17-alpha-hydroxyprogesterone

17α-Hydroxyprogesterone

Names
IUPAC name (8R,9S,10R,13S,14S,17R)-17-acetyl-17-hydroxy-10,13-dimethyl-2,6,7,8,9,11,12,14,15,16-decahydro-1H-cyclopenta[a]phenanthren-3-one
Other names 17α-Hydroxypregn-4-ene-3,20-dione, Hydroxyprogesterone (INN)
Identifiers
CAS Number	68-96-2
3D model (JSmol)	Interactive image
ChEBI	CHEBI:17252
ChemSpider	6002
ECHA InfoCard	100.000.636
IUPHAR/BPS	5104
PubChem CID	6238
UNII	21807M87J2
InChI InChI=1S/C21H30O3/c1-13(22)21(24)11-8-18-16-5-4-14-12-15(23)6-9-19(14,2)17(16)7-10-20(18,21)3/h12,16-18,24H,4-11H2,1-3H3/t16-,17+,18+,19+,20+,21+/m1/s1 Key: DBPWSSGDRRHUNT-CEGNMAFCSA-N
SMILES CC(=O)C1(CCC2C1(CCC3C2CCC4=CC(=O)CCC34C)C)O
Properties
Chemical formula	C21H30O3
Molar mass	330.46 g/mol
Melting point	219.5
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

17α-Hydroxyprogesterone (17α-OHP), or hydroxyprogesterone (OHP), is an endogenous progestogen steroid hormone related to progesterone. It is also a chemical intermediate in the biosynthesis of many other endogenous steroids, including androgens, estrogens, glucocorticoids, and mineralocorticoids, as well as neurosteroids.

17α-OHP is an agonist of the progesterone receptor (PR) similarly to progesterone, albeit weakly in comparison. In addition, it is an antagonist of the mineralocorticoid receptor (MR) as well as a partial agonist of the glucocorticoid receptor (GR), albeit with very low potency (EC₅₀ >100-fold less relative to cortisol) at the latter site, also similarly to progesterone.

17α-OHP is derived from progesterone via 17α-hydroxylase (encoded by CYP17A1)

17α-OHP increases in the third trimester of pregnancy primarily due to fetal adrenal production.

This steroid is primarily produced in the adrenal glands and to some degree in the gonads, specifically the corpus luteum of the ovary. Normal levels are 3-90 ng/dl in children, and in women, 20-100 ng/dl prior to ovulation, and 100-500 ng/dl during the luteal phase.