Norethindrone acetate | CAS#51-98-9 | conraceptive

MedKoo Cat#: 599152 | Name: Norethindrone acetate

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Description:

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

Norethindrone acetate is used in combination with estrogen as a contraceptive (oral). It is reasonably anticipated to be a human carcinogen.

Chemical Structure

Norethindrone acetate

CAS#51-98-9 (acetate)

Theoretical Analysis

MedKoo Cat#: 599152

Name: Norethindrone acetate

CAS#: 51-98-9 (acetate)

Chemical Formula: C22H28O3

Exact Mass: 340.2038

Molecular Weight: 340.46

Elemental Analysis: C, 77.61; H, 8.29; O, 14.10

Price and Availability

Size	Price	Availability	Quantity
100mg	USD 285.00	2 weeks
500mg	USD 550.00	2 weeks

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Related CAS #

51-98-9 (acetate) 53016-31-2

Synonym

Norethindrone acetate; ENTA; NSC 22844; NSC-22844; NSC22844; Primolut-Nor;

IUPAC/Chemical Name

(8R,9S,10R,13S,14S,17S)-17-ethynyl-13-methyl-3-oxo-2,3,6,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl acetate

InChi Key

IMONTRJLAWHYGT-REGVOWLASA-N

InChi Code

InChI=1S/C22H28O3/c1-4-22(25-14(2)23)12-10-20-19-7-5-15-13-16(24)6-8-17(15)18(19)9-11-21(20,22)3/h1,13,17-20H,5-12H2,2-3H3/t17-,18+,19+,20-,21-,22+/m0/s1

SMILES Code

C#C[C@@]1(OC(C)=O)CC[C@@]2([H])[C@]3([H])CCC4=CC(CC[C@]4([H])[C@@]3([H])CC[C@]12C)=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

>3 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

2934.99.03.00

More Info

Product Data

Product Data

Instruction

View handling instruction

Biological target:

Norethindrone acetate is a female hormone used for the research of endometriosis.

In vitro activity:

Assays of cell viability, proliferation, migration, apoptosis, and colony formation were performed to investigate the pro-tumorigenesis effect of NET (norethisterone) and the effects of miR-181a on human breast epithelial MCF10A cells. NET significantly increased MCF10A cell viability, proliferation, migration, and colony formation, but reduced cellular apoptosis. In addition, NET increased the expression of progesterone receptor membrane component 1 (PGRMC1), EGFR, B-cell lymphoma 2, cyclin D1, and proliferating cell nuclear antigen, but decreased the expression of pro-apoptosis factors, such as Bax, caspase-7, and caspase-9. Reference: Transl Oncol. 2021 Jun;14(6):101068. https://pubmed.ncbi.nlm.nih.gov/33730679/

In vivo activity:

Norethindrone acetate administration led to significant and proportional reductions of the concentrations of triglycerides, cholesterol and phospholipids of plasma lipoproteins of density less than 1.006 of rats fed a high carbohydrate diet. Norethindrone acetate (0.1 mM) also significantly inhibited the incorporation of both [9,10(-3)H] palmitate and [U-14C]glycerol into triglycerides of isolated hepatocytes from fed rats, by 11 to 16% (P less than 0.001). Reference: Atherosclerosis. 1983 Jan;46(1):41-8. https://pubmed.ncbi.nlm.nih.gov/6838693/

	Solvent	mg/mL	mM
Solubility
	DMSO	84.0	246.72
	Ethanol	68.0	199.73
	Water	0.7	1.97

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 340.46 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. Cai G, Wang Y, Houda T, Yang C, Wang L, Gu M, Mueck A, Croteau S, Ruan X, Hardy P. MicroRNA-181a suppresses norethisterone-promoted tumorigenesis of breast epithelial MCF10A cells through the PGRMC1/EGFR-PI3K/Akt/mTOR signaling pathway. Transl Oncol. 2021 Jun;14(6):101068. doi: 10.1016/j.tranon.2021.101068. Epub 2021 Mar 14. PMID: 33730679; PMCID: PMC7974027. 2. Brosnan JF, Sheppard BL, Kelly LA, O'Leary JJ, Norris LA. Norethisterone acetate alters coagulation gene expression in vitro in human cell culture. Thromb Res. 2013 Jan;131(1):72-7. doi: 10.1016/j.thromres.2012.09.006. Epub 2012 Sep 19. PMID: 22999413. 3. Cheng DC, Wolfe BM. Norethindrone acetate inhibition of triglyceride synthesis and release by rat hepatocytes. Atherosclerosis. 1983 Jan;46(1):41-8. doi: 10.1016/0021-9150(83)90162-4. PMID: 6838693.

In vitro protocol:

In vivo protocol:

1. Cheng DC, Wolfe BM. Norethindrone acetate inhibition of triglyceride synthesis and release by rat hepatocytes. Atherosclerosis. 1983 Jan;46(1):41-8. doi: 10.1016/0021-9150(83)90162-4. PMID: 6838693.

1: Vercellini P, Bracco B, Mosconi P, Roberto A, Alberico D, Dhouha D, Somigliana E. Norethindrone acetate or dienogest for the treatment of symptomatic endometriosis: a before and after study. Fertil Steril. 2016 Mar;105(3):734-743.e3. doi: 10.1016/j.fertnstert.2015.11.016. Epub 2015 Dec 8. PubMed PMID: 26677792. 2: Pohl O, Bestel E, Gotteland JP. Synergistic effects of E2MATE and norethindrone acetate on steroid sulfatase inhibition: a randomized phase I proof-of-principle clinical study in women of reproductive age. Reprod Sci. 2014 Oct;21(10):1256-65. doi: 10.1177/1933719114522526. Epub 2014 Mar 6. PubMed PMID: 24604234. 3: DiVasta AD, Feldman HA, Sadler Gallagher J, Stokes NA, Laufer MR, Hornstein MD, Gordon CM. Hormonal Add-Back Therapy for Females Treated With Gonadotropin-Releasing Hormone Agonist for Endometriosis: A Randomized Controlled Trial. Obstet Gynecol. 2015 Sep;126(3):617-27. doi: 10.1097/AOG.0000000000000964. PubMed PMID: 26181088; PubMed Central PMCID: PMC4545413. 4: Archer DF, Nakajima ST, Sawyer AT, Wentworth J, Trupin S, Koltun WD, Gilbert RD, Ellman H. Norethindrone acetate 1.0 milligram and ethinyl estradiol 10 micrograms as an ultra low-dose oral contraceptive. Obstet Gynecol. 2013 Sep;122(3):601-7. doi: 10.1097/AOG.0b013e3182a1741c. PubMed PMID: 23921878. 5: Cheng G, Butler R, Warner M, Gustafsson JÅ, Wilczek B, Landgren BM. Effects of short-term estradiol and norethindrone acetate treatment on the breasts of normal postmenopausal women. Menopause. 2013 May;20(5):496-503. doi: 10.1097/GME.0b013e318276c4ea. PubMed PMID: 23615640. 6: Symons J, Kempfert N, Speroff L. Vaginal bleeding in postmenopausal women taking low-dose norethindrone acetate and ethinyl estradiol combinations. The FemHRT Study Investigators. Obstet Gynecol. 2000 Sep;96(3):366-72. PubMed PMID: 10960627. 7: Kaser DJ, Missmer SA, Berry KF, Laufer MR. Use of norethindrone acetate alone for postoperative suppression of endometriosis symptoms. J Pediatr Adolesc Gynecol. 2012 Apr;25(2):105-108. doi: 10.1016/j.jpag.2011.09.013. Epub 2011 Dec 11. PubMed PMID: 22154396. 8: Polisseni AF, Andrade AT, Ribeiro LC, Castro IQ, Brandão M, Polisseni F, Guerra Mde O. Effects of a continuous-combined regimen of low-dose hormone therapy (oestradiol and norethindrone acetate) and tibolone on the quality of life in symptomatic postmenopausal women: a double-blind, randomised study. Maturitas. 2013 Feb;74(2):172-8. doi: 10.1016/j.maturitas.2012.11.001. Epub 2012 Nov 30. PubMed PMID: 23201326. 9: Archer DF, Dorin MH, Heine W, Nanavati N, Arce JC. Uterine bleeding in postmenopausal women on continuous therapy with estradiol and norethindrone acetate. Endometrium Study Group. Obstet Gynecol. 1999 Sep;94(3):323-9. PubMed PMID: 10472853. 10: Simon JA, Liu JH, Speroff L, Shumel BS, Symons JP. Reduced vaginal bleeding in postmenopausal women who receive combined norethindrone acetate and low-dose ethinyl estradiol therapy versus combined conjugated equine estrogens and medroxyprogesterone acetate therapy. Am J Obstet Gynecol. 2003 Jan;188(1):92-9. PubMed PMID: 12548201. 11: Soliman AM, Bonafede M, Farr AM, Castelli-Haley J, Winkel C. Analysis of Adherence, Persistence, and Surgery Among Endometriosis Patients Treated with Leuprolide Acetate Plus Norethindrone Acetate Add-Back Therapy. J Manag Care Spec Pharm. 2016 May;22(5):573-87. doi: 10.18553/jmcp.2016.22.5.573. PubMed PMID: 27123918. 12: Archer DF, Furst K, Tipping D, Dain MP, Vandepol C. A randomized comparison of continuous combined transdermal delivery of estradiol-norethindrone acetate and estradiol alone for menopause. CombiPatch Study Group. Obstet Gynecol. 1999 Oct;94(4):498-503. PubMed PMID: 10511348. 13: Chwalisz K, Surrey E, Stanczyk FZ. The hormonal profile of norethindrone acetate: rationale for add-back therapy with gonadotropin-releasing hormone agonists in women with endometriosis. Reprod Sci. 2012 Jun;19(6):563-71. doi: 10.1177/1933719112438061. Epub 2012 Mar 27. Review. PubMed PMID: 22457429. 14: Muneyyirci-Delale O, Jalou S, Rahman M, Nacharaju V. Can we decrease breakthrough bleeding in patients with endometriosis on norethindrone acetate? Int J Fertil Womens Med. 2003 Jan-Feb;48(1):32-6. PubMed PMID: 12643518. 15: Portman DJ, Symons JP, Wilborn W, Kempfert NJ. A randomized, double-blind, placebo-controlled, multicenter study that assessed the endometrial effects of norethindrone acetate plus ethinyl estradiol versus ethinyl estradiol alone. Am J Obstet Gynecol. 2003 Feb;188(2):334-42. PubMed PMID: 12592236. 16: Kurman RJ, Félix JC, Archer DF, Nanavati N, Arce J, Moyer DL. Norethindrone acetate and estradiol-induced endometrial hyperplasia. Obstet Gynecol. 2000 Sep;96(3):373-9. PubMed PMID: 10960628. 17: Singh H, Uniyal JP, Jha P, Murugesan K, Takkar D, Hingorani V, Laumas KR. Pharmacokinetics of norethindrone acetate in women. Am J Obstet Gynecol. 1979 Oct 1;135(3):409-14. PubMed PMID: 484634. 18: Notelovitz M, Cassel D, Hille D, Furst KW, Dain MP, VandePol C, Skarinsky D. Efficacy of continuous sequential transdermal estradiol and norethindrone acetate in relieving vasomotor symptoms associated with menopause. Am J Obstet Gynecol. 2000 Jan;182(1 Pt 1):7-12. PubMed PMID: 10649149. 19: Vercellini P, Pietropaolo G, De Giorgi O, Pasin R, Chiodini A, Crosignani PG. Treatment of symptomatic rectovaginal endometriosis with an estrogen-progestogen combination versus low-dose norethindrone acetate. Fertil Steril. 2005 Nov;84(5):1375-87. PubMed PMID: 16275232. 20: Speroff L, Symons J, Kempfert N, Rowan J; femhrt Study Investigators. The effect of varying low-dose combinations of norethindrone acetate and ethinyl estradiol (femhrt) on the frequency and intensity of vasomotor symptoms. Menopause. 2000 Nov-Dec;7(6):383-90. PubMed PMID: 11127760.