Tadalafil

A summary of the most common chemical descriptors (InChI Key and SMILES codes) for Tadalafil are summarized together with 3D and 2D structures and relevant physico-chemical properties.

What is the Tadalafil?

The molecule Tadalafil presents a molecular formula of C22H19N3O4 and its IUPAC name is (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.

Tadalafil is a molecule used to treat erectile dysfunction and benign prostatic hyperplasia. It is a phosphodiesterase 5 (PDE5) inhibitor. Tadalafil was approved for use in the United States in 2003. It exists as a generic drug..

Tadalafil is used to treat erectile dysfunction (ED) and benign prostatic hyperplasia (BPH). ED is the inability to get or maintain an erection. BPH is an enlarged prostate. Tadalafil is thought to work by relaxing the smooth muscle in the prostate and bladder. This decreases urine retention and helps to relieve symptoms of BPH..

Tadalafil exists as an oral tablet. It is usually taken once a day with or without food. The dose is usually 10 mg to 20 mg per day. The maximum recommended dose is 100 mg per day..

Tadalafil can cause side effects. The most common side effects are headache, flushing, upset stomach, and muscle aches. These side effects usually go away after a few hours. Tadalafil can also cause back pain and dizziness. These side effects usually go away after a few days..

If you have any questions about tadalafil, please talk with your doctor, nurse, pharmacist, or other health care provider..

3D structure

Cartesian coordinates

Geometry of Tadalafil in x, y and z coordinates (Å units) to copy/paste elsewhere. Generated with Open Babel software.

2D drawing

 

Tadalafil WOXKDUGGOYFFRN-IIBYNOLFSA-N chemical compound 2D structure molecule svg
Tadalafil

 

Molecule descriptors

 
IUPAC name(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 codeInChI=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
SMILESCN1CC(=O)N2[C@H](Cc3c([nH]c4ccccc34)[C@H]2c2ccc3c(c2)OCO3)C1=O

Other names (synonyms)

IUPAC nomenclature provides a standardized method for naming chemical compounds. Although this system is widely used in chemistry, many chemical compounds have also other names commonly used in different contexts. These synonyms can come from a variety of sources and are used for a variety of purposes.

One common source of synonyms for chemical compounds is the common or trivial names, assigned on the basis of appearance, properties, or origin of the molecule.

Another source of synonyms are historical or obsolete names employed in the past, however replaced nowadays by more modern or standardized names.

In addition to common and historical names, chemical compounds may also have synonyms that are specific to a particular field or industry.

  • (-)-Tadalafil (6R ,12aS) diastereomer
  • (-)-Tadalafil (6R)
  • (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
  • (2R,8R)-2-(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(16),12,14-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
  • (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,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)-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,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
  • (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-(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-(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
  • (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
  • (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
  • (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
  • 1,3-benzodioxol-5-yl(methyl)[?]dione
  • 1242099-07-5
  • 171488-03-2
  • 171596-29-5
  • 1xoz
  • 596T295
  • 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
  • 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
  • 742SXX0ICT
  • A23556
  • AB00639969-08
  • AB00639969_09
  • AB00639969_10
  • AB42193
  • ADCIRCA
  • AMY10321
  • AR-270/43507798
  • BDBM14777
  • BT164435
  • CCG-100973
  • CS-1414
  • Cialis
  • Cialis, Tadalafil
  • D02008
  • DB00820
  • DSSTox_CID_26786
  • DSSTox_GSID_46786
  • DSSTox_RID_81904
  • ENTADFI COMPONENT TADALAFIL
  • EX-A2644
  • GF 196960
  • GF-196960
  • GF196960
  • GTPL7299
  • HMS2051N17
  • HMS2235L21
  • HMS3884G19
  • HSDB 7303
  • HY-90009A
  • IC 351
  • IC-351
  • ICOS 351
  • Ic351
  • KS-1117
  • LY-450190
  • LY450190
  • MFCD07771966
  • MLS000759426
  • MLS001165782
  • MLS001195644
  • MLS001424132
  • MLS006010126
  • NC00223
  • NCGC00168781-01
  • NCGC00263909-02
  • NSC 750236
  • NSC 759172
  • NSC-750236
  • NSC-759172
  • NSC750236
  • NSC759172
  • 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)-
  • Pharmakon1600-01505639
  • 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',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)-
  • Q424156
  • SMR000466321
  • SR-05000001940
  • SR-05000001940-1
  • SW197603-2
  • TADALAFIL COMPONENT OF ENTADFI
  • TADALAFIL; CIALIS
  • TILDENAFIL
  • Tadalafil
  • Tadalafil (6R ,12aS)- Lilly
  • Tadalafil (Cialis)
  • Tadalafil (JAN/USP/INN)
  • Tadalafil 1.0 mg/ml in Acetonitrile
  • Tadalafil Lilly
  • Tadalafil mylan
  • Tadalafil solution
  • Tadalafil specified impurity A
  • Tadalafil(Cialis)
  • Tadalafil- Bio-X
  • Tadalafila
  • Tadalafilo
  • Tadanafil
  • Taldalafil
  • Trans-tadalafil
  • 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
  • s1512

Reference codes for other databases

There exist several different chemical codes commonly used in orded to identify molecules:
  • ZINC3993855
  • CAS-171596-29-5
  • UNII-742SXX0ICT
  • AKOS015892559
  • BRD-K93645900-001-04-8
  • DTXSID9046786
  • CHEMBL779
  • CHEBI:71940
  • Tox21_112642
  • Tox21_112642_1
  • SCHEMBL33333

Physico-Chemical properties

IUPAC name(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
Molecular formulaC22H19N3O4
Molecular weight389.404
Melting point (ºC)
Boiling point (ºC)
Density (g/cm3)
Molar refractivity112.61
LogP2.1
Topological polar surface area74.9

LogP and topological polar surface area (TPSA) values were estimated using Open Babel software.

The n-octanol/water partition coeficient (Kow) data is applied in toxicology and drug research. Kow values are used, to guess the environmental fate of persistent organic pollutants. High partition coefficients values, tend to accumulate in the fatty tissue of organisms. Molecules with a log(Kow) (or LogP) greater than 5 are considered to bioaccumulate.

TPSA values are the sum of the surface area over all polar atoms or molecules, mainly oxygen and nitrogen, also including hydrogen atoms.

In medicinal chemistry, TPSA is used to assess the ability of a drug to permeabilise cells.

For molecules to penetrate the blood-brain barrier (and act on receptors in the central nervous system), TPSA values below 90 Å2 are required. Thus, molecules with a polar surface area greater than 140 Å2 tend to be poorly permeable to cell membranes.