17α-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
Identifiers
CAS Number	68-96-2
3D model (Jmol)	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) (INN, BAN), also known as 17α-hydroxypregn-4-ene-3,20-dione, 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.

Under the brand name Gestageno, 17α-OHP has been marketed for clinical use in Argentina. However, esters of 17α-OHP, including hydroxyprogesterone caproate, as well as hydroxyprogesterone acetate and hydroxyprogesterone heptanoate to a much lesser extent, have been used far more widely in comparison, and when "hydroxyprogesterone" is referenced from the standpoint of medical use, what is usually being referred to is actually, in general, hydroxyprogesterone caproate.

17α-OHP is also the parent compound of a class of progestins referred to as the 17α-hydroxyprogesterone derivatives. Among others, this class of drugs includes chlormadinone acetate, cyproterone acetate, hydroxyprogesterone caproate, medroxyprogesterone acetate, and megestrol acetate.