A prodrug form of 3-keto allylestrenol
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Allylestrenol

Item No. 46192

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
(17β)-17-(2-propen-1-yl)-estr-4-en-17-ol
CAS Number
432-60-0
Synonyms
  • 17α-Allyl-17β-hydroxy-4-estren
  • NSC 37723
Molecular Formula
C21H32O
Formula Weight
300.5
Purity
≥98%
Formulation (Request formulation change)
A solid
Solubility(Learn about Variance in Solubility)
DMSO: Soluble: ≥10 mg/mlEthanol: Slightly soluble: 0.1-1 mg/ml
SMILES
C[C@@]12[C@](CC[C@@]2(O)CC=C)([H])[C@@]3([H])[C@]([C@]4([H])C(CC3)=CCCC4)([H])CC1
InChi Code
InChI=1S/C21H32O/c1-3-12-21(22)14-11-19-18-9-8-15-6-4-5-7-16(15)17(18)10-13-20(19,21)2/h3,6,16-19,22H,1,4-5,7-14H2,2H3/t16-,17+,18+,19-,20-,21-/m0/s1
InChi Key
ATXHVCQZZJYMCF-XUDSTZEESA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    50 mg

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    100 mg

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    250 mg

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    Product Description

    Allylestrenol is a prodrug form of the progesterone receptor agonist 3-keto allylestrenol.1,2 Unlike 3-keto allylestrenol, allylestrenol is a weak agonist of androgen and progesterone receptors in reporter assays (EC50s = 663 and 381 nM, respectively), and it does not bind to estrogen or glucocorticoid receptors. Allylestrenol protects against embryo resorptions and decreases in serum progesterone levels, fetal weight, and placental weight induced by misoprostol (Item No. 13820) in mice.3 It decreases ventral prostate and seminal vesicle weight in mature male rats and inhibits testosterone propionate-induced ventral prostate and seminal vesicle growth in castrated immature rats.4 Neonatal administration of allylestrenol (17.5 µg/animal) decreases bone mineral content in female rats and increases it in male rats but does not affect bone mineral density in either female or male rats.5

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. McRobb, L., Handelsman, D.J., Kazlauskas, R., et al. Structure-activity relationships of synthetic progestins in a yeast-based in vitro androgen bioassay. J. Steroid Biochem. Mol. Biol. 110(1-2), 39-47 (2008).

    2. Bergink, E.W., Loonen, P.B., and Kloosterboer, H.J. Receptor binding of allylestrenol, a progestagen of the 19-nortestosterone series without androgenic properties. J. Steroid Biochem. 23(2), 165-168 (1985).

    3. Long, Z., and Xia, H. Allylestrenol prevents misoprostol-induced abortion in mice via progesterone receptor-dependent anti-inflammatory and anti-apoptotic pathways. Biol. Reprod. 114(6), 1842-1855 (2026).

    4. Yasuda, N., Fujino, K., Shiraji, T., et al. Effects of steroid 5α-reductase inhibitor ONO-9302 and anti-androgen allylestrenol on the prostatic growth, and plasma and prostatic hormone levels in rats. Jpn. J. Pharmacol. 74(3), 243-252 (1997).

    5. Karabélyos, C., Horváth, C., Holló, I., et al. Effect of perinatal synthetic steroid hormone (allylestrenol, diethylstilbestrol) treatment (hormonal imprinting) on the bone mineralization of the adult male and female rat. Life Sci. 64(9), PL105-PL110 (1999).