20β-Dihydroprogesterone

20β-Dihydroprogesterone
Names
	IUPAC name (8S,9S,10R,13S,14S,17S)-17-[(1R)-1-Hydroxyethyl]-10,13-dimethyl-1,2,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-3-one
	Other names 20β-DHP; 20β-Hydroxyprogesterone; 20β-OHP; 20β-Hydroxypregn-4-en-3-one; Pregn-4-en-20β-ol-3-one
Identifiers
CAS Number	145-15-3;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:36729;
ChEMBL	ChEMBL2112756;
ChemSpider	8612;
PubChem CID	92747;
	InChI 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/h12-13,16-19,22H,4-11H2,1-3H3/t13-,16+,17-,18+,19+,20+,21-/m1/s1 Key: RWBRUCCWZPSBFC-SJOKZOANSA-N;
	SMILES C[C@H]([C@H]1CC[C@@H]2[C@@]1(CC[C@H]3[C@H]2CCC4=CC(=O)CC[C@]34C)C)O;
Properties
Chemical formula	C21H32O2
Molar mass	316.485 g/mol
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
	Infobox references

20β-Dihydroprogesterone (20β-DHP), also known as 20β-hydroxyprogesterone (20β-OHP), is an endogenous metabolite of progesterone which is formed by 20β-hydroxysteroid dehydrogenase (20β-HSD).[1] It is a progestogen similarly to progesterone, with about 20 to 50% of the progestogenic activity of progesterone.[1] It can be converted by 20β-HSD into progesterone in the uterus.[2] The effects of 20β-HSD on the uterus, mammary glands, and in maintaining pregnancy have been studied.[2][3][4] The progestogenic activity of 20β-HSD has also been characterized in women.[5][3]

References

Bertram G. Katzung (30 November 2017). Basic and Clinical Pharmacology 14th Edition. McGraw-Hill Education. p. 728. ISBN 978-1-259-64116-9. In addition to progesterone, 20α- and 20β-hydroxyprogesterone (20α- and 20β-hydroxy-4-pregnene-3-one) also are found. These compounds have about one-fifth the progestational activity of progesterone in humans and other species.
Lisboa, B. P.; Holtermann, M. (1976). "METABOLISM OF 20β-HYDROXY-4-PREGNEN-3-ONE IN UTERINE TISSUE OF NON-PREGNANT RATS IN VITRO". Acta Endocrinologica. 83 (3): 604–620. doi:10.1530/acta.0.0830604. ISSN 0804-4643.
Lauritzen, Christian (1963). "BIOLOGISCHE WIRKUNGEN DES 20β-HYDROXY-PREGN-4-EN-3-ON". Acta Endocrinologica. 44 (2): 225–236. doi:10.1530/acta.0.0440225. ISSN 0804-4643.
Kumaresan, P.; Turner, C. W. (1968). "A Comparison of 20 -hydroxy-pregn-4-ene-3-one and Progesterone on Mammary Gland Growth of the Rat". Experimental Biology and Medicine. 129 (3): 955–956. doi:10.3181/00379727-129-33466. ISSN 1535-3702.
Besch, Paige K.; Barry, Roger D.; Vorys, Nichols; Stevens, Vernon; Ullery, John C. (1965). "A review of some aspects of the metabolism of progestational agents". Metabolism. 14 (3): 432–443. doi:10.1016/0026-0495(65)90031-4. ISSN 0026-0495.

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[Katzung2017-1] Bertram G. Katzung (30 November 2017). Basic and Clinical Pharmacology 14th Edition. McGraw-Hill Education. p. 728. ISBN 978-1-259-64116-9. In addition to progesterone, 20α- and 20β-hydroxyprogesterone (20α- and 20β-hydroxy-4-pregnene-3-one) also are found. These compounds have about one-fifth the progestational activity of progesterone in humans and other species.

[LisboaHoltermann1976-2] Lisboa, B. P.; Holtermann, M. (1976). "METABOLISM OF 20β-HYDROXY-4-PREGNEN-3-ONE IN UTERINE TISSUE OF NON-PREGNANT RATS IN VITRO". Acta Endocrinologica. 83 (3): 604–620. doi:10.1530/acta.0.0830604. ISSN 0804-4643.

[Lauritzen1963-3] Lauritzen, Christian (1963). "BIOLOGISCHE WIRKUNGEN DES 20β-HYDROXY-PREGN-4-EN-3-ON". Acta Endocrinologica. 44 (2): 225–236. doi:10.1530/acta.0.0440225. ISSN 0804-4643.

[KumaresanTurner1968-4] Kumaresan, P.; Turner, C. W. (1968). "A Comparison of 20 -hydroxy-pregn-4-ene-3-one and Progesterone on Mammary Gland Growth of the Rat". Experimental Biology and Medicine. 129 (3): 955–956. doi:10.3181/00379727-129-33466. ISSN 1535-3702.

[BeschBarry1965-5] Besch, Paige K.; Barry, Roger D.; Vorys, Nichols; Stevens, Vernon; Ullery, John C. (1965). "A review of some aspects of the metabolism of progestational agents". Metabolism. 14 (3): 432–443. doi:10.1016/0026-0495(65)90031-4. ISSN 0026-0495.

20β-Dihydroprogesterone

See also

References