Dutasteride

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

What is the Dutasteride?

The molecule Dutasteride presents a molecular formula of C27H30F6N2O2 and its IUPAC name is (1S,3aS,3bS,5aR,9aR,9bS,11aS)-N-[2,5-bis(trifluoromethyl)phenyl]-9a,11a-dimethyl-7-oxo-1,2,3,3a,3b,4,5,5a,6,9b,10,11-dodecahydroindeno[5,4-f]quinoline-1-carboxamide.

Dutasteride is a synthetic 4-azasteroid compound that is a selective inhibitor of both the type 1 and type 2 isoforms of steroid 5α-reductase, an intracellular enzyme that converts testosterone to DHT. Dutasteride is marketed under the brand names Avodart and Jalyn. It is used to treat benign prostatic hyperplasia (BPH) in men with an enlarged prostate..

DHT is the main cause of prostate growth. Dutasteride inhibits the production of DHT, which leads to a decrease in the size of the prostate and a reduction in BPH symptoms..

Dutasteride was approved by the US Food and Drug Administration (FDA) in 2001 for the treatment of BPH. It exists in capsules of 0.5 mg. The recommended dose is 0.5 mg once daily..

Dutasteride has been shown to be effective in reducing the risk of acute urinary retention and the need for BPH-related surgery. It may also improve symptoms of BPH..

The most common side effects of dutasteride include decreased libido, erectile dysfunction, ejaculatory dysfunction, and breast tenderness and enlargement. These side effects are more common in men younger than 55 years of age..

Dutasteride is a prescription medication. It is not available over-the-counter..

3D structure

Cartesian coordinates

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

2D drawing

 

Dutasteride JWJOTENAMICLJG-QWBYCMEYSA-N chemical compound 2D structure molecule svg
Dutasteride

 

Molecule descriptors

 
IUPAC name(1S,3aS,3bS,5aR,9aR,9bS,11aS)-N-[2,5-bis(trifluoromethyl)phenyl]-9a,11a-dimethyl-7-oxo-1,2,3,3a,3b,4,5,5a,6,9b,10,11-dodecahydroindeno[5,4-f]quinoline-1-carboxamide
InChI codeInChI=1S/C27H30F6N2O2/c1-24-11-9-17-15(4-8-21-25(17,2)12-10-22(36)35-21)16(24)6-7-19(24)23(37)34-20-13-14(26(28,29)30)3-5-18(20)27(31,32)33/h3,5,10,12-13,15-17,19,21H,4,6-9,11H2,1-2H3,(H,34,37)(H,35,36)/t15-,16-,17-,19+,21+,24-,25+/m0/s1
InChI KeyJWJOTENAMICLJG-QWBYCMEYSA-N
SMILESC[C@]12CC[C@H]3[C@@H](CC[C@H]4NC(=O)C=C[C@]34C)[C@@H]1CC[C@@H]2C(=O)Nc1cc(C(F)(F)F)ccc1C(F)(F)F

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.

  • (1S,2R,7R,10S,11S,14S,15S)-N-[2,5-bis(trifluoromethyl)phenyl]-2,15-dimethyl-5-oxo-6-azatetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-3-ene-14-carboxamide
  • (1S,3aS,3bS,5aR,9aR,11aS)-N-[2,5-bis(trifluoromethyl)phenyl]-9a,11a-dimethyl-7-oxo-1,2,3,3a,3b,4,5,5a,6,9b,10,11-dodecahydroindeno[5,4-f]quinoline-1-carboxamide
  • (1S,3aS,3bS,5aR,9aR,9bS,11aS)-N-[2,5-bis(trifluoromethyl)phenyl]-9a,11a-dimethyl-7-oxo-1,2,3,3a,3b,4,5,5a,6,9b,10,11-dodecahydroindeno[5,4-f]quinoline-1-carboxamide
  • (4aR,4bS,6aS,7S,9aS,9bS,11aR)-N-(2,5-Bis(trifluoromethyl)phenyl)-4a,6a-dimethyl-2-oxo-2,4a,4b,5,6,6a,7,8,9,9a,9b,10,11,11a-tetradecahydro-1H-indeno[5,4-f]quinoline-7-carboxamide
  • (5.ALPHA.,17.BETA.)-N-(2,5-BIS(TRIFLUOROMETHYL)PHENYL)-3-OXO-4-AZAANDROST-1-ENE-17-CARBOXAMIDE
  • (5.alpha.,5 bis(trifluoromethyl)phenyl}-3-oxo-4-azaandrost-1-ene-17-carboxamide;dutasteride;Avodart;
  • (5alpha,17beta)-N-(2,5-Bis(trifluoromethyl)phenyl)-3-oxo-4-azaandrost-1-ene-17-carboxamide
  • (5alpha,17beta)-N-{2,5-bis(trifluoromethyl)-phenyl}-3-oxo-4-azaandrost-1-ene-17-carboxamide
  • .ALPHA.,.ALPHA.,.ALPHA.,.ALPHA.',.ALPHA.',.ALPHA.'-HEXAFLUORO-3-OXO-4-AZA-5.ALPHA.-ANDROST-1-ENE-17.BETA.-CARBOXY-2',5'-XYLIDIDE
  • 164656-23-9
  • 1H-Indeno(5,4-f)quinoline-7-carboxamide, N-(2,5-bis(trifluoromethyl)phenyl)-2,4a,4b,5,6,6a,7,8,9,9a,9b,10,11,11a-tetradecahydro-4a,6a-dimethyl-2-oxo-, (4aR,4bS,6aS,7S,9aS,9bS,11aR)-
  • 1H-Indeno[5,4-f]quinoline-7-carboxamide, N-[2,5-bis(trifluoromethyl)phenyl]-2,4a,4b,5,6,6a,7,8,9,9a,9b,10,11,11a-tetradecahydro-4a,6a-dimethyl-2-oxo-, (4aR,4bS,6aS,7S,9aS,9bS,11aR)-
  • 4-Azaandrost-1-ene-17-carboxaMide, N-[2,5-bis(trifluoroMethyl)phenyl]-3-oxo-, (5a,17b)-
  • 656D239
  • A810580
  • AB01274774-01
  • AB01274774_02
  • Avidart
  • Avodart
  • Avolve
  • BCP02344
  • BCP9000630
  • BCPP000248
  • BD164398
  • BDBM50340481
  • CCG-269904
  • CS-1542
  • D03820
  • D5973
  • DB01126
  • DSSTox_CID_26452
  • DSSTox_GSID_46452
  • DSSTox_RID_81626
  • DUTASTERIDE COMPONENT OF JALYN
  • Duagen
  • Duastride
  • Dutasteride
  • Dutasteride (JAN/USP/INN)
  • Dutasteride- Bio-X
  • EX-A1952
  • GG 745
  • GG-745
  • GI 198745
  • GI-198745
  • GI-198745X
  • GI198745
  • GS-3565
  • GTPL7457
  • HY-13613
  • JALYN COMPONENT DUTASTERIDE
  • MFCD00937869
  • N-[2,5-bis(trifluoromethyl)phenyl]-3-oxo-4-aza-5alpha-androst-1-ene-17beta-carboxamide
  • NCGC00164571-01
  • NSC 740477
  • NSC 759880
  • NSC-740477
  • NSC-759880
  • NSC740477
  • O0J6XJN02I
  • Q-201052
  • Q424760
  • Z1563146168
  • alpha,alpha,alpha,alpha',alpha',alpha'-Hexafluoro-3-oxo-4-aza-5alpha-androst-1-ene-17beta-carboxy-2',5'-xylidide
  • s1202

Reference codes for other databases

There exist several different chemical codes commonly used in orded to identify molecules:
  • ZINC3932831
  • CAS-164656-23-9
  • UNII-O0J6XJN02I
  • AKOS015920136
  • AKOS015924431
  • BRD-K30373883-001-02-8
  • DTXSID8046452
  • CHEMBL1200969
  • CHEBI:521033
  • Tox21_112199
  • SCHEMBL5903

Physico-Chemical properties

IUPAC name(1S,3aS,3bS,5aR,9aR,9bS,11aS)-N-[2,5-bis(trifluoromethyl)phenyl]-9a,11a-dimethyl-7-oxo-1,2,3,3a,3b,4,5,5a,6,9b,10,11-dodecahydroindeno[5,4-f]quinoline-1-carboxamide
Molecular formulaC27H30F6N2O2
Molecular weight528.53
Melting point (ºC)
Boiling point (ºC)
Density (g/cm3)
Molar refractivity129.94
LogP7.0
Topological polar surface area58.2

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.