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Merck

SML0356

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
NACRES:
NA.77
PubChem Substance ID:
329825358
UNSPSC Code:
51111800
EC Number:
258-936-2
MDL number:
MFCD00867863

Product Name

Etonogestrel, ≥98% (HPLC)

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

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

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

Quality Level

100

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 progestin, contraceptive.
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

signalword

Danger

hcodes

H351,H360

Hazard Classifications

Carc. 2 - Repr. 1B

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)

Lot/Batch Number
0000106917
0000114722
0000103749
0000058518
047M4731V

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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.
Pharmacokinetics of etonogestrel released from the contraceptive implant Implanon
Wenzl R, et al.
Contraception, 58(5), 283-288 (1998)
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
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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