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N1200000

Norethisterone

European Pharmacopoeia (EP) 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:
68-22-4
Molecular Weight:
298.42
Beilstein:
1915671
MDL number:
MFCD00067596
UNSPSC Code:
41116107
PubChem Substance ID:
329818523
NACRES:
NA.24

grade

pharmaceutical primary standard

API family

norethisterone

manufacturer/tradename

EDQM

mp

205-206 °C (lit.)

application(s)

pharmaceutical (small molecule)

format

neat

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

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

Gene Information

human ... PGR(5241)

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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.

Application

Norethisterone EP Reference standard, intended for use in laboratory tests only as specifically prescribed in the European Pharmacopoeia.

Biochem/physiol Actions

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

Packaging

The product is delivered as supplied by the issuing Pharmacopoeia. For the current unit quantity, please visit the EDQM reference substance catalogue.

Other Notes

Sales restrictions may apply.

Pictograms

Health hazardEnvironment
GHS08,GHS09

Signal Word

Danger

Hazard Statements

H351,H360FD,H362,H410

Hazard Classifications

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

Storage Class Code

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

WGK

WGK 3

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Lot/Batch Number

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Sigma-Aldrich

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Karl van den Broeck et al.
The European journal of contraception & reproductive health care : the official journal of the European Society of Contraception, 17(5), 321-328 (2012-09-15)
Ferdinand Peeters, a practising gynaecologist from Turnhout, near Antwerp (Belgium), had a pivotal role in the development of a practical and viable modality of oral contraception, striking the balance between efficacy and an acceptably low incidence and severity of side
Kelli Stidham Hall et al.
Contraception, 86(6), 653-658 (2012-06-12)
Progestin-only contraceptive pills (POPs) offer a safe and effective contraceptive option, particularly for women at increased risk of venous thromboembolism. However, the prevalence of POP use among women in the United States is unknown. We analyzed population-based data from 12,279
Chelsea B Polis et al.
The Lancet. Infectious diseases, 13(9), 797-808 (2013-07-23)
Whether or not the use of hormonal contraception affects risk of HIV acquisition is an important question for public health. We did a systematic review, searching PubMed and Embase, aiming to explore the possibility of an association between various forms
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
F Z Stanczyk et al.
Contraception, 42(1), 67-96 (1990-07-01)
There is limited information on the metabolism of levonorgestrel, norethindrone and structurally related contraceptive steroids. Both levonorgestrel and norethindrone undergo extensive reduction of the alpha, beta-unsaturated ketone in ring A. Levonorgestrel also undergoes hydroxylation at carbons 2 and 16. The
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