Solid dosage forms that contain clathrates of 17.alpha.-ethinyl

Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Carbohydrate doai

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514 58, 514182, A61K 31705, A61K 31565

Patent

active

057983380

DESCRIPTION:

BRIEF SUMMARY
The invention relates to solid dosage forms that contain steroidal sex hormones.
As is generally known, natural and especially synthetically derived sex hormones are generally highly effective active ingredients of pharmaceutical agents. Consequently, in most cases solid dosage forms contain these active ingredients at very low dosages; these are usually 0.01 .mu.g to 500 .mu.g and especially 0.1 .mu.g to 200 .mu.g per single-dosed dosage form. This means that both the preparation and the storage and use of these dosage forms are often problematical in nature.
In the preparation of such low-dosed dosage forms, strong fluctuations of the active ingredient concentrations in the dosage units occur almost unavoidably (inadequate content uniformity), which manifest themselves more strongly, the smaller the amount of the active ingredient.
In the storage of such low-dosed preparations, moreover, a reduction in the active ingredient concentration is often additionally observed as a result of, in most cases, oxidative degradation reactions of the active ingredient.
In addition, at such low dosage the bioavailability of the active ingredient is subject to a pronounced first-pass effect and exhibits great inter- and intra-individual fluctuations.
It has now been found that the drawbacks that are observed especially in the preparation and storage of dosage forms which contain low-dosed steroidal sex hormones can be avoided, at least to a large extent, if dosage forms are prepared that contain powdery cyclodextrin clathrates of these active ingredients.
Steroidal sex hormones that are suitable for the production of dosage forms according to the invention are estrogenically, gestagenically, androgen-anabolically, antiestrogenically, antigestagenically, and antiandrogenically active compounds, as well as mixtures of these substances.
For example, estrone, estradiol, estriol, 17.alpha.-ethinylestradiol, mestranol, 14.alpha.,17.alpha.-ethanoestra-1,3,5(10)-triene-3,17.beta.-diol (WO88/012 75), 14.alpha.,17.alpha.-ethanoestra-1,3,5(10)-triene-3,16.alpha.,17.beta.-trio l (WO and their esters such as estradiol-dipropionate, estradiol-dihexanoate and estradiol-didecanoate (EP-A 163 596) can be mentioned as examples of suitable estrogens.
Suitable gestagens are, for example, norethisterone, levonorgestrel, gestodene, desorgestrel, and 3-ketodesorgestrel.
Suitable androgen-anabolically active compounds are, i.a., testosterone, mesterolone, methenolone, and esters of these substances, such as testosterone propionate, testosterone enanthate, testosterone nicotinate, and testosterone phenylacetate.
Suitable antiestrogens are, i.a., 1-methyl-androsta-1,4-diene-3,17-dione (atamestane) and -triene-3,17.beta.-diol (ICI 182780).
As suitable antigestagens, ropyl)-13.alpha.-estra-4,9-dien-3-one (onapristone) and estra-4,9-dien-3-one (mifepristone) can be mentioned.
Antiandrogenically active compounds that are suitable for the production of dosage forms according to the invention are, for example, 17.alpha.-acetoxy-6-chloro-pregna-4,6-diene-3,20-dione (chloromadinone acetate), na-1,4,6-triene-3,20-diene (cyproterone acetate) (topterone) and 17.beta.-hydroxy-1.alpha.-methyl-17.alpha.-propyl-androstan-3-one (propylmesterolone).
It was already mentioned that the dosage forms according to the invention contain powdery cyclodextrin clathrates of these active ingredients.
Cyclodextrins that are suitable for the production of these clathrates are, for example, those of general formula ##STR1## in which R.sub.1 means a hydrogen atom, a methyl group, a 2-hydroxyethyl group, or a 2-hydroxypropyl group also a methyl group, and
Such cyclodextrins are preferably .alpha.-cyclodextrin, .gamma.-cyclodextrin, dimethyl-.beta.-cyclodextrin, 2-hydroxyethyl-.beta.-cyclodextrin, 2-hydroxypropyl-.beta.-cyclodextrin and especially .beta.-cyclodextrin (Drug Dev. and Ind. Pharm., 17, 1991, 1503-1549, J. Incl. Phenom., 1, 1983, 135-150 and WO 93/13138). For the production of clathrates, the steroid hormones can be very intimately mixed with the cyclodextrin, option

REFERENCES:
patent: 4877774 (1989-10-01), Pitha et al.
Pitha et al., Int. J. Pharm., 29(1), 73-82 (1986).

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