1. 13-ethyl-17-hydroxy-11-methylene-18,19-dinor-17alpha-pregn-4-en-20-yn-3-one
2. 18,19-dinorpregn-4-en-20-yn-3-one, 13-ethyl-17-hydroxy-11-methylene-, (17-alpha)-
3. 3-keto-desogestrel
4. 3-ketodesogestrel
5. 3-oxo Desogestrel
6. 3-oxodesogestrel
7. Implanon
8. Nexplanon
9. Org-3236
1. Implanon
2. 54048-10-1
3. 3-oxodesogestrel
4. Nexplanon
5. 3-ketodesogestrel
6. 3-keto-desogestrel
7. Org-3236
8. Org 3236
9. (8s,9s,10r,13s,14s,17r)-13-ethyl-17-ethynyl-17-hydroxy-11-methylidene-2,6,7,8,9,10,12,14,15,16-decahydro-1h-cyclopenta[a]phenanthren-3-one
10. 304gth6rnh
11. Chebi:50777
12. 18,19-dinorpregn-4-en-20-yn-3-one,13-ethyl-17-hydroxy-11-methylene-, (17a)-
13. Etonogestrelum
14. Implanon (tn)
15. Etonogestrel (usan/inn)
16. Unii-304gth6rnh
17. Etonogestrel [usan:inn:ban]
18. Ncgc00168777-01
19. Einecs 258-936-2
20. 17-ethinyl-17-beta-hydroxy-18-methyl-11-methylene-4-estren-3-one
21. Etonogestrel [mi]
22. Etonogestrel [inn]
23. Etonogestrel [usan]
24. 13-ethyl-17-hydroxy-11-methylene-18,19-dinor-17alpha-pregn-4-en-20-yn-3-one
25. Chembl1531
26. Dsstox_cid_26782
27. Dsstox_rid_81900
28. Etonogestrel [vandf]
29. Dsstox_gsid_46782
30. Desogestrel Impurity D
31. Etonogestrel [mart.]
32. Desogestrel Related Compound C
33. Etonogestrel [usp-rs]
34. Etonogestrel [who-dd]
35. Schembl117703
36. Gtpl7590
37. Dtxsid9046782
38. Etonogestrel (3-ketodesogestrel)
39. Etonogestrel, >=98% (hplc)
40. Etonogestrel [orange Book]
41. Bcp28481
42. Hy-b0652
43. 3-oxodesogestrel;3-keto-desogestrel
44. Tox21_112638
45. Bdbm50423516
46. S4673
47. Zinc11680067
48. Nuvaring Component Etonogestrel
49. 13-ethyl-11-methylene-18,19-dinor-17-alpha-pregn-4-en-20-yn-3-one
50. 17alpha-ethynyl-17beta-hydroxy-11-methylidene-18a-homo-estr-4-en-3-one
51. Ccg-267753
52. Db00294
53. (17-alpha)-13-ethyl-17-hydroxy-11-methylene-18,19-dinorpregn-4-en-20-yn-3-one
54. (17alpha)-13-ethyl-17-hydroxy-11-methylene-18,19-dinorpregn-4-en-20-yn-3-one
55. 18,19-dinorpregn-4-en-20-yn-3-one, 13-ethyl-17-hydroxy-11-methylene-, (17-alpha)-
56. Etonogestrel Component Of Nuvaring
57. Ncgc00168777-04
58. As-73246
59. Cas-54048-10-1
60. Desogestrel Impurity D [ep Impurity]
61. C75537
62. D04104
63. Desogestrel Related Compound C [usp-rs]
64. 048e101
65. A829925
66. Q3733839
67. Etonogestrel, United States Pharmacopeia (usp) Reference Standard
68. (17-alpha)-13-ethyl-17-hydroxy-11-methylene-18,19-dinorpregn-4-en-20-yn-3-on
69. 13-ethyl-17-hydroxy-11-methylene-18,19-dinor-17.alpha.-pregn-4-en-20-yn-3-one
70. 18,19-dinor-17alpha-pregn-4-en-20-yn-3-one, 13-ethyl-17-hydroxy-11-methylene-
71. Desogestrel Related Compound C, United States Pharmacopeia (usp) Reference Standard
72. (1r,3as,3bs,9ar,9bs,11as)-11a-ethyl-1-ethynyl-1-hydroxy-10-methylidene-1h,2h,3h,3ah,3bh,4h,5h,7h,8h,9h,9ah,9bh,10h,11h,11ah-cyclopenta[a]phenanthren-7-one
73. (1s,2r,10s,11s,14r,15s)-15-ethyl-14-ethynyl-14-hydroxy-17-methylidenetetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-6-en-5-one
74. (8s,9s,13s,14s,17r)-13-ethyl-17-ethynyl-17-hydroxy-11-methylene-6,7,8,9,10,11,12,13,14,15,16,17-dodecahydro-1h-cyclopenta[a]phenanthren-3(2h)-one
75. 13-ethyl-17-hydroxy-11-methylidene-18,19-dinor-17alpha-pregn-4-en-20-yn-3-one (3-ketodesogestrel)
76. 18,19-dinor-17.alpha.-pregn-4-en-20-yn-3-one, 13-ethyl-17-hydroxy-11-methylene-
| Molecular Weight | 324.5 g/mol |
|---|---|
| Molecular Formula | C22H28O2 |
| XLogP3 | 3.3 |
| Hydrogen Bond Donor Count | 1 |
| Hydrogen Bond Acceptor Count | 2 |
| Rotatable Bond Count | 2 |
| Exact Mass | 324.208930132 g/mol |
| Monoisotopic Mass | 324.208930132 g/mol |
| Topological Polar Surface Area | 37.3 Ų |
| Heavy Atom Count | 24 |
| Formal Charge | 0 |
| Complexity | 677 |
| Isotope Atom Count | 0 |
| Defined Atom Stereocenter Count | 6 |
| Undefined Atom Stereocenter Count | 0 |
| Defined Bond Stereocenter Count | 0 |
| Undefined Bond Stereocenter Count | 0 |
| Covalently Bonded Unit Count | 1 |
| 1 of 4 | |
|---|---|
| Drug Name | Implanon |
| PubMed Health | Etonogestrel (Implantation) |
| Drug Classes | Contraceptive, Progestin |
| Drug Label | IMPLANON (etonogestrel implant) is a progestin-only, soft, flexible implant preloaded in a sterile, disposable applicator for subdermal use. The implant is off-white, non-biodegradable and 4 cm in length with a diameter of 2 mm (see Figure 22). Each... |
| Active Ingredient | Etonogestrel |
| Dosage Form | Implant |
| Route | Implantation |
| Strength | 68mg/implant |
| Market Status | Prescription |
| Company | Organon Usa |
| 2 of 4 | |
|---|---|
| Drug Name | Nexplanon |
| PubMed Health | Etonogestrel (Implantation) |
| Drug Classes | Contraceptive, Progestin |
| Drug Label | NEXPLANON is a radiopaque, progestin-only, soft, flexible implant preloaded in a sterile, disposable applicator for subdermal use. The implant is white/off-white, non-biodegradable and 4 cm in length with a diameter of 2 mm (see Figure 18). Each impl... |
| Active Ingredient | Etonogestrel |
| Dosage Form | Implant |
| Route | Implantation |
| Strength | 68mg/implant |
| Market Status | Prescription |
| Company | Organon Usa |
| 3 of 4 | |
|---|---|
| Drug Name | Implanon |
| PubMed Health | Etonogestrel (Implantation) |
| Drug Classes | Contraceptive, Progestin |
| Drug Label | IMPLANON (etonogestrel implant) is a progestin-only, soft, flexible implant preloaded in a sterile, disposable applicator for subdermal use. The implant is off-white, non-biodegradable and 4 cm in length with a diameter of 2 mm (see Figure 22). Each... |
| Active Ingredient | Etonogestrel |
| Dosage Form | Implant |
| Route | Implantation |
| Strength | 68mg/implant |
| Market Status | Prescription |
| Company | Organon Usa |
| 4 of 4 | |
|---|---|
| Drug Name | Nexplanon |
| PubMed Health | Etonogestrel (Implantation) |
| Drug Classes | Contraceptive, Progestin |
| Drug Label | NEXPLANON is a radiopaque, progestin-only, soft, flexible implant preloaded in a sterile, disposable applicator for subdermal use. The implant is white/off-white, non-biodegradable and 4 cm in length with a diameter of 2 mm (see Figure 18). Each impl... |
| Active Ingredient | Etonogestrel |
| Dosage Form | Implant |
| Route | Implantation |
| Strength | 68mg/implant |
| Market Status | Prescription |
| Company | Organon Usa |
Etonogestrel is administered in subdermal implants as long-acting reversible contraception. It is known to be effective in postpartum insertion including breastfeeding women. Etonogestrel is part of the long-acting contraceptive implants that prevent pregnancy. The implant's effect can remain for 5 years.
FDA Label
Etonogestrel attains its therapeutic effect inhibiting fertility by impairing the release of the luteinizing hormone which is one of the most important reproductive hormones for ovulation. As well, etonogestrel is known to increase the viscosity of the cervical mucus hindering the passage of the spermatozoa and altering the lining in the uterus to prevent the implantation of the fertilized eggs in the endometrium. In clinical trials, etonogestrel was implanted and reported to avoid 100% of pregnancies over a three year period. When the implant was removed, normal periods were reinstalled within 90 days in 91% of the individuals. Fertility was established quickly with 20 reported pregnancies within 3 months of implant removal. The implants of etonogestrel release 40 mcg of etonogestrel daily and they usually provide a continuous contraception effect for 3 years. When the implant is administered, the failure rate is reported to be 0.1%. Some non-contraceptive effects are improved dysmenorrhea. All data of etonogestrel comes from patients between 80-130% of the body mass.
Contraceptive Agents, Female
Chemical substances or agents with contraceptive activity in females. Use for female contraceptive agents in general or for which there is no specific heading. (See all compounds classified as Contraceptive Agents, Female.)
Contraceptive Agents, Hormonal
Contraceptive agents that act on the ENDOCRINE SYSTEM. (See all compounds classified as Contraceptive Agents, Hormonal.)
G03AC08
S76 | LUXPHARMA | Pharmaceuticals Marketed in Luxembourg | Pharmaceuticals marketed in Luxembourg, as published by d'Gesondheetskeess (CNS, la caisse nationale de sante, www.cns.lu), mapped by name to structures using CompTox by R. Singh et al. (in prep.). List downloaded from https://cns.public.lu/en/legislations/textes-coordonnes/liste-med-comm.html. Dataset DOI:10.5281/zenodo.4587355
G - Genito urinary system and sex hormones
G03 - Sex hormones and modulators of the genital system
G03A - Hormonal contraceptives for systemic use
G03AC - Progestogens
G03AC08 - Etonogestrel
Absorption
Vaginal administration of etonogestrel is known to be significantly absorbed through the vaginal epithelium but it does not increase the levels of etonogestrel in the urine. On the other hand, oral administration is absorbed in the GI tract and it goes through the first-pass metabolism. When etonogestrel is administered subdermally it is absorbed rapidly into the bloodstream and it presents a bioavailability of 82%. It is reported that the implant releases around 60 mcg per day in the first 3 months and then decreases steady reaching a concentration of 30 mcg at the end of year 2.
Route of Elimination
The elimination of etonogestrel and its metabolites is mainly done renally.
Volume of Distribution
The apparent volume of distribution of etonogestrel is of around 201 L.
Clearance
The clearance rate of etonogestrel is reported to be of 7.5 L/h.
Etonogestrel is highly metabolized in the liver by the action of the cytochrome isoenzyme 3A4 mainly by the presence of hydroxylation, sulfate conjugation and glucuronide conjugation reactions.
The elimination half-life of etonogestrel is reported to be of 25 hours which indicates a reversible contraceptive effect.
Etonogestrel binds with high affinity to the progesterone and estrogen receptors in the target organs. From the target organs, they include the female reproductive tract, mammary gland, hypothalamus, and pituitary. Once bound, this drug changes the synthesis of different proteins which in order decreases the level of gonadotropin-releasing hormone and the luteinizing hormone.
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