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SML0292

Sigma-Aldrich

Gestodene

≥98% (HPLC)

Synonym(s):

(17α)-13-Ethyl-17-hydroxy-18,19-Dinorpregna-4,15-dien-20-yn-3-one, Gestinol, SHB 331, WL 70

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About This Item

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

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

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

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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Pasquale Florio et al.
Gynecological endocrinology : the official journal of the International Society of Gynecological Endocrinology, 27(6), 434-438 (2011-01-06)
In a retrospective case-control study, we compared the effectiveness of hysteroscopic correction and hormonal treatment to improve symptoms [postmestrual abnormal uterine bleeding (PAUB), pelvic pain localized in suprapubic site] associated with isthmocele. Women (n = 39; mean age ± SD
Ana Cristina Rebelo et al.
The European journal of contraception & reproductive health care : the official journal of the European Society of Contraception, 16(4), 289-297 (2011-07-22)
To evaluate the influence of oral contraceptives (OCs) containing 20 μg ethinylestradiol (EE) and 150 μg gestodene (GEST) on the autonomic modulation of heart rate (HR) in women. One-hundred and fifty-five women aged 24 ± 2 years were divided into
Vincenzo De Leo et al.
Contraception, 82(3), 276-280 (2010-08-14)
This randomized study's aim was to compare the effect of four oral contraceptives (OCs) containing 30 mcg of ethinylestradiol (EE) and different progestogens [drospirenone, (DRSP), chlormadinone acetate (CMA), desogestrel (DSG), gestodene (GSD)] on biochemical and hormonal parameters of hyperandrogenism and
Øjvind Lidegaard et al.
BMJ (Clinical research ed.), 343, d6423-d6423 (2011-10-27)
To assess the risk of venous thromboembolism from use of combined oral contraceptives according to progestogen type and oestrogen dose. National historical registry based cohort study. Four registries in Denmark. Non-pregnant Danish women aged 15-49 with no history of thrombotic
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
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