A progesterone receptor agonist and metabolite of progesterone
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5β-Dihydroprogesterone

Item No. 34644

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
(5β)-pregnane-3,20-dione
CAS Number
128-23-4
Synonyms
  • 5β-DHP
  • NSC 82868
  • 5β-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-/m1/s1
InChi Key
XMRPGKVKISIQBV-XWOJZHJZSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    100 mg

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    Product Description

    5β-Dihydroprogesterone (5β-DHP) is a progesterone receptor agonist and metabolite of progesterone (Item No. 15876).1,2 It is formed from progesterone by 5β-reductase.2 5β-DHP inhibits spontaneous contractions in isolated rat uterus when used at a concentration of 10 µg/ml, an effect that can be blocked by the progesterone receptor antagonist RU486 (mifepristone; Item No. 10006317) but not the GABAA receptor antagonist picrotoxin (Item No. 20771).1 It is a negative modulator of homooligomeric ρ1 subunit-containing GABAA receptors, inhibiting GABA-induced currents in X. laevis oocytes expressing these receptors (IC50 = 5.02 µM).3 Plasma levels of 5β-DHP decrease at the onset of spontaneous human labor.4

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Putnam, C.D., Brann, D.W., Kolbeck, R.C., et al. Inhibition of uterine contractility by progesterone and progesterone metabolites: Mediation by progesterone and gamma amino butyric acidA receptor systems. Biol. Reprod. 45(2), 266-272 (1991).

    2. Bumke-Vogt, C., Bähr, V., Diederich, S., et al. Expression of the progesterone receptor and progesterone- metabolising enzymes in the female and male human kidney. J. Endocrinol. 175(2), 349-364 (2002).

    3. Morris, K.D., Moorefield, C.N., and Amin, J. Differential modulation of the γ-aminobutyric acid type C receptor by neuroactive steroids. Mol. Pharmacol. 56(4), 752-759 (1999).

    4. Sheehan, P.M., Rice, G.E., Moses, E.K., et al. 5β-dihydroprogesterone and steroid 5β-reductase decrease in association with human parturition at term. Mol. Hum. Reprod. 11(7), 495-501 (2005).