A progesterone receptor agonist and progesterone metabolite
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5α-Dihydroprogesterone

Item No. 31505

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
(5α)-pregnane-3,20-dione
CAS Number
566-65-4
Synonyms
  • 5α-DHP
  • NSC 18319
  • 5α-Pregnanedione
Molecular Formula
C21H32O2
Formula Weight
316.5
Purity
≥95%
Formulation
A solid
Solubility(Learn about Variance in Solubility)
Chloroform: 30 mg/ml
SMILES
C[C@@]12[C@]3([H])[C@](CC[C@@]1([H])CC(CC2)=O)([H])[C@@]4([H])[C@](CC3)([C@H](CC4)C(C)=O)C
InChi Code
InChI=1S/C21H32O2/c1-13(22)17-6-7-18-16-5-4-14-12-15(23)8-10-20(14,2)19(16)9-11-21(17,18)3/h14,16-19H,4-12H2,1-3H3/t14-,16-,17+,18-,19-,20-,21+/m0/s1
InChi Key
XMRPGKVKISIQBV-BJMCWZGWSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    500 mg

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    Product Description

    5α-Dihydroprogesterone (5α-DHP) is a progesterone receptor agonist and metabolite of progesterone (Item No. 15876).1 It is formed from progesterone by 5α-reductase.2 It induces gene expression mediated by the progesterone receptor (PR) in reporter assays using HepG2 cells expressing equine PR or human PR (EC50s = 14 and 23.1 nM, respectively).1 5α-DHP (0.7 mg/kg) maintains equine pregnancy in the absence of luteal progesterone. It increases proliferation of C4HD murine mammary cells when used at a concentration of 1 µM and induces tumor formation in a C4HD mouse model of tumorigenesis in a dose-dependent manner.3 5α-DHP levels increase locally following spinal cord injury or traumatic brain injury in rats and ischemic brain injury in mice.2

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Scholtz, E.L., Krishnan, S., Ball, B.A., et al. Pregnancy without progesterone in horses defines a second endogenous biopotent progesterone receptor agonist, 5α-dihydroprogesterone. Proc. Natl. Acad. Sci. USA 111(9), 3365-3370 (2014).

    2. Guennoun, R., Labombarda, F., Gonzalez Deniselle, M.C., et al. Progesterone and allopregnanolone in the central nervous system: Response to injury and implication for neuroprotection. J. Steroid Biochem. Mol. Biol. 146, 48-61 (2015).

    3. Wiebe, J.P., Rivas, M.A., Mercogliano, M.F., et al. Progesterone-induced stimulation of mammary tumorigenesis is due to the progesterone metabolite, 5α-dihydroprogesterone (5αP) and can be suppressed by the 5α-reductase inhibitor, finasteride. J. Steroid Biochem. Mol. Biol. 149, 27-34 (2015).