Tadalafil

Tadalafil
Clinical data


Pronunciation	/təˈdæləfɪl/ tə-DAL-ə-fil
Trade names	Cialis, others
AHFS/Drugs.com	Monograph
MedlinePlus	a604008
License data	US DailyMed: Tadalafil
Pregnancy category	AU: B1
Routes of administration	By mouth
Drug class	PDE5 inhibitor
ATC code	G04BE08 (WHO)
Legal status
Legal status	AU: S4 (Prescription only) UK: POM (Prescription only) US: ℞-only EU: Rx-only In general: ℞ (Prescription only)
Pharmacokinetic data
Bioavailability	Varies
Protein binding	94%
Metabolism	Liver (predominantly CYP3A4)
Metabolites	Catechol metabolite
Onset of action	30 minutes
Elimination half-life	17.5 hours
Duration of action	≤ 36 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
KEGG	D02008^Y
ChEBI	CHEBI:71940^Y
ChEMBL	ChEMBL779^Y
PDB ligand	CIA (PDBe, RCSB PDB)
CompTox Dashboard (EPA)	DTXSID9046786
ECHA InfoCard	100.214.024
Chemical and physical data
Formula	C₂₂H₁₉N₃O₄
Molar mass	389.411 g·mol⁻¹
3D model (JSmol)	Interactive image
SMILES CN1CC(=O)N2[C@H](Cc3c([nH]c4ccccc34)[C@H]2c2ccc3c(c2)OCO3)C1=O
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
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