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Etonogestrel

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8 FDA Orange Book
8 Europe
3 Canada
1 Australia
2 South Africa
1 Listed Dossiers

DRUG PRODUCT COMPOSITIONS

RING;VAGINAL - 0.015MG/24HR;0.12MG/24HR, IMPLANT;IMPLANTATION - 68MG/IMPLANT

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RING;VAGINAL - 0.015MG/24HR;0.12MG/24HR
IMPLANT;IMPLANTATION - 68MG/IMPLANT

RELATED EXCIPIENT COMPANIES

1 Faran Shimi Pharmaceutical, 1 Gangwal Healthcare, 1 Anhui Sunhere Pharmaceutical Excipients Co.,Ltd, 5 Microlex e.U, 1 Pluviaendo, 1 Prachin Chemical, 1 Shanghai Shenmei Pharmaceutical Technology Co., Ltd, 1 Vasa Pharmachem

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1 Prachin Chemical
1 Shanghai Shenmei Pharmaceutical Technology Co., Ltd
1 Vasa Pharmachem

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1 US Medicaid Prescriptions, 4 Finished Drug Prices, 15 Annual Reports

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ANALYTICAL

1 BioAnalytical Methods

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1 BioAnalytical Methods

Aspen Etonogestrel

Synopsis

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12 RELATED EXCIPIENT COMPANIES

18EXCIPIENTS BY APPLICATIONS

Chemistry

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Also known as: Implanon, 54048-10-1, 3-oxodesogestrel, Nexplanon, 3-ketodesogestrel, 3-keto-desogestrel

Molecular Formula

C₂₂H₂₈O₂

Molecular Weight

324.5 g/mol

InChI Key

GCKFUYQCUCGESZ-BPIQYHPVSA-N

FDA UNII

304GTH6RNH

Etonogestrel is a synthetic form of the naturally occurring female sex hormone progesterone. 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 is a Progestin.

1 2D Structure

Etonogestrel

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

(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

2.1.2 InChI

InChI=1S/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

2.1.3 InChI Key

GCKFUYQCUCGESZ-BPIQYHPVSA-N

2.1.4 Canonical SMILES

CCC12CC(=C)C3C(C1CCC2(C#C)O)CCC4=CC(=O)CCC34

2.1.5 Isomeric SMILES

CC[C@]12CC(=C)[C@H]3[C@H]([C@@H]1CC[C@]2(C#C)O)CCC4=CC(=O)CC[C@H]34

2.2 Other Identifiers

2.2.1 UNII

304GTH6RNH

2.3 Synonyms

2.3.1 MeSH Synonyms

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

2.3.2 Depositor-Supplied Synonyms

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-

2.4 Create Date

2006-07-28

3 Chemical and Physical Properties

Molecular Formula	C₂₂H₂₈O₂
Molecular Weight	324.5 g/mol
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 Å²
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

4 Drug and Medication Information

4.1 Drug Information

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

4.2 Drug Indication

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

5 Pharmacology and Biochemistry

5.1 Pharmacology

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.

5.2 MeSH Pharmacological Classification

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.)

5.3 FDA Pharmacological Classification

5.3.1 Active Moiety

ETONOGESTREL

5.3.2 FDA UNII

304GTH6RNH

5.3.3 Pharmacological Classes

Progestin [EPC]; Progesterone Congeners [CS]

5.4 ATC Code

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

5.5 Absorption, Distribution and Excretion

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.

5.6 Metabolism/Metabolites

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.

5.7 Biological Half-Life

The elimination half-life of etonogestrel is reported to be of 25 hours which indicates a reversible contraceptive effect.

5.8 Mechanism of Action

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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