A metabolite of progesterone
Related Products
Isomer(s)
3589811α-Hydroxyprogesterone
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11β-Hydroxyprogesterone

Item No. 36031

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
11β-hydroxy-pregn-4-ene-3,20-dione
CAS Number
600-57-7
Synonyms
  • 21-deoxy Corticosterone
  • 11β-OHP
  • NSC 15469
  • U-1701
Molecular Formula
C21H30O3
Formula Weight
330.5
Purity
≥98%
Formulation
A solid
Solubility(Learn about Variance in Solubility)
Acetone: slightly solubleChloroform: slightly solubleMethanol: slightly soluble
SMILES
C[C@@]12[C@]3([H])[C@](CCC1=CC(CC2)=O)([H])[C@@]4([H])[C@](C[C@@H]3O)([C@H](CC4)C(C)=O)C
InChi Code
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
InChi Key
BFZHCUBIASXHPK-ATWVFEABSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    1 mg

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    Product Description

    11β-Hydroxyprogesterone (11β-OHP) is a metabolite of progesterone (Item No. 15876).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

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description 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).