Tadalafil (CED0003193)

Record Information
Version1.0
Creation Date2016-05-22 05:56:58 UTC
Update Date2026-08-21 21:21:09 UTC
Accession NumberCHEM019251
Identification
Common NameTadalafil
ClassSmall Molecule
Description
Tadalafil is an organic compound with the formula C22H19N3O4 and an average molecular weight of 389.40 g/mol. Tadalafil belongs to the pyridoindoles, a subclass of indoles and derivatives within the organic compounds. It is classified as an organoheterocyclic compound. The substance has three recorded protein targets, acting as an inhibitor of cGMP-specific 3',5'-cyclic phosphodiesterase (PDE5A), as well as targeting dual 3',5'-cyclic-AMP and -GMP phosphodiesterase 11A (PDE11A) and retinal rod rhodopsin-sensitive cGMP 3',5'-cyclic phosphodiesterase subunit gamma (PDE6G). Regarding health effects, it is associated with a decrease in hypotension (PMC12454544). Tadalafil is found in or released from 35 recorded sources. Within healthcare, pharmaceuticals, and veterinary products, it is used in urologicals, antihypertensives, and drugs used in benign prostatic hypertrophy. Other sources include building and construction materials such as floors, ceilings, roofs, fencing, and stairs and ramps. It is also associated with food, food processing, and cookware, specifically the treatment of hops and the processing of meats and fish, as well as the preparation of sparkling wine or wine. Household cleaning and consumer products include pipe accessories, tobacco pipes, other smoking requisites, and non electric simulated smoking devices. Additionally, it is found in electrical and electronic equipment, including antennas, coils, discharge lamps, amplifiers, and colour television systems. The recorded exposure route for this compound is oral.
Contaminant Type
  • Human Neurotoxin
Chemical Structure
Synonyms
ValueSource
(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-dioneChEBI
(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-dioneChEBI
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-dioneChEBI
AdcircaChEBI
CialisChEBI
ZalutiaKegg
ICOS 351HMDB
TadanafilHMDB
351, ICHMDB
Chemical FormulaC22H19N3O4
Average Molecular Mass389.404 g/mol
Monoisotopic Mass389.138 g/mol
CAS Registry Number171596-29-5
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
Traditional Nametadalafil
SMILES[H][C@]12CC3=C(NC4=CC=CC=C34)[C@H](N1C(=O)CN(C)C2=O)C1=CC2=C(OCO2)C=C1
InChI IdentifierInChI=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
InChI KeyWOXKDUGGOYFFRN-IIBYNOLFSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as beta carbolines. Beta carbolines 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
  • Alpha-amino acid or derivatives
  • 3-alkylindole
  • Benzodioxole
  • Indole
  • 2,5-dioxopiperazine
  • Dioxopiperazine
  • N-methylpiperazine
  • N-alkylpiperazine
  • Benzenoid
  • Piperazine
  • 1,4-diazinane
  • Tertiary carboxylic acid amide
  • Pyrrole
  • Heteroaromatic compound
  • Carboxamide group
  • Lactam
  • Acetal
  • Carboxylic acid derivative
  • Oxacycle
  • Azacycle
  • Hydrocarbon derivative
  • Organic nitrogen compound
  • Organic oxide
  • Carbonyl group
  • Organopnictogen compound
  • Organic oxygen compound
  • Organooxygen compound
  • Organonitrogen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Organoleptic EffectsNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.25 g/LALOGPS
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 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity104.08 m³·mol⁻¹ChemAxon
Polarizability40.92 ųChemAxon
Number of Rings6ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyDeposition DateView
Predicted GC-MSPredicted GC-MS Spectrumsplash10-0006-3097000000-803ff86b2ce502e2bc83Not AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-02t9-2890000000-0be3708ad44a8a467cc5Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-03di-0090000000-c52485d22b5893fc60a2Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-03di-0090000000-2f6ad2194cd2932b0761Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0i0r-0291000000-a4ae40141abccfc86710Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0j59-0290000000-86095fe2d98833db9d0bNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0uy0-0429200000-641774545afc89315134Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0uy0-0429200000-f223c860e93cceeeacd8Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-014i-0292000000-0563bdd5b0be8c1cfa47Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-02t9-2890000000-0be3708ad44a8a467cc5Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-014i-0391000000-2d53d99ea189cbcf20bfNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0f6x-0009000000-bea170f3de4098be75e0Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-001i-0191000000-b10465a3e1f68719ab50Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0udi-0019000000-989b326813e322333fa5Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-004i-0119000000-28b2b617eb618183d5c8Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-001i-0791000000-5534e9b8d8ed5169e623Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-000i-0009000000-844cd3bb8e0273b1caddNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-03di-0091000000-612762fb281177438c8eNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0006-0009000000-cfa5abcf4ec76ea41d68Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0006-1019000000-59cc81b34404c6ecd167Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0006-0291000000-20d1a51d47c7345d5742Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-000i-2009000000-721840625f2b26eb19a7Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-052r-4019000000-5dff72997668963ef319Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-01pc-2191000000-f8bd70ef77444b35f09bNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0006-0029000000-5ec0e4346a39de6e6582Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0006-0009000000-565961b51e5cb53f55d4Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0f6x-2092000000-b5fa1e583c414d28641aNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-000i-0009000000-478dc5844ab3ecb4550aNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-03dr-0089000000-ff3a16cb65ef0de89aa3Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-05fr-1049000000-53eb81cc5c1384d3c581Not AvailableView Spectrum
Toxicity Profile
Mechanism of ToxicityNot Available
Carcinogenicity (IARC Classification)Not Available
Minimum Risk LevelNot Available
SymptomsNot Available
TreatmentNot Available
Toxicity Values
Toxicity ValueUnitValue RangeOrganismDose DescriptorRoute of ExposurePredicted or ExperimentalReference
763.0Log mg/kg[430:1400]RatLD50oralpredictedNot Available
Health Effects
Health EffectRelationshipDirectionReference
hypotensionassociated_withdecreasePMC12454544
Exposure Sources
Source IDSourceSectorReference
289AntihypertensivesHealthcare, pharmaceuticals & veterinary productsNot Available
326UrologicalsHealthcare, pharmaceuticals & veterinary productsNot Available
327Drugs used in benign prostatic hypertrophyHealthcare, pharmaceuticals & veterinary productsNot Available
495CeilingsBuilding & ConstructionNot Available
496FencingBuilding & ConstructionNot Available
497FloorsBuilding & ConstructionNot Available
499RoofsBuilding & ConstructionNot Available
500Stairs And RampsBuilding & ConstructionNot Available
501Sunshades Awnings Or Outside ScreensBuilding & ConstructionNot Available
502Sunshades Awnings Or Outside ScreensBuilding & ConstructionNot Available
505AmplifiersElectrical & Electronic EquipmentNot Available
506AntennasElectrical & Electronic EquipmentNot Available
508CoilsElectrical & Electronic EquipmentNot Available
509Colour Television SystemsElectrical & Electronic EquipmentNot Available
514Discharge LampsElectrical & Electronic EquipmentNot Available
516Electric Hearing AidsElectrical & Electronic EquipmentNot Available
520Emergency Protective DevicesElectrical & Electronic EquipmentNot Available
525Line Transmission SystemsElectrical & Electronic EquipmentNot Available
527MagnetsElectrical & Electronic EquipmentNot Available
530Radio Transmission SystemsElectrical & Electronic EquipmentNot Available
531RelaysElectrical & Electronic EquipmentNot Available
532SelectorsElectrical & Electronic EquipmentNot Available
534Still Video CamerasElectrical & Electronic EquipmentNot Available
535Superconducting Magnets And Superconducting CoilsElectrical & Electronic EquipmentNot Available
537Television SystemsElectrical & Electronic EquipmentNot Available
538Thin Magnetic FilmsElectrical & Electronic EquipmentNot Available
539Video GamesElectrical & Electronic EquipmentNot Available
549Preparation Of Wine Or Sparkling WineFood, food processing & cookwareNot Available
551Processing FishFood, food processing & cookwareNot Available
552Processing MeatsFood, food processing & cookwareNot Available
553Treatment Of HopsFood, food processing & cookwareNot Available
559Non Electric Simulated Smoking DevicesHousehold cleaning & consumer productsNot Available
560Other Smoking RequisitesHousehold cleaning & consumer productsNot Available
562Pipe AccessoriesHousehold cleaning & consumer productsNot Available
566Tobacco PipesHousehold cleaning & consumer productsNot Available
579Manufacture Of Iron Or SteelIndustrial manufacturing & chemical processingNot Available
583Anchoring EquipmentMarine, shipping & aquacultureNot Available
584BuoysMarine, shipping & aquacultureNot Available
586Fishing BoatsMarine, shipping & aquacultureNot Available
592Marine Propulsion Or SteeringMarine, shipping & aquacultureNot Available
593Nautical InstrumentsMarine, shipping & aquacultureNot Available
598Fertiliser DistributorsAgriculture & land managementNot Available
620Card GamesRecreation & sports surfacesNot Available
621Chutes And SlidesRecreation & sports surfacesNot Available
625Racing SportsRecreation & sports surfacesNot Available
630ToysRecreation & sports surfacesNot Available
643HeadwearTextiles, leather & furnishingsNot Available
650Purses Luggage Hand BagsTextiles, leather & furnishingsNot Available
651Purses Money Bags WalletsTextiles, leather & furnishingsNot Available
653SewingTextiles, leather & furnishingsNot Available
Pathways
1 pathway
Targets
StructureProteinUniProt IDOrganismRelationshipDetails
High affinity 3',5'-cyclic-AMP phosphodiesterase 7A structureClick to view 3D structureHigh affinity 3',5'-cyclic-AMP phosphodiesterase 7AQ13946HumansPredicted (SEA)3.73676
High affinity cAMP-specific and IBMX-insensitive 3',5'-cyclic phosphodiesterase 8A structureClick to view 3D structureHigh affinity cAMP-specific and IBMX-insensitive 3',5'-cyclic phosphodiesterase 8AO60658HumansPredicted (SEA)2.49118
Acetylcholinesterase structureClick to view 3D structureAcetylcholinesteraseP22303HumansPredicted (SEA)64.6149
Click to view 3D structureDual specificity calcium/calmodulin-dependent 3',5'-cyclic nucleotide phosphodiesterase 1AP54750HumansPredicted (SEA)6.15009
Click to view 3D structureAcetylcholinesteraseP37136Rattus norvegicusPredicted (SEA)75.358
cGMP-inhibited 3',5'-cyclic phosphodiesterase 3B structureClick to view 3D structurecGMP-inhibited 3',5'-cyclic phosphodiesterase 3BQ13370HumansPredicted (SEA)4.67095
Click to view 3D structureCholinesteraseP81908Equus caballusPredicted (SEA)241.722
Alpha-1A adrenergic receptor structureClick to view 3D structureAlpha-1A adrenergic receptorP35348HumansPredicted (SEA)361.843
Click to view 3D structureAlpha-1B adrenergic receptorP35368HumansPredicted (SEA)284.617
Click to view 3D structureAlpha-1D adrenergic receptorP25100HumansPredicted (SEA)246.86
Nuclear receptor subfamily 2 group E member 1 structureClick to view 3D structureNuclear receptor subfamily 2 group E member 1Q9Y466HumansPredicted (SEA)0.0778492
D(2) dopamine receptor structureClick to view 3D structureD(2) dopamine receptorP14416HumansPredicted (SEA)1009.0
Alpha-2B adrenergic receptor structureClick to view 3D structureAlpha-2B adrenergic receptorP18089HumansPredicted (SEA)367.76
Alpha-2A adrenergic receptor structureClick to view 3D structureAlpha-2A adrenergic receptorP08913HumansPredicted (SEA)543.154
Alpha-2C adrenergic receptor structureClick to view 3D structureAlpha-2C adrenergic receptorP18825HumansPredicted (SEA)400.223
cGMP-specific 3',5'-cyclic phosphodiesterase structureClick to view 3D structurecGMP-specific 3',5'-cyclic phosphodiesteraseO76074HumansPredicted (SEA)0.622794
Click to view 3D structureDual 3',5'-cyclic-AMP and -GMP phosphodiesterase 11AQ9HCR9HumansPredicted (SEA)0.233548
Click to view 3D structurecGMP-specific 3',5'-cyclic phosphodiesteraseQ28156Bos taurusPredicted (SEA)0.467095
Cone cGMP-specific 3',5'-cyclic phosphodiesterase subunit alpha' structureClick to view 3D structureCone cGMP-specific 3',5'-cyclic phosphodiesterase subunit alpha'P51160HumansPredicted (SEA)0.622794
3',5'-cyclic-AMP phosphodiesterase 4A structureClick to view 3D structure3',5'-cyclic-AMP phosphodiesterase 4AP27815HumansPredicted (SEA)0.778492
Click to view 3D structurecGMP-specific 3',5'-cyclic phosphodiesteraseO54735Rattus norvegicusPredicted (SEA)0.0778492
cGMP-dependent 3',5'-cyclic phosphodiesterase structureClick to view 3D structurecGMP-dependent 3',5'-cyclic phosphodiesteraseO00408HumansPredicted (SEA)4.12601
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A structureClick to view 3D structurecAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10AQ9Y233HumansPredicted (SEA)4.7488
Click to view 3D structurePhosphodiesterase 3BE1BN64Bos taurusPredicted (SEA)0.311397
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A structureClick to view 3D structureHigh affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9AO76083HumansPredicted (SEA)4.98235
Concentrations
Not Available
External Links
DrugBank IDDB00820
HMDB IDHMDB0014958
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDCIA
Wikipedia LinkTadalafil
Chemspider ID99301
ChEBI ID71940
PubChem Compound ID110635
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. 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.
2. Naeije R, Huez S: Expert opinion on available options treating pulmonary arterial hypertension. Expert Opin Pharmacother. 2007 Oct;8(14):2247-65.
3. 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.
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=21056623
5. https://www.ncbi.nlm.nih.gov/pubmed/?term=21680058
6. https://www.ncbi.nlm.nih.gov/pubmed/?term=22014651
7. https://www.ncbi.nlm.nih.gov/pubmed/?term=22328305
8. https://www.ncbi.nlm.nih.gov/pubmed/?term=22494518
9. https://www.ncbi.nlm.nih.gov/pubmed/?term=22776546
10. https://www.ncbi.nlm.nih.gov/pubmed/?term=22816778
11. https://www.ncbi.nlm.nih.gov/pubmed/?term=22971615
12. https://www.ncbi.nlm.nih.gov/pubmed/?term=22982422
13. https://www.ncbi.nlm.nih.gov/pubmed/?term=22996758
14. https://www.ncbi.nlm.nih.gov/pubmed/?term=23033484
15. https://www.ncbi.nlm.nih.gov/pubmed/?term=23072271
16. https://www.ncbi.nlm.nih.gov/pubmed/?term=23118430
17. https://www.ncbi.nlm.nih.gov/pubmed/?term=23140258
18. https://www.ncbi.nlm.nih.gov/pubmed/?term=23190275
19. https://www.ncbi.nlm.nih.gov/pubmed/?term=23216015
20. https://www.ncbi.nlm.nih.gov/pubmed/?term=23219525
21. https://www.ncbi.nlm.nih.gov/pubmed/?term=23234619
22. https://www.ncbi.nlm.nih.gov/pubmed/?term=23312193
23. https://www.ncbi.nlm.nih.gov/pubmed/?term=23346990
24. https://www.ncbi.nlm.nih.gov/pubmed/?term=23347176