Dutasteride - CAS 164656-23-9
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CAS 164656-23-9 Dutasteride

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1. Resonance-assisted amide protonation in dutasteride hydrochloride salt
Jagadeesh Babu Nanubolu, Balasubramanian Sridhar and Krishnan Ravikumar*. CrystEngComm, 2012, 14, 2571–2578
Dutasteride (5, 17-N-{2,5-bis(trifluoromethyl)phenyl}-3-oxo-4-azaandrost-1-ene-17-carboxamide) is a pharmaceutically active compound, used for the treatment of benign prostatic hyperplasia, a condition found primarily in men over the age of 50. The only other approved in this class is finasteride which predominantly inhibits type II 5-alpha reductase. Compared to finasteride, dutasteride is more potent and causes greater reduction in dihydrotestosterone concentration at equipotent doses. Dutasteride is reported to exist in three polymorph modifications as noted in 2004 and 2009 patents, and these forms are confirmed by powder X-ray diffraction. Attempts to grow single crystals of polymorphs have yielded a novel form of dutasteride from ethanol. The simulated pattern of this form has many similarities to the pattern reported in 2009 patent. It is confirmed as hemihydrate which crystallised in the orthorhombic P212121 space group. The asymmetric unit is composed of two dutasteride molecules (A and B) and one water molecule (Fig. 1). The two dutasteride molecules are symmetry independent and PLATON confirmed that therewas no additional overlooked symmetry. The two molecules differ only in the orientation of the phenyl ring, as can be expressed by the torsion angle C20–N21–C22–C27, of 28.3(8) and 48.7(7)o for molecules A and B, respectively.
2. Phase transition studies of dutasteride crystalline forms
M. Łaszcz,* K. Trzcińska, A. Witkowska, E. Lipiec-Abramska and W. J. Szczepek. CrystEngComm,2015, 17, 2346–2352
According to patent publications US 7022854 B2 and WO 2009/083258 A2 dutasteride exhibits polymorphism (form I and form II) and exists as a hemihydrate (form III) as well as an amorphous form. The synthesis of dutasteride forms 1 and 2 was described by Satyanarayana et al. Diffractogram comparisons of forms I with 1 and II with 2 proved that they are the same crystalline forms (Fig. A2). X-ray studies of dutasteride hemihydrate were described by Nanubolu et al. Dutasteride hemihydrate crystallizes in the orthorhombic space group P212121 with the following unit cell parameters: a = 8.2124(7), b = 18.5162IJ17), c = 34.876(3) Å. A diffractogram comparison of form III revealed in the International Patent Application with a simulated powder diffractogram obtained from single crystal data deposited by Nanubolu et al. in the Cambridge Crystallographic Data Centre (refcode LATSIK) proved the existence of the same crystalline structures (Fig. A3).