Ethynodiol diacetate

Sample preparation Powder tablets (60 mesh), weigh out amount equivalent to one tablet, add 2 mL 50 (jig/mL BHT in MeCN water 80 20, shake 30 min, centrifuge 

Column 250 x 3.2 Altex RP-2 express series Mobile phase MeCN water 38 62 Flow rate 1.75 Ipjection volume 20 Detector UV 210 UV 280 

Simultaneous degradation products, ethinyl estradiol, mestranol 

Carignan, G. Lodge, B.A. Skakum, W. Quantitative analysis of ethynodiol diacetate and ethinyl estra-diol/mestranol in oral contraceptive tablets by high-performance liquid chromatography. J.Pharm.Sci., 1982, 71, 264-266 

Column 50 x 4.6 5 pm Supelcosil LC-DP Mobile phase MeCN THF water 26 14 60 Flow rate 1 Injection volume 20 Detector UV 220 

Therapeutic Function Progestin oral contraceptive ingredient Chemical Name 3(3,17(3-diacetoxy-17tt-ethynyl-4-estrene Common Name - 

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EthynodlolDia.ceta.te, Ethynodiol diacetate has been used alone, and in combination with an strogen, as an oral contraceptive and to treat disorders associated with progesterone deficiency (76). It may be crystallised from aqueous methanol (77) and is soluble in chloroform, ether, and ethanol sparingly soluble in fixed oils and insoluble in water (76). Extensive spectral and chromatographic data have been compiled (78). 

Ethynodiol diacetate (53) is prepared by reduction of the 3-oxo group of norethindrone (28) with lithium tributoxyalurninum hydride, followed by acylation with acetic anhydride-pyridine (78,79). It has been reported that higher yields can be obtained in the reduction step by using triethylanainoalurninum hydride (80). 

In further modifications of these norprogestins, reaction of norethindrone with acetic anhydride in the presence of p-toluene-sulfonic acid, followed by hydrolysis of the first-formed enol acetate, affords norethindrone acetate (41). This in turn affords, on reaction with excess cyclopentanol in the presence of phosphorus pentoxide, the 3-cyclopentyl enol ether (42) the progestational component of Riglovic . Reduction of norethindrone affords the 3,17-diol. The 33-hydroxy compound is the desired product since reactions at 3 do not show nearly the stereoselectivity of those at 17 by virtue of the relative lack of stereo-directing proximate substituents, the formation of the desired isomer is engendered by use of a bulky reducing agent, lithium aluminum-tri-t-butoxide. Acetylation of the 33,173-diol iffords ethynodiol diacetate, one of the most potent oral proves tins (44). ... 

MonophasicOral Contraceptives 50 meg ethinyl estradiol acetate img norethindrone 50 meg ethinyl estradiol, 1 mg ethynodiol diacetate 50 meg ethinyl estradiol, 0.5 mg norgestrel 35 mg ethinyl estradiol, 1 mg norethindrone 35 meg ethinyl estradiol, 0.5 mg norethindrone 35 meg ethinyl estradiol, 0.4 mg norethindrone 35 meg ethinyl estradiol, 0.25 mg norgestimate 35 meg ethinyl estradiol, 1 mg ethynodiol diacetate... 

Desogen (Organon) Estrostep (Parke Davis) Ethynodiol Diacetate and Ethinyl Estradiol (Watson) Levlen (Berlex)... 

Diphenhydramine hydrochloride, 3,173 Diphenoxylate hydrochloride, 7,149 Disulflram, 4, 168 Dobutamine hydrochloride, 8,139 Droperidol, 7,171 Echothiophate iodide, 3,233 Epinephrine, 7, 193 Ergotamine tartrate, 6,113 Erythromycin, 8,139 Erythromycin estolate, 1, 101 2, 573 Estradiol valerate, 4,192 Ethambutol hydrochloride, 7,231 Ethynodiol diacetate, 3,253 Fenoprofen calcium, 6,161 Flucytosine, 5,115 Fludrocortisone acetate, 3, 281 Fluorouracil, 2,221 Fluoxymesterone, 7,251 Fluphenazine enanthate, 2, 245 4,523 Fluphenazine hydrochloride, 2,263 4,518 Gluthethimide,5,139 Gramicidin, 8,179 Griseofulvin, 8,219 Halcinonide, 8,251 Halothane, 1, 119 2,573 Hexetidine, 7,277 Hydralazine hydrochloride, 8,283 Hydroflumethiazide, 7,297 Hydroxyprogesterone caproate, 4,209 Hydroxyzine dihydrochloride, 7,319 Iodipamide, 3,333 Isocarboxazid, 2, 295... 

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