Abstract
Androsta-1,4-dien-17β-ol-3-one, also known as boldenone, is an anabolic-androgenic steroid derived from testosterone. The crystal structures of boldenone base, boldenone acetate, boldenone propionate, boldenone cypionate and a boldenone acetate polymorph obtained by high throughput screening were investigated. Hirshfeld surfaces and fingerprint plots breakdown revealed that the molecular packing in the crystals are driven by dominant H⋯H intermolecular contacts, followed by O⋯H/H⋯O contacts and to a lesser degree C⋯H/H⋯C contacts. The steroid skeleton rings, for all the reported compounds, adopt the following conformation: planar in A, chair in B and C, whereas C(13) envelope conformations are found for the five-membered D rings. The total lattice energies were calculated as a sum of four terms (Coulombic, polarization, dispersion, repulsion).
Acknowledgements
Financial support from the Ministry of Research and Innovation – MCI, Core Programme, Project PN19 35 02 01.
References
[1] S. R. Vippagunta, H. G. Brittain, D. J. W. Grant, Adv. Drug Deliv. Rev.2001, 48, 3.10.1016/S0169-409X(01)00097-7Search in Google Scholar
[2] N. T. Shahidi, Clin. Ther.2001, 23, 1355.10.1016/S0149-2918(01)80114-4Search in Google Scholar
[3] J. Elks, C. R. Ganellin, The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies, 1st ed., Springer US, Easton, 1990.Search in Google Scholar
[4] C. Arts, R. Schilt, M. Schreurs, L. van Ginkel. in Proceedings of the EuroResidue III Conference, (Eds. N. Haagsma and A. Ruiter) Utrecht, The Netherlands University of Utrecht, p. 212, 1996.Search in Google Scholar
[5] Index Nominum, International Drug Directory, 17th ed. Swiss Pharmaceutical Society, Medpharm Scientific Publishers, Stuttgart, 2000.Search in Google Scholar
[6] W. Llewellyn, Anabolics, 10th ed. Molecular Nutrition Llc., Jupiter, Florida, 2011.Search in Google Scholar
[7] P. Teale, E. Houghton, Biol. Mass. Spectrom.1991, 20, 109.10.1002/bms.1200200303Search in Google Scholar PubMed
[8] W. Schänzer, Clin. Chem.1996, 42, 1001.10.1093/clinchem/42.7.1001Search in Google Scholar
[9] W. Schänzer, M. Donike, Biol. Mass. Spectrom.1992, 21, 3.10.1002/bms.1200210104Search in Google Scholar PubMed
[10] D. R. Mottram, A. J. George, Best Pract. Res. Clin. Endocrinol. Metab.2000, 14, 55.10.1053/beem.2000.0053Search in Google Scholar PubMed
[11] A. Vermeulen, Acta Clin Belg.1975, 30, 48.10.1080/17843286.1975.11716973Search in Google Scholar PubMed
[12] N. William, M. D. Taylor, Anabolic Steroids and the Athlete, 2nd ed., McFarland & Company, Jefferson, North Carolina, and London, 2002.Search in Google Scholar
[13] J. M. Ohrt, B. A. Haner, D. A. Norton, Acta Cryst.1965, 19, 479.10.1107/S0365110X65003663Search in Google Scholar
[14] Z. Gałdecki, P. Grochulski, Z. Wawrzak, A. Szyczewski, J. Crystallogr. Spectrosc. Res. 1989, 19, 933.10.1007/BF01160875Search in Google Scholar
[15] C. R. Groom, I. J. Bruno, M. P. Lightfoot, S. C. Ward, Acta Crystallogr.2016, B72, 171.Search in Google Scholar
[16] CrysAlis PRO, Rigaku Oxford Diffraction, Yarnton, Oxfordshire, England, 2015.Search in Google Scholar
[17] O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard, H. Puschmann, J. Appl. Cryst.2009, 42, 339.10.1107/S0021889808042726Search in Google Scholar
[18] G. M. Sheldrick, Acta Crystallogr.2008, A64, 112.10.1107/S0108767307043930Search in Google Scholar PubMed
[19] G. M. Sheldrick, Acta Crystallogr.2015, A71, 3.Search in Google Scholar
[20] G. M. Sheldrick, Acta Crystallogr.2015, C71, 3.Search in Google Scholar
[21] M. A. Spackman, J. J. McKinnon, CrystEngComm. 2002, 4, 378.10.1039/B203191BSearch in Google Scholar
[22] J. J. McKinnon, M. A. Spackman, A. S. Mitchell, Acta Crystallogr.2004, B60, 627.10.1107/S0108768104020300Search in Google Scholar PubMed
[23] M. J. Turner, J. J. McKinnon, S. K. Wolff, D. J. Grimwood, P. R. Spackman, D. Jayatilaka, M. A. Spackman, CrystalExplorer17. University of Western Australia, The Nedlands, Western Australia, 2017.Search in Google Scholar
[24] J. J. McKinnon, D. Jayatilaka, M. A. Spackman, Chem. Commun.2007, 3814.10.1039/b704980cSearch in Google Scholar PubMed
[25] J. J. McKinnon, F. P. A Fabbiani, M. A. Spackman, Cryst. Growth Des.2007, 7, 755.10.1021/cg060773kSearch in Google Scholar
[26] K. Durka, A. A. Hoser, R. Kaminski, S. Lulinski, J. Serwatowski, W. Kozminski, K. Wozniak, Cryst. Growth Des.2011, 11, 1835.10.1021/cg200032eSearch in Google Scholar
[27] A. Tarahhomi, M. Pourayoubi, J. A. Golen, P. Zargaran, B. Elahi, A. L. Rheingold, M. A. L. Ramirez, T. M. Percino, Acta Crystallogr.2013, B69, 260.Search in Google Scholar
[28] A. Gavezzotti, New J. Chem.2011, 35, 1360.10.1039/c0nj00982bSearch in Google Scholar
[29] J. F. Griffin, W. L. Duax, C. M. Weeks, Atlas of Steroid Structure, 2nd ed., IFI/PLENUM, New York-Washington-London, 1984.10.1007/978-1-4757-0426-6Search in Google Scholar
[30] C. Altona, M. Sundaralingam, J. Am. Chem. Soc.1972, 94, 8205.10.1021/ja00778a043Search in Google Scholar PubMed
[31] C. F. Macrae, I. J. Bruno, J. A. Chisholm, P. R. Edgington, P. McCabe, E. Pidcock, L. Rodriguez-Monge, R. Taylor, J. van de Streek, P. A. Wood, J. Appl. Cryst.2008, 41, 466.10.1107/S0021889807067908Search in Google Scholar
[32] D. F. Rendle, J. Trotter, J. Chem. Soc. Perkin II. 1974, 847.10.1039/P29740000847Search in Google Scholar
[33] N. W. Isaacs, W. D. S. Motherwell, J. C. Coppola, O. Kennard, J. Chem. Soc. Perkin II.1972, 2331.10.1039/p29720002331Search in Google Scholar
[34] P. J. Roberts, J. C. Coppola, N. W. Isaacs, O. Kennard, J. Chem. Soc. Perkin II. 1973, 774.10.1039/P29730000774Search in Google Scholar
[35] V. R. Hathwar, M. Sist, M. R. V. Jørgensen, A. H. Mamakhel, X. Wang, C. M. Hoffmann, K. Sugimoto, J. Overgaard, B. B. Iversen, IUCrJ.2015, 2, 563.10.1107/S2052252515012130Search in Google Scholar PubMed PubMed Central
Supplementary Material
The online version of this article offers supplementary material (https://doi.org/10.1515/zkri-2019-0030).
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