54048-10-1

Usage

Uses

Used in Contraceptive Applications:
Etonogestrel is used as the progestin component in implantable contraceptives for the purpose of preventing pregnancy. It is a key ingredient in Implanon, a newer implantable contraceptive device that provides long-term birth control.
Used in Vaginal Contraceptive Rings:
Etonogestrel is also used as the progestin component in vaginal contraceptive rings, such as NuvaRing, for the purpose of providing a convenient and non-invasive method of birth control.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, Etonogestrel is used as an active ingredient in the development of hormonal contraceptive products, contributing to their effectiveness in preventing unwanted pregnancies.

Biochem/physiol Actions

Etonogestrel is a lipophilic molecule. Pharmacokinetics studies reveal that etonogestrel is bound to protein albumin in the blood. This remains independent of both endogenous and exogenous concentration of estradiol.

InChI:InChI=1/C22H28O2/c1-4-21-13-14(3)20-17-9-7-16(23)12-15(17)6-8-18(20)19(21)10-11-22(21,24)5-2/h2,12,17-20,24H,3-4,6-11,13H2,1H3/t17-,18-,19-,20+,21-,22-/m0/s1

Upstream product

• 54024-22-5 desogestrel 
• 1066-54-2 trimethylsilylacetylene 
• 65032-27-1 ethynylmagnesium chloride 
• 170901-07-2 13-ethyl-11-hydroxygon-4-ene-3,17-dione 
• 100071-90-7 18-methyl-estra-4-en-3,11,17-trione 
• 170901-07-2 C₁₉H₂₆O₃ 
• 7370-08-3 11α,17β-Dihydroxy-18a-homo-estr-4-en-3-one 
• 54024-21-4 11-methylene-18a-homo-estr-4-en-17-one 
• 160683-92-1 18a-homo-estr-4-ene-11α,17β-diol 
• 187538-71-2 Acetic acid (8S,9S,10R,13S,14S,17R)-13-ethyl-17-ethynyl-11-methylene-3-oxo-2,3,6,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl ester 
• 160683-94-3 17,17-<(2,2-dimethyl)propane-1,3-dioxy>-18a-homo-estr-4-en-11-one 
• 160683-96-5 Acetic acid (8S,9S,10R,13S,14S,17R)-13-ethyl-17-ethynyl-11-methylene-2,3,6,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl ester 
• 160683-95-4 11-methylene-17-<(2,2-dimethyl)propane-1,3-dioxy>-18a-homo-estr-4-ene 
• 160683-91-0 3,3-ethylenedithio-18a-homo-estr-4-ene-11α,17β-diol 

Downstream Products

• 70805-85-5 3alpha-Hydroxydesogestrel 
• 70805-85-5 13-ethyl-11-methylene-18,19-dinor-17α-pregn-4-en-20-yne-3β-17β-diol 

Relevant academic research and scientific papers

PROCESS AND NEW INTERMEDIATES FOR THE PREPARATION OF 11-METHYLENE STEROIDS

The invention relates to a process for the preparation of 11 -methylene steroids through selective olefination of the ketone at position 11. The resulting products are useful intermediates in the preparation of several pharmaceutically active agents, such as Etonogestrel and Desogestrel.

COMBINED SYNTHESIS ROUTE FOR ETONOGESTREL AND DESOGESTREL

The present invention relates to a synthesis route and to steroid derivatives of general formula VI and VII useful in the synthesis of desogestrel and etonogestrel.

Pharmaceutical combined preparation, kit and method for hormonal contraception

PCT No. PCT/DE96/01192 Sec. 371 Date Jun. 3, 1998 Sec. 102(e) Date Jun. 3, 1998 PCT Filed Jun. 27, 1996 PCT Pub. No. WO97/01342 PCT Pub. Date Jan. 16, 1997The present invention describes a two-stage pharmaceutical combined preparation for hormonal contraception containing at least 30 daily unit doses, which preparation, in its first stage, comprises as hormonal active ingredient a combination of an oestrogen preparation and, in a dose that is at least sufficient to inhibit ovulation, a gestagen preparation, in single stage form and, in the second stage comprises as hormonal active ingredient an oestrogen preparation only, wherein the first stage comprises a minimum of 25 and a maximum of 77 daily discrete or continuous unit doses and the second stage comprises 5, 6 or 7 daily discrete or continuous unit doses, and wherein the total number of daily units is equal to the total number of days of the desired cycle of a minimum of 30 and a maximum of 84 days. This combined preparation, in the form of a monthly pack, which is used for female fertility control, permits as low as possible an oestrogen content in each individual unit dose and also has a low total hormone content per cycle of administration, with high contraceptive reliability, low incidence of follicle development, and satisfactory cycle control with reliable avoidance of intermediate bleeding as well as undesired side effects.

Pharmaceutical combination preparation for hormonal contraception

The invention provides a pharmaceutical combination preparation with two hormone components in a packaging unit and intended for time-sequential oral administration, comprising a number of daily dosage units physically separate and individually removable in the packaging unit, whereby as a hormonal active ingredient a first hormone component contains in combination an estrogen preparation and in at least a dosage that is sufficient to inhibit ovulation a gestagen preparation, and as a hormonal active ingredient the second hormone component contains only an estrogen preparation, whereby the first hormone component comprises 23 or 24 daily units and the second hormone component comprises 4, 3 or 2 daily units, and between these two hormone components, 2 or 1 active ingredient-free daily units are present or 2 or 1 blank pill days are indicated, and the total number of hormone daily units and the active ingredient-free daily units or the blank pill days is equal to the total number of days of the desired cycle, but at least 28 days in length. This combination preparation is useful for female birth control, and allows for an estrogen content that is as low as possible in each individual dosage unit and also has a low total hormone content per administration cycle, with high contraceptive reliability, low incidence of follicular development, and satisfactory cycle control, with reliable avoidance of intracyclic menstrual bleeding as well as of undesirable side-effects.

Pharmaceutical combination preparation for hormonal contraception

A pharmaceutical combination preparation with two hormone components that are manufactured physically separately in a packaging unit and that are intended for time-sequential oral administration, which in each case consist of a number of daily dosage units that are placed physically separately and are individually removable in the packaging unit. As a hormonal active ingredient, a first hormone component contains in combination an estrogen preparation and, in at least a dosage that is sufficient to inhibit ovulation, a gestagen preparation, and as a hormonal active ingredient the second hormone component contains only an estrogen preparation. The first hormone component comprises 23 or 24 daily units and the second hormone component comprises 4 to 10 daily units. The total number of hormone daily units is equal to the total number of days of the desired cycle, but at least 28 days in length. This combination preparation is used for female birth control, and allows for an estrogen content that is as low as possible in each individual dosage unit and also has a low total hormone content per administration cycle, with high contraceptive reliability, low incidence of follicular development, and satisfactory cycle control, with reliable avoidance of intracyclic menstrual bleeding as well as of undesirable side-effects.

Synthesis of 13-Ethyl-11-methylene-18,19-dinor-17α-pregn-4-en-20-yn-17-ol (Desogestrel) and its Main Metabolite 3-Oxo-Desogestrel

A synthesis of the steroid hormone desogestrel (25) from the 18a-homo steroid 1 is described. 25 was transformed into 3-oxo-desogestrel (28) by allyl oxidation.