{"ATC Code":["G04BE08","G - Genito urinary system and sex hormones","G04 - Urologicals","G04B - Urologicals","G04BE - Drugs used in erectile dysfunction","G04BE08 - Tadalafil","QG - Genito urinary system and sex hormones","QG04 - Urologicals","QG04B - Urologicals","QG04BE - Drugs used in erectile dysfunction","QG04BE08 - Tadalafil"],"Absorption, Distribution and Excretion":"Tadalafil has a tmax of 0.5-6h with a median of 2h in healthy adults. The tmax in adults with PAH is reported as 2-8h with a median of 4h. There does not appear to be a significant effect on absorption when tadalafil is taken with food.","Adverse Effects":"Common Adverse Effects","Aliases":["Tadalafil","Cialis","Ic351","ADCIRCA","IC 351","IC-351","Tadalafilo","Tadalafil mylan","Trans-tadalafil","CHEWTADZY","NSC-750236","NSC-759172","Dtxsid9046786","LY-450190","(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","(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","LY450190","(6R,12aR)-2,3,6,7,12,12a-Hexahydro-2-methyl-6-(3,4-methylenedioxyphenyl)pyrazino(1',2':1,6)pyrido(3,4-b)indole-1,4-dione","Dtxcid7026786","Chebi:71940","Entadfi component tadalafil","Opsynvi component tadalafil","Pyrazino(1',2':1,6)pyrido(3,4-b)indole-1,4-dione, 6-(1,3-benzodioxol-5-yl)-2,3,6,7,12,12a-hexahydro-2-methyl-, (6R,12aR)-","Pyrazino(1',2':1,6)pyrido(3,4-b)indole-1,4-dione, 6-(1,3-benzodioxol-5-yl)-2,3,6,7,12,12a-hexahydro-2-methyl-, (6R-trans)-","Pyrazino[1',2':1,6]pyrido[3,4-b]indole-1,4-dione, 6-(1,3-benzodioxol-5-yl)-2,3,6,7,12,12a-hexahydro-2-methyl-, (6R,12aR)-","tadalafilum","(2R,8R)-2-(2H-1,3-benzodioxol-5-yl)-6-methyl-3,6,17-triazatetracyclo(8.7.0.0^(3,8).0^(11,16))heptadeca-1(10),11,13,15-tetraene-4,7-dione","(2R,8R)-2-(2H-1,3-benzodioxol-5-yl)-6-methyl-3,6,17-triazatetracyclo[8.7.0.0^{3,8}.0^{11,16}]heptadeca-1(10),11,13,15-tetraene-4,7-dione","Pyrazino[1',2':1,6]pyrido[3,4-b]indole-1,4-dione, 6-(1,3-benzodioxol-5-yl)-2,3,6,7,12,12a-hexahydro-2-methyl-, (6R-trans)-","ALYQ","TADLIQ","G04BE08","(6R,12aR)-6-(Benzo[d][1,3]dioxol-5-yl)-2-methyl-2,3,12,12a-tetrahydropyrazino[1',2':1,6]pyrido[3,4-b]indole-1,4(6H,7H)-dione","ICOS 351","Tadanafil","GF 196960","Tadalafil(Cialis)","Mfcd07771966","CHEMBL779","GF-196960","(6R,12aR)-6-(1,3-Benzodioxol-5-yl)-2,3,6,7,12,12a-hexahydro-2-methylpyrazino[1',2':1,6]pyrido[3,4-b]indole-1,4-dione","(6R,12aR)-6-(benzo[d][1,3]dioxol-5-yl)-2-methyl-2,3,6,7,12,12a-hexahydropyrazino[1',2':1,6]pyrido[3,4-b]indole-1,4-dione","C22H19N3O4","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","Tadalafil Lilly","(6R,12aR)-6-(1,3-benzodioxol-5-yl)-2-methyl-2,3,6,7,12,12a-hexahydropyrazino[1',2':1,6]pyrido[3,4-b]indole-1,4-dione","CIA","Smr000466321","Cas-171596-29-5","HSDB 7303","Unii-742sxx0ict","Tadalafila","Tadalafil bulk","Tadalafil?","Tadalafil API","Tadalafil CRS","Tadalafil USP","1xoz","Cialis, Tadalafil","Tadalafil anhydrous","Ncgc00168781-01","Adcirca","Zalutia","Tadalafil raw powder","KS-1117","Tadalafil; cialis","Schembl33333","Mls000759426","Mls001165782","Mls001195644","Mls001424132","Mls006010126","Tadalafil - Bio-X trade mark","GTPL7299","orb1308738","orb3140154","Schembl29358190","Schembl29427554","BDBM14777","GLXC-07318","HMS2051N17","HMS2235L21","HMS3884G19","HY-90009AR","Pharmakon1600-01505639","EX-A2644","MSK10246","Tox21_112642","EBC-09118","HY-90009A","NSC750236","NSC759172","s1512","Tadalafil 1.0 mg/ml in Acetonitrile","Akos015892559","Tox21_112642_1","AB42193","CCG-100973","CS-1414","DB00820","FB02802","NC00223","NSC 750236","NSC 759172","1,3-benzodioxol-5-yl(methyl)[?]dione","Ncgc00263909-02","Tadalafil 100 microg/mL in Acetonitrile","BT164435","NS00006532","SW197603-2","D02008","Ab00639969-08","Ab00639969_09","Ab00639969_10","Ar-270/43507798","Sr-05000001940","Sr-05000001940-1","Brd-k93645900-001-04-8","Brd-k93645900-001-11-3","Brd-k93645900-001-12-1","Z1501485354","(2R,8R)-2-(2H-1,3-benzodioxol-5-yl)-6-methyl-3,6,17-triazatetracyclo[8.7.0.0^{3,8}.0^{11,16}]heptadeca-1(10),11(16),12,14-tetraene-4,7-dione","(6R,12 aR)-6-(1,3-benzodioxol-5-yl)-2,3,6,7,12,12a-hexahydro-2-methylpyrazino[1',2':1,6]pyrido[3,4-b]indole-1,4-dione","(6R,12?R)-6-(Benzo[d][1,3]dioxol-5-yl)-2-methyl-2,3,12,12?-tetrahydropyrazino[1',2':1,6]pyrido[3,4-?]indole-1,4(6H,7H)-dione","(6R,12aR) 6-(1,3-benzodioxol-5-yl)-2,3,6,7,12,12a-hexahydro-2-methylpyrazino [1',2':1,6] pyrido[3,4-b]indole-1,4-dione","(6R,12aR) 6-(1,3-benzodioxol-5-yl)-2,3,6,7,12,12a-hexahydro-2-methylpyrazino[1',2':1,6]pyrido[3,4-b]indole-1,4-dione","(6R,12aR)-6-(1,3-Benzodioxol-5-yl)-2,3,6,7,12,12a-hexahydro-2-methylpyrazino[1,2:1,6]pyrido[3,4-b]indole-1,4-dione","(6R,12aR)-6-(1,3-benzodioxol-5-yl)-2-methyl-2,3,6,7,12,12a-hexahydropyrazino[1,2,1,6]pyrido[3,4-b]indole-1,4-dione","(6R,12aR)-6-(2H-1,3-Benzodioxol-5-yl)-2-methyl-2,3,6,7,12,12a-hexahydropyrazino[1',2':1,6]pyrido[3,4-b]indole-1,4-dione","(6R,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","1242099-07-5","171488-03-2","6-(1,3-benzodioxol-5-yl)-2-methyl-2,3,6,7,12,12a-hexahydropyrazino[2',1':6,1]pyrido[3,4-b]indole-1,4-dione","Pyrazino[1',6]pyrido[3,4-b]indole-1,4-dione, 6-(1,3-benzodioxol-5-yl)-2,3,6,7,12,12ahexahydro-2-methyl-, (6R,12aR)-","rel-(6R,12aR)-6-(Benzo[d][1,3]dioxol-5-yl)-2-methyl-2,3,12,12a-tetrahydropyrazino[1',2':1,6]pyrido[3,4-b]indole-1,4(6H,7H)-dione"],"Biological Half-Life":"The mean half-life of elimination of tadalafil is 15-17.5h in healthy adults. The mean half-life of elimination in adults with PAH is reported as 35h.","CAS":"171596-29-5","ChemicalClasses":["β-carboline","methylenedioxyphenethylamine"],"Chirality":"achiral","DBI-IGS":["Tadalafil"],"Dosing Info":[{"Method":"Oral","Tiers":{"Common":{"Entries":13,"Lower":12.5,"Percentage":15.3,"Unit":"mg","Upper":15},"Extreme":{"Entries":4,"Lower":20,"Percentage":4.7,"Unit":"mg","Upper":20},"Heavy":{"Entries":0,"Lower":20,"Percentage":0,"Unit":"mg","Upper":20},"Light":{"Entries":34,"Lower":12.5,"Percentage":40,"Unit":"mg","Upper":12.5},"Strong":{"Entries":34,"Lower":15,"Percentage":40,"Unit":"mg","Upper":20}}}],"Drug Classes":"PDE5 Inhibitors","Drug Indication":"Tadalafil is indicated for the treatment of erectile dysfunction (ED) and either alone or in combination with [finasteride] for the treatment of benign prostatic hypertrophy (BPH). It is also indicated for the treatment of pulmonary arterial hypertension (PAH) both alone and in combination with [macitentan] or other endothelin-1 antagonists.","Drug Warnings":"The Food and Drug Administration ... approved updated labeling for Cialis, Levitra and Viagra to reflect a small number of post-marketing reports of sudden vision loss, attributed to NAION (non arteritic ischemic optic neuropathy), a condition where blood flow is blocked to the optic nerve.  FDA advises patients to stop taking these medicines, and call a doctor or healthcare provider right away if they experience sudden or decreased vision loss in one or both eyes. Further, patients taking or considering taking these products should inform their health care professionals if they have ever had severe loss of vision, which might reflect a prior episode of NAION. Such patients are at an increased risk of developing NAION again.","DurationOfAction":"≤ 36 hours","EliminationHalfLife":"17.5 hours","Esters":[],"European Community (EC) Number":"687-782-2","FDA Pharmacological Classification":[{"Name":"FDA UNII","ReferenceNumber":35,"Value":{"StringWithMarkup":[{"String":"742SXX0ICT"}]}},{"Name":"Active Moiety","ReferenceNumber":35,"Value":{"StringWithMarkup":[{"String":"TADALAFIL"}]}},{"Name":"Pharmacological Classes","ReferenceNumber":35,"Value":{"StringWithMarkup":[{"String":"Established Pharmacologic Class [EPC] - Phosphodiesterase 5 Inhibitor"}]}},{"Name":"Pharmacological Classes","ReferenceNumber":35,"Value":{"StringWithMarkup":[{"String":"Mechanisms of Action [MoA] - Phosphodiesterase 5 Inhibitors"}]}},{"Name":"FDA Pharmacology Summary","ReferenceNumber":35,"Value":{"StringWithMarkup":[{"Markup":[{"Extra":"CID-110635","Length":9,"Start":0,"Type":"PubChem Internal Link","URL":"https://pubchem.ncbi.nlm.nih.gov/compound/Tadalafil"},{"Extra":"CID-110635","Length":9,"Start":73,"Type":"PubChem Internal Link","URL":"https://pubchem.ncbi.nlm.nih.gov/compound/tadalafil"}],"String":"Tadalafil is a Phosphodiesterase 5 Inhibitor. The mechanism of action of tadalafil is as a Phosphodiesterase 5 Inhibitor."}]}},{"Name":"Non-Proprietary Name","ReferenceNumber":54,"Value":{"StringWithMarkup":[{"String":"TADALAFIL"}]}},{"Name":"Pharmacological Classes","ReferenceNumber":54,"Value":{"StringWithMarkup":[{"String":"Phosphodiesterase 5 Inhibitor [EPC]; Phosphodiesterase 5 Inhibitors [MoA]"}]}}],"Formating":[],"HMDB ID":"HMDB0014958","HeavyAtomCount":29,"Human Drugs":"FDA approved drugs -\u003e Active ingredient","IUPACName":"(2R,8R)-2-(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","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","InChIKey":"WOXKDUGGOYFFRN-IIBYNOLFSA-N","Interactions":"Simultaneous administration of an antacid (magnesium hydroxide/aluminum hydroxide) and tadalafil reduced the apparent rate of absorption of tadalafil without altering the exposure (AUC) to tadalafil.","MeSH Headers":[{"Id":"M0431130","Link":"https://id.nlm.nih.gov/mesh/M0431130.html","Name":"Tadalafil","Ref":85},{"Id":"M0392386","Link":"https://id.nlm.nih.gov/mesh/M0392386.html","Name":"IC351","Ref":87},{"Id":"M0392387","Link":"https://id.nlm.nih.gov/mesh/M0392387.html","Name":"Cialis","Ref":88},{"Id":"DescTree","Link":"https://www.nlm.nih.gov/mesh/meshhome.html","Name":"MeSH Tree","Ref":89},{"Id":"M0022559","Link":"https://id.nlm.nih.gov/mesh/M0022559.html","Name":"Vasodilator Agents","Ref":115},{"Id":"M0545665","Link":"https://id.nlm.nih.gov/mesh/M0545665.html","Name":"Phosphodiesterase 5 Inhibitors","Ref":116},{"Id":"M0584314","Link":"https://id.nlm.nih.gov/mesh/M0584314.html","Name":"Urological Agents","Ref":117}],"MeSH Pharmacological Classification":[{"Id":"M0022559","Link":"https://id.nlm.nih.gov/mesh/M0022559.html","Name":"Vasodilator Agent","Ref":115},{"Id":"M0545665","Link":"https://id.nlm.nih.gov/mesh/M0545665.html","Name":"Phosphodiesterase 5 Inhibitor","Ref":116},{"Id":"M0584314","Link":"https://id.nlm.nih.gov/mesh/M0584314.html","Name":"Urological Agent","Ref":117}],"Mechanism of Action":"Tadalafil is a selective phosphodiesterase-5 (PDE5) inhibitor that produces several downstream effects with the most common therapeutic effect being smooth muscle relaxation. Patients may experience ED due to a variety of causes including psychogenic, neurogenic, vasculogenic, iatrogenic, or endocrine. These causes result in dysfunction of penile smooth muscle relaxation through either disrupted neuronal signaling or direct influence on smooth muscle cells. During sexual arousal, non-adrenergic non-cholinergic (NANC) neurons release nitric oxide (NO). Nitric oxide stimulates guanylate cyclase which converts guanosine triphosphate to cyclic guanosine monophosphate (cGMP). cGMP activates the cGMP-dependent kinase (PKG) in a signal cascade which activates K+ channels leading to inhibition of Ca2+ channels, inhibits platelet activation, and inhibits smooth muscle cell proliferation while inducing apoptosis. This signal cascade is attenuated by PDE5 which breaks the phosphodiester bond of cGMP, converting it to GMP. Inhibition of PDE5 by tadalafil increases signaling via the PKG cascade which supports penile smooth muscle relaxation during sexual arousal by decreasing Ca2+ entry into smooth muscle cells. This smooth muscle relaxation allows blood to fill the corpus cavernosum thereby producing an erection.  In PAH, blood pressure in the pulmonary arteries is raised due to a variety of mechanisms stemming from endothelial dysfunction. Decreased production of NO and prostacyclin reduce vasodilatory signaling while overproduction of endothelin-1 and thromboxane increase vasoconstriction. Inflammation, thromboses, and hypoxia later contribute to vascular remodeling which further reduces luminal size. The resultant increase in blood pressure reduces the capacity for gas exchange and increases afterload at the right ventricle, producing symptoms of dyspnea, fatigue, and dizziness as well as leading to right-sided heart failure. Tadalafil exerts its therapeutic effect in PAH through boosting NO-cGMP signaling to contribute to smooth muscle relaxation as with ED.  Lastly, tadalafil is used to treat BPH. BPH produces urinary dysfunction through hyperproliferation of the epithelial and smooth muscle layers of the prostate. The increased size of the prostate blocks urine flow through the urethra resulting in higher residual volumes due to incomplete emptying. Tadalafil does not appear to exert its benefit via smooth muscle relaxation of the prostate. It may instead exert its effect through a mix of increased oxygenation and decreased inflammation, which decreases tissue remodeling, and inhibition of cell proliferation through the cGMP cascade.  The decreased affinity for PDE6 compared to other PDE5 inhibitors may explain the decreased incidence of visual side effects as PDE6 is present in the eye and contributes to color vision.","Melting Point":"301-302 °C","Metabolism/Metabolites":"Tadalafil undergoes hepatic metabolism via CYP3A4 to a catechol metabolite. This catechol metabolite undergoes subsequent methylation and glucuronidation with the methyl-glucuronide metabolite becoming the primary metabolite in circulation. None of the known metabolites are considered to be active.","MolecularFormula":"C\u003csub\u003e22\u003c/sub\u003eH\u003csub\u003e19\u003c/sub\u003eN\u003csub\u003e3\u003c/sub\u003eO\u003csub\u003e4\u003c/sub\u003e","MolecularWeight":"389.4 g/mol","Pharmacodynamics":"Tadalafil exerts a therapeutic effect in ED by increasing sexual stimulation-dependant smooth muscle relaxation in the penis, allowing the corpus cavernosum to fill with blood to produce an erection. Smooth muscle relaxation in the pulmonary vasculature helps to produce vasodilation in PAH which reduces blood pressure in the pulmonary arteries. In BPH, tadalafil may contribute to decreased smooth muscle cell proliferation which may reduce the size of the prostate and relieve the anatomical obstruction which produces urinary symptoms of BPH. The decreased affinity of tadalafil for PDE6 compared to other PDE5 inhibitors may explain the reduced incidence of visual side effects.","Physical Description":"Solid","PubChemId":110635,"RefChem":"6280","RefCount":3,"RefCur":"","References":[{"Name":"Wikipedia","Urls":[{"Link":"https://en.wikipedia.org/wiki/Tadalafil","Name":"Tadalafil","Sub":false}]},{"Name":"Wikidata","Urls":[{"Link":"https://www.wikidata.org/wiki/Q424156","Name":"Tadalafil","Sub":false}]},{"Name":"DrugBank","Urls":[{"Link":"https://go.drugbank.com/DB00820","Name":"Tadalafil","Sub":false}]},{"Name":"PubChem","Urls":[{"Link":"https://pubchem.ncbi.nlm.nih.gov/compound/110635","Name":"Tadalafil","Sub":false}]},{"Name":"Common Chemistry","Urls":[{"Link":"https://commonchemistry.cas.org/detail?cas_rn=171596-29-5","Name":"Tadalafil","Sub":false}]},{"Name":"HMDB","Urls":[{"Link":"https://hmdb.ca/metabolites/HMDB0014958","Name":"Tadalafil","Sub":false}]},{"Name":"KEGG","Urls":[{"Link":"https://www.kegg.jp/entry/D02008","Name":"Tadalafil","Sub":false}]},{"Name":"UNII","Urls":[{"Link":"https://gsrs.ncats.nih.gov/ginas/app/ui/substances/742SXX0ICT","Name":"Tadalafil","Sub":false}]},{"Name":"EPA DSSTox","Urls":[{"Link":"https://comptox.epa.gov/dashboard/chemical/details/DTXSID9046786","Name":"Tadalafil","Sub":false}]}],"Refs":["National Center for Biotechnology Information. PubChem Compound Summary for CID 110635, Tadalafil. Accessed April 11, 2026. \u003ca href=https://pubchem.ncbi.nlm.nih.gov/compound/110635\u003ehttps://pubchem.ncbi.nlm.nih.gov/compound/110635\u003c/a\u003e","Cialis 10mg film-coated tablets - Summary of Product Characteristics (SmPC). April 26, 2017. Accessed April 11, 2026. \u003ca href=https://www.medicines.org.uk/emc/product/7431/smpc\u003ehttps://www.medicines.org.uk/emc/product/7431/smpc\u003c/a\u003e"],"SMILES":"CN1CC(=O)N2[C@@H](C1=O)CC3=C([C@H]2C4=CC5=C(C=C4)OCO5)NC6=CC=CC=C36","SaltData":[],"Salts":[],"Scheduling":[{"gov":"Australia","ref":[],"schedule":"S4 substance"},{"gov":"United Kingdom","ref":["2"],"schedule":"prescription only substance"},{"gov":"United States","ref":[],"schedule":"prescription only substance"},{"gov":"European Union","ref":[],"schedule":"prescription only substance"}],"Solubility":"Practically insoluble in water","StereoisomerData":[],"Stereoisomers":[],"Structure":"\u003csvg xmlns=\"http://www.w3.org/2000/svg\" preserveAspectRatio=\"none\" style=\"display:block\" viewBox=\"0 0 107.827 120.461\"\u003e\u003crect width=\"100%\" height=\"100%\" fill=\"#fff\"/\u003e\u003cdesc\u003eGenerated by the Chemistry Development Kit (http://github.com/cdk)\u003c/desc\u003e\u003cg fill=\"#ff0d0d\" stroke=\"#000\" 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labeling/","Title":"Tadalafil","UNII":"742SXX0ICT","Wikidata":"Q424156","Wikipedia":"Tadalafil","XLogP":2.3}