WARNING: This product is for research use only, not for human or veterinary use.
Hodoodo CAT#: H317857
CAS#: 54048-10-1
Description: Etonogestrel is a steroidal progestin used in hormonal contraceptives, most notably the subdermal implant Nexplanon and the vaginal ring NuvaRing. Etonogestrel is the active metabolite of the inactive prodrug desogestrel, one of two third-generation progestins found in some epidemiological studies of combined oral contraceptive pills to be associated with a higher risk of venous thrombosis than combined oral contraceptive pills containing certain second-generation progestins. Because hormones are released continuously from NuvaRing, peak and total estrogen and progestin doses are significantly lower than with combined oral contraceptives, although it is not known whether this lowers the risk of blood clots. It is effective within the first 24 hours. Antibiotics make it less effective.
Hodoodo Cat#: H317857
Name: Etonogestrel
CAS#: 54048-10-1
Chemical Formula: C22H28O2
Exact Mass: 324.21
Molecular Weight: 324.460
Elemental Analysis: C, 81.44; H, 8.70; O, 9.86
Synonym: ORG 3236; ORG-3236; ORG3236; Etonogestrel, Implanon, nexplanon, 3-keto-desogestrel, 3-ketodesogestrel, 3-oxo desogestrel, 3-oxodesogestrel
IUPAC/Chemical 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
InChi Key: GCKFUYQCUCGESZ-BPIQYHPVSA-N
InChi Code: 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
SMILES Code: CC[C@]12CC(=C)[C@H]3[C@H]([C@@H]1CC[C@]2(C#C)O)CCC4=CC(=O)CC[C@H]34
Appearance: Solid powder
Purity: >98% (or refer to the Certificate of Analysis)
Shipping Condition: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility: Soluble in DMSO, not in water
Shelf Life: >2 years if stored properly
Drug Formulation: This drug may be formulated in DMSO
Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code: 2934.99.9001
More Info:
| Biological target: | Etonogestrel (Implanon, Nexplanon, 3-Oxodesogestrel, 3-keto-Desogestrel) binds to the cytoplasmic progesterone receptors in the reproductive system and subsequently activates progesterone receptor mediated gene expression. |
| In vitro activity: | As demonstrated in Figure 1A, MPA exerted a significant inhibitory effect on the production of IFNγ by CD2/CD3/CD28-stimulated PBMCs at a concentration of 10−8 M and higher. At 10−6 M, ETG (Etonogestrel) displayed a significant inhibition of T cell function compared to untreated control but not compared to cells treated with P4. Reference: Contraception. 2014 Aug; 90(2): 123–129. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4874781/ |
| In vivo activity: | The main result of this study is that under metabolic acidosis conditions, in DBS preparations, ETO (Etonogestrel) induced a significant strengthening of the increase in fR compared to that observed in DBS preparations exposed to DMSO (approximately +50%; +78.22 ± 21.91%, n = 7 with ETO vs. +27.84 ± 5.66%, n = 7 with DMSO, p < 0.001; Fig. 3(D1 and D2 and C1 and C2)) and compared to that observed in DBS preparations superfused with free-DMSO/free-ETO-metabolic acidosis-aCSF (approximately +42%; +78.22 ± 21.91%, n = 7 with ETO vs. +36.08 ± 8.85%, n = 7 with free-DMSO/free-ETO, p < 0.01). Thus, ETO may act on one or more of these structures and activate or over-activate a supramedullary mechanism. Reference: Neurosci Lett. 2014 May 1;567:63-7. https://pubmed.ncbi.nlm.nih.gov/24686181/ |
| Solvent | Max Conc. mg/mL | Max Conc. mM | |
|---|---|---|---|
| Solubility | |||
| DMSO | 65.0 | 200.33 | |
| Ethanol | 13.5 | 41.61 |
The following data is based on the product molecular weight 324.46 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.
| Concentration / Solvent Volume / Mass | 1 mg | 5 mg | 10 mg |
|---|---|---|---|
| 1 mM | 1.15 mL | 5.76 mL | 11.51 mL |
| 5 mM | 0.23 mL | 1.15 mL | 2.3 mL |
| 10 mM | 0.12 mL | 0.58 mL | 1.15 mL |
| 50 mM | 0.02 mL | 0.12 mL | 0.23 mL |
| Formulation protocol: | 1. Huijbregts RP, Michel KG, Hel Z. Effect of progestins on immunity: medroxyprogesterone but not norethisterone or levonorgestrel suppresses the function of T cells and pDCs. Contraception. 2014 Aug;90(2):123-9. doi: 10.1016/j.contraception.2014.02.006. Epub 2014 Feb 26. Erratum in: Contraception. 2016 Nov;94(5):578. PMID: 24674041; PMCID: PMC4874781. 3. Loiseau C, Osinski D, Joubert F, Straus C, Similowski T, Bodineau L. The progestin etonogestrel enhances the respiratory response to metabolic acidosis in newborn rats. Evidence for a mechanism involving supramedullary structures. Neurosci Lett. 2014 May 1;567:63-7. doi: 10.1016/j.neulet.2014.03.040. Epub 2014 Mar 29. PMID: 24686181. 4. Tasdemir N, Kilic S, Lortlar N, Yuksel B, Goker U, Ozaksit G. Time dependent influence of etonogestrel on the caspase-3 immunoreactivity and apoptotic indexes of rat uterus and ovaries. Gynecol Endocrinol. 2012 Jun;28(6):463-7. doi: 10.3109/09513590.2011.633652. Epub 2012 Feb 17. PMID: 22578029. |
| In vitro protocol: | 1. Huijbregts RP, Michel KG, Hel Z. Effect of progestins on immunity: medroxyprogesterone but not norethisterone or levonorgestrel suppresses the function of T cells and pDCs. Contraception. 2014 Aug;90(2):123-9. doi: 10.1016/j.contraception.2014.02.006. Epub 2014 Feb 26. Erratum in: Contraception. 2016 Nov;94(5):578. PMID: 24674041; PMCID: PMC4874781. |
| In vivo protocol: | 1. Loiseau C, Osinski D, Joubert F, Straus C, Similowski T, Bodineau L. The progestin etonogestrel enhances the respiratory response to metabolic acidosis in newborn rats. Evidence for a mechanism involving supramedullary structures. Neurosci Lett. 2014 May 1;567:63-7. doi: 10.1016/j.neulet.2014.03.040. Epub 2014 Mar 29. PMID: 24686181. 2. Tasdemir N, Kilic S, Lortlar N, Yuksel B, Goker U, Ozaksit G. Time dependent influence of etonogestrel on the caspase-3 immunoreactivity and apoptotic indexes of rat uterus and ovaries. Gynecol Endocrinol. 2012 Jun;28(6):463-7. doi: 10.3109/09513590.2011.633652. Epub 2012 Feb 17. PMID: 22578029. |
1: In brief: etonogestrel (nexplanon) contraceptive implant. Med Lett Drugs Ther. 2012 Feb 6;54(1383):12. Review. PubMed PMID: 22354222.
2: Mansour D, Bahamondes L, Critchley H, Darney P, Fraser IS. The management of unacceptable bleeding patterns in etonogestrel-releasing contraceptive implant users. Contraception. 2011 Mar;83(3):202-10. doi: 10.1016/j.contraception.2010.08.001. Epub 2010 Sep 17. Review. PubMed PMID: 21310280.
3: Wagner MS, Arias RD, Nucatola DL. The combined etonogestrel/ethinyl estradiol contraceptive vaginal ring. Expert Opin Pharmacother. 2007 Aug;8(11):1769-77. Review. PubMed PMID: 17685892.
4: Gaffield ME, Curtis KM, Mohllajee AP, Peterson HB. Medical eligibility criteria for new contraceptive methods: combined hormonal patch, combined hormonal vaginal ring and the etonogestrel implant. Contraception. 2006 Feb;73(2):134-44. Epub 2005 Oct 20. Review. PubMed PMID: 16413844.
5: Etonogestrel implant (Implanon) for contraception. Drug Ther Bull. 2001 Aug;39(8):57-9. Review. PubMed PMID: 11526801.
6: Varma R, Mascarenhas L. Endometrial effects of etonogestrel (Implanon) contraceptive implant. Curr Opin Obstet Gynecol. 2001 Jun;13(3):335-41. Review. PubMed PMID: 11396660.
7: Bennink HJ. The pharmacokinetics and pharmacodynamics of Implanon, a single-rod etonogestrel contraceptive implant. Eur J Contracept Reprod Health Care. 2000 Sep;5 Suppl 2:12-20. Review. PubMed PMID: 11246602.
