A neurosteroid and an active metabolite of pregnenolone
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Isomer(s)
34295Epipregnanolone
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Pregnanolone

Item No. 42751

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
(3α,5β)-3-hydroxy-pregnan-20-one
CAS Number
128-20-1
Synonyms
  • Eltanolone
  • NSC 82867
  • 3α,5β-P
  • 5β-Pregnan-3α-ol-20-one
  • SKF 6455
  • 3α,5β-Tetrahydroprogesterone
  • U-2340
Molecular Formula
C21H34O2
Formula Weight
318.5
Purity
≥95%
Formulation
A solid
Solubility(Learn about Variance in Solubility)
DMSO: Soluble: ≥10 mg/mlEthanol: Soluble: ≥10 mg/ml
SMILES
C[C@@]12[C@](CC[C@@H]2C(C)=O)([H])[C@]3([H])CC[C@]4([H])C[C@H](O)CC[C@]4(C)[C@@]3([H])CC1
InChi Code
InChI=1S/C21H34O2/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/h14-19,23H,4-12H2,1-3H3/t14-,15-,16+,17-,18+,19+,20+,21-/m1/s1
InChi Key
AURFZBICLPNKBZ-YZRLXODZSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    1 mg

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    Product Description

    Pregnanolone is a neurosteroid and an active metabolite of pregnenolone (Item No. 19864).1,2,3 It is formed from pregnenolone via the intermediates progesterone (Item No. 15876) and 5β-dihydroprogesterone (Item No. 34644).3 Pregnanolone enhances the binding of flunitrazepam to GABAA receptors in rat brain homogenate (EC50 = 237 nM) and inhibits currents induced by GABA in Xenopus oocytes expressing ρ1 subunit-containing GABAC receptors (IC50 = 550 nM).2,1 It protects against seizures induced by pentylenetetrazole (PTZ; Item No. 18682) in a rat model of perimenstrual catamenial epilepsy (ED50 = 2.16 mg/kg).4 Pregnanolone (20 mg/kg) increases the number of entries into and percentage of time spent in the open arms of the elevated plus maze in mice, indicating anxiolytic activity.5 It induces anesthesia in rats.6

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. 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).

    2. Prince, R.J., and Simmonds, M.A. 5β-pregnan-3β-ol-20-one, a specific antagonist at the neurosteroid site of the GABAA receptor-complex. Neurosci. Lett. 135(2), 273-275 (1992).

    3. Hill, M., Cibula, D., Havlíkova, H., et al. Circulating levels of pregnanolone isomers during the third trimester of human pregnancy. J. Steroid Biochem. Mol. Biol. 105(1-5), 166-175 (2007).

    4. Reddy, D.S., and Rogawski, M.A. Enhanced anticonvulsant activity of neuroactive steroids in a rat model of catamenial epilepsy. Epilepsia 42(3), 337-344 (2001).

    5. Rodgers, R.J., and Johnson, N.J. Behaviorally selective effects of neuroactive steroids on plus-maze anxiety in mice. Pharmacol. Biochem. Behav. 59(1), 221-232 (1998).

    6. Zhu, D., Wang, M.D., Bäckström, T., et al. Evaluation and comparison of the pharmacokinetic and pharmacodynamic properties of allopregnanolone and pregnanolone at induction of anaesthesia in the male rat. Br. J. Anaesth. 86(3), 403-412 (2001).