Etonogestrel | ORG-3236 | CAS#54048-10-1 | steroidal progestin

MedKoo Cat#: 317857 | Name: Etonogestrel

Description:

WARNING: This product is for research use only, not for human or veterinary use.

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.

Chemical Structure

Etonogestrel

CAS#54048-10-1

Theoretical Analysis

MedKoo Cat#: 317857

Name: Etonogestrel

CAS#: 54048-10-1

Chemical Formula: C22H28O2

Exact Mass: 324.2089

Molecular Weight: 324.46

Elemental Analysis: C, 81.44; H, 8.70; O, 9.86

Price and Availability

Size	Price	Availability
10mg	USD 90.00	Ready to ship
25mg	USD 180.00	Ready to ship
50mg	USD 250.00	Ready to ship
100mg	USD 400.00	Ready to ship
200mg	USD 650.00	Ready to ship
500mg	USD 950.00	Ready to ship
1g	USD 1,550.00	Ready to ship
2g	USD 2,550.00	Ready to ship
5g	USD 3,450.00	Ready to ship

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Related CAS #

No Data

Synonym

ORG 3236; ORG-3236; ORG3236; 3-Keto-Org 2969; 3-keto-Desogestrel; 3-Ketodesogestrel; Etonogestrel; Implanon; 3-Oxodesogestrel; Nexplanon;

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

Product Data

Product Data

Certificate of Analysis

View CoA: current batch, Lot#A20T11K19

QC Data

View QC data: current batch, Lot#A20T11K19

Safety Data Sheet (SDS)

View Safety Data Sheet (SDS)

Instruction

View handling instruction

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	mg/mL	mM
Solubility
	DMSO	65.0	200.33
	Ethanol	13.5	41.61

Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

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:

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: Moray KV, Chaurasia H, Sachin O, Joshi B. A systematic review on clinical effectiveness, side-effect profile and meta-analysis on continuation rate of etonogestrel contraceptive implant. Reprod Health. 2021 Jan 6;18(1):4. doi: 10.1186/s12978-020-01054-y. PMID: 33407632; PMCID: PMC7788930. 2: Carvalho N, Margatho D, Cursino K, Benetti-Pinto CL, Bahamondes L. Control of endometriosis-associated pain with etonogestrel-releasing contraceptive implant and 52-mg levonorgestrel-releasing intrauterine system: randomized clinical trial. Fertil Steril. 2018 Nov;110(6):1129-1136. doi: 10.1016/j.fertnstert.2018.07.003. PMID: 30396557. 3: Dugré N, Choksi N, Kirkwood J. Etonogestrel implant effectiveness. Can Fam Physician. 2022 Aug;68(8):594. doi: 10.46747/cfp.6808594. PMID: 35961721; PMCID: PMC9374080. 4: Clermidy H, Fabre D, Hugues JN, Alonso CG, Mitilian D, Mercier O, Brenot P, Charbonneau P, Fadel E. Management of Etonogestrel implant migration into the pulmonary artery. Contraception. 2022 Sep;113:62-67. doi: 10.1016/j.contraception.2022.03.017. Epub 2022 Mar 26. PMID: 35351447. 5: Müller A, Sailer M, Colli E, Regidor PA. Safety, efficacy and quality of life of the novel vaginal contraceptive ring containing etonogestrel/ethinylestradiol 11.0/3.474 mg after 3 years of "real life" experience. Eur Rev Med Pharmacol Sci. 2020 Nov;24(22):11810-11819. doi: 10.26355/eurrev_202011_23838. PMID: 33275253. 6: Wong S, Naresh A. Etonogestrel Subdermal Implant-Associated Regression of Endometrial Intraepithelial Neoplasia. Obstet Gynecol. 2019 Apr;133(4):780-782. doi: 10.1097/AOG.0000000000003152. PMID: 30870304. 7: Rosenthal MA, McQuillan SK. Adolescent contraception. CMAJ. 2021 Aug 9;193(31):E1218. doi: 10.1503/cmaj.202413. PMID: 34373270; PMCID: PMC8367427. 8: Kreitchmann R, Stek A, Best BM, Capparelli E, Wang J, Shapiro D, Chakhtoura N, Mirochnick M, Eke AC; IMPAACT P1026s protocol team. Interactions between etonogestrel-releasing contraceptive implant and 3 antiretroviral regimens. Contraception. 2022 Jan;105:67-74. doi: 10.1016/j.contraception.2021.08.006. Epub 2021 Aug 15. PMID: 34407424; PMCID: PMC8678338. 9: Etonogestrel implant (Implanon) for contraception. Drug Ther Bull. 2001 Aug;39(8):57-9. PMID: 11526801. 10: Petro G, Spence T, Patel M, Gertz AM, Morroni C. Difficult etonogestrel implant removals in South Africa: A review of 74 referred cases. Contraception. 2020 Aug;102(2):129-132. doi: 10.1016/j.contraception.2020.04.013. Epub 2020 Apr 24. PMID: 32339484; PMCID: PMC8221391. 11: Zigler RE, McNicholas C. Unscheduled vaginal bleeding with progestin-only contraceptive use. Am J Obstet Gynecol. 2017 May;216(5):443-450. doi: 10.1016/j.ajog.2016.12.008. Epub 2016 Dec 14. PMID: 27988268. 12: In brief: etonogestrel (nexplanon) contraceptive implant. Med Lett Drugs Ther. 2012 Feb 6;54(1383):12. PMID: 22354222. 13: Bahamondes L, Brache V, Ali M, Habib N; WHO study group on contraceptive implants for women. A multicenter randomized clinical trial of etonogestrel and levonorgestrel contraceptive implants with nonrandomized copper intrauterine device controls: effect on weight variations up to 3 years after placement. Contraception. 2018 Sep;98(3):181-187. doi: 10.1016/j.contraception.2018.05.009. Epub 2018 May 16. PMID: 29777663. 14: Berlan ED, Richards MJ, Vieira CS, Creinin MD, Kaunitz AM, Fraser IS, Edelman A, Mansour D. Best Practices for Counseling Adolescents about the Etonogestrel Implant. J Pediatr Adolesc Gynecol. 2020 Oct;33(5):448-454. doi: 10.1016/j.jpag.2020.06.022. Epub 2020 Jul 2. PMID: 32621879. 15: Wagner MS, Arias RD, Nucatola DL. The combined etonogestrel/ethinyl estradiol contraceptive vaginal ring. Expert Opin Pharmacother. 2007 Aug;8(11):1769-77. doi: 10.1517/14656566.8.11.1769. PMID: 17685892. 16: Rodrigues ML, Branco R, Landim E. Ectopic pregnancy with etonogestrel implant. BMJ Case Rep. 2021 Nov 16;14(11):e245175. doi: 10.1136/bcr-2021-245175. PMID: 34785516; PMCID: PMC8596039. 17: Lew J, Sheeder J, Lazorwitz A. Etonogestrel contraceptive implant uptake and safety among solid organ transplant recipients. Contraception. 2021 Nov;104(5):556-560. doi: 10.1016/j.contraception.2021.06.007. Epub 2021 Jun 18. PMID: 34147509; PMCID: PMC8502202. 18: Varma R, Mascarenhas L. Endometrial effects of etonogestrel (Implanon) contraceptive implant. Curr Opin Obstet Gynecol. 2001 Jun;13(3):335-41. doi: 10.1097/00001703-200106000-00015. PMID: 11396660. 19: Chapa HO, Ramirez A, Dawson D. Etonogestrel contraceptive implant-associated secondary anorgasmia. Contraception. 2017 Oct;96(4):254-256. doi: 10.1016/j.contraception.2017.06.008. Epub 2017 Jun 27. PMID: 28666796. 20: Lazorwitz A, Pena M, Sheeder J, Teal S. Effect of Topiramate on Serum Etonogestrel Concentrations Among Contraceptive Implant Users. Obstet Gynecol. 2022 Apr 1;139(4):579-587. doi: 10.1097/AOG.0000000000004697. Epub 2022 Mar 10. PMID: 35594123; PMCID: PMC9140306.