organisms
  • Not Available

SNP Mediated Adverse Drug Reactions
  • Not Available

Pharmacoeconomics

Manufacturers:
  • Eli lilly co
  • Eli lilly and co
  • Eli Lilly and Company

Packagers:
Dosage forms
FormRouteStrength
Tabletoral20 mg/1
Tabletoral10 mg
Tabletoral2.5 mg
Tabletoral20 mg
Tabletoral5.0 mg
Tablet, film coatedoral10 mg/1
Tablet, film coatedoral2.5 mg/1
Tablet, film coatedoral20 mg/1
Tablet, film coatedoral5 mg/1

Prices
Unit descriptionCostUnit
Cialis 2.5 mg tablet$4.76tablet
Cialis 5 mg tablet$4.76tablet
Cialis 10 mg tablet$20.92tablet
Cialis 20 mg tablet$20.92tablet
Cialis 30 5 mg tablet Box$140.77box

Patents
CountryPatent NumberApprovedExpires (estimated)
2181377Canada2002-05-282015-01-19
2379948Canada2008-03-252020-04-26
6140329United States1996-07-112016-07-11
6821975United States2000-11-192020-11-19

Interactions

Drug Interactions
DrugInteraction
AcebutololTadalafil may increase the antihypertensive activities of Acebutolol.
AlfuzosinTadalafil may increase the hypotensive activities of Alfuzosin.
AliskirenTadalafil may increase the antihypertensive activities of Aliskiren.
AlprostadilThe risk or severity of adverse effects can be increased when Tadalafil is combined with Alprostadil.
AmilorideTadalafil may increase the antihypertensive activities of Amiloride.
AmlodipineTadalafil may increase the antihypertensive activities of Amlodipine.
Amyl NitriteTadalafil may increase the vasodilatory activities of Amyl Nitrite.
AprepitantThe serum concentration of Tadalafil can be increased when it is combined with Aprepitant.
AtazanavirThe serum concentration of Tadalafil can be increased when it is combined with Atazanavir.
AtenololTadalafil may increase the antihypertensive activities of Atenolol.
AvanafilThe risk or severity of adverse effects can be increased when Tadalafil is combined with Avanafil.
Azilsartan medoxomilTadalafil may increase the antihypertensive activities of Azilsartan medoxomil.
BenazeprilTadalafil may increase the antihypertensive activities of Benazepril.
BendroflumethiazideTadalafil may increase the antihypertensive activities of Bendroflumethiazide.
BetaxololTadalafil may increase the antihypertensive activities of Betaxolol.
BisoprololTadalafil may increase the antihypertensive activities of Bisoprolol.
BoceprevirThe serum concentration of Tadalafil can be increased when it is combined with Boceprevir.
BosentanThe serum concentration of Tadalafil can be decreased when it is combined with Bosentan.
BumetanideTadalafil may increase the antihypertensive activities of Bumetanide.
CandesartanTadalafil may increase the antihypertensive activities of Candesartan.
CaptoprilTadalafil may increase the antihypertensive activities of Captopril.
CarbamazepineThe serum concentration of Tadalafil can be decreased when it is combined with Carbamazepine.
CarvedilolTadalafil may increase the antihypertensive activities of Carvedilol.
CeritinibThe serum concentration of Tadalafil can be increased when it is combined with Ceritinib.
ChlorothiazideTadalafil may increase the antihypertensive activities of Chlorothiazide.
ChlorthalidoneTadalafil may increase the antihypertensive activities of Chlorthalidone.
CilazaprilTadalafil may increase the antihypertensive activities of Cilazapril.
ClarithromycinThe serum concentration of Tadalafil can be increased when it is combined with Clarithromycin.
ClevidipineTadalafil may increase the antihypertensive activities of Clevidipine.
ClonidineTadalafil may increase the antihypertensive activities of Clonidine.
CobicistatThe serum concentration of Tadalafil can be increased when it is combined with Cobicistat.
ConivaptanThe serum concentration of Tadalafil can be increased when it is combined with Conivaptan.
DapoxetineDapoxetine may increase the orthostatic hypotensive activities of Tadalafil.
DarunavirThe serum concentration of Tadalafil can be increased when it is combined with Darunavir.
DasatinibThe serum concentration of Tadalafil can be increased when it is combined with Dasatinib.
DiltiazemTadalafil may increase the antihypertensive activities of Diltiazem.
DoxazosinTadalafil may increase the hypotensive activities of Doxazosin.
EnalaprilTadalafil may increase the antihypertensive activities of Enalapril.
EnalaprilatTadalafil may increase the antihypertensive activities of Enalaprilat.
EnzalutamideThe serum concentration of Tadalafil can be decreased when it is combined with Enzalutamide.
EplerenoneTadalafil may increase the antihypertensive activities of Eplerenone.
EprosartanTadalafil may increase the antihypertensive activities of Eprosartan.
Erythrityl TetranitrateTadalafil may increase the vasodilatory activities of Erythrityl Tetranitrate.
EsmololTadalafil may increase the antihypertensive activities of Esmolol.
Ethacrynic acidTadalafil may increase the antihypertensive activities of Ethacrynic acid.
EthanolEthanol may increase the hypotensive activities of Tadalafil.
EtravirineThe serum concentration of Tadalafil can be decreased when it is combined with Etravirine.
FelodipineTadalafil may increase the antihypertensive activities of Felodipine.
FluconazoleThe serum concentration of Tadalafil can be increased when it is combined with Fluconazole.
FosaprepitantThe serum concentration of Tadalafil can be increased when it is combined with Fosaprepitant.
FosinoprilTadalafil may increase the antihypertensive activities of Fosinopril.
FosphenytoinThe serum concentration of Tadalafil can be decreased when it is combined with Fosphenytoin.
FurosemideTadalafil may increase the antihypertensive activities of Furosemide.
Fusidic AcidThe serum concentration of Tadalafil can be increased when it is combined with Fusidic Acid.
GuanfacineTadalafil may increase the antihypertensive activities of Guanfacine.
HydralazineTadalafil may increase the antihypertensive activities of Hydralazine.
HydrochlorothiazideTadalafil may increase the antihypertensive activities of Hydrochlorothiazide.
IdelalisibThe serum concentration of Tadalafil can be increased when it is combined with Idelalisib.
IndapamideTadalafil may increase the antihypertensive activities of Indapamide.
IndinavirThe serum concentration of Tadalafil can be increased when it is combined with Indinavir.
IrbesartanTadalafil may increase the antihypertensive activities of Irbesartan.
IsosorbideTadalafil may increase the vasodilatory activities of Isosorbide.
Isosorbide DinitrateTadalafil may increase the vasodilatory activities of Isosorbide Dinitrate.
Isosorbide MononitrateTadalafil may increase the vasodilatory activities of Isosorbide Mononitrate.
IsradipineTadalafil may increase the antihypertensive activities of Isradipine.
ItraconazoleThe serum concentration of Tadalafil can be increased when it is combined with Itraconazole.
IvacaftorThe serum concentration of Tadalafil can be increased when it is combined with Ivacaftor.
KetoconazoleThe serum concentration of Tadalafil can be increased when it is combined with Ketoconazole.
LabetalolTadalafil may increase the antihypertensive activities of Labetalol.
LisinoprilTadalafil may increase the antihypertensive activities of Lisinopril.
LorcaserinThe risk or severity of adverse effects can be increased when Lorcaserin is combined with Tadalafil.
LosartanTadalafil may increase the antihypertensive activities of Losartan.
LuliconazoleThe serum concentration of Tadalafil can be increased when it is combined with Luliconazole.
MannitolTadalafil may increase the antihypertensive activities of Mannitol.
MecamylamineTadalafil may increase the antihypertensive activities of Mecamylamine.
MethyclothiazideTadalafil may increase the antihypertensive activities of Methyclothiazide.
MethyldopaTadalafil may increase the antihypertensive activities of Methyldopa.
MetolazoneTadalafil may increase the antihypertensive activities of Metolazone.
MetoprololTadalafil may increase the antihypertensive activities of Metoprolol.
MifepristoneThe serum concentration of Tadalafil can be increased when it is combined with Mifepristone.
MinoxidilTadalafil may increase the antihypertensive activities of Minoxidil.
MitotaneThe serum concentration of Tadalafil can be decreased when it is combined with Mitotane.
MoexiprilTadalafil may increase the antihypertensive activities of Moexipril.
MolsidomineMolsidomine may increase the hypotensive activities of Tadalafil.
MoxonidineTadalafil may increase the antihypertensive activities of Moxonidine.
NadololTadalafil may increase the antihypertensive activities of Nadolol.
NebivololTadalafil may increase the antihypertensive activities of Nebivolol.
NefazodoneThe serum concentration of Tadalafil can be increased when it is combined with Nefazodone.
NelfinavirThe serum concentration of Tadalafil can be increased when it is combined with Nelfinavir.
NetupitantThe serum concentration of Tadalafil can be increased when it is combined with Netupitant.
NicardipineTadalafil may increase the antihypertensive activities of Nicardipine.
NifedipineTadalafil may increase the antihypertensive activities of Nifedipine.
NimodipineTadalafil may increase the antihypertensive activities of Nimodipine.
NisoldipineTadalafil may increase the antihypertensive activities of Nisoldipine.
NitroglycerinTadalafil may increase the vasodilatory activities of Nitroglycerin.
NitroprussideTadalafil may increase the antihypertensive activities of Nitroprusside.
OlmesartanTadalafil may increase the antihypertensive activities of Olmesartan.
PalbociclibThe serum concentration of Tadalafil can be increased when it is combined with Palbociclib.
PenbutololTadalafil may increase the antihypertensive activities of Penbutolol.
PerindoprilTadalafil may increase the antihypertensive activities of Perindopril.
PhenobarbitalThe serum concentration of Tadalafil can be decreased when it is combined with Phenobarbital.
PhenoxybenzamineTadalafil may increase the hypotensive activities of Phenoxybenzamine.
PhentolamineTadalafil may increase the hypotensive activities of Phentolamine.
PhenytoinThe serum concentration of Tadalafil can be decreased when it is combined with Phenytoin.
PindololTadalafil may increase the antihypertensive activities of Pindolol.
PosaconazoleThe serum concentration of Tadalafil can be increased when it is combined with Posaconazole.
PrazosinTadalafil may increase the hypotensive activities of Prazosin.
PrimidoneThe serum concentration of Tadalafil can be decreased when it is combined with Primidone.
PropranololTadalafil may increase the antihypertensive activities of Propranolol.
QuinaprilTadalafil may increase the antihypertensive activities of Quinapril.
RamiprilTadalafil may increase the antihypertensive activities of Ramipril.
ReserpineTadalafil may increase the antihypertensive activities of Reserpine.
RifabutinThe serum concentration of Tadalafil can be decreased when it is combined with Rifabutin.
RifampicinThe serum concentration of Tadalafil can be decreased when it is combined with Rifampicin.
RifapentineThe serum concentration of Tadalafil can be decreased when it is combined with Rifapentine.
RiociguatTadalafil may increase the hypotensive activities of Riociguat.
RitonavirThe serum concentration of Tadalafil can be increased when it is combined with Ritonavir.
SaquinavirThe serum concentration of Tadalafil can be increased when it is combined with Saquinavir.
SildenafilThe risk or severity of adverse effects can be increased when Tadalafil is combined with Sildenafil.
SilodosinTadalafil may increase the hypotensive activities of Silodosin.
SimeprevirThe serum concentration of Tadalafil can be increased when it is combined with Simeprevir.
SotalolTadalafil may increase the antihypertensive activities of Sotalol.
SpironolactoneTadalafil may increase the antihypertensive activities of Spironolactone.
StiripentolThe serum concentration of Tadalafil can be increased when it is combined with Stiripentol.
TamsulosinTadalafil may increase the hypotensive activities of Tamsulosin.
TelaprevirThe serum concentration of Tadalafil can be increased when it is combined with Telaprevir.
TelithromycinThe serum concentration of Tadalafil can be increased when it is combined with Telithromycin.
TelmisartanTadalafil may increase the antihypertensive activities of Telmisartan.
TerazosinTadalafil may increase the hypotensive activities of Terazosin.
TetrahydrobiopterinTetrahydrobiopterin may increase the hypotensive activities of Tadalafil.
TimololTadalafil may increase the antihypertensive activities of Timolol.
TipranavirThe serum concentration of Tadalafil can be increased when it is combined with Tipranavir.
TorasemideTadalafil may increase the antihypertensive activities of Torasemide.
TrandolaprilTadalafil may increase the antihypertensive activities of Trandolapril.
TriamtereneTadalafil may increase the antihypertensive activities of Triamterene.
ValsartanTadalafil may increase the antihypertensive activities of Valsartan.
VardenafilThe risk or severity of adverse effects can be increased when Vardenafil is combined with Tadalafil.
VerapamilTadalafil may increase the antihypertensive activities of Verapamil.
VoriconazoleThe serum concentration of Tadalafil can be increased when it is combined with Voriconazole.

Food Interactions:
  • Not Available

Taxonomy

Kingdom: Organic compounds
Super Class: Not Available
Class: Not Available
Sub Class: Not Available
Direct Parent: Not Available
Alternative Parents:
  • 2,5-dioxopiperazines
  • Acetals
  • Azacyclic compounds
  • Benzenoids
  • Benzodioxoles
  • Carbonyl compounds
  • Heteroaromatic compounds
  • Hydrocarbon derivatives
  • Indoles
  • Lactams
  • N-methylpiperazines
  • Oxacyclic compounds
  • Pyrroles
  • Tertiary amines
  • Tertiary carboxylic acid amides

substituent:
  • 1,4-diazinane
  • 2,5-dioxopiperazine
  • Acetal
  • Amine
  • Aromatic heteropolycyclic compound
  • Azacycle
  • Benzenoid
  • Benzodioxole
  • Beta-carboline
  • Carbonyl group
  • Carboxamide group
  • Carboxylic acid derivative
  • Dioxopiperazine
  • Heteroaromatic compound
  • Hydrocarbon derivative
  • Indole
  • Lactam
  • N-alkylpiperazine
  • N-methylpiperazine
  • Organonitrogen compound
  • Organooxygen compound
  • Oxacycle
  • Piperazine
  • Pyrrole
  • Tertiary amine
  • Tertiary carboxylic acid amide

References

Synthesis Reference: Ben-Zion Dolitzky, Dov Diller, "Preparation of tadalafil intermediates." U.S. Patent US20060276652, issued December 07, 2006.
General Reference: # Naeije R, Huez S: Expert opinion on available options treating pulmonary arterial hypertension. Expert Opin Pharmacother. 2007 Oct;8(14):2247-65. "Pubmed":http://www.ncbi.nlm.nih.gov/pubmed/17927481 # Burnett AL: Molecular Pharmacotherapeutic Targeting of PDE5 for Preservation of Penile Health. J Androl. 2007 Oct 17;. "Pubmed":http://www.ncbi.nlm.nih.gov/pubmed/17942972 # Guazzi M, Samaja M: The role of PDE5-inhibitors in cardiopulmonary disorders: from basic evidence to clinical development. Curr Med Chem. 2007;14(20):2181-91. "Pubmed":http://www.ncbi.nlm.nih.gov/pubmed/17691956
External Links:
ResourceLink
RxListhttp://www.rxlist.com/cgi/generic3/cialis.htm
PDRhealthhttp://www.pdrhealth.com/drug_info/rxdrugprofiles/drugs/cia1687.shtml
Drugs.comhttp://www.drugs.com/tadalafil.html

ATC Codes:
  • Array

AHFS Codes:
  • 24:12.12

MSDS: Download
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