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P7754

Sigma-Aldrich

5α-Pregnane-3,20-dione (allo)

progesterone metabolite

Synonyme(s) :

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

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About This Item

Formule empirique (notation de Hill):
C21H32O2
Numéro CAS:
566-65-4
Poids moléculaire :
316.48
Numéro CE :
209-297-3
Numéro MDL:
MFCD00067132
Code UNSPSC :
51111800
ID de substance PubChem :
24898872
Nomenclature NACRES :
NA.77

Niveau de qualité

200

Forme

powder

Chaîne SMILES 

[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

Clé InChI

XMRPGKVKISIQBV-BJMCWZGWSA-N

Actions biochimiques/physiologiques

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.

Code de la classe de stockage

11 - Combustible Solids

Classe de danger pour l'eau (WGK)

WGK 3

Point d'éclair (°F)

Not applicable

Point d'éclair (°C)

Not applicable

Équipement de protection individuelle

Eyeshields, Gloves, type N95 (US)

Certificats d'analyse (COA)

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5-Pregnen-3β-ol-20-one ≥98%

Sigma-Aldrich

P9129

5-Pregnen-3β-ol-20-one

Pregnenolone solution 100 μg/mL in acetonitrile, certified reference material, Cerilliant®

Supelco

P-104

Pregnenolone solution

Acétylacétone for synthesis

Sigma-Aldrich

8.00023

Acétylacétone

Pregnenolone Avanti Research™ - A Croda Brand

Avanti

700142P

Pregnenolone

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
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
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
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
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