Pregnanediol

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Pregnanediol
Pregnanediol.svg
Names
IUPAC name
(3R,5R,8R,9S,10S,13S,14S,17S)-17-[(1S)-1-Hydroxyethyl]-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-ol
Other names
5β-Pregnane-3α,20α-diol; Pregnandiol
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
ECHA InfoCard 100.001.195 Edit this at Wikidata
UNII
  • InChI=1S/C21H36O2/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/h13-19,22-23H,4-12H2,1-3H3/t13-,14+,15+,16-,17+,18-,19-,20-,21+/m0/s1 checkY
    Key: YWYQTGBBEZQBGO-BERLURQNSA-N checkY
  • InChI=1/C21H36O2/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/h13-19,22-23H,4-12H2,1-3H3/t13-,14+,15+,16-,17+,18-,19-,20-,21+/m0/s1
    Key: YWYQTGBBEZQBGO-BERLURQNBW
  • O[C@@H]4CC[C@]3([C@H](CC[C@H]2[C@@H]1CC[C@@H]([C@@]1(C)CC[C@@H]23)[C@@H](O)C)C4)C
Properties
C21H36O2
Molar mass 320.517 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

Pregnanediol, or 5β-pregnane-3α,20α-diol, is an inactive metabolic product of progesterone. A test can be done to measure the amount of pregnanediol in urine, which offers an indirect way to measure progesterone levels in the body.[1]

In 1936, Venning and Browne demonstrated the presence of pregnanediol, specifically the glucuronide of pregnanediol in pregnancy urine. Their study extracted pregnanediol from pregnancy urine and revealed that pregnanediol concentration in urine indicates the amount of progesterone excreted. Since progesterone levels indicate the functionality of a corpus luteum, and pregnanediol concentration represents 40-45% of the progesterone excreted, estimations of pregnanediol reveal the functionality of a corpus luteum. However, pregnanediol concentrations vary with menstrual cycle phases, so it is essential to consider the menstrual cycle phase when examining them.[2] Furthermore, current research has demonstrated that pregnanediol concentration in urine is also a measure of ovarian activity.[3]

Chemistry[edit]

See also[edit]

References[edit]

  1. ^ Smith, Melanie N. (May 1, 2007). "Pregnanediol". A.D.A.M., Inc.
  2. ^ Hain, A.; Robertson, Edwin (June 17, 1939). "Pregnanediol Excretion in the Menstrual Cycle" Check |url= value (help). The British Medical Journal – via PubMed.
  3. ^ Blackwell, Leonard; Cooke, Delwyn; Brown, Simon (May 31, 2018). "The Use of Estrone-3-Glucuronide and Pregnanediol-3-Glucuronide Excretion Rates to Navigate the Continuum of Ovarian Activity" Check |url= value (help). Frontiers in Public Health – via PubMed.