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SML0356

Sigma-Aldrich

Etonogestrel

≥98% (HPLC)

Synonym(s):

(17α)-13-Ethyl-17-hydroxy-11-methylene-18,19-dinorpregn-4-en-20-yn-3-one, 3-Keto-desogestrel, 3-Oxo-desogestrel

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About This Item

Empirical Formula (Hill Notation):
C22H28O2
CAS Number:
54048-10-1
Molecular Weight:
324.46
EC Number:
258-936-2
MDL number:
MFCD00867863
UNSPSC Code:
51111800
PubChem Substance ID:
329825358
NACRES:
NA.77

Quality Level

100

Assay

≥98% (HPLC)

form

powder

optical activity

[α]/D +80 to +95°, c = 1 (CHCl3)

color

white to beige

solubility

DMSO: >5 mg/mL

storage temp.

−20°C

SMILES string

CC[C@]12CC(=C)[C@H]3[C@@H](CCC4=CC(=O)CC[C@H]34)[C@@H]1CC[C@@]2(O)C#C

InChI

1S/C22H28O2/c1-4-21-13-14(3)20-17-9-7-16(23)12-15(17)6-8-18(20)19(21)10-11-22(21,24)5-2/h2,12,17-20,24H,3-4,6-11,13H2,1H3/t17-,18-,19-,20+,21-,22-/m0/s1

InChI key

GCKFUYQCUCGESZ-BPIQYHPVSA-N

Gene Information

human ... PGR(5241)

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Biochem/physiol Actions

Etonogestrel is a lipophilic molecule. Pharmacokinetics studies reveal that etonogestrel is bound to protein albumin in the blood. This remains independent of both endogenous and exogenous concentration of estradiol.
Etonogestrel is a third-generation progestin contraceptive. Etonogestrel is used as a contraceptive itself and is also the active metabolite of the drug desogestrel used in some combination contraceptives.

Features and Benefits

This compound is featured on the Nuclear Receptors (Steroids) page of the Handbook of Receptor Classification and Signal Transduction. To browse other handbook pages, click here.

Pictograms

Health hazard
GHS08

Signal Word

Danger

Hazard Statements

H351,H360

Precautionary Statements

P201 - P308 + P313

Hazard Classifications

Carc. 2 - Repr. 1B

Storage Class Code

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

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Diana Mansour et al.
Contraception, 83(3), 202-210 (2011-02-12)
The aim of this guidance is to review the management of unacceptable vaginal bleeding patterns in etonogestrel (ENG)-releasing contraceptive implant users concentrating, where possible, on the evidence for pharmacological treatments and identifying a pragmatic approach where this is not possible.
Anne Calhoun et al.
Headache, 52(8), 1246-1253 (2012-07-14)
To determine whether extended-cycle dosing of an ultralow dose vaginal ring contraceptive decreases frequency of migraine aura and prevents menstrual related migraine (MRM). Many women are denied therapy with combined hormonal contraceptives due to published guidelines that recommend against their
Hanna Xu et al.
Obstetrics and gynecology, 120(1), 21-26 (2012-06-09)
To estimate the contraceptive failure rates of the etonogestrel subdermal contraceptive implant in overweight and obese women and compare failure rates with women of normal weight and women using intrauterine devices (IUDs). The Contraceptive CHOICE Project is a large prospective
Milena B Brito et al.
Thrombosis research, 130(3), 355-360 (2012-05-01)
The puerperium is the period of highest risk for thrombosis during a woman's reproductive life and it is an important time for initiating an effective contraceptive method in order to increase intergestational interval. Thus, the objective of the present study
Matthew Brown et al.
Contraception, 86(5), 591-593 (2012-07-10)
The etonogestrel contraceptive implant (Implanon®) is an effective, long-acting subdermal method of hormonal contraception for women. We describe a case of forearm pain and hypoesthesia associated with the insertion of the Implanon® contraceptive implant in a healthy 26-year-old female. These
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