Crystal structure of isotibolone: a major degradation product of tibolone

Author(s)

Gomez, Ariel ^[1] ; Antonio, Selma Gutierrez ^[2] ; Barros de Araujo, Gabriel Lima ^[3] ; Ferreira, Fabio Furlan ^[4] ; Paiva-Santos, Carlos Oliveira ^[2]

Affiliation

^[1] Univ Guelph, Dept Phys, Guelph, ON N1G 2W1 - Canada

^[2] Univ Estadual Paulista, Inst Quim, Depto Fis Quim, BR-14801970 Araraquara, SP - Brazil

^[3] Univ Sao Paulo, Fac Ciencias Farmaceut, Sao Paulo - Brazil

^[4] Univ Fed ABC, Ctr Ciencias Nat & Humanas, BR-09210170 Santo Andre, SP - Brazil

• Document type: Journal article
• Source: CrystEngComm; v. 14, n. 8, p. 2826-2830, 2012.
• Web of Science Citations: 8

Abstract

Isotibolone is frequently found as an impurity in tibolone, a drug used for hormone reposition of post-menopause women, due to some inadequate tibolone synthesis or as a result of degradation during drug storage. The presence of isotibolone impurities should be detected and quantified in active pharmaceutical ingredient products of tibolone before its use in the manufacturing of medicaments. The X-ray powder diffraction technique offers the possibility of quantifying isotibolone amounts at different stages of drug production and storage, from the chemical synthesis to the final formulation. In the course of a study involving the quantitative analysis of isotibolone by X-ray powder diffraction, the authors determined the structure of the title compound using a recently developed approach (A. Gomez and S. Kycia, J. Appl. Crystallogr. 2011, 44, 708-713). The structure is monoclinic, space group P2(1) (4), with unit cell parameters a = 6.80704(7) angstrom, b = 20.73858(18) angstrom, c = 6.44900(6) angstrom, beta = 76.4302(5)degrees, V = 884.980(15) angstrom(3) and two molecules per unit cell (Z = 2). The molecules are hydrogen bonded in the ab plane forming layers that are held together in the crystal by van der Waals interactions along the c-axis. (AU)

• FAPESP's process: 10/06849-0 - Medicament control through X-ray powder diffraction
• Grantee: Selma Gutierrez Antonio
• Support Opportunities: Scholarships in Brazil - Post-Doctoral
• FAPESP's process: 08/10537-3 - Study of crystalline pharmaceuticals polymorphs by X-ray powder diffraction and the Rietveld method
• Grantee: Fabio Furlan Ferreira
• Support Opportunities: Research Grants - Young Investigators Grants