Synonym
Epipregnanolone; NSC 21450; NSC21450; NSC-21450; 5β-Pregnan-3β-ol-20-one; Pregnanolone I; 5beta-Pregnanolone
IUPAC/Chemical Name
1-((3S,5R,8R,9S,10S,13S,14S,17S)-3-hydroxy-10,13-dimethylhexadecahydro-1H-cyclopenta[a]phenanthren-17-yl)ethan-1-one
InChi Key
AURFZBICLPNKBZ-GRWISUQFSA-N
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
SMILES Code
C[C@@]12[C@@]3([C@]([H])([C@]4([C@]([C@@H](C(C)=O)CC4)(C)CC3)[H])CC[C@@]1(C[C@@H](O)CC2)[H])[H]
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
To be determined
Shelf Life
>2 years if stored properly
Drug Formulation
To be determined
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
Biological target:
A neurosteroid and an active metabolite of pregnenolone.
In vivo activity:
Pretreatment with epipregnanolone (0.10-0.30 mg/kg) significantly blocked the development of tolerance to the motor impairing and hypothermic effects induced by ethanol in mice. Considering tolerance to ethanol-induced motor impairment, epipregnanolone (0.15 mg/kg) reversed the stimulatory action of dehydroepiandrosterone sulfate (0.15 mg/kg), but did not affect the actions of pregnenolone sulfate (0.08 mg/kg). Moreover, epipregnanolone prevented the inhibitory action of allotetrahydrodeoxycorticosterone (0.10 mg/kg). In relation to ethanol-induced hypothermia, the results showed that pretreatment with epipregnanolone (0.30 mg/kg) significantly prevented the stimulatory action of dehydroepiandrosterone sulfate and pregnenolone sulfate, as well as the inhibitory action of allotetrahydrodeoxicorticosterone (0.20 mg/kg), on tolerance to this effect.
Reference: Braz J Psychiatry. 2007 Dec;29(4):337-45. https://pubmed.ncbi.nlm.nih.gov/18200398/
|
Solvent |
mg/mL |
mM |
| Solubility |
| DMF |
30.0 |
94.19 |
| DMSO |
30.0 |
94.19 |
| Ethanol |
5.0 |
15.70 |
Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.
Preparing Stock Solutions
The following data is based on the
product
molecular weight
318.50
Batch specific molecular weights may vary
from batch to batch
due to the degree of hydration, which will
affect the solvent
volumes required to prepare stock solutions.
| Concentration / Solvent Volume / Mass |
1 mg |
5 mg |
10 mg |
| 1 mM |
1.15 mL |
5.76 mL |
11.51 mL |
| 5 mM |
0.23 mL |
1.15 mL |
2.3 mL |
| 10 mM |
0.12 mL |
0.58 mL |
1.15 mL |
| 50 mM |
0.02 mL |
0.12 mL |
0.23 mL |
Formulation protocol:
1. Barbosa AD, Morato GS. Influence of epipregnanolone on the modulation of rapid tolerance to ethanol by neurosteroids. Braz J Psychiatry. 2007 Dec;29(4):337-45. doi: 10.1590/s1516-44462007000400008. PMID: 18200398.
2. O'Dell LE, Purdy RH, Covey DF, Richardson HN, Roberto M, Koob GF. Epipregnanolone and a novel synthetic neuroactive steroid reduce alcohol self-administration in rats. Pharmacol Biochem Behav. 2005 Jul;81(3):543-50. doi: 10.1016/j.pbb.2005.03.020. PMID: 15950269.
In vivo protocol:
1. Barbosa AD, Morato GS. Influence of epipregnanolone on the modulation of rapid tolerance to ethanol by neurosteroids. Braz J Psychiatry. 2007 Dec;29(4):337-45. doi: 10.1590/s1516-44462007000400008. PMID: 18200398.
2. O'Dell LE, Purdy RH, Covey DF, Richardson HN, Roberto M, Koob GF. Epipregnanolone and a novel synthetic neuroactive steroid reduce alcohol self-administration in rats. Pharmacol Biochem Behav. 2005 Jul;81(3):543-50. doi: 10.1016/j.pbb.2005.03.020. PMID: 15950269.
1: Bukanova J, Solntseva E, Kondratenko R, Kudova E. Epipregnanolone as a Positive Modulator of GABAA Receptor in Rat Cerebellar and Hippocampus Neurons. Biomolecules. 2021 May 24;11(6):791. doi: 10.3390/biom11060791. PMID: 34074021.
2: Joksimovic SL, Donald RR, Park JY, Todorovic SM. Inhibition of multiple voltage-gated calcium channels may contribute to spinally mediated analgesia by epipregnanolone in a rat model of surgical paw incision. Channels (Austin). 2019 Dec;13(1):48-61. doi: 10.1080/19336950.2018.1564420. PMID: 30672394; PMCID: PMC6380214.
3: Ayoola C, Hwang SM, Hong SJ, Rose KE, Boyd C, Bozic N, Park JY, Osuru HP, DiGruccio MR, Covey DF, Jevtovic-Todorovic V, Todorovic SM. Inhibition of CaV3.2 T-type calcium channels in peripheral sensory neurons contributes to analgesic properties of epipregnanolone. Psychopharmacology (Berl). 2014 Sep;231(17):3503-3515. doi: 10.1007/s00213-014-3588-0. Epub 2014 May 7. PMID: 24800894; PMCID: PMC4135044.
4: Barbosa AD, Morato GS. Influence of epipregnanolone on the modulation of rapid tolerance to ethanol by neurosteroids. Braz J Psychiatry. 2007 Dec;29(4):337-45. doi: 10.1590/s1516-44462007000400008. PMID: 18200398.
5: Cerný I, Pouzar V, Hill M, Havlíková H, Hampl R. Syntheses of 19-[O-(carboxymethyl)oxime] haptens of epipregnanolone and pregnanolone. Steroids. 2006 Feb;71(2):120-8. doi: 10.1016/j.steroids.2005.09.002. Epub 2005 Oct 20. PMID: 16242742.
6: O'Dell LE, Purdy RH, Covey DF, Richardson HN, Roberto M, Koob GF. Epipregnanolone and a novel synthetic neuroactive steroid reduce alcohol self- administration in rats. Pharmacol Biochem Behav. 2005 Jul;81(3):543-50. doi: 10.1016/j.pbb.2005.03.020. PMID: 15950269.
7: Barbosa AD, Morato GS. Effect of epipregnanolone and pregnenolone sulfate on chronic tolerance to ethanol. Pharmacol Biochem Behav. 2000 Nov;67(3):459-64. doi: 10.1016/s0091-3057(00)00372-5. PMID: 11164072.
8: Pignataro L, Fiszer de Plazas S. Epipregnanolone acts as a partial agonist on a common neurosteroid modulatory site of the GABA(A) receptor complex in avian CNS. Neurochem Res. 1997 Feb;22(2):221-5. doi: 10.1023/a:1027327910138. PMID: 9016849.
9: Prince RJ, Simmonds MA. Differential antagonism by epipregnanolone of alphaxalone and pregnanolone potentiation of [3H]flunitrazepam binding suggests more than one class of binding site for steroids at GABAA receptors. Neuropharmacology. 1993 Jan;32(1):59-63. doi: 10.1016/0028-3908(93)90130-u. PMID: 8381526.
10: Bauer HC, Bauer H. Effects of progesterone, epipregnanolone and RU 38486 on potassium uptake in cultured cortical neurons. J Steroid Biochem. 1990 Jul 4;36(4):269-72. doi: 10.1016/0022-4731(90)90216-f. PMID: 2168007.
