Names | |
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IUPAC name
20α-Hydroxypregn-4-en-3-one
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Systematic IUPAC name
(1S,3aS,3bS,9aR,9bS,11aS)-1-[(1S)-1-Hydroxyethyl]-9a,11a-dimethyl-1,2,3,3a,3b,4,5,8,9,9a,9b,10,11,11a-tetradecahydro-7H-cyclopenta[a]phenanthren-7-one | |
Other names
20α-DHP; 20α-Hydroxyprogesterone; 20α-OHP; Pregn-4-en-20α-ol-3-one
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Identifiers | |
3D model (
JSmol)
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ChemSpider | |
EC Number |
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MeSH | 20-alpha-Dihydroprogesterone |
PubChem
CID
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UNII | |
CompTox Dashboard (
EPA)
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Properties | |
C21H32O2 | |
Molar mass | 316.478 g/mol |
Except where otherwise noted, data are given for materials in their
standard state (at 25 °C [77 °F], 100 kPa).
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20α-Dihydroprogesterone (20α-DHP), also known as 20α-hydroxyprogesterone (20α-OHP), is a naturally occurring, endogenous progestogen. [1] [2] [3] It is a metabolite of progesterone, formed by the 20α-hydroxysteroid dehydrogenases (20α-HSDs) AKR1C1, AKR1C2, and AKR1C3 and the 17β-hydroxysteroid dehydrogenase (17β-HSD) HSD17B1. [4] [5] 20α-DHP can be transformed back into progesterone by 20α-HSDs and by the 17β-HSD HSD17B2. [6] [7] HSD17B2 is expressed in the human endometrium and cervix among other tissues. [8] [9] [10] [7] In animal studies, 20α-DHP has been found to be selectively taken up into and retained in target tissues such as the uterus, brain, and skeletal muscle. [6]
20α-DHP has very low affinity for the progesterone receptor and is much less potent as a progestogen in comparison to progesterone, with about one-fifth of the relative progestogenic activity. [1] [2] [3] [11] [12] [6] [13] It has also been found to act as an aromatase inhibitor and to inhibit the production of estrogen in breast tissue in vitro. [14]
A single 200-mg oral dose of micronized progesterone has been found to result in peak levels of 20α-DHP of around 1 ng/mL after 2 hours. [15] In another study however, peak levels of 20α-DHP were around 10 ng/mL during therapy with 300 mg/day oral micronized progesterone. [16] 20α-DHP is formed from progesterone in the liver and in target tissues such as the endometrium. [16] It appears to be more slowly eliminated than progesterone. [16]
Levels of 5α-DHP have been quantified. [17]
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.
Names | |
---|---|
IUPAC name
20α-Hydroxypregn-4-en-3-one
| |
Systematic IUPAC name
(1S,3aS,3bS,9aR,9bS,11aS)-1-[(1S)-1-Hydroxyethyl]-9a,11a-dimethyl-1,2,3,3a,3b,4,5,8,9,9a,9b,10,11,11a-tetradecahydro-7H-cyclopenta[a]phenanthren-7-one | |
Other names
20α-DHP; 20α-Hydroxyprogesterone; 20α-OHP; Pregn-4-en-20α-ol-3-one
| |
Identifiers | |
3D model (
JSmol)
|
|
ChemSpider | |
EC Number |
|
MeSH | 20-alpha-Dihydroprogesterone |
PubChem
CID
|
|
UNII | |
CompTox Dashboard (
EPA)
|
|
| |
| |
Properties | |
C21H32O2 | |
Molar mass | 316.478 g/mol |
Except where otherwise noted, data are given for materials in their
standard state (at 25 °C [77 °F], 100 kPa).
|
20α-Dihydroprogesterone (20α-DHP), also known as 20α-hydroxyprogesterone (20α-OHP), is a naturally occurring, endogenous progestogen. [1] [2] [3] It is a metabolite of progesterone, formed by the 20α-hydroxysteroid dehydrogenases (20α-HSDs) AKR1C1, AKR1C2, and AKR1C3 and the 17β-hydroxysteroid dehydrogenase (17β-HSD) HSD17B1. [4] [5] 20α-DHP can be transformed back into progesterone by 20α-HSDs and by the 17β-HSD HSD17B2. [6] [7] HSD17B2 is expressed in the human endometrium and cervix among other tissues. [8] [9] [10] [7] In animal studies, 20α-DHP has been found to be selectively taken up into and retained in target tissues such as the uterus, brain, and skeletal muscle. [6]
20α-DHP has very low affinity for the progesterone receptor and is much less potent as a progestogen in comparison to progesterone, with about one-fifth of the relative progestogenic activity. [1] [2] [3] [11] [12] [6] [13] It has also been found to act as an aromatase inhibitor and to inhibit the production of estrogen in breast tissue in vitro. [14]
A single 200-mg oral dose of micronized progesterone has been found to result in peak levels of 20α-DHP of around 1 ng/mL after 2 hours. [15] In another study however, peak levels of 20α-DHP were around 10 ng/mL during therapy with 300 mg/day oral micronized progesterone. [16] 20α-DHP is formed from progesterone in the liver and in target tissues such as the endometrium. [16] It appears to be more slowly eliminated than progesterone. [16]
Levels of 5α-DHP have been quantified. [17]
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.