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SML0292

Sigma-Aldrich

Gestodene

≥98% (HPLC)

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Synonym(s):
(17α)-13-Ethyl-17-hydroxy-18,19-Dinorpregna-4,15-dien-20-yn-3-one, Gestinol, SHB 331, WL 70
Empirical Formula (Hill Notation):
C21H26O2
CAS Number:
60282-87-3
Molecular Weight:
310.43
EC Number:
262-145-8
MDL number:
MFCD00867858
UNSPSC Code:
51111800
PubChem Substance ID:
329825299
NACRES:
NA.77

Quality Level

100

Assay

≥98% (HPLC)

form

powder

optical activity

[α]/D -175 to -195° (DCM)

color

white to off-white

solubility

DMSO: >20 mg/mL

storage temp.

−20°C

SMILES string

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

InChI

1S/C21H26O2/c1-3-20-11-9-17-16-8-6-15(22)13-14(16)5-7-18(17)19(20)10-12-21(20,23)4-2/h2,10,12-13,16-19,23H,3,5-9,11H2,1H3/t16-,17+,18+,19-,20-,21-/m0/s1

InChI key

SIGSPDASOTUPFS-XUDSTZEESA-N

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Biochem/physiol Actions

Gestodene is a synthetic progestin used as a contraceptive. Gestodene displays a high binding affinity to the progesterone receptor, and also binds strongly to adrogen and glucocorticoid receptors.

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

Warning

Hazard Statements

H361fd

Hazard Classifications

Repr. 2

WGK

WGK 3

Regulatory Information

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Ana Cristina S Rebelo et al.
Contraception, 81(4), 309-315 (2010-03-17)
The purpose of this study was to evaluate the effect of long-term use of oral contraceptives (OC) containing 0.20 mg of ethinylestradiol (EE) combined with 0.15 mg of gestodene (GEST) on the peak aerobic capacity and at the anaerobic threshold
Lothar A J Heinemann et al.
Contraception, 81(5), 401-407 (2010-04-20)
This study investigated whether gestodene-containing oral contraceptives (OCs) carry a higher risk of venous thromboembolism (VTE) than OCs containing progestins other than desogestrel and gestodene. The study was conducted based on the hypothesis that the biases and confounding factors that
Xiao-Fen Liu et al.
Yao xue xue bao = Acta pharmaceutica Sinica, 45(1), 87-92 (2011-03-01)
To establish a sensitive and specific method for simultaneous determination of gestodene, etonogestrel and ethinylestradiol in plasma by LC-MS/MS, plasma samples were extracted and derivatized before injection. An ESI ion source was used and operated in the positive ion mode
Sille Vaiksaar et al.
Perceptual and motor skills, 113(3), 764-772 (2012-03-13)
Eight female rowers (M age = 21.0 yr., SD = 2.8), using a monophasic oral-contraceptive pill, performed a 1-hr. rowing ergometer test (intensity: 70% VO2max) during the active-pill and non active-pill phases of the oral contraceptive cycle. No significant differences
Ettore Caroppo et al.
Journal of assisted reproduction and genetics, 29(9), 973-977 (2012-06-13)
To report the long-term management of a case of premature ovarian insufficiency of unknown origin in a young woman with Crohn's disease. Here is reported the case of a 20 years old woman with Crohn's disease presenting with two years
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