Tadalafil

Tadalafil

Clinical data
Pronunciation	ta-DAL-a-fil
Trade names	Cialis, Adcirca
AHFS/Drugs.com	Monograph
MedlinePlus	a604008
Pregnancy category	B
Routes of administration	By mouth (tablets)
ATC code	G04BE08 (WHO)
Legal status
Legal status	℞ (Prescription only)
Pharmacokinetic data
Bioavailability	Varies
Protein binding	94%
Metabolism	Liver (predominantly CYP3A4)
Metabolites	Catechol metabolite
Biological half-life	17.5 hours
Excretion	Feces (~61%), urine (~36%)
Identifiers
IUPAC name (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
CAS Number	171596-29-5 Y
PubChem (CID)	110635
IUPHAR/BPS	7299
DrugBank	DB00820 Y
ChemSpider	99301 Y
UNII	742SXX0ICT Y
KEGG	D02008 Y
ChEBI	CHEBI:71940 Y
ChEMBL	CHEMBL779 Y
PDB ligand ID	CIA (PDBe, RCSB PDB)
ECHA InfoCard	100.214.024
Chemical and physical data
Formula	C22H19N3O4
Molar mass	389.404 g/mol
3D model (Jmol)	Interactive image
SMILES O=C1N(CC(N2[C@@H]1CC3=C([C@H]2C4=CC5=C(OCO5)C=C4)NC6=C3C=CC=C6)=O)C
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 Y Key:WOXKDUGGOYFFRN-IIBYNOLFSA-N Y

Tadalafil (INN) is a PDE5 inhibitor marketed in pill form for treating erectile dysfunction (ED) under the name Cialis see-AL-iss, and under the name Adcirca ad-SUR-kuh 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 world-wide 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 daily.

Tadalafil is also manufactured and sold under the name of Tadacip by the Indian pharmaceutical company Cipla in doses of 10 mg and 20 mg.

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 (Viagra) and vardenafil (Levitra)). Like sildenafil and vardenafil, tadalafil is recommended as an 'as needed' medication. Cialis is the only one of the three that is also offered as a once-daily medication.