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MedKoo Cat#: 462860 | Name: 5α-Dihydroprogesterone
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Description:

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

5α-Dihydroprogesterone is a progesterone receptor agonist and metabolite of progesterone. It is formed from progesterone by 5α-reductase. It induces gene expression mediated by the progesterone receptor in reporter assays using HepG2 cells expressing equine PR or human PR.1 5α-DHP 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. 5α-DHP levels increase locally following spinal cord injury or traumatic brain injury in rats and ischemic brain injury in mice.

Chemical Structure

5α-Dihydroprogesterone
5α-Dihydroprogesterone
CAS#566-65-4

Theoretical Analysis

MedKoo Cat#: 462860

Name: 5α-Dihydroprogesterone

CAS#: 566-65-4

Chemical Formula: C21H32O2

Exact Mass: 316.2402

Molecular Weight: 316.49

Elemental Analysis: C, 79.70; H, 10.19; O, 10.11

Price and Availability

Size Price Availability Quantity
500mg USD 350.00 2 Weeks
1g USD 650.00 2 Weeks
5g USD 1,650.00 2 Weeks
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Related CAS #
No Data
Synonym
5α-DH PROG; 5α-DHP; 5α-Pregnanedione; NSC 18319; NSC18319; NSC-18319; 5alpha-Pregnane-3,20-dione; 5a-Pregnane-3,20-dione
IUPAC/Chemical Name
(5S,8R,9S,10S,13S,14S,17S)-17-acetyl-10,13-dimethylhexadecahydro-3H-cyclopenta[a]phenanthren-3-one
InChi Key
XMRPGKVKISIQBV-BJMCWZGWSA-N
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
SMILES Code
C[C@@]12[C@@]3([C@]([H])([C@]4([C@]([C@@H](C(C)=O)CC4)(C)CC3)[H])CC[C@]1(CC(CC2)=O)[H])[H]
Appearance
Solid powder
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
Soluble in DMSO
Shelf Life
>3 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

Preparing Stock Solutions

The following data is based on the product molecular weight 316.49 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
1: Conley AJ, Scholtz EL, Legacki EL, Corbin CJ, Knych HK, Dujovne GD, Ball BA, Moeller BC, Stanley SD. 5α-dihydroprogesterone concentrations and synthesis in non-pregnant mares. J Endocrinol. 2018 Jul;238(1):25-32. doi: 10.1530/JOE-18-0215. PMID: 29853526. 2: Wu YV, Burnham WM. The anti-seizure effects of IV 5α-dihydroprogesterone on amygdala-kindled seizures in rats. Epilepsy Res. 2018 Oct;146:132-136. doi: 10.1016/j.eplepsyres.2018.07.022. Epub 2018 Jul 29. PMID: 30149307. 3: Wynn MAA, Ball BA, Legacki E, Conley A, Loux S, May J, Esteller-Vico A, Stanley S, Scoggin K, Squires E, Troedsson M. Inhibition of 5α-reductase alters pregnane metabolism in the late pregnant mare. Reproduction. 2018 Mar;155(3):251-258. doi: 10.1530/REP-17-0380. Epub 2018 Jan 16. PMID: 29339451. 4: Wiebe JP, Rivas MA, Mercogliano MF, Elizalde PV, Schillaci R. 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. 2015 May;149:27-34. doi: 10.1016/j.jsbmb.2015.01.004. Epub 2015 Jan 13. PMID: 25595041. 5: Conley AJ, Ball BA. Steroids in the establishment and maintenance of pregnancy and at parturition in the mare. Reproduction. 2019 Dec;158(6):R197-R208. doi: 10.1530/REP-19-0179. PMID: 31252409. 6: Corbin CJ, Legacki EL, Ball BA, Scoggin KE, Stanley SD, Conley AJ. Equine 5α-reductase activity and expression in epididymis. J Endocrinol. 2016 Oct;231(1):23-33. doi: 10.1530/JOE-16-0175. Epub 2016 Jul 27. PMID: 27466384. 7: Schumacher M, Mattern C, Ghoumari A, Oudinet JP, Liere P, Labombarda F, Sitruk-Ware R, De Nicola AF, Guennoun R. Revisiting the roles of progesterone and allopregnanolone in the nervous system: resurgence of the progesterone receptors. Prog Neurobiol. 2014 Feb;113:6-39. doi: 10.1016/j.pneurobio.2013.09.004. Epub 2013 Oct 27. PMID: 24172649. 8: Rasmusson AM, King MW, Valovski I, Gregor K, Scioli-Salter E, Pineles SL, Hamouda M, Nillni YI, Anderson GM, Pinna G. Relationships between cerebrospinal fluid GABAergic neurosteroid levels and symptom severity in men with PTSD. Psychoneuroendocrinology. 2019 Apr;102:95-104. doi: 10.1016/j.psyneuen.2018.11.027. Epub 2018 Nov 22. PMID: 30529908; PMCID: PMC6584957. 9: Ando T, Nishiyama T, Takizawa I, Miyashiro Y, Hara N, Tomita Y. A carbon 21 steroidal metabolite from progestin, 20β-hydroxy-5α-dihydroprogesterone, stimulates the androgen receptor in prostate cancer cells. Prostate. 2018 Feb;78(3):222-232. doi: 10.1002/pros.23460. Epub 2017 Dec 1. PMID: 29194690. 10: Drugs and Lactation Database (LactMed) [Internet]. Bethesda (MD): National Library of Medicine (US); 2006–. Brexanolone. 2020 Jul 20. PMID: 31038852. 11: Irwin RW, Brinton RD. Allopregnanolone as regenerative therapeutic for Alzheimer's disease: translational development and clinical promise. Prog Neurobiol. 2014 Feb;113:40-55. doi: 10.1016/j.pneurobio.2013.08.004. Epub 2013 Sep 14. PMID: 24044981. 12: Meletti S, Lucchi C, Monti G, Giovannini G, Bedin R, Trenti T, Rustichelli C, Biagini G. Low levels of progesterone and derivatives in cerebrospinal fluid of patients affected by status epilepticus. J Neurochem. 2018 Oct;147(2):275-284. doi: 10.1111/jnc.14550. Epub 2018 Aug 30. PMID: 30005125. 13: Zamora-Sánchez CJ, Hernández-Vega AM, Gaona-Domínguez S, Rodríguez-Dorantes M, Camacho-Arroyo I. 5alpha-dihydroprogesterone promotes proliferation and migration of human glioblastoma cells. Steroids. 2020 Jul 28;163:108708. doi: 10.1016/j.steroids.2020.108708. Epub ahead of print. PMID: 32730775. 14: Scholtz EL, Krishnan S, Ball BA, Corbin CJ, Moeller BC, Stanley SD, McDowell KJ, Hughes AL, McDonnell DP, Conley AJ. Pregnancy without progesterone in horses defines a second endogenous biopotent progesterone receptor agonist, 5α-dihydroprogesterone. Proc Natl Acad Sci U S A. 2014 Mar 4;111(9):3365-70. doi: 10.1073/pnas.1318163111. Epub 2014 Feb 18. PMID: 24550466; PMCID: PMC3948269. 15: Wiebe JP, Pawlak KJ, Kwok A. Mechanism of action of the breast cancer- promoter hormone, 5α-dihydroprogesterone (5αP), involves plasma membrane- associated receptors and MAPK activation. J Steroid Biochem Mol Biol. 2016 Jan;155(Pt A):166-76. doi: 10.1016/j.jsbmb.2015.10.021. Epub 2015 Oct 28. PMID: 26519986. 16: Zhu X, Fréchou M, Liere P, Zhang S, Pianos A, Fernandez N, Denier C, Mattern C, Schumacher M, Guennoun R. A Role of Endogenous Progesterone in Stroke Cerebroprotection Revealed by the Neural-Specific Deletion of Its Intracellular Receptors. J Neurosci. 2017 Nov 8;37(45):10998-11020. doi: 10.1523/JNEUROSCI.3874-16.2017. Epub 2017 Oct 6. PMID: 28986464; PMCID: PMC6596486. 17: Wiebe JP, Beausoleil M, Zhang G, Cialacu V. Opposing actions of the progesterone metabolites, 5alpha-dihydroprogesterone (5alphaP) and 3alpha- dihydroprogesterone (3alphaHP) on mitosis, apoptosis, and expression of Bcl-2, Bax and p21 in human breast cell lines. J Steroid Biochem Mol Biol. 2010 Jan;118(1-2):125-32. doi: 10.1016/j.jsbmb.2009.11.005. Epub 2009 Nov 17. PMID: 19931389. 18: Hankele AK, Rehm K, Berard J, Schuler G, Bigler L, Ulbrich SE. Progestogen profiling in plasma during the estrous cycle in cattle using an LC-MS based approach. Theriogenology. 2020 Jan 15;142:376-383. doi: 10.1016/j.theriogenology.2019.10.005. Epub 2019 Oct 10. PMID: 31708192. 19: Fry JP, Li KY, Devall AJ, Cockcroft S, Honour JW, Lovick TA. Fluoxetine elevates allopregnanolone in female rat brain but inhibits a steroid microsomal dehydrogenase rather than activating an aldo-keto reductase. Br J Pharmacol. 2014 Dec;171(24):5870-80. doi: 10.1111/bph.12891. Epub 2014 Nov 24. PMID: 25161074; PMCID: PMC4290723. 20: Wynn MAA, Ball BA, May J, Esteller-Vico A, Canisso I, Squires E, Troedsson M. Changes in maternal pregnane concentrations in mares with experimentally- induced, ascending placentitis. Theriogenology. 2018 Dec;122:130-136. doi: 10.1016/j.theriogenology.2018.09.001. Epub 2018 Sep 7. PMID: 30265893.