An androgen and progesterone receptor ligand used to treat endometriosis
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Gestrinone

Item No. 10006488

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
13-ethyl-17α-hydroxy-18,19-dinorpregna-4,9,11-trien-20-yn-3-one
CAS Number
16320-04-0
Molecular Formula
C21H24O2
Formula Weight
308.4
Purity
≥98%
Formulation
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMF: 20 mg/mlDMSO: 20 mg/mlEthanol: 20 mg/mlEthanol:PBS (pH 7.2) (1:5): 0.25 mg/ml
λmax
238, 341 nm
SMILES
O[C@@]1(C#C)CC[C@@]2([H])[C@]3([H])CCC4=CC(CCC4=C3C=C[C@@]21CC)=O
InChi Code
InChI=1S/C21H24O2/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/h2,9,11,13,18-19,23H,3,5-8,10,12H2,1H3/t18-,19+,20+,21+/m1/s1
InChi Key
BJJXHLWLUDYTGC-ANULTFPQSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    Product Description

    Endometriosis is common disease characterized by the presence of endometrial tissue outside the uterus which affects approximately 10% of premenopausal women. Gestrinone is a synthetic steroid used occasionally to treat endometriosis.1 It acts centrally on the hypothalamic-pituitary system to suppress release of lutenizing hormone (LH) and follicle-stimulating hormone (FSH), thus reducing estrogen synthesis.1 It also binds to androgen (AR), progesterone (PR), and estrogen (ER) receptors in the human endometrial tissue but not to steroid hormone binding globulin or corticord-binding globulin.2 Gestrinone binds to AR and PR with EC50 values of approximately 20 and 30 nM, respectively.3 These values reflect approximately 5-6 fold lower affinity than testosterone and progesterone, the natural AR and PR ligands, for these receptors.3

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Moghissi, K.S. Medical treatment of endometriosis. Clin. Obstet. Gynecol. 45(3), 620-633 (1999).

    2. Tamaya, T., Fujimoto, J., Watanabe, Y., et al. Gestrinone (R2323) binding to steroid receptors in human uterine endometrial cytosol. Acta Obstet. Gynecol. Scand. 65(5), 439-441 (1986).

    3. Death, A.K., mcGrath, K.C.Y., Kazluskas, R., et al. Tetrahydrogestrinone is a potent androgen and progestin. J. Clin. Endocrinol. Metab. 89(5), 2498-2500 (2004).