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N4128

Sigma-Aldrich

19-Norethindrone

≥98%, powder

Synonym(s):

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/REAXYS Number:
1915671
EC Number:
200-681-6
MDL number:
MFCD00067596
UNSPSC Code:
12352211
PubChem Substance ID:
24897669
NACRES:
NA.77

biological source

synthetic (organic)

sterility

non-sterile

assay

≥98%

form

powder

storage condition

protect from light

color

white to off-white

mp

205-206 °C (lit.)

solubility

chloroform: ≥50 mg/mL, clear, colorless

shipped in

ambient

storage temp.

room temp

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 ... AR(367) , PGR(5241)
rat ... Ar(24208)

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Biochem/physiol Actions

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

pictograms

Health hazardEnvironment
GHS08,GHS09

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_germany

WGK 3

ppe

Eyeshields, Gloves, type P3 (EN 143) respirator cartridges

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Susan M Fetherston et al.
The Journal of antimicrobial chemotherapy, 68(2), 394-403 (2012-10-31)
The non-nucleoside reverse transcriptase inhibitor MC1220 has potent in vitro activity against HIV type 1 (HIV-1). A liposome gel formulation of MC1220 has previously been reported to partially protect rhesus macaques against vaginal challenge with a simian HIV (SHIV). Here
Moa Säfholm et al.
Philosophical transactions of the Royal Society of London. Series B, Biological sciences, 369(1656) (2014-11-19)
Most amphibians breed in water, including the terrestrial species, and may therefore be exposed to water-borne pharmaceuticals during critical phases of the reproductive cycle, i.e. sex differentiation and gamete maturation. The objectives of this paper were to (i) review available
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
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
Louise Lind Schierbeck et al.
BMJ (Clinical research ed.), 345, e6409-e6409 (2012-10-11)
To investigate the long term effect of hormone replacement therapy on cardiovascular outcomes in recently postmenopausal women. Open label, randomised controlled trial. Denmark, 1990-93. 1006 healthy women aged 45-58 who were recently postmenopausal or had perimenopausal symptoms in combination with
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