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Identification
NameTadalafil
Accession NumberDB00820  (APRD00071)
TypeSmall Molecule
GroupsApproved, Investigational
DescriptionTadalafil 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
Thumb
Synonyms
(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
(6R,12AR)-2,3,6,7,12,12a-hexahydro-2-methyl-6-(3,4-(methylenedioxy)phenyl) pyrazino(1',2':1,6)pyrido(3,4-b)indole-1,4-dione
6-BENZO[1,3]dioxol-5-yl-2-methyl-2,3,6,7,12,12a-hexahydro-pyrazino[1',2':1,6]pyrido[3,4-b]indole-1,4-dione
Adcirca
Cialis
ICOS 351
Tadanafil
External Identifiers Not Available
Approved Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Act Tadalafiltablet20 mgoralActavis Pharma Company2016-07-12Not applicableCanada
Act Tadalafiltablet2.5 mgoralActavis Pharma Company2016-07-12Not applicableCanada
Act Tadalafiltablet5 mgoralActavis Pharma Company2016-07-12Not applicableCanada
Act Tadalafiltablet10 mgoralActavis Pharma Company2016-07-12Not applicableCanada
Adcircatablet20 mgoralEli Lilly Canada Inc2010-01-19Not applicableCanada
Adcircatablet20 mg/1oralUnited Therapeutics Corporation2009-08-03Not applicableUs
AdcircaFilm-coated tablet20 mgOral useEli Lilly Nederland B.V.2008-10-01Not applicableEu
Auro-tadalafiltablet10 mgoralAuro Pharma Inc2016-07-14Not applicableCanada
Auro-tadalafiltablet20 mgoralAuro Pharma Inc2016-07-14Not applicableCanada
Auro-tadalafiltablet2.5 mgoralAuro Pharma Inc2016-07-14Not applicableCanada
Auro-tadalafiltablet5 mgoralAuro Pharma Inc2016-07-14Not applicableCanada
Cialistablet, film coated20 mg/1oralPd Rx Pharmaceuticals, Inc.2003-11-26Not applicableUs
CialisFilm-coated tablet20 mgOral useEli Lilly Nederland B.V.2002-11-12Not applicableEu
Cialistablet, film coated5 mg/1oralEli Lilly and Company2003-11-26Not applicableUs
Cialistablet, film coated5 mg/1oralbryant ranch prepack2003-11-26Not applicableUs
Cialistablet, film coated5 mg/1oralPhysicians Total Care, Inc.2008-10-23Not applicableUs
CialisFilm-coated tablet5 mgOral useEli Lilly Nederland B.V.2002-11-12Not applicableEu
Cialistablet, film coated10 mg/1oralSTAT Rx USA LLC2003-11-26Not applicableUs
Cialistablet20 mgoralEli Lilly Canada Inc2003-11-25Not applicableCanada
CialisFilm-coated tablet10 mgOral useEli Lilly Nederland B.V.2002-11-12Not applicableEu
Cialistablet, film coated20 mg/1oralAphena Pharma Solutions Tennessee, Llc2003-11-26Not applicableUs
CialisFilm-coated tablet20 mgOral useEli Lilly Nederland B.V.2002-11-12Not applicableEu
Cialistablet, film coated10 mg/1oralEli Lilly and Company2003-11-26Not applicableUs
CialisFilm-coated tablet20 mgOral useEli Lilly Nederland B.V.2002-11-12Not applicableEu
Cialistablet, film coated5 mg/1oralCardinal Health2003-11-26Not applicableUs
CialisFilm-coated tablet20 mgOral useEli Lilly Nederland B.V.2002-11-12Not applicableEu
Cialistablet, film coated10 mg/1oralRebel Distributors Corp.2003-11-26Not applicableUs
Cialistablet2.5 mgoralEli Lilly Canada Inc2008-01-18Not applicableCanada
Cialistablet, film coated10 mg/1oralPhysicians Total Care, Inc.2003-12-03Not applicableUs
CialisFilm-coated tablet2.5 mgOral useEli Lilly Nederland B.V.2002-11-12Not applicableEu
Cialistablet, film coated20 mg/1oralEli Lilly and Company2003-11-26Not applicableUs
Cialistablet, film coated20 mg/1oralDispensing Solutions, Inc.2003-11-26Not applicableUs
Cialistablet, film coated20 mg/1oralbryant ranch prepack2003-11-26Not applicableUs
Cialistablet5.0 mgoralEli Lilly Canada Inc2008-01-18Not applicableCanada
CialisFilm-coated tablet20 mgOral useEli Lilly Nederland B.V.2002-11-12Not applicableEu
Cialistablet, film coated20 mg/1oralRebel Distributors Corp.2003-11-26Not applicableUs
Cialistablet, film coated20 mg/1oralPhysicians Total Care, Inc.2003-12-11Not applicableUs
CialisFilm-coated tablet5 mgOral useEli Lilly Nederland B.V.2002-11-12Not applicableEu
Cialistablet, film coated2.5 mg/1oralEli Lilly and Company2008-01-07Not applicableUs
Cialistablet10 mgoralEli Lilly Canada Inc2003-12-11Not applicableCanada
Cialistablet, film coated2.5 mg/1oralbryant ranch prepack2008-01-07Not applicableUs
Dom-tadalafiltablet5 mgoralDominion PharmacalNot applicableNot applicableCanada
Dom-tadalafiltablet10 mgoralDominion PharmacalNot applicableNot applicableCanada
Dom-tadalafiltablet20 mgoralDominion PharmacalNot applicableNot applicableCanada
Dom-tadalafiltablet2.5 mgoralDominion PharmacalNot applicableNot applicableCanada
Ipg-tadalafiltablet5 mgoralMarcan Pharmaceuticals IncNot applicableNot applicableCanada
Ipg-tadalafiltablet10 mgoralMarcan Pharmaceuticals IncNot applicableNot applicableCanada
Ipg-tadalafiltablet20 mgoralMarcan Pharmaceuticals IncNot applicableNot applicableCanada
Ipg-tadalafiltablet2.5 mgoralMarcan Pharmaceuticals IncNot applicableNot applicableCanada
Jamp-tadalafiltablet2.5 mgoralJamp Pharma Corporation2016-07-13Not applicableCanada
Jamp-tadalafiltablet5 mgoralJamp Pharma Corporation2016-07-13Not applicableCanada
Jamp-tadalafiltablet10 mgoralJamp Pharma Corporation2016-07-13Not applicableCanada
Jamp-tadalafiltablet20 mgoralJamp Pharma Corporation2016-07-13Not applicableCanada
Mar-tadalafiltablet5 mgoralMarcan Pharmaceuticals Inc2016-07-13Not applicableCanada
Mar-tadalafiltablet10 mgoralMarcan Pharmaceuticals Inc2016-07-13Not applicableCanada
Mar-tadalafiltablet20 mgoralMarcan Pharmaceuticals Inc2016-07-13Not applicableCanada
Mar-tadalafiltablet2.5 mgoralMarcan Pharmaceuticals Inc2016-07-13Not applicableCanada
Mint-tadalafiltablet2.5 mgoralMint Pharmaceuticals IncNot applicableNot applicableCanada
Mint-tadalafiltablet10 mgoralMint Pharmaceuticals IncNot applicableNot applicableCanada
Mint-tadalafiltablet5 mgoralMint Pharmaceuticals Inc2016-07-14Not applicableCanada
Mint-tadalafiltablet20 mgoralMint Pharmaceuticals Inc2016-07-14Not applicableCanada
Mylan-tadalafiltablet20 mgoralMylan Pharmaceuticals Ulc2016-07-12Not applicableCanada
Mylan-tadalafiltablet2.5 mgoralMylan Pharmaceuticals Ulc2016-07-12Not applicableCanada
Mylan-tadalafiltablet5 mgoralMylan Pharmaceuticals Ulc2016-07-12Not applicableCanada
Mylan-tadalafiltablet10 mgoralMylan Pharmaceuticals Ulc2016-07-12Not applicableCanada
PMS-tadalafiltablet20 mgoralPharmascience Inc2016-07-12Not applicableCanada
PMS-tadalafiltablet2.5 mgoralPharmascience Inc2016-07-12Not applicableCanada
PMS-tadalafiltablet5 mgoralPharmascience Inc2016-07-12Not applicableCanada
PMS-tadalafiltablet10 mgoralPharmascience Inc2016-07-12Not applicableCanada
Priva-tadalafiltablet20 mgoralPharmapar Inc2016-07-13Not applicableCanada
Priva-tadalafiltablet2.5 mgoralPharmapar Inc2016-07-13Not applicableCanada
Priva-tadalafiltablet5 mgoralPharmapar Inc2016-07-13Not applicableCanada
Priva-tadalafiltablet10 mgoralPharmapar Inc2016-07-13Not applicableCanada
Ran-tadalafiltablet20 mgoralRanbaxy Pharmaceuticals Canada Inc.2016-07-15Not applicableCanada
Ran-tadalafiltablet5 mgoralRanbaxy Pharmaceuticals Canada Inc.2016-07-12Not applicableCanada
Ran-tadalafiltablet2.5 mgoralRanbaxy Pharmaceuticals Canada Inc.2016-07-12Not applicableCanada
Ran-tadalafiltablet10 mgoralRanbaxy Pharmaceuticals Canada Inc.2016-07-12Not applicableCanada
Riva-tadalafiltablet5 mgoralLaboratoire Riva Inc2016-07-13Not applicableCanada
Riva-tadalafiltablet2.5 mgoralLaboratoire Riva IncNot applicableNot applicableCanada
Riva-tadalafiltablet20 mgoralLaboratoire Riva Inc2016-07-13Not applicableCanada
Riva-tadalafiltablet10 mgoralLaboratoire Riva IncNot applicableNot applicableCanada
Tadalafiltablet5 mgoralPro Doc LimiteeNot applicableNot applicableCanada
Tadalafiltablet10 mgoralPro Doc LimiteeNot applicableNot applicableCanada
Tadalafiltablet20 mgoralPro Doc LimiteeNot applicableNot applicableCanada
Teva-tadalafiltablet10 mgoralTeva Canada Limited2016-07-12Not applicableCanada
Teva-tadalafiltablet20 mgoralTeva Canada Limited2016-07-12Not applicableCanada
Teva-tadalafiltablet2.5 mgoralTeva Canada Limited2016-07-12Not applicableCanada
Teva-tadalafiltablet5 mgoralTeva Canada Limited2016-07-12Not applicableCanada
Approved Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Apo-tadalafiltablet20 mgoralApotex Inc2016-07-12Not applicableCanada
Apo-tadalafiltablet2.5 mgoralApotex Inc2016-07-12Not applicableCanada
Apo-tadalafiltablet5 mgoralApotex Inc2016-07-12Not applicableCanada
Apo-tadalafiltablet10 mgoralApotex Inc2016-07-12Not applicableCanada
Apo-tadalafil Pahtablet20 mgoralApotex Inc2015-10-15Not applicableCanada
Tadalafil MylanFilm-coated tablet20 mgOral useGenerics (Uk) Limited2014-11-21Not applicableEu
Tadalafil MylanFilm-coated tablet5 mgOral useGenerics (Uk) Limited2014-11-21Not applicableEu
Tadalafil MylanFilm-coated tablet2.5 mgOral useGenerics (Uk) Limited2014-11-21Not applicableEu
Tadalafil MylanFilm-coated tablet5 mgOral useGenerics (Uk) Limited2014-11-21Not applicableEu
Tadalafil MylanFilm-coated tablet20 mgOral useGenerics (Uk) Limited2014-11-21Not applicableEu
Tadalafil MylanFilm-coated tablet5 mgOral useGenerics (Uk) Limited2014-11-21Not applicableEu
Tadalafil MylanFilm-coated tablet2.5 mgOral useGenerics (Uk) Limited2014-11-21Not applicableEu
Tadalafil MylanFilm-coated tablet10 mgOral useGenerics (Uk) Limited2014-11-21Not applicableEu
Tadalafil MylanFilm-coated tablet20 mgOral useGenerics (Uk) Limited2014-11-21Not applicableEu
Tadalafil MylanFilm-coated tablet5 mgOral useGenerics (Uk) Limited2014-11-21Not applicableEu
Tadalafil MylanFilm-coated tablet10 mgOral useGenerics (Uk) Limited2014-11-21Not applicableEu
Tadalafil MylanFilm-coated tablet20 mgOral useGenerics (Uk) Limited2014-11-21Not applicableEu
Tadalafil MylanFilm-coated tablet20 mgOral useGenerics (Uk) Limited2014-11-21Not applicableEu
Tadalafil MylanFilm-coated tablet5 mgOral useGenerics (Uk) Limited2014-11-21Not applicableEu
Tadalafil MylanFilm-coated tablet10 mgOral useGenerics (Uk) Limited2014-11-21Not applicableEu
Approved Over the Counter ProductsNot Available
Unapproved/Other Products Not Available
International BrandsNot Available
Brand mixturesNot Available
SaltsNot Available
Categories
UNII742SXX0ICT
CAS number171596-29-5
WeightAverage: 389.404
Monoisotopic: 389.137556111
Chemical FormulaC22H19N3O4
InChI KeyInChIKey=WOXKDUGGOYFFRN-IIBYNOLFSA-N
InChI
InChI=1S/C22H19N3O4/c1-24-10-19(26)25-16(22(24)27)9-14-13-4-2-3-5-15(13)23-20(14)21(25)12-6-7-17-18(8-12)29-11-28-17/h2-8,16,21,23H,9-11H2,1H3/t16-,21-/m1/s1
IUPAC Name
(2R,8R)-2-(2H-1,3-benzodioxol-5-yl)-6-methyl-3,6,17-triazatetracyclo[8.7.0.0³,⁸.0¹¹,¹⁶]heptadeca-1(10),11,13,15-tetraene-4,7-dione
SMILES
[H][C@]12CC3=C(NC4=CC=CC=C34)[[email protected]](N1C(=O)CN(C)C2=O)C1=CC2=C(OCO2)C=C1
Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as beta carbolines. These are compounds containing a 9H-pyrido[3,4-b]indole moiety.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassIndoles and derivatives
Sub ClassPyridoindoles
Direct ParentBeta carbolines
Alternative Parents
Substituents
  • Beta-carboline
  • Indole
  • Benzodioxole
  • 2,5-dioxopiperazine
  • Dioxopiperazine
  • N-alkylpiperazine
  • N-methylpiperazine
  • Benzenoid
  • Piperazine
  • 1,4-diazinane
  • Heteroaromatic compound
  • Tertiary carboxylic acid amide
  • Pyrrole
  • Tertiary amine
  • Lactam
  • Carboxamide group
  • Oxacycle
  • Azacycle
  • Carboxylic acid derivative
  • Acetal
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Carbonyl group
  • Amine
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Pharmacology
IndicationUsed for the treatment of erectile dysfunction.
PharmacodynamicsTadalafil is used to treat male erectile dysfunction (impotence) and pulmonary arterial hypertension (PAH). Part of the physiological process of erection involves the release of nitric oxide (NO) in the corpus cavernosum. This then activates the enzyme guanylate cyclase which results in increased levels of cyclic guanosine monophosphate (cGMP), leading to smooth muscle relaxation in the corpus cavernosum, resulting in increased inflow of blood and an erection. Tadalafil is a potent and selective inhibitor of cGMP specific phosphodiesterase type 5 (PDE5) which is responsible for degradation of cGMP in the corpus cavernosum. This means that, with tadalafil on board, normal sexual stimulation leads to increased levels of cGMP in the corpus cavernosum which leads to better erections. Without sexual stimulation and no activation of the NO/cGMP system, tadalafil should not cause an erection.
Mechanism of actionTadalafil 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.
Related Articles
AbsorptionAfter 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 binding94%
Metabolism

Tadalafil is predominantly metabolized by CYP3A4 to a catechol metabolite. The catechol metabolite undergoes extensive methylation and glucuronidation to form the methylcatechol and methylcatechol glucuronide conjugate, respectively. In vitro data suggests the metabolites are not expected to be pharmacologically active at observed metabolite concentrations.

Route of eliminationTadalafil 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 life17.5 hours
Clearance
  • oral cl=2.5 L/hr
ToxicityOral, Rat LD50 = 2000 mg/kg, no deaths or toxicity.
Affected organisms
  • Humans and other mammals
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9933
Blood Brain Barrier+0.7821
Caco-2 permeable+0.5
P-glycoprotein substrateSubstrate0.6581
P-glycoprotein inhibitor INon-inhibitor0.59
P-glycoprotein inhibitor IINon-inhibitor0.775
Renal organic cation transporterNon-inhibitor0.7165
CYP450 2C9 substrateNon-substrate0.8742
CYP450 2D6 substrateNon-substrate0.9116
CYP450 3A4 substrateSubstrate0.7407
CYP450 1A2 substrateNon-inhibitor0.7447
CYP450 2C9 inhibitorInhibitor0.5566
CYP450 2D6 inhibitorNon-inhibitor0.6788
CYP450 2C19 inhibitorInhibitor0.6998
CYP450 3A4 inhibitorNon-inhibitor0.6981
CYP450 inhibitory promiscuityHigh CYP Inhibitory Promiscuity0.7235
Ames testNon AMES toxic0.6466
CarcinogenicityNon-carcinogens0.931
BiodegradationNot ready biodegradable0.8906
Rat acute toxicity2.6521 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.976
hERG inhibition (predictor II)Non-inhibitor0.8734
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397 )
Pharmacoeconomics
Manufacturers
  • Eli lilly co
  • Eli lilly and co
  • Eli Lilly and Company
Packagers
Dosage forms
FormRouteStrength
Film-coated tabletOral use20 mg
Tabletoral20 mg/1
Film-coated tabletOral use10 mg
Film-coated tabletOral use2.5 mg
Film-coated tabletOral use5 mg
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
Tabletoral5 mg
Prices
Unit descriptionCostUnit
Cialis 30 5 mg tablet Box140.77USD box
Cialis 10 mg tablet20.92USD tablet
Cialis 20 mg tablet20.92USD tablet
Cialis 2.5 mg tablet4.76USD tablet
Cialis 5 mg tablet4.76USD tablet
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
Patent NumberPediatric ExtensionApprovedExpires (estimated)
CA2181377 No2002-05-282015-01-19Canada
CA2379948 No2008-03-252020-04-26Canada
US5859006 No1997-11-212017-11-21Us
US6140329 No1996-07-112016-07-11Us
US6821975 No2000-11-192020-11-19Us
US6943166 No2000-04-262020-04-26Us
US7182958 No2000-04-262020-04-26Us
Properties
StateSolid
Experimental Properties
PropertyValueSource
melting point301-302 °CNot Available
water solubilityPractically insoluble in waterNot Available
logP1.7Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.25 mg/mLALOGPS
logP2.36ALOGPS
logP1.64ChemAxon
logS-3.2ALOGPS
pKa (Strongest Acidic)15.17ChemAxon
pKa (Strongest Basic)-4.2ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area74.87 Å2ChemAxon
Rotatable Bond Count1ChemAxon
Refractivity104.08 m3·mol-1ChemAxon
Polarizability40.92 Å3ChemAxon
Number of Rings6ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Not Available
Spectra
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot Available
References
Synthesis Reference

Ben-Zion Dolitzky, Dov Diller, “Preparation of tadalafil intermediates.” U.S. Patent US20060276652, issued December 07, 2006.

US20060276652
General References
  1. Naeije R, Huez S: Expert opinion on available options treating pulmonary arterial hypertension. Expert Opin Pharmacother. 2007 Oct;8(14):2247-65. [PubMed:17927481 ]
  2. Burnett AL: Molecular pharmacotherapeutic targeting of PDE5 for preservation of penile health. J Androl. 2008 Jan-Feb;29(1):3-14. Epub 2007 Oct 17. [PubMed:17942972 ]
  3. 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:17691956 ]
External Links
ATC CodesG04BE08
AHFS Codes
  • 24:12.12
PDB EntriesNot Available
FDA labelDownload (287 KB)
MSDSDownload (73.7 KB)
Interactions
Drug Interactions
Drug
AcebutololTadalafil may increase the antihypertensive activities of Acebutolol.
AlfuzosinTadalafil may increase the hypotensive activities of Alfuzosin.
AliskirenTadalafil may increase the antihypertensive activities of Aliskiren.
AlprenololTadalafil may increase the antihypertensive activities of Alprenolol.
AlprostadilThe risk or severity of adverse effects can be increased when Tadalafil is combined with Alprostadil.
AmbrisentanTadalafil may increase the antihypertensive activities of Ambrisentan.
AmiodaroneThe serum concentration of Tadalafil can be increased when it is combined with Amiodarone.
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.
AtomoxetineThe metabolism of Tadalafil can be decreased when combined with Atomoxetine.
BenazeprilTadalafil may increase the antihypertensive activities of Benazepril.
BendroflumethiazideTadalafil may increase the antihypertensive activities of Bendroflumethiazide.
BepridilTadalafil may increase the antihypertensive activities of Bepridil.
BetaxololTadalafil may increase the antihypertensive activities of Betaxolol.
BethanidineTadalafil may increase the antihypertensive activities of Bethanidine.
BexaroteneThe serum concentration of Tadalafil can be decreased when it is combined with Bexarotene.
BimatoprostTadalafil may increase the antihypertensive activities of Bimatoprost.
BisoprololTadalafil may increase the antihypertensive activities of Bisoprolol.
BoceprevirThe serum concentration of Tadalafil can be increased when it is combined with Boceprevir.
BortezomibThe metabolism of Tadalafil can be decreased when combined with Bortezomib.
BosentanThe serum concentration of Tadalafil can be decreased when it is combined with Bosentan.
BosentanTadalafil may increase the antihypertensive activities of Bosentan.
BretyliumTadalafil may increase the antihypertensive activities of Bretylium.
BrimonidineTadalafil may increase the antihypertensive activities of Brimonidine.
BupranololTadalafil may increase the antihypertensive activities of Bupranolol.
CandesartanTadalafil may increase the antihypertensive activities of Candesartan.
CandoxatrilTadalafil may increase the antihypertensive activities of Candoxatril.
CaptoprilTadalafil may increase the antihypertensive activities of Captopril.
CarbamazepineThe serum concentration of Tadalafil can be decreased when it is combined with Carbamazepine.
CarteololTadalafil may increase the antihypertensive activities of Carteolol.
CarvedilolTadalafil may increase the antihypertensive activities of Carvedilol.
CeliprololTadalafil may increase the antihypertensive activities of Celiprolol.
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.
ClemastineThe metabolism of Tadalafil can be decreased when combined with Clemastine.
ClonidineTadalafil may increase the antihypertensive activities of Clonidine.
ClotrimazoleThe metabolism of Tadalafil can be decreased when combined with Clotrimazole.
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.
CrizotinibThe metabolism of Tadalafil can be decreased when combined with Crizotinib.
CryptenamineTadalafil may increase the antihypertensive activities of Cryptenamine.
CyclosporineThe metabolism of Tadalafil can be decreased when combined with Cyclosporine.
CyclothiazideTadalafil may increase the antihypertensive activities of Cyclothiazide.
DabrafenibThe serum concentration of Tadalafil can be decreased when it is combined with Dabrafenib.
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.
DebrisoquinTadalafil may increase the antihypertensive activities of Debrisoquin.
DeferasiroxThe serum concentration of Tadalafil can be decreased when it is combined with Deferasirox.
DelavirdineThe metabolism of Tadalafil can be decreased when combined with Delavirdine.
DeserpidineTadalafil may increase the antihypertensive activities of Deserpidine.
DexamethasoneThe serum concentration of Tadalafil can be decreased when it is combined with Dexamethasone.
DiazoxideTadalafil may increase the antihypertensive activities of Diazoxide.
DihydroergotamineThe metabolism of Tadalafil can be decreased when combined with Dihydroergotamine.
DiltiazemTadalafil may increase the antihypertensive activities of Diltiazem.
DiltiazemThe metabolism of Tadalafil can be decreased when combined with Diltiazem.
DorzolamideTadalafil may increase the antihypertensive activities of Dorzolamide.
DoxazosinTadalafil may increase the antihypertensive activities of Doxazosin.
DoxycyclineThe metabolism of Tadalafil can be decreased when combined with Doxycycline.
DronedaroneThe metabolism of Tadalafil can be decreased when combined with Dronedarone.
EfavirenzThe serum concentration of Tadalafil can be decreased when it is combined with Efavirenz.
EfonidipineTadalafil may increase the antihypertensive activities of Efonidipine.
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.
EpoprostenolTadalafil may increase the antihypertensive activities of Epoprostenol.
EprosartanTadalafil may increase the antihypertensive activities of Eprosartan.
Erythrityl TetranitrateTadalafil may increase the vasodilatory activities of Erythrityl Tetranitrate.
ErythromycinThe metabolism of Tadalafil can be decreased when combined with Erythromycin.
Eslicarbazepine acetateThe serum concentration of Tadalafil can be decreased when it is combined with Eslicarbazepine acetate.
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.
FenoldopamTadalafil may increase the antihypertensive activities of Fenoldopam.
FluconazoleThe serum concentration of Tadalafil can be increased when it is combined with Fluconazole.
FluvoxamineThe metabolism of Tadalafil can be decreased when combined with Fluvoxamine.
FosamprenavirThe metabolism of Tadalafil can be decreased when combined with Fosamprenavir.
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.
Fusidic AcidThe serum concentration of Tadalafil can be increased when it is combined with Fusidic Acid.
GuanabenzTadalafil may increase the antihypertensive activities of Guanabenz.
GuanadrelTadalafil may increase the antihypertensive activities of Guanadrel.
GuanethidineTadalafil may increase the antihypertensive activities of Guanethidine.
GuanfacineTadalafil may increase the antihypertensive activities of Guanfacine.
HexamethoniumTadalafil may increase the antihypertensive activities of Hexamethonium.
HydralazineTadalafil may increase the antihypertensive activities of Hydralazine.
HydrochlorothiazideTadalafil may increase the antihypertensive activities of Hydrochlorothiazide.
HydroflumethiazideTadalafil may increase the antihypertensive activities of Hydroflumethiazide.
IdelalisibThe serum concentration of Tadalafil can be increased when it is combined with Idelalisib.
ImatinibThe metabolism of Tadalafil can be decreased when combined with Imatinib.
IndapamideTadalafil may increase the antihypertensive activities of Indapamide.
IndenololTadalafil may increase the antihypertensive activities of Indenolol.
IndinavirThe serum concentration of Tadalafil can be increased when it is combined with Indinavir.
IndoraminTadalafil may increase the antihypertensive activities of Indoramin.
IrbesartanTadalafil may increase the antihypertensive activities of Irbesartan.
IsavuconazoniumThe metabolism of Tadalafil can be decreased when combined with Isavuconazonium.
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.
IsradipineThe metabolism of Tadalafil can be decreased when combined with 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.
LacidipineTadalafil may increase the antihypertensive activities of Lacidipine.
LatanoprostTadalafil may increase the antihypertensive activities of Latanoprost.
LercanidipineTadalafil may increase the antihypertensive activities of Lercanidipine.
LisinoprilTadalafil may increase the antihypertensive activities of Lisinopril.
LofexidineTadalafil may increase the antihypertensive activities of Lofexidine.
LopinavirThe serum concentration of Tadalafil can be increased when it is combined with Lopinavir.
LorcaserinThe risk or severity of adverse effects can be increased when Lorcaserin is combined with Tadalafil.
LosartanTadalafil may increase the antihypertensive activities of Losartan.
LovastatinThe metabolism of Tadalafil can be decreased when combined with Lovastatin.
LuliconazoleThe serum concentration of Tadalafil can be increased when it is combined with Luliconazole.
MacitentanTadalafil may increase the antihypertensive activities of Macitentan.
ManidipineTadalafil may increase the antihypertensive activities of Manidipine.
MecamylamineTadalafil may increase the antihypertensive activities of Mecamylamine.
MethyldopaTadalafil may increase the antihypertensive activities of Methyldopa.
MetipranololTadalafil may increase the antihypertensive activities of Metipranolol.
MetolazoneTadalafil may increase the antihypertensive activities of Metolazone.
MetoprololTadalafil may increase the antihypertensive activities of Metoprolol.
MibefradilTadalafil may increase the antihypertensive activities of Mibefradil.
MifepristoneThe metabolism of Tadalafil can be decreased when 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.
ModafinilThe serum concentration of Tadalafil can be decreased when it is combined with Modafinil.
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.
NafcillinThe serum concentration of Tadalafil can be decreased when it is combined with Nafcillin.
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.
NevirapineThe metabolism of Tadalafil can be decreased when combined with Nevirapine.
NicardipineTadalafil may increase the antihypertensive activities of Nicardipine.
NicorandilTadalafil may increase the antihypertensive activities of Nicorandil.
NiguldipineTadalafil may increase the antihypertensive activities of Niguldipine.
NilotinibThe metabolism of Tadalafil can be decreased when combined with Nilotinib.
NilvadipineTadalafil may increase the antihypertensive activities of Nilvadipine.
NimodipineTadalafil may increase the antihypertensive activities of Nimodipine.
NintedanibThe serum concentration of Nintedanib can be increased when it is combined with Tadalafil.
NisoldipineTadalafil may increase the antihypertensive activities of Nisoldipine.
NitrendipineTadalafil may increase the antihypertensive activities of Nitrendipine.
NitroglycerinTadalafil may increase the vasodilatory activities of Nitroglycerin.
NitroprussideTadalafil may increase the antihypertensive activities of Nitroprusside.
OlaparibThe metabolism of Tadalafil can be decreased when combined with Olaparib.
OlmesartanTadalafil may increase the antihypertensive activities of Olmesartan.
OmapatrilatTadalafil may increase the antihypertensive activities of Omapatrilat.
OsimertinibThe serum concentration of Tadalafil can be increased when it is combined with Osimertinib.
OxprenololTadalafil may increase the antihypertensive activities of Oxprenolol.
PalbociclibThe serum concentration of Tadalafil can be increased when it is combined with Palbociclib.
PargylineTadalafil may increase the antihypertensive activities of Pargyline.
PenbutololTadalafil may increase the antihypertensive activities of Penbutolol.
PentobarbitalThe serum concentration of Tadalafil can be decreased when it is combined with Pentobarbital.
PentoliniumTadalafil may increase the antihypertensive activities of Pentolinium.
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 antihypertensive activities of Phenoxybenzamine.
PhentolamineTadalafil may increase the antihypertensive activities of Phentolamine.
PhenytoinThe serum concentration of Tadalafil can be decreased when it is combined with Phenytoin.
PinacidilTadalafil may increase the antihypertensive activities of Pinacidil.
PindololTadalafil may increase the antihypertensive activities of Pindolol.
PolythiazideTadalafil may increase the antihypertensive activities of Polythiazide.
PosaconazoleThe serum concentration of Tadalafil can be increased when it is combined with Posaconazole.
PrazosinTadalafil may increase the antihypertensive 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.
RanolazineThe metabolism of Tadalafil can be decreased when combined with Ranolazine.
RemikirenTadalafil may increase the antihypertensive activities of Remikiren.
RescinnamineTadalafil may increase the antihypertensive activities of Rescinnamine.
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.
SaprisartanTadalafil may increase the antihypertensive activities of Saprisartan.
SapropterinSapropterin may increase the hypotensive activities of Tadalafil.
SaquinavirThe serum concentration of Tadalafil can be increased when it is combined with Saquinavir.
SelexipagTadalafil may increase the antihypertensive activities of Selexipag.
SildenafilThe risk or severity of adverse effects can be increased when Sildenafil is combined with Tadalafil.
SilodosinTadalafil may increase the hypotensive activities of Silodosin.
SiltuximabThe serum concentration of Tadalafil can be decreased when it is combined with Siltuximab.
SimeprevirThe serum concentration of Tadalafil can be increased when it is combined with Simeprevir.
SitaxentanTadalafil may increase the antihypertensive activities of Sitaxentan.
SpiraprilTadalafil may increase the antihypertensive activities of Spirapril.
St. John's WortThe serum concentration of Tadalafil can be decreased when it is combined with St. John's Wort.
StiripentolThe serum concentration of Tadalafil can be increased when it is combined with Stiripentol.
SulfisoxazoleThe metabolism of Tadalafil can be decreased when combined with Sulfisoxazole.
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.
TemocaprilTadalafil may increase the antihypertensive activities of Temocapril.
TerazosinTadalafil may increase the hypotensive activities of Terazosin.
TerlipressinTadalafil may increase the antihypertensive activities of Terlipressin.
TiboloneTadalafil may increase the antihypertensive activities of Tibolone.
TiclopidineThe metabolism of Tadalafil can be decreased when combined with Ticlopidine.
TicrynafenTadalafil may increase the antihypertensive activities of Ticrynafen.
TimololTadalafil may increase the antihypertensive activities of Timolol.
TipranavirThe serum concentration of Tadalafil can be increased when it is combined with Tipranavir.
TocilizumabThe serum concentration of Tadalafil can be decreased when it is combined with Tocilizumab.
TolazolineTadalafil may increase the antihypertensive activities of Tolazoline.
TorasemideTadalafil may increase the antihypertensive activities of Torasemide.
TrandolaprilTadalafil may increase the antihypertensive activities of Trandolapril.
TravoprostTadalafil may increase the antihypertensive activities of Travoprost.
TreprostinilTadalafil may increase the antihypertensive activities of Treprostinil.
TrichlormethiazideTadalafil may increase the antihypertensive activities of Trichlormethiazide.
TrimazosinTadalafil may increase the antihypertensive activities of Trimazosin.
TrimethaphanTadalafil may increase the antihypertensive activities of Trimethaphan.
UdenafilThe risk or severity of adverse effects can be increased when Tadalafil is combined with Udenafil.
UnoprostoneTadalafil may increase the antihypertensive activities of Unoprostone.
ValsartanTadalafil may increase the antihypertensive activities of Valsartan.
VardenafilThe risk or severity of adverse effects can be increased when Tadalafil is combined with Vardenafil.
VenlafaxineThe metabolism of Tadalafil can be decreased when combined with Venlafaxine.
VerapamilThe metabolism of Tadalafil can be decreased when combined with Verapamil.
VoriconazoleThe serum concentration of Tadalafil can be increased when it is combined with Voriconazole.
XylometazolineTadalafil may increase the antihypertensive activities of Xylometazoline.
ZiprasidoneThe metabolism of Tadalafil can be decreased when combined with Ziprasidone.
Food InteractionsNot Available

Targets

Kind
Protein
Organism
Human
Pharmacological action
yes
Actions
inhibitor
General Function:
Metal ion binding
Specific Function:
Plays a role in signal transduction by regulating the intracellular concentration of cyclic nucleotides. This phosphodiesterase catalyzes the specific hydrolysis of cGMP to 5'-GMP (PubMed:9714779, PubMed:15489334). Specifically regulates nitric-oxide-generated cGMP (PubMed:15489334).
Gene Name:
PDE5A
Uniprot ID:
O76074
Molecular Weight:
99984.14 Da
References
  1. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]
  2. Curran M, Keating G: Tadalafil. Drugs. 2003;63(20):2203-12; discussion 2213-4. [PubMed:14498756 ]
  3. Eardley I, Cartledge J: Tadalafil (Cialis) for men with erectile dysfunction. Int J Clin Pract. 2002 May;56(4):300-4. [PubMed:12074215 ]
  4. Montorsi F, Salonia A, Deho' F, Cestari A, Guazzoni G, Rigatti P, Stief C: Pharmacological management of erectile dysfunction. BJU Int. 2003 Mar;91(5):446-54. [PubMed:12603396 ]
  5. Rotella DP: Tadalafil Lilly ICOS. Curr Opin Investig Drugs. 2003 Jan;4(1):60-5. [PubMed:12625031 ]
  6. Roumeguere T, Sternon J, Schulman CC: [Erectile dysfunction and phosphodiesterase type 5 inhibitors]. Rev Med Brux. 2003 Jun;24(3):169-75. [PubMed:12891884 ]
  7. Zoraghi R, Francis SH, Corbin JD: Critical amino acids in phosphodiesterase-5 catalytic site that provide for high-affinity interaction with cyclic guanosine monophosphate and inhibitors. Biochemistry. 2007 Nov 27;46(47):13554-63. Epub 2007 Nov 3. [PubMed:17979301 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
inhibitor
General Function:
Metal ion binding
Specific Function:
Plays a role in signal transduction by regulating the intracellular concentration of cyclic nucleotides cAMP and cGMP. Catalyzes the hydrolysis of both cAMP and cGMP to 5'-AMP and 5'-GMP, respectively.
Gene Name:
PDE11A
Uniprot ID:
Q9HCR9
Molecular Weight:
104750.64 Da
References
  1. Weeks JL 2nd, Corbin JD, Francis SH: Interactions between cyclic nucleotide phosphodiesterase 11 catalytic site and substrates or tadalafil and role of a critical Gln-869 hydrogen bond. J Pharmacol Exp Ther. 2009 Oct;331(1):133-41. doi: 10.1124/jpet.109.156935. Epub 2009 Jul 29. [PubMed:19641165 ]
  2. Weeks JL 2nd, Zoraghi R, Francis SH, Corbin JD: N-Terminal domain of phosphodiesterase-11A4 (PDE11A4) decreases affinity of the catalytic site for substrates and tadalafil, and is involved in oligomerization. Biochemistry. 2007 Sep 11;46(36):10353-64. Epub 2007 Aug 16. [PubMed:17696499 ]

Enzymes

Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
substrateinhibitor
General Function:
Vitamin d3 25-hydroxylase activity
Specific Function:
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation reactions (e.g. caffeine 8-oxidation, omeprazole sulphoxidation, midazolam 1'-hydroxylation and midazolam 4-hydroxylation) of structurally unrelated compounds, including steroids, fatty acids, and xenobiot...
Gene Name:
CYP3A4
Uniprot ID:
P08684
Molecular Weight:
57342.67 Da
References
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]
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Drug created on June 13, 2005 07:24 / Updated on September 30, 2016 02:26