11β-Hydroxyprogesterone

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11β-Hydroxyprogesterone
11β-hydroxyprogesterone molecular structure
Names
IUPAC name
11β-Hydroxypregn-4-ene-3,20-dione
Systematic IUPAC name
(1S,3aS,3bS,9aR,9bS,10S,11aS)-1-Acetyl-10-hydroxy-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
11β-OHP; 21-Deoxycorticosterone; 21-Desoxycorticosterone
Identifiers
3D model (
JSmol
)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard
 100.009.088 Edit this at Wikidata
KEGG
  • InChI=1S/C21H30O3/c1-12(22)16-6-7-17-15-5-4-13-10-14(23)8-9-20(13,2)19(15)18(24)11-21(16,17)3/h10,15-19,24H,4-9,11H2,1-3H3/t15-,16+,17-,18-,19+,20-,21+/m0/s1
    Key: BFZHCUBIASXHPK-ATWVFEABSA-N
  • CC(=O)[C@H]1CC[C@@H]2[C@@]1(C[C@@H]([C@H]3[C@H]2CCC4=CC(=O)CC[C@]34C)O)C
Properties
C21H30O3
Molar mass 330.468 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

11β-Hydroxyprogesterone (11β-OHP), also known as 21-deoxycorticosterone, as well as 11β-hydroxypregn-4-ene-3,20-dione, is a

derivative of progesterone.[1] It is a potent mineralocorticoid.[1] Syntheses of 11β-OHP from progesterone is catalyzed by the steroid 11β-hydroxylase (CYP11B1) enzyme,[2][3] and, to a lesser extent, by the aldosterone synthase enzyme (CYP11B2).[2]

Function

Along with its

11β-hydroxysteroid dehydrogenase (11β-HSD).[4][5]

Outcome of 21-hydroxylase deficiency

It has been known since 1987 that increased levels of 11β-OHP occur in

21-deoxycortisol, respectively.[10] In the 2017 study mentioned above, serum progesterone concentrations in boys (10 days to 18 years old) with 21-hydroxylase deficiency reached levels similar to female luteal values (up to 10.14 ng/mL, depending on severity and treatment), while in the control group of boys progesterone was 0.07 ng/mL (0.22 nmol/L) on average, ranged from 0.05 to 0.40 ng/mL.[8]

In a 2016 study, classical CAH patients receiving glucocorticoid therapy had C19 11-oxygenated steroid serum levels that were elevated 3-4 fold compared to healthy controls.[11] In that same study, the levels of C19 11-oxygenated androgens correlated positively with conventional androgens in women but negatively in men. The levels of 11KT were four times higher than that of T in women with the condition. In adult women with CAH, the ratio of DHT produced in a backdoor pathway to that produced in a conventional pathway increases as control of androgen excess by glucocorticoid therapy deteriorates.[12] In CAH patients with poor disease control, 11-oxygenated androgens remain elevated for longer than 17OHP, thus serving as a better biomarker for the effectiveness of the disease control.[13][14] In males with CAH, 11-oxygenated androgen levels may indicate the presence testicular adrenal rest tumors.[14][15][16]

While studies suggest that 11β-OHP, also known as 21-deoxycorticosterone, can be used as marker for adrenal 21-hydroxylase deficiency,

17α-hydroxyprogesterone) gained acceptance for this purpose.[17][18][19]

See also

References

  1. ^ a b "Human Metabolome Database: Showing metabocard for 11b-Hydroxyprogesterone (HMDB04031)". hmdb.ca. Archived from the original on 21 December 2016. Retrieved 16 December 2016.
  2. ^
    PMID 23322723
    .
  3. S2CID 3700135
    .
  4. PMID 7895695
    .
  5. PMID 8698448
    .
  6. ^
    PMID 3546944
    .
  7. PMID 2537337
    .
  8. ^
    PMID 29264476
    .
  9. PMID 28057154
    .
  10. PMID 26038201
    .
  11. PMID 26865584
    .
  12. PMID 24780050
    .
  13. PMID 34867794
    .
  14. ^
    PMID 28472487
    .
  15. PMID 34390337
    .
  16. S2CID 257943362. This article incorporates text from this source, which is available under the CC BY 4.0
    license.
  17. PMID 37873849
    .
  18. PMID 14689562
    .
  19. PMID 31016162
    .

External links
Retrieved from "https://en.wikipedia.org/w/index.php?title=11β-Hydroxyprogesterone&oldid=1218316130"