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ChemSpider 2D Image | Dutasteride | C27H30F6N2O2

Dutasteride

  • Molecular FormulaC27H30F6N2O2
  • Average mass528.530 Da
  • Monoisotopic mass528.221130 Da
  • ChemSpider ID5293502
  • defined stereocentres - 7 of 7 defined stereocentres


More details:



Featured data source



Validated by Experts, Validated by Users, Non-Validated, Removed by Users

(4aR,4bS,6aS,7S,9aS,9bS,11aR)-N-[2,5-Bis(trifluormethyl)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]chinolin-7-carboxamid [German] [ACD/IUPAC Name]
(4aR,4bS,6aS,7S,9aS,9bS,11aR)-N-[2,5-Bis(trifluorométhyl)phényl]-4a,6a-diméthyl-2-oxo-2,4a,4b,5,6,6a,7,8,9,9a,9b,10,11,11a-tétradécahydro-1H-indéno[5,4-f]quinoléine-7-carboxamide [French] [ACD/IUPAC Name]
(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 [ACD/IUPAC Name]
(5a,17b)-N-(2,5-Bis(trifluoromethyl)phenyl)-3-oxo-4-azaandrost-1-ene-17-carboxamide
(5α,17β)-N-(2,5-Bis(trifluoromethyl)phenyl)-3-oxo-4-azaandrost-1-ene-17-carboxamide
(5α,17β)-N-[2,5-Bis(trifluoromethyl)phenyl]-3-oxo-4-azaandrost-1-ene-17-carboxamide
164656-23-9 [RN]
17β-N-[2,5-Bis(trifluoromethyl)phenyl]carbamoyl-4-aza-5α-androst-1-en-3-one
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)- [ACD/Index Name]
7586
More...

Validated by Experts, Validated by Users, Non-Validated, Removed by Users

GG 745 [DBID]
GI 198745 [DBID]
D03820 [DBID]
GG-745 [DBID]
GI-198745 [DBID]
  • Experimental Physico-chemical Properties
  • Miscellaneous
    • Safety:

      G04CB02 Wikidata Q424760
      IRRITANT Matrix Scientific 076047
    • Chemical Class:

      An aza-steroid that is inasteride in which the tert-butyl group is replaced by a 2,5-bis(trifluoromethyl)phenyl group. A synthetic 4-azasteroid, dutasteride is a selective inhibitor of bo; th the type 1 and type 2 isoforms of steroid 5alpha-reductase, an intracellular enzyme that converts testosterone to 5alpha-dihydrotestosterone. Dutasteride is used f; or the treatment of symptomatic benign pros tatic hyperplasia in men with an enlarged prostate gland. ChEBI https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:521033
      Finasteride in which the <ital>tert</ital>-butyl group is replaced by a 2,5-bis(trifluoromethyl)phenyl group. A synthetic 4-azasteroid, dutasteride is a selective inhibitor of both the type 1 and type 2 isoforms of steroid 5<stereo>alpha</stereo>-reductase, an intracellular enzyme that converts testosterone to 5<stereo>alpha</stereo>-dihydrotestosterone. Dutasteride is used for the treatment of sy mptomatic benign prostatic hyperplasia in men with an enlarged prostate gland. ChEBI CHEBI:521033
    • Bio Activity:

      5 alpha Reductase MedChem Express HY-13613
      Dutasteride (GG745) is a potent inhibitor of both 5 alpha-reductase isozymes. MedChem Express HY-13613
      Dutasteride (GG745) is a potent inhibitor of both 5 alpha-reductase isozymes. Dutasteride may possess off-target effects on the androgen receptor (AR) due to its structural similarity to DHT.;IC50 Value:;Target: 5 alpha-reductase;In vitro: Dutasteride inhibited (3)H-T conversion to (3)H-DHT and, as anticipated, inhibited T-induced secretion of PSA and proliferation. However the drug also inhibited DHT-induced PSA secretion and cell proliferation (IC(50) approximately 1 microM). Dutasteride competed for binding the LNCaP cell AR with an IC(50) approximately 1.5 microM. High concentrations of dutasteride (10-50 microM), but not finasteride, in steroid-free medium, resulted in enhanced cell death, possibly by apoptosis [1]. Dutasteride reduces cell viability and cell proliferation in both cell lines tested (androgen-responsive (LNCaP) and androgen-unresponsive (DU145) human prostate cancer (PCa)) [2].;In vivo: GG745 has a terminal half-life of approximately 240 hr, and single doses MedChem Express HY-13613
      Metabolism/Protease MedChem Express HY-13613
      Metabolism/Protease; MedChem Express HY-13613
      Under investigation for treatment of benign prostatic hyperplasia Zerenex Molecular [ZBioX-0158]

Predicted data is generated using the ACD/Labs Percepta Platform - PhysChem Module

Density: 1.3±0.1 g/cm3
Boiling Point: 620.3±55.0 °C at 760 mmHg
Vapour Pressure: 0.0±1.8 mmHg at 25°C
Enthalpy of Vaporization: 91.9±3.0 kJ/mol
Flash Point: 329.0±31.5 °C
Index of Refraction: 1.523
Molar Refractivity: 124.0±0.3 cm3
#H bond acceptors: 4
#H bond donors: 2
#Freely Rotating Bonds: 4
#Rule of 5 Violations: 2
ACD/LogP: 5.61
ACD/LogD (pH 5.5): 4.99
ACD/BCF (pH 5.5): 3660.32
ACD/KOC (pH 5.5): 12369.74
ACD/LogD (pH 7.4): 4.99
ACD/BCF (pH 7.4): 3660.32
ACD/KOC (pH 7.4): 12369.74
Polar Surface Area: 58 Å2
Polarizability: 49.1±0.5 10-24cm3
Surface Tension: 38.1±3.0 dyne/cm
Molar Volume: 405.6±3.0 cm3

Click to predict properties on the Chemicalize site






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