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Safety Information

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

Regulatory Information

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Certificates of Analysis (COA)

Lot/Batch Number
0000106917
0000114722
0000103749
0000058518
047M4731V

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Kristina M Tocce et al.
American journal of obstetrics and gynecology, 206(6), 481-481 (2012-05-29)
The purpose of this study was to determine contraceptive continuation and repeat pregnancy rates in adolescents who are offered immediate postpartum etonogestrel implant (IPI) insertion. Participants in an adolescent prenatal-postnatal program were enrolled in a prospective observational study of IPI
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
Pharmacokinetics of etonogestrel released from the contraceptive implant Implanon
Wenzl R, et al.
Contraception, 58(5), 283-288 (1998)
Mary E Gaffield et al.
Contraception, 73(2), 134-144 (2006-01-18)
To review evidence on the combined hormonal patch, combined hormonal vaginal ring and the etonogestrel implant, with a focus on safety and effectiveness of use among women with special health conditions, we searched MEDLINE, Pre-MEDLINE and the Cochrane Library for
View All Related Papers

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