Description
5α-Pregnane-3β,6α-diol-20-one is a mitogenic metabolite of progesterone, and it can be produced in starved androgen-responsive prostate cancer cells.
Product information
CAS Number: 21853-11-2
Molecular Weight: 334.49
Formula: C21H34O3
Chemical Name: 1-[(1S,3aS,3bR,5S,5aS,7S,9aR,9bS,11aS)-3a,3b,5a,9b-tetrahydrogenio-5,7-dihydroxy-9a,11a-dimethyl-hexadecahydro-1H-cyclopenta[a]phenanthren-1-yl]ethan-1-one
Smiles: C[C@]12CC[C@H]3[C@@H](C[C@H](O)[C@H]4C[C@@H](O)CC[C@@]43C)[C@@H]1CC[C@@H]2C(C)=O
InChiKey: HHUZGDMRRLQZIQ-WAXVQEINSA-N
InChi: InChI=1S/C21H34O3/c1-12(22)15-4-5-16-14-11-19(24)18-10-13(23)6-8-21(18,3)17(14)7-9-20(15,16)2/h13-19,23-24H,4-11H2,1-3H3/t13-,14-,15+,16-,17-,18+,19-,20+,21+/m0/s1
Technical Data
Appearance: Solid Power
Purity: ≥98% (or refer to the Certificate of Analysis)
Solubility: DMSO : 100 mg/mL (298.96 mM; Need ultrasonic).
Shipping Condition: Shipped under ambient temperature as non-hazardous chemical or refer to Certificate of Analysis
Storage Condition: Dry, dark and -20 oC for 1 year or refer to the Certificate of Analysis.
Shelf Life: ≥12 months if stored properly.
Stock Solution Storage: 0 - 4 oC for 1 month or refer to the Certificate of Analysis.
Drug Formulation: To be determined
HS Tariff Code: 382200
How to use
In Vitro:
Progesterone is converted to 5α-pregnane-3β,6α-diol-20-one in human fibroblasts. Pregnenolone and progesterone are avidly metabolized to 5α-pregnan-3β,6α-diol-20-one in the C4.2 cell line, with nearly complete conversions at 24 h and 18 h, respectively. Preferential 5α-pregnan-3β,6α-diol-20-one formation from early steroid precursors is independent of CYP17A1 but rather relies on 3β-HSD activity.
References:
- Zhang J, et al. Progesterone metabolism in human fibroblasts is independent of P-glycoprotein levels and Niemann-Pick type C disease. J Steroid Biochem Mol Biol. 1999 Sep-Oct;70(4-6):123-31.
- de Mello Martins AGG, et al. CYP17A1-independent production of the neurosteroid-derived 5α-pregnan-3β,6α-diol-20-one in androgen-responsive prostate cancer cell lines under serum starvation and inhibition by Abiraterone. J Steroid Biochem Mol Biol. 2017 Nov;174:183-191.
Products are for research use only. Not for human use.
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