Etonogestrel Chemical Properties

Melting point:

182-184°C

Boiling point:

473.1±45.0 °C(Predicted)

alpha 

D +87.6°

Density 

1.13±0.1 g/cm3(Predicted)

storage temp. 

-20°C

solubility 

DMSO: >5mg/mL

pka

13.04±0.40(Predicted)

form 

powder

color 

white to beige

optical activity

[α]/D +80 to +95°, c = 1 (CHCl3)

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-/s3

InChIKey

GCKFUYQCUCGESZ-BPIQYHPVSA-N

SMILES

C([C@]12CC(=C)[C@]3([H])[C@@]4([H])CCC(=O)C=C4CC[C@@]3([H])[C@]1([H])CC[C@@]2(O)C#C)C |&1:1,5,7,17,19,23,r|

CAS DataBase Reference

54048-10-1(CAS DataBase Reference)

Safety Information

Risk Statements 

60-40

WGK Germany 

3

RTECS 

JF8290000

HS Code 

2937230000

Etonogestrel Usage And Synthesis

Description

Etonogestrel molecule is a 3-ketodesogestrel or 19-nortestosterone which is a synthetic biologically active metabolite of progestin desogestrel. The first product including etonogestrel was developed by the Merck subsidiary Organon and FDA approved in 2001.

Chemical Properties

White Solid

Uses

A biologically active metabolite of Desogestrel.

Definition

ChEBI: Etonogestrel is a 17beta-hydroxy steroid, a 3-oxo-Delta(4) steroid and a terminal acetylenic compound. It has a role as a contraceptive drug, a progestin and a female contraceptive drug.

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.

Mode of action

Etonogestrel binds to the cytoplasmic progesterone receptors in the reproductive system and subsequently activates progesterone receptor mediated gene expression. As a result of the negative feedback mechanism, luteinizing hormone (LH) release is inhibited, which leads to an inhibition of ovulation and an alteration in the cervical mucus and endometrium.

Etonogestrel(54048-10-1)Related Product Information

• Gestrinone
• Trinexapac-ethyl
• Ethyl propiolate
• Ethyl acetate
• Altrenogest
• Desogestrel
• Gestodene
• CHLOROPHOSPHONAZO III
• Ethylparaben
• Ethyl acrylate
• Ethyl cyanoacetate
• Ethanol
• ISOXADIFEN-ETHYL
• Eprinomectin
• Ectoine
• Brexpiprazole
• Levonorgestrel
• Norgestrel