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P7754

Sigma-Aldrich

5α-Pregnane-3,20-dione (allo)

progesterone metabolite

Synonym(s):

5α-Dihydroprogesterone, Allopregnane-3,20-dione

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About This Item

Empirical Formula (Hill Notation):
C21H32O2
CAS Number:
566-65-4
Molecular Weight:
316.48
EC Number:
209-297-3
MDL number:
MFCD00067132
UNSPSC Code:
51111800
PubChem Substance ID:
24898872
NACRES:
NA.77

form

powder

SMILES string

[H][C@@]12CC[C@@]3([H])[C@]4([H])CC[C@H](C(C)=O)[C@@]4(C)CC[C@]3([H])[C@@]1(C)CCC(=O)C2

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

InChI key

XMRPGKVKISIQBV-BJMCWZGWSA-N

Biochem/physiol Actions

A high-level metabolite of progesterone in breast cancer tissue (but not normal breast tissue); promotes cell proliferation and detachment. Receptors appear only on the cell surface of MCF-7 breast cancer cells, not on nuclei where most other steroid receptors are located.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

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Oscar González-Flores et al.
Hormones and behavior, 58(2), 223-229 (2010-03-24)
This study tested the hypothesis that the Src/Raf/MAPK signaling pathway is involved in the facilitation of the lordosis and proceptive behaviors induced by progesterone (P) and its ring A-reduced metabolites in ovariectomized, estradiol-primed rats. Intraventricular (icv) infusion of PP2 (7.5
Laurence Meyer et al.
Cellular and molecular life sciences : CMLS, 67(17), 3017-3034 (2010-05-01)
Painful neuropathy is a major side-effect limiting cancer chemotherapy. Therefore, novel strategies are required to suppress the neuropathic effects of anticancer drugs without altering their chemotherapeutic effectiveness. By combining biochemical, neuroanatomical/neurochemical, electrophysiological and behavioral methods, we demonstrated that progesterone-derived neurosteroids
George Wittemyer et al.
Hormones and behavior, 51(3), 346-354 (2007-02-27)
Non-invasive endocrine methods enable investigation of the relationship between ecological variation and ovarian activity and how this impacts on demographic processes. The underlying physiological factors driving high variation in inter-calving intervals among multi-parous African elephants offer an interesting system for
Ahmad A Jamshidi et al.
Steroids, 72(13), 843-850 (2007-09-04)
Oxytocin receptor (OTR) expression is suppressed by progesterone (P4) during the luteal phase of the estrous cycle and then it increases at the time of luteolysis, but its regulation is still not completely understood. The objective of this work was
J Zhang et al.
The Journal of steroid biochemistry and molecular biology, 70(4-6), 123-131 (2000-01-06)
Progesterone inhibits intracellular transport of lysosomal cholesterol in cultured cells, and thus at least in part mimics the biochemical phenotype of Niemann-Pick type C disease (NPC) in human fibroblasts. The goal of this study was to determine whether metabolism of
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