A Study of the Complexation Between Danazol and Hydrophilic Cyclodextrin Derivatives

Sherif I.F. Badawy, Amanda Marshall, Mahmoud M. Ghorab, Christianah Moji Adeyeye
In: Drug Development and Industrial Pharmacy · 1996 · vol. 22(9-10) , pp. 959–966 · doi:10.3109/03639049609065926 · W2001425273
Lab / animal OA: closed CC0 ⤵ 2 in-corpus citations
View on OpenAlex View at publisher
⚙ AI-generated summary by gemini-2.5-flash-lite, 2026-06-08 ⓘ

Danazol complexation with HPCD and SBE was investigated, revealing a 1:1 complex where the isoxazole ring is included in the cyclodextrin cavity, impacting danazol's solid state and dissolution rates.

One-sentence paraphrase of the abstract; not a substitute for reading it. No clinical advice. How this works

Abstract

Complexation between danazol, a steroid used for endometriosis, and both hydroxypropyl- β-cyclodextrin (HPCD) and sulfobutyl ether-β-cyclodextrin (SBE) was studied in solution and solid state. Complexation was evaluated in solution using solubility studies and proton magnetic resonance (1H NMR) spectroscopy, and in the solid state using x-ray diffraction, Fourier-transform infrared spectroscopy (FTIR)), and dissolution studies. Solubility studies suggested the existence of a 1:1 complex between danazol and either HPCD or SBE. 1H NMR showed that complexation occurs by inclusion of the isoxazole ring of danazol into the cyclodextrin cavity in both cases. Powder x-ray diffraction indicated that danazol existed in a crystalline noncomplexed form at low danazol-to-cyclodextrin ratios in the coprecipitates prepared by solvent evaporation method, while at higher ratios danazol existed in an amorphous complexed form. This ratio was 1:10 w/w for HPCD and 1:20 for SBE; the higher ratio in the case of SBE is attributed to early precipitation of danazol from the solvent used for preparation. FTIR studies showed that the complexation was accompanied by a shift of the O-H stretching of danatol hydroxyl group to a higher frequency, which is attributed to the disruption of the intermolecular hydrogen bonding. The dissolution rate of danazol from HPCD coprecipitates was higher than crystalline danazol in aqueous-isopropanolic medium, while SBE coprecipitates showed reduced dissolution rates due to the low solubility of SBE in isopropanol. However, SBE coprecipitates showed higher dissolution rates in water than in the isopropanolic medium.

My notes (saved in your browser only)

Condition tags

endometriosis

Citation neighborhood (2-hop)

Papers in the corpus that this work cites (lower rings, blue) and that cite this one (upper rings, green). Dot size scales with the paper's in-corpus citation count — bigger dot = more influential within the endo/adeno field. Click a dot to open that paper. Outer rings show 2-hop neighbours — papers reached through the immediate citers/citees. [ collapse to 1-hop ]

References (11)

Cited by (2)

Source provenance

openalex
last seen: 2026-05-10T11:52:25.947030+00:00
License: CC0 · commercial use OK