11β-Hydroxyprogesterone

11β-Hydroxyprogesterone
Names
	IUPAC name (8S,9S,10R,11S,13S,14S,17S)-17-acetyl-11-hydroxy-10,13-dimethyl-1,2,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-3-one
	Other names 11β-OHP; 21-Deoxycorticosterone; 21-Desoxycorticosterone; 11β-Hydroxypregn-4-ene-3,20-dione
Identifiers
CAS Number	600-57-7;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:28247;
ChEMBL	ChEMBL2440888;
ChemSpider	91968;
ECHA InfoCard	100.009.088
KEGG	C05498;
PubChem CID	101788;
	InChI 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;
	SMILES 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
Chemical formula	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). Infobox references

11β-Hydroxyprogesterone (11β-OHP), also known as 21-deoxycorticosterone, as well as 11β-hydroxypregn-4-ene-3,20-dione, is a naturally occurring, endogenous steroid and derivative of progesterone.^[1] It is a potent mineralocorticoid.^[1] Increased levels of 11β-OHP occur in 21-hydroxylase deficiency.^[1]

Along with its epimer 11α-hydroxyprogesterone (11α-OHP), 11β-OHP has been identified as a very potent competitive inhibitor of both isoforms (1 and 2) of 11β-hydroxysteroid dehydrogenase (11β-HSD).^[2]^[3]

References

^ ^a ^b ^c "Human Metabolome Database: Showing metabocard for 11b-Hydroxyprogesterone (HMDB04031)". hmdb.ca. Retrieved 2016-12-16.
^ Souness GW, Latif SA, Laurenzo JL, Morris DJ (1995). "11 alpha- and 11 beta-hydroxyprogesterone, potent inhibitors of 11 beta-hydroxysteroid dehydrogenase (isoforms 1 and 2), confer marked mineralocorticoid activity on corticosterone in the ADX rat". Endocrinology. 136 (4): 1809–12. doi:10.1210/endo.136.4.7895695. PMID 7895695.
^ Souness GW, Morris DJ (1996). "11 alpha- and 11 beta-hydroxyprogesterone, potent inhibitors of 11 beta-hydroxysteroid dehydrogenase, possess hypertensinogenic activity in the rat". Hypertension. 27 (3 Pt 1): 421–5. PMID 8698448.

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