Norgestrel | CAS#6533-00-2 | steroid

MedKoo Cat#: 584397 | Name: Norgestrel

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Description:

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

Norgestrel is a synthetic progestin used primarily in hormonal contraceptives and exhibits high progestational activity via binding to the human progesterone receptor (PR). It acts as a full agonist with a binding affinity (Ki) of approximately 5–10 nM for the PR, and displays minimal to no estrogenic or androgenic activity at therapeutic concentrations. Norgestrel also binds weakly to androgen receptors (AR), with a Ki of ~100–300 nM, contributing to mild androgenic effects in some users. It shows negligible glucocorticoid or mineralocorticoid receptor activity. In vitro assays and receptor-binding studies confirm its potency in suppressing ovulation, primarily through negative feedback on the hypothalamic-pituitary-gonadal axis, reducing luteinizing hormone (LH) and follicle-stimulating hormone (FSH) levels. Norgestrel is used clinically in both racemic form and as its biologically active levo-isomer, levonorgestrel, which is about twice as potent.

Chemical Structure

Norgestrel

CAS#6533-00-2

Theoretical Analysis

MedKoo Cat#: 584397

Name: Norgestrel

CAS#: 6533-00-2

Chemical Formula: C21H28O2

Exact Mass: 312.2089

Molecular Weight: 312.45

Elemental Analysis: C, 80.73; H, 9.03; O, 10.24

Price and Availability

Size	Price	Availability
500mg	USD 350.00	2 Weeks
1g	USD 550.00	2 Weeks
2g	USD 950.00	2 Weeks
5g	USD 1,650.00	2 Weeks

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Related CAS #

797-64-8 (rotation+) 6533-00-2

Synonym

Norgestrel; SH 70850; SH 850; Wy 3707; Wy-3707; FH 122-A

IUPAC/Chemical Name

dl-13-beta-Ethyl-17-alpha-ethynyl-17-beta-hydroxygon-4-en-3-one

InChi Key

WWYNJERNGUHSAO-XUDSTZEESA-N

InChi Code

InChI=1S/C21H28O2/c1-3-20-11-9-17-16-8-6-15(22)13-14(16)5-7-18(17)19(20)10-12-21(20,23)4-2/h2,13,16-19,23H,3,5-12H2,1H3/t16-,17+,18+,19-,20-,21-/m0/s1

SMILES Code

O=C1CC[C@]2([H])[C@@]3([H])CC[C@]4(CC)[C@](O)(C#C)CC[C@@]4([H])[C@]3([H])CCC2=C1

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:

Norgestrel is a synthetic progestational agent with actions similar to those of PROGESTERONE.

In vitro activity:

This work identifies the potential of Norgestrel to rescue stressed 661W photoreceptor-like cells and ex vivo retinal explants from cell death over 24 h. Analysis of 661W cells in vitro by real-time polymerase chain reaction (rt-PCR), enzyme-linked immunosorbent assay (ELISA) and Western blotting revealed an upregulation of bFGF in response to Norgestrel over 6 h. Furthermore, Norgestrel initiated a bFGF-dependent inactivation of glycogen synthase kinase 3β (GSK3β) through phosphorylation at serine 9. The effects of Norgestrel on GSK3β were dependent on protein kinase A (PKA) pathway activation. Specific inhibition of both the PKA and GSK3β pathways prevented Norgestrel-mediated neuroprotection of stressed photoreceptor cells in vitro. Reference: Eur J Neurosci. 2016 Apr;43(7):899-911. https://pubmed.ncbi.nlm.nih.gov/26750157/

In vivo activity:

Using the well-established rd10 mouse model of RP, this study administered a norgestrel-supplemented diet at postnatal day (P)30, following widespread loss of rod photoreceptors and at the outset of cone degeneration. While cone cell degeneration was widespread in the untreated rd10 retina, this study observed profound preservation of cone photoreceptor morphology in the norgestrel-treated mice for at least 50 days, out to P80. Reference: Invest Ophthalmol Vis Sci. 2019 Jul 1;60(8):3221-3235. https://pubmed.ncbi.nlm.nih.gov/31335948/

	Solvent	mg/mL	mM
Solubility
	DMF	10.0	32.01
	DMF:PBS (pH 7.2) (1:6)	0.3	0.80
	DMSO	55.7	178.16
	Ethanol	10.6	34.01

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 312.45 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. Byrne AM, Ruiz-Lopez AM, Roche SL, Moloney JN, Wyse-Jackson AC, Cotter TG. The synthetic progestin norgestrel modulates Nrf2 signaling and acts as an antioxidant in a model of retinal degeneration. Redox Biol. 2016 Dec;10:128-139. doi: 10.1016/j.redox.2016.10.002. Epub 2016 Oct 4. PMID: 27744118; PMCID: PMC5065647. 2. Wyse Jackson AC, Cotter TG. The synthetic progesterone Norgestrel is neuroprotective in stressed photoreceptor-like cells and retinal explants, mediating its effects via basic fibroblast growth factor, protein kinase A and glycogen synthase kinase 3β signalling. Eur J Neurosci. 2016 Apr;43(7):899-911. doi: 10.1111/ejn.13166. Epub 2016 Feb 11. PMID: 26750157. 3. Roche SL, Kutsyr O, Cuenca N, Cotter TG. Norgestrel, a Progesterone Analogue, Promotes Significant Long-Term Neuroprotection of Cone Photoreceptors in a Mouse Model of Retinal Disease. Invest Ophthalmol Vis Sci. 2019 Jul 1;60(8):3221-3235. doi: 10.1167/iovs.19-27246. PMID: 31335948.

In vitro protocol:

In vivo protocol:

1. Roche SL, Kutsyr O, Cuenca N, Cotter TG. Norgestrel, a Progesterone Analogue, Promotes Significant Long-Term Neuroprotection of Cone Photoreceptors in a Mouse Model of Retinal Disease. Invest Ophthalmol Vis Sci. 2019 Jul 1;60(8):3221-3235. doi: 10.1167/iovs.19-27246. PMID: 31335948.

1: Bifano M, Sevinsky H, Hwang C, Kandoussi H, Jiang H, Grasela D, Bertz R. Effect of the coadministration of daclatasvir on the pharmacokinetics of a combined oral contraceptive containing ethinyl estradiol and norgestimate. Antivir Ther. 2014;19(5):511-9. doi: 10.3851/IMP2718. Epub 2013 Dec 17. PubMed PMID: 24343001. 2: Larrañaga A, Sartoretto JN, Winterhalter M, Navas Filho F. Clinical evaluation of two biphasic and one triphasic norgestrel/ethinyl estradiol regimens. Int J Fertil. 1978;23(3):193-9. PubMed PMID: 40893. 3: Kaunitz AM, Archer DF, Mishell DR Jr, Foegh M. Safety and tolerability of a new low-dose contraceptive patch in obese and nonobese women. Am J Obstet Gynecol. 2015 Mar;212(3):318.e1-8. doi: 10.1016/j.ajog.2014.09.014. Epub 2014 Sep 16. PubMed PMID: 25220709. 4: Fåhraeus L, Larsson-Cohn U, Wallentin L. L-norgestrel and progesterone have different influences on plasma lipoproteins. Eur J Clin Invest. 1983 Dec;13(6):447-53. PubMed PMID: 6416861. 5: Sánchez-Borrego R, Balasch J. Ethinyl oestradiol plus dl-norgestrel or levonorgestrel in the Yuzpe method for post-coital contraception: results of an observational study. Hum Reprod. 1996 Nov;11(11):2449-53. PubMed PMID: 8981131. 6: Yuzpe AA, Lancee WJ. Ethinylestradiol and dl-norgestrel as a postcoital contraceptive. Fertil Steril. 1977 Sep;28(9):932-6. PubMed PMID: 892044. 7: Elder MG, Myatt L, Chaudhuri G. The effect of norgestrel and clogestone on the spontaneous motility of the human fallopian tube. Int J Fertil. 1978;23(1):61-4. PubMed PMID: 30711. 8: El-Mahgoub. D-norgestrel slow-releasing T device as an intrauterine contraceptive. Am J Obstet Gynecol. 1975 Sep 15;123(2):133-8. PubMed PMID: 1163576. 9: Hagag P, Steinschneider M, Weiss M. Role of the combination spironolactone-norgestimate-estrogen in Hirsute women with polycystic ovary syndrome. J Reprod Med. 2014 Sep-Oct;59(9-10):455-63. PubMed PMID: 25330687. 10: Bateson D, McNamee K, Briggs P. Newer non-oral hormonal contraception. BMJ. 2013 Feb 14;346:f341. doi: 10.1136/bmj.f341. PubMed PMID: 23412438. 11: Yuzpe AA, Smith RP, Rademaker AW. A multicenter clinical investigation employing ethinyl estradiol combined with dl-norgestrel as postcoital contraceptive agent. Fertil Steril. 1982 Apr;37(4):508-13. PubMed PMID: 7040117. 12: Darwish M, Bond M, Ricciotti N, Hsieh J, Fiedler-Kelly J, Grasela T. A comparison of the pharmacokinetic profile of an ascending-dose, extended-regimen combined oral contraceptive to those of other extended regimens. Reprod Sci. 2014 Nov;21(11):1401-10. doi: 10.1177/1933719114526472. Epub 2014 Mar 19. PubMed PMID: 24647707. 13: Lamparczyk H, Zarzycki PK, Nowakowska J. Effect of temperature on separation of norgestrel enantiomers by high-performance liquid chromatography. J Chromatogr A. 1994 May 13;668(2):413-7. PubMed PMID: 8032490. 14: Schmutz JL, Barbaud A, Trechot P. [Systemic photosensibility and contraception]. Ann Dermatol Venereol. 2011;138(4):367-8. doi: 10.1016/j.annder.2010.12.011. Epub 2011 Jan 22. French. PubMed PMID: 21497270. 15: Bukvic N, Susca F, Bukvic D, Fanelli M, Guanti G. 17-alpha-ethinylestradiol and norgestrel in combination induce micronucleus increases and aneuploidy in human lymphocyte and fibroblast cultures. Teratog Carcinog Mutagen. 2000;20(3):147-59. PubMed PMID: 10820425. 16: Hümpel M, Kühne G, Schulze PE, Speck U. Injectable depot contraceptives on d-norgestrel basis. I. Pharmacokinetic studies in dog and baboons. Contraception. 1977 Apr;15(4):401-12. PubMed PMID: 880816. 17: Song IH, Borland J, Chen S, Wajima T, Peppercorn AF, Piscitelli SC. Dolutegravir Has No Effect on the Pharmacokinetics of Oral Contraceptives With Norgestimate and Ethinyl Estradiol. Ann Pharmacother. 2015 Jul;49(7):784-9. doi: 10.1177/1060028015580637. Epub 2015 Apr 10. PubMed PMID: 25862012; PubMed Central PMCID: PMC4472613. 18: Borsos A, Lampé L. [Contraception with d-norgestrel]. Orv Hetil. 1980 Jun 22;121(25):1495-8. Hungarian. PubMed PMID: 7454258. 19: Blye RP, Kim HK, Lindberg MC, Mitra SB, Naqvi RH, Peterson DM, Rao PN. Development and use of a radioimmunoassay for D-(-)-norgestrel 17 beta-cyclopentanecarboxylate. Steroids. 1986 Jul-Aug;48(1-2):27-45. PubMed PMID: 3660438. 20: McQuarrie HG, Harris JW, Ellsworth HS, Stone RA, Anderson AE 3rd. Evaluation of d-norgestrel 1.0 mg in cyclic regimen. J Reprod Med. 1973 Apr;10(4):200-2. PubMed PMID: 4695502.