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 ;
PubChem CID	110635;
IUPHAR/BPS	7299;
DrugBank	DB00820 ;
ChemSpider	99301 ;
UNII	742SXX0ICT;
KEGG	D02008 ;
ChEBI	CHEBI:71940 ;
ChEMBL	ChEMBL779 ;
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 ; Key:WOXKDUGGOYFFRN-IIBYNOLFSA-N ;
	(verify)

^ "Tadalafil Use During Pregnancy". Drugs.com. 14 March 2019. Archived from the original on 1 December 2020. Retrieved 20 August 2020.
^ Cite error: The named reference Cialis tadalafil PI was invoked but never defined (see the help page).
^ "Cialis 10mg film-coated tablets - Summary of Product Characteristics (SmPC)". (emc). 26 April 2017. Archived from the original on 1 December 2020. Retrieved 20 August 2020.
^ ^a ^b "Cialis- tadalafil tablet, film coated". DailyMed. 12 June 2020. Archived from the original on 21 September 2019. Retrieved 20 August 2020.
^ "Adcirca- tadalafil tablet". DailyMed. 23 June 2022. Archived from the original on 6 March 2023. Retrieved 10 April 2023.
^ "Cialis EPAR". European Medicines Agency (EMA). 17 September 2018. Archived from the original on 7 January 2021. Retrieved 20 August 2020.