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Structure Database (LMSD)

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Common Name

11beta-hydroxyprogesterone

Systematic Name

11β-hydroxypregn-4-ene-3,20-dione

Synonyms

(11beta)-11-hydroxypregn-4-ene-3,20-dione
11beta-Hydroxyprogesterone
21-deoxycorticosterone

LM ID

LMST02030168

Formula

C₂₁H₃₀O₃

Exact Mass

Calculate m/z

330.219495

Sum Composition

ST 21:3;O3

Status

Curated

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Classification

Biological Context

11β-Hydroxyprogesterone (11β-OHP) is a metabolite of progesterone .¹ It is an agonist of the mineralocorticoid receptor (MR) that induces MR transactivation in a reporter assay (EC50 = 0.05 µM for COS-7 cells expressing the human receptor).² It increases sodium absorption in mpkCCDc14 murine renal cortical collecting duct cells. 11β-OHP is an inhibitor of 11β-hydroxysteroid dehydrogenase type 2 (11β-HSD2) and 11β-HSD1 (IC50s = 0.140 and 1 µM, respectively).³ It increases blood pressure in rats when administered subcutaneously at a rate of 10 µg/hour.⁴ Serum levels of 11β-OHP are increased in patients with 21-hydroxylase deficiency, a type of congenital adrenal hyperplasia (CAH), characterized by masculinized genitals in female infants, irregular menses in adult females, and accelerated bone age in adolescent males.⁵

This information has been provided by Cayman Chemical

References

1. van Rooyen, D., Gent, R., Barnard, L., et al. The in vitro metabolism of 11β-hydroxyprogesterone and 11-ketoprogesterone to 11-ketodihydrotestosterone in the backdoor pathway. J. Steroid Biochem. Mol. Biol. 178, 203-212 (2018).

2. Rafestin-Oblin, M.-E., Fagart, J., Souque, A., et al. 11β-hydroxyprogesterone acts as a mineralocorticoid agonist in stimulating Na+ absorption in mammalian principal cortical collecting duct cells. Mol. Pharmacol. 62(6), 1306-1313 (2002).

3. Souness, G.W., Latif, S.A., Laurenzo, J.L., et al. 11α- and 11β-hydroxyprogesterone, potent inhibitors of 11β-hydroxysteroid dehydrogenase (isoforms 1 and 2), confer marked mineralocorticoid activity on corticosterone in the ADX rat. Endocrinology 136(4), 1809-1812 (1995).

4. Souness, G.W., and Morris, D.J. 11α- and 11β-hydroxyprogesterone, potent inhibitors of 11β-hydroxysteroid dehydrogenase, possess hypertensinogenic activity in the rat. Hypertension 27(3 Pt 1), 421-425 (1996).

5. Turcu, A.F., Rege, J., Chomic, R., et al. Profiles of 21-carbon steroids in 21-hydroxylase deficiency. J. Clin. Endocrinol. Metab. 100(6), 2283-2290 (2015).

String Representations

InChiKey (Click to copy)

BFZHCUBIASXHPK-ATWVFEABSA-N

InChi (Click to copy)

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

SMILES (Click to copy)

C1CC2[C@@](C)([C@@]3([H])[C@@H](O)C[C@@]4([C@H](CC[C@@]4([H])[C@]13[H])C(=O)C)C)CCC(=O)C=2