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Merck

1469005

USP

Norethindrone

United States Pharmacopeia (USP) Reference Standard

Synonym(s):

19-Norethindrone, 17α-Ethynyl-19-nortestosterone, 17-Hydroxy-19-nor-17α-4-pregnen-20-yn-3-one, 17α-Ethynyl-17β-hydroxy-19-nor-4-androsten-3-one, 19-Nor-17α-ethynyl-4-androsten-17β-ol-3-one, 19-Norethisterone

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About This Item

Empirical Formula (Hill Notation):
C20H26O2
CAS Number:
Molecular Weight:
298.42
UNSPSC Code:
41116107
NACRES:
NA.24
PubChem Substance ID:
EC Number:
200-681-6
Beilstein/REAXYS Number:
1915671
MDL number:

Product Name

Norethindrone, United States Pharmacopeia (USP) Reference Standard

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/h1,12,15-18,22H,4-11H2,2H3/t15-,16+,17+,18-,19-,20-/m0/s1

InChI key

VIKNJXKGJWUCNN-XGXHKTLJSA-N

SMILES string

[H][C@]12CCC(=O)C=C1CC[C@]3([H])[C@]2([H])CC[C@@]4(C)[C@@]3([H])CC[C@@]4(O)C#C

grade

pharmaceutical primary standard

API family

norethindrone

manufacturer/tradename

USP

mp

205-206 °C (lit.)

application(s)

pharmaceutical (small molecule)

format

neat

Gene Information

human ... PGR(5241)

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Analysis Note

These products are for test and assay use only. They are not meant for administration to humans or animals and cannot be used to diagnose, treat, or cure diseases of any kind.  ​

Application

Norethindrone USP reference standard, intended for use in specified quality tests and assays as specified in the USP compendia. Also, for use with USP monographs such as:
  • Norethindrone Tablets
  • Norethindrone Acetate Tablets
  • Norethindrone and Mestranol Tablets
  • Norethindrone and Ethinyl Estradiol Tablets
  • Fluocinolone Acetonide Cream
  • Fluoxymesterone Tablets

Biochem/physiol Actions

19-norethindrone is an oral contraceptive involved in the inhibition of cytosolic sulfotransferases (SULT).

General description

This product is provided as delivered and specified by the issuing Pharmacopoeia. All information provided in support of this product, including SDS and any product information leaflets have been developed and issued under the Authority of the issuing Pharmacopoeia.For further information and support please go to the website of the issuing Pharmacopoeia.

Other Notes

Sales restrictions may apply.

pictograms

Health hazardEnvironment

signalword

Danger

Hazard Classifications

Aquatic Acute 1 - Aquatic Chronic 1 - Carc. 2 - Lact. - Repr. 1A

Storage Class

6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable


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Certificates of Analysis (COA)

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H F Taitel et al.
International journal of fertility and menopausal studies, 40(4), 207-223 (1995-07-01)
Norethindrone is utilized for numerous noncontraceptive therapies, especially during the menopause. Through an analysis of the literature we have described the pharmacological profile of norethindrone and the potential therapeutic implications of low-dose therapies, with an emphasis on endometrial pathology, climacteric
Rajesh Rajput et al.
Journal of obstetrics and gynaecology Canada : JOGC = Journal d'obstetrique et gynecologie du Canada : JOGC, 30(8), 680-683 (2008-09-13)
The association between the progestin-only pill used for treatment of menstrual disorders and central venous sinus thrombosis (CVST) has rarely been reported in the literature. This report describes a case of central venous sinus thrombosis following intake of norethindrone acetate
L R Wiseman et al.
Drugs & aging, 4(3), 238-256 (1994-03-01)
The combined transdermal estradiol/norethisterone therapeutic system is designed to deliver both estradiol and norethisterone into the systemic circulation at a constant rate for up to 4 days when affixed to the skin. Transdermal administration avoids hepatic first-pass metabolism, allowing therapeutic
Colleen L Casey et al.
Clinical interventions in aging, 3(1), 9-16 (2008-05-21)
Abstract: The goal ofpostmenopausal hormone therapy is to alleviate the symptoms that are associated with the loss of estrogen. Many formulations of estrogen and progestin are available, depending on the needs and circumstances of each individual woman. For postmenopausal women
Kristof Chwalisz et al.
Reproductive sciences (Thousand Oaks, Calif.), 19(6), 563-571 (2012-03-30)
Gonadotropin-releasing hormone agonists (GnRHa) are an effective treatment of endometriosis-associated pelvic pain. The use of hormonal add-back therapy can alleviate the hypoestrogenic symptoms associated with GnRHa therapy, while preserving therapeutic efficacy. Norethindrone acetate (NETA) is a unique progestin that has

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