54048-10-1

Basic information

• Product Name: Etonogestrel
• Synonyms: Desogestrel Related CoMpound C;(17-alpha)-13-ethyl-17-hydroxy-11-methylene-18,19-dinorpregn-4-en-20-yn-3-on;13-ethyl-11-methylene-18,19-dinor-17-alpha-pregn-4-en-20-yn-3-one;17-ethinyl-17-beta-hydroxy-18-methyl-11-methylene-4-estren-3-one;19-dinorpregn-4-en-20-yn-3-one,13-ethyl-17-hydroxy-11-methylene-1(17-alpha;3-oxodesogestrel;org3236;13-ethyl-17-ethynyl-17-hydroxy-11-methylidene-2,6,7,8,9,10,12,13,14,15,16,17-dodecahydro-1h-cyclopenta[a]phenanthren-3-one
• CAS NO: 54048-10-1
• Molecular Formula: C₂₂H₂₈O₂
• Molecular Weight: 324.46
• EINECS: 258-936-2
• Product Categories: Hormone Drugs;API;Inhibitors;Various Metabolites and Impurities;Intermediates & Fine Chemicals;Metabolites & Impurities;Pharmaceuticals;Steroids
• Mol File: 54048-10-1.mol
• Article Data: 7

Chemical Properties

• Melting Point: 182-184°C
• Boiling Point: 473.1 °C at 760 mmHg
• Flash Point: 201.1 °C
• Appearance: white to beige/
• Density: 1.13 g/cm³
• Vapor Pressure: 6.13E-11mmHg at 25°C
• Refractive Index: 1.574
• Storage Temp.: -20°C
• Solubility: DMSO: >5mg/mL
• PKA: 13.04±0.40(Predicted)
• CAS DataBase Reference: Etonogestrel(CAS DataBase Reference)
• NIST Chemistry Reference: Etonogestrel(54048-10-1)
• EPA Substance Registry System: Etonogestrel(54048-10-1)

Safety Data

• Statements: 60-40
• WGK Germany: 3
• RTECS: JF8290000
• Hazardous Substances Data: 54048-10-1(Hazardous Substances Data)

Usage

Chemical Properties

White Solid

Uses

A biologically active metabolite of Desogestrel.

Brand name

Implanon (Organon).

General Description

Etonogestrel, 17α-13-ethyl-17hydroxy-11-methylene-18,19-dinorpregn-4-en-20-yn-3-one,3-ketodesogestrel, is the active metabolite of desogestrel. It isthe progestin component in a newer implantable contraceptive(Implanon) and in the vaginal contraceptive ring (NuvaRing).

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

• 100071-90-7 18-methyl-estra-4-en-3,11,17-trione 
• 170901-07-2 13-ethyl-11-hydroxygon-4-ene-3,17-dione 
• 65032-27-1 ethynylmagnesium chloride 
• 1066-54-2 trimethylsilylacetylene 
• 170901-07-2 C₁₉H₂₆O₃ 
• 7370-08-3 11α,17β-Dihydroxy-18a-homo-estr-4-en-3-one 
• 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 
• 160683-85-2 3-methoxy-18a-homo-estra-2,5(10)-diene-11α,17β-diol 
• 160683-93-2 18a-homo-estr-4-ene-11,17-dione 
• 54024-21-4 11-methylene-18a-homo-estr-4-en-17-one 
• 160683-92-1 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 articles and documents

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.

KIT FOR FEMALE MAMMALS, COMPRISING A COMBINATION OF GESTAGEN AND OESTROGEN

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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.