Norethynodrel | CAS#68-23-5 | Synthetic progestin

MedKoo Cat#: 464018 | Name: Norethynodrel

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Description:

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

Noretynodrel, or norethynodrel, sold under the brand name Enovid among others, is a progestin medication which was previously used in birth control pills and in the treatment of gynecological disorders but is now no longer marketed. It was available both alone and in combination with an estrogen. The medication is taken by mouth.

Chemical Structure

Norethynodrel

CAS#68-23-5

Theoretical Analysis

MedKoo Cat#: 464018

Name: Norethynodrel

CAS#: 68-23-5

Chemical Formula: C20H26O2

Exact Mass: 298.1933

Molecular Weight: 298.43

Elemental Analysis: C, 80.50; H, 8.78; O, 10.72

Price and Availability

Size	Price	Availability	Quantity
1mg	USD 350.00	2 Weeks
5mg	USD 950.00	2 Weeks

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Related CAS #

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Synonym

Norethynodrel; Noretynodrel; Norethinodrel; NSC 15432; NSC15432; NSC-15432; SC-4642; SC4642; SC 4642;

IUPAC/Chemical Name

(8R,9S,13S,14S,17R)-17-ethynyl-17-hydroxy-13-methyl-1,2,4,6,7,8,9,11,12,13,14,15,16,17-tetradecahydro-3H-cyclopenta[a]phenanthren-3-one

InChi Key

ICTXHFFSOAJUMG-SLHNCBLASA-N

InChi Code

InChI=1S/C20H26O2/c1-3-20(22)11-9-18-17-6-4-13-12-14(21)5-7-15(13)16(17)8-10-19(18,20)2/h1,16-18,22H,4-12H2,2H3/t16-,17-,18+,19+,20+/m1/s1

SMILES Code

C[C@]12CC[C@H]3[C@H]([C@@H]1CC[C@]2(C#C)O)CCC4=C3CCC(C4)=O

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

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

Instruction

View handling instruction

Biological target:

Norethynodrel (Enidre) is a 19-nortestosterone derivative to be used as a progestagen.

In vitro activity:

TBD

In vivo activity:

TBD

	Solvent	mg/mL	mM
Solubility
	Soluble in DMSO	0.0	100.00

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 298.43 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:

TBD

In vitro protocol:

TBD

In vivo protocol:

TBD

1: Drugs and Lactation Database (LactMed) [Internet]. Bethesda (MD): National Library of Medicine (US); 2006–. Norethynodrel. 2020 Dec 21. PMID: 30000402. 2: Penning TM, Chen M, Jin Y. Promiscuity and diversity in 3-ketosteroid reductases. J Steroid Biochem Mol Biol. 2015 Jul;151:93-101. doi: 10.1016/j.jsbmb.2014.12.003. Epub 2014 Dec 10. PMID: 25500069; PMCID: PMC4458445. 3: Jayaraman A, Pike CJ. Differential effects of synthetic progestagens on neuron survival and estrogen neuroprotection in cultured neurons. Mol Cell Endocrinol. 2014 Mar 25;384(1-2):52-60. doi: 10.1016/j.mce.2014.01.003. Epub 2014 Jan 11. PMID: 24424444; PMCID: PMC3954450. 4: Kubli-Garfias C, González-Flores O, Gómora-Arrati P, González-Mariscal G, Vázquez-Ramírez R, Beyer C. Bimodal binding and free energy of the progesterone receptor in the induction of female sexual receptivity by progesterone and synthetic progestins. J Steroid Biochem Mol Biol. 2013 Jan;133:43-50. doi: 10.1016/j.jsbmb.2012.08.010. Epub 2012 Aug 31. PMID: 22960752. 5: Jin Y, Duan L, Chen M, Penning TM, Kloosterboer HJ. Metabolism of the synthetic progestogen norethynodrel by human ketosteroid reductases of the aldo- keto reductase superfamily. J Steroid Biochem Mol Biol. 2012 Apr;129(3-5):139-44. doi: 10.1016/j.jsbmb.2011.12.002. Epub 2011 Dec 28. PMID: 22210085; PMCID: PMC3303946. 6: Balssa F, Fischer M, Bonnaire Y. Easy stereoselective synthesis of 5α-estrane-3β,17α-diol, the major metabolite of nandrolone in the horse. Steroids. 2011 Jun;76(7):667-8. doi: 10.1016/j.steroids.2011.03.004. Epub 2011 Mar 16. PMID: 21419146. 7: Liu L, Zhao L, She H, Chen S, Wang JM, Wong C, McClure K, Sitruk-Ware R, Brinton RD. Clinically relevant progestins regulate neurogenic and neuroprotective responses in vitro and in vivo. Endocrinology. 2010 Dec;151(12):5782-94. doi: 10.1210/en.2010-0005. Epub 2010 Oct 13. PMID: 20943809; PMCID: PMC2999493. 8: Freyberger A, Wilson V, Weimer M, Tan S, Tran HS, Ahr HJ. Assessment of a robust model protocol with accelerated throughput for a human recombinant full length estrogen receptor-alpha binding assay: protocol optimization and intralaboratory assay performance as initial steps towards validation. Reprod Toxicol. 2010 Aug;30(1):50-9. doi: 10.1016/j.reprotox.2010.01.001. Epub 2010 Jan 13. PMID: 20074635. 9: Freyberger A, Witters H, Weimer M, Lofink W, Berckmans P, Ahr HJ. Screening for (anti)androgenic properties using a standard operation protocol based on the human stably transfected androgen sensitive PALM cell line. First steps towards validation. Reprod Toxicol. 2010 Aug;30(1):9-17. doi: 10.1016/j.reprotox.2009.10.002. Epub 2009 Oct 27. PMID: 19836445. 10: Freyberger A, Weimer M, Tran HS, Ahr HJ. Assessment of a recombinant androgen receptor binding assay: initial steps towards validation. Reprod Toxicol. 2010 Aug;30(1):2-8. doi: 10.1016/j.reprotox.2009.10.001. Epub 2009 Oct 13. PMID: 19833195. 11: Oesterheld JR, Cozza K, Sandson NB. Oral contraceptives. Psychosomatics. 2008 Mar-Apr;49(2):168-75. doi: 10.1176/appi.psy.49.2.168. PMID: 18354071. 12: Kuhl H, Wiegratz I. Can 19-nortestosterone derivatives be aromatized in the liver of adult humans? Are there clinical implications? Climacteric. 2007 Aug;10(4):344-53. doi: 10.1080/13697130701380434. PMID: 17653961. 13: Sinkkonen J, Liimatainen J, Karonen M, Wiinamäki K, Eklund P, Sjöholm R, Pihlaja K. A sesquineolignan with a spirodienone structure from Pinus sylvestris L. Angew Chem Int Ed Engl. 2007;46(22):4148-50. doi: 10.1002/anie.200605115. PMID: 17455178. 14: Notelovitz M. Postmenopausal tibolone therapy: biologic principles and applied clinical practice. MedGenMed. 2007 Jan 3;9(1):2. PMID: 17435612; PMCID: PMC1924982. 15: Raobaikady B, Parsons MF, Reed MJ, Purohit A. Lack of aromatisation of the 3-keto-4-ene metabolite of tibolone to an estrogenic derivative. Steroids. 2006 Jul;71(7):639-46. doi: 10.1016/j.steroids.2006.03.006. Epub 2006 May 18. PMID: 16712888. 16: Djerassi C. Chemical birth of the pill. 1992. Am J Obstet Gynecol. 2006 Jan;194(1):290-8. doi: 10.1016/j.ajog.2005.06.010. PMID: 16389046. 17: Siddique YH, Afzal M. Evaluation of genotoxic potential of norethynodrel in human lymphocytes in vitro. J Environ Biol. 2005 Jun;26(2 Suppl):387-92. PMID: 16334272. 18: Zuo M, Gao MJ, Liu Z, Cai L, Duan GL. Stereoselectivity in metabolic 3-reduction of tibolone in healthy Chinese female volunteers. Acta Pharmacol Sin. 2005 Dec;26(12):1527-30. doi: 10.1111/j.1745-7254.2005.00228.x. PMID: 16297354. 19: Brodeur JC, Woodburn KB, Klecka GM. Potentiation of the vitellogenic response to 17alpha-ethinylestradiol by cortisol in the fathead minnow Pimephales promelas. Environ Toxicol Chem. 2005 May;24(5):1125-32. doi: 10.1897/04-309r.1. PMID: 16110990. 20: Fenske M, Maack G, Schäfers C, Segner H. An environmentally relevant concentration of estrogen induces arrest of male gonad development in zebrafish, Danio rerio. Environ Toxicol Chem. 2005 May;24(5):1088-98. doi: 10.1897/04-096r1.1. PMID: 16110986.