Pregnanediol

Pregnanediol
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
CAS Number	80-92-2 ;
3D model (JSmol)	Interactive image;
ChEMBL	ChEMBL269897 ;
ChemSpider	190585 ;
ECHA InfoCard	100.001.195
PubChem CID	219833;
UNII	JR3JD1Y22C ;
CompTox Dashboard (EPA)	DTXSID6046218 ;
	InChI 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 Key: YWYQTGBBEZQBGO-BERLURQNSA-N ; 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;
	SMILES 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
Chemical formula	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).

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

References

^ Smith, Melanie N. (May 1, 2007). "Pregnanediol". A.D.A.M., Inc.
^ Hain, A.; Robertson, Edwin (June 17, 1939). "Pregnanediol Excretion in the Menstrual Cycle". The British Medical Journal – via PubMed.
^ 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". Frontiers in Public Health – via PubMed.

[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". 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". Frontiers in Public Health – via PubMed.

[1]

[2]

[3]

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
CAS Number	80-92-2
3D model (JSmol)	Interactive image
ChEMBL	ChEMBL269897
ChemSpider	190585
ECHA InfoCard	100.001.195
PubChem CID	219833
UNII	JR3JD1Y22C
CompTox Dashboard (EPA)	DTXSID6046218
InChI 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 Key: YWYQTGBBEZQBGO-BERLURQNSA-N 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
SMILES 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
Chemical formula	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).

Pregnanediol

Chemistry

See also

References