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MedKoo Cat#: 326987 | Name: Pregnanolone
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Description:

WARNING: This product is for research use only, not for human or veterinary use.

Pregnanolone, also known as 3a5b-Pregnanolone; Kabi-2213, SKF 6455, Eltanolone, is a cell membrane modulator potentially for the treatment of pain. Pregnanolone is an endogenous neurosteroid that is biosynthesized from progesterone. It is a positive allosteric modulator of the GABAA receptor, as well as a negative allosteric modulator of the glycine receptor, and is known to have sedative, anxiolytic, anesthetic, and anticonvulsant effects.

Chemical Structure

Pregnanolone
CAS#128-20-1

Theoretical Analysis

MedKoo Cat#: 326987

Name: Pregnanolone

CAS#: 128-20-1

Chemical Formula: C21H34O2

Exact Mass: 318.2559

Molecular Weight: 318.50

Elemental Analysis: C, 79.19; H, 10.76; O, 10.05

Price and Availability

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25mg USD 750.00 2 Weeks
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Synonym
Pregnanolone; Kabi-2213; Kabi 2213; Kabi2213; SKF 6455; SKF6455; Eltanolone; 3a5b-Pregnanolone;
IUPAC/Chemical Name
1-((3R,5R,8R,9S,10S,13S,14S,17S)-3-hydroxy-10,13-dimethylhexadecahydro-1H-cyclopenta[a]phenanthren-17-yl)ethan-1-one
InChi Key
AURFZBICLPNKBZ-YZRLXODZSA-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
CC([C@H]1CC[C@@]2([H])[C@]3([H])CC[C@]4([H])C[C@H](O)CC[C@]4(C)[C@@]3([H])CC[C@]12C)=O
Appearance
Solid powder
Purity
>95% (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
Soluble in DMSO
Shelf Life
>2 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
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
More Info
Product Data
Product Data
Certificate of Analysis
View CoA: current batch, Lot#T8R10B15
Safety Data Sheet (SDS)
View Safety Data Sheet (SDS)
Instruction
View handling instruction
Biological target:
Pregnanolone, also known as 3a5b-Pregnanolone; Kabi-2213, SKF 6455, Eltanolone, is a cell membrane modulator potentially for the treatment of pain.
In vitro activity:
Pregnanolone sulfate and pregnanolone potentiate glutamate release downstream of presynaptic Ca2+ influx, resembling the action of a phorbol ester PDBu. PDBu partially occludes the effect of pregnanolone, but not of pregnanolone sulfate. Calphostin C, an inhibitor that disrupts DAG binding to its targets, reduces the effect PDBu and pregnanolone, but not of pregnanolone sulfate, suggesting that pregnanolone might interact with a well-known DAG/phorbol ester target Munc13-1. Reference: Br J Pharmacol. 2021 Oct;178(19):3888-3904. https://pubmed.ncbi.nlm.nih.gov/33988248/
In vivo activity:
The results demonstrated the strong age-related anticonvulsive effect of PA-G (pregnanolone glutamate) in a model of pentylenetetrazol-induced seizures. PA-G significantly decreased seizure severity in 12-day-old rats, but only after the highest dose in 25-day-old animals. Interestingly, the anticonvulsant effect of PA-G differed both qualitatively and quantitatively from that of zuranolone, an investigational neurosteroid acting as a potent positive allosteric modulator of GABAARs. Next, this study identified 17-hydroxy-pregnanolone (17-OH-PA) as a major metabolite of PA-G in 12-day-old animals. Finally, the administration of PA-G demonstrated direct modulation of unexpected neurosteroid levels, namely pregnenolone and dehydroepiandrosterone sulfate. Reference: Pharmaceuticals (Basel). 2021 Dec 30;15(1):49. https://pubmed.ncbi.nlm.nih.gov/35056106/
Solvent mg/mL mM comments
Solubility
Ethanol 31.9 100.00
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.

Recalculate based on batch purity %
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. Smejkalova T, Korinek M, Krusek J, Hrcka Krausova B, Candelas Serra M, Hajdukovic D, Kudova E, Chodounska H, Vyklicky L. Endogenous neurosteroids pregnanolone and pregnanolone sulfate potentiate presynaptic glutamate release through distinct mechanisms. Br J Pharmacol. 2021 Oct;178(19):3888-3904. doi: 10.1111/bph.15529. Epub 2021 Jun 22. PMID: 33988248; PMCID: PMC8518729. 2. Kussius CL, Kaur N, Popescu GK. Pregnanolone sulfate promotes desensitization of activated NMDA receptors. J Neurosci. 2009 May 27;29(21):6819-27. doi: 10.1523/JNEUROSCI.0281-09.2009. PMID: 19474309; PMCID: PMC3150747. 3. Kudova E, Mares P, Hill M, Vondrakova K, Tsenov G, Chodounska H, Kubova H, Vales K. The Neuroactive Steroid Pregnanolone Glutamate: Anticonvulsant Effect, Metabolites and Its Effect on Neurosteroid Levels in Developing Rat Brains. Pharmaceuticals (Basel). 2021 Dec 30;15(1):49. doi: 10.3390/ph15010049. PMID: 35056106; PMCID: PMC8780580. 4. Holubova K, Nekovarova T, Pistovcakova J, Sulcova A, Stuchlík A, Vales K. Pregnanolone Glutamate, a Novel Use-Dependent NMDA Receptor Inhibitor, Exerts Antidepressant-Like Properties in Animal Models. Front Behav Neurosci. 2014 Apr 16;8:130. doi: 10.3389/fnbeh.2014.00130. PMID: 24795582; PMCID: PMC3997017.
In vitro protocol:
1. Smejkalova T, Korinek M, Krusek J, Hrcka Krausova B, Candelas Serra M, Hajdukovic D, Kudova E, Chodounska H, Vyklicky L. Endogenous neurosteroids pregnanolone and pregnanolone sulfate potentiate presynaptic glutamate release through distinct mechanisms. Br J Pharmacol. 2021 Oct;178(19):3888-3904. doi: 10.1111/bph.15529. Epub 2021 Jun 22. PMID: 33988248; PMCID: PMC8518729. 2. Kussius CL, Kaur N, Popescu GK. Pregnanolone sulfate promotes desensitization of activated NMDA receptors. J Neurosci. 2009 May 27;29(21):6819-27. doi: 10.1523/JNEUROSCI.0281-09.2009. PMID: 19474309; PMCID: PMC3150747.
In vivo protocol:
1. Kudova E, Mares P, Hill M, Vondrakova K, Tsenov G, Chodounska H, Kubova H, Vales K. The Neuroactive Steroid Pregnanolone Glutamate: Anticonvulsant Effect, Metabolites and Its Effect on Neurosteroid Levels in Developing Rat Brains. Pharmaceuticals (Basel). 2021 Dec 30;15(1):49. doi: 10.3390/ph15010049. PMID: 35056106; PMCID: PMC8780580. 2. Holubova K, Nekovarova T, Pistovcakova J, Sulcova A, Stuchlík A, Vales K. Pregnanolone Glutamate, a Novel Use-Dependent NMDA Receptor Inhibitor, Exerts Antidepressant-Like Properties in Animal Models. Front Behav Neurosci. 2014 Apr 16;8:130. doi: 10.3389/fnbeh.2014.00130. PMID: 24795582; PMCID: PMC3997017.
1: Okechukwu NG, Klein C, Jamann H, Maitre M, Patte-Mensah C, Mensah-Nyagan AG. Monomeric Amyloid Peptide-induced Toxicity in Human Oligodendrocyte Cell Line and Mouse Brain Primary Mixed-glial Cell Cultures: Evidence for a Neuroprotective Effect of Neurosteroid 3α-O-allyl-allopregnanolone. Neurotox Res. 2024 Aug 5;42(4):37. doi: 10.1007/s12640-024-00715-1. PMID: 39102123. 2: Çulcu EA, Demiryürek Ş, Demiryürek AT. An update on approved and emerging drugs for the treatment of postpartum depression. Ideggyogy Sz. 2024 Jul 30;77(7-8):227-235. English. doi: 10.18071/isz.77.0227. PMID: 39082257. 3: Ma M, Xu H, Ye L, Li C, Zhu H, Jiang W, Wang W, Yang H, Yang Y, Wang Y, Tian J. Synthesis and evaluation of neuroactive steroids with novel pharmacophore at C-21 let identify a compound with advantageous PK profile and higher EC50 and Emax as PAM on GABAA receptor. Eur J Med Chem. 2024 Oct 5;276:116602. doi: 10.1016/j.ejmech.2024.116602. Epub 2024 Jun 22. PMID: 38971049. 4: Downs J, Jacoby P, Specchio N, Cross H, Amin S, Bahi-Buisson N, Rajaraman R, Suter B, Devinsky O, Aimetti A, Busse G, Olson HE, Demarest S, Benke TA, Pestana-Knight E. Effects of ganaxolone on non-seizure outcomes in CDKL5 Deficiency Disorder: Double-blind placebo-controlled randomized trial. Eur J Paediatr Neurol. 2024 Jul;51:140-146. doi: 10.1016/j.ejpn.2024.06.005. Epub 2024 Jun 17. PMID: 38959712; PMCID: PMC11283350. 5: Izumi Y, O'Dell KA, Cashikar AG, Paul SM, Covey DF, Mennerick SJ, Zorumski CF. Neurosteroids mediate and modulate the effects of pro-inflammatory stimulation and toll-like receptors on hippocampal plasticity and learning. PLoS One. 2024 Jun 14;19(6):e0304481. doi: 10.1371/journal.pone.0304481. PMID: 38875235; PMCID: PMC11178232. 6: Geng X, Wang X, Liu K, Xing Y, Xu J, Li Z, Zhang H, Hu M, Gao P, Chen D, Liu W, Li K, Wei S. ShuYu capsule alleviates emotional and physical symptoms of premenstrual dysphoric disorder: Impact on ALLO decline and GABAA receptor δ subunit in the PAG area. Phytomedicine. 2024 Jul 25;130:155549. doi: 10.1016/j.phymed.2024.155549. Epub 2024 Mar 19. PMID: 38810551. 7: Fayoud AM, Orebi HA, Elshnoudy IA, Elsebaie MAT, Elewidi MMM, Sabra HK. The efficacy and safety of Zuranolone for treatment of depression: A systematic review and meta-analysis. Psychopharmacology (Berl). 2024 Jul;241(7):1299-1317. doi: 10.1007/s00213-024-06611-y. Epub 2024 May 28. Erratum in: Psychopharmacology (Berl). 2024 Sep;241(9):1937. doi: 10.1007/s00213-024-06642-5. PMID: 38802705; PMCID: PMC11199213. 8: McCurry MD, D'Agostino GD, Walsh JT, Bisanz JE, Zalosnik I, Dong X, Morris DJ, Korzenik JR, Edlow AG, Balskus EP, Turnbaugh PJ, Huh JR, Devlin AS. Gut bacteria convert glucocorticoids into progestins in the presence of hydrogen gas. Cell. 2024 Jun 6;187(12):2952-2968.e13. doi: 10.1016/j.cell.2024.05.005. Epub 2024 May 24. PMID: 38795705; PMCID: PMC11179439. 9: Gautier KN, Higley SL, Mendoza JM, Morrison KE. The impact of pubertal stress and adult hormone exposure on the transcriptome of the developing hypothalamus. Stress. 2024 Jan;27(1):2357330. doi: 10.1080/10253890.2024.2357330. Epub 2024 May 22. PMID: 38775373; PMCID: PMC11323331. 10: Blakely KK. First Oral Treatment Specific for Postpartum Depression. Nurs Womens Health. 2024 Aug;28(4):315-318. doi: 10.1016/j.nwh.2024.03.003. Epub 2024 May 18. PMID: 38768648. 11: Grötsch MK, Ehlert U. Allopregnanolone in the peripartum: Correlates, concentrations, and challenges - A systematic review. Psychoneuroendocrinology. 2024 Aug;166:107081. doi: 10.1016/j.psyneuen.2024.107081. Epub 2024 May 16. PMID: 38759520. 12: Deligiannidis KM, Bullock A, Nandy I, Dunbar J, Lasser R, Witte M, Leclair B, Wald J. Zuranolone Concentrations in the Breast Milk of Healthy, Lactating Individuals: Results From a Phase 1 Open-Label Study. J Clin Psychopharmacol. 2024 Jul-Aug 01;44(4):337-344. doi: 10.1097/JCP.0000000000001873. Epub 2024 May 13. PMID: 38739007. 13: Hitt EM. Zuranolone: A Narrative Review of a New Oral Treatment for Postpartum Depression. Clin Ther. 2024 May;46(5):433-438. doi: 10.1016/j.clinthera.2024.04.001. Epub 2024 May 1. PMID: 38697873. 14: Mitchell SJ, Phillips GD, Tench B, Li Y, Belelli D, Martin SJ, Swinny JD, Kelly L, Atack JR, Paradowski M, Lambert JJ. Neurosteroid Modulation of Synaptic and Extrasynaptic GABAA Receptors of the Mouse Nucleus Accumbens. Biomolecules. 2024 Apr 9;14(4):460. doi: 10.3390/biom14040460. PMID: 38672476; PMCID: PMC11048561. 15: Hamidovic A, Cho S, Davis J. Positive association between dehydroepiandrosterone (DHEA) and gene expression of the gamma-aminobutyric acid (GABA-A) receptor δ subunit. J Steroid Biochem Mol Biol. 2024 Jul;241:106525. doi: 10.1016/j.jsbmb.2024.106525. Epub 2024 Apr 16. PMID: 38636682. 16: Bäckström T, Doverskog M, Blackburn TP, Scharschmidt BF, Felipo V. Allopregnanolone and its antagonist modulate neuroinflammation and neurological impairment. Neurosci Biobehav Rev. 2024 Jun;161:105668. doi: 10.1016/j.neubiorev.2024.105668. Epub 2024 Apr 10. PMID: 38608826. 17: Khan P, Saini S, Hussain S, Majid H, Gupta S, Agarwal N. A systematic review and meta-analysis on efficacy and safety of Ganaxolone in epilepsy. Expert Opin Pharmacother. 2024 Apr;25(5):621-632. doi: 10.1080/14656566.2024.2342413. Epub 2024 Apr 17. PMID: 38606458. 18: Amin SN, Shaltout SA, El Gazzar WB, Abdel Latif NS, Al-Jussani GN, Alabdallat YJ, Albakri KA, Elberry DA. Impact of NMDA receptors block versus GABA-A receptors modulation on synaptic plasticity and brain electrical activity in metabolic syndrome. Adv Med Sci. 2024 Mar;69(1):176-189. doi: 10.1016/j.advms.2024.03.008. Epub 2024 Mar 30. PMID: 38561071. 19: Guard M, Labonte AK, Mendoza M, Myers MJ, Duncan M, Drysdale AT, Mukherji E, Rahman T, Tandon M, Kelly JC, Cooke E, Rogers CE, Lenze S, Sylvester CM. Brexanolone Treatment in a Real-World Patient Population: A Case Series and Pilot Feasibility Study of Precision Neuroimaging. J Clin Psychopharmacol. 2024 May-Jun 01;44(3):240-249. doi: 10.1097/JCP.0000000000001859. Epub 2024 Mar 28. PMID: 38551454; PMCID: PMC11177577. 20: Guillén-Ruiz G, Bernal-Morales B, Limón-Vázquez AK, Olmos-Vázquez OJ, Rodríguez-Landa JF. Involvement of the GABAA Receptor in the Antidepressant-Like Effects Produced by Low and High Doses of the Flavonoid Chrysin in the Rat: A Longitudinal Study. J Integr Neurosci. 2024 Mar 4;23(3):51. doi: 10.31083/j.jin2303051. PMID: 38538228.