Hydroxyprogesterone acetate

Hydroxyprogesterone acetate

Clinical data
ATC code	None
Identifiers
IUPAC name 17α-Acetoxypregn-4-ene-3,20-dione
Synonyms	Hydroxyprogesterone acetate, acetoxyprogesterone, 17α-acetoxyprogesterone
CAS Number	302-23-8
PubChem CID	10156152
ChemSpider	8331660
ECHA InfoCard	100.005.564
Chemical and physical data
Formula	C23H32O4
Molar mass	372.498 g/mol
3D model (Jmol)	Interactive image
SMILES O=C4\C=C2/[C@]([C@H]1CC[C@@]3([C@@](OC(=O)C)(C(=O)C)CC[C@H]3[C@@H]1CC2)C)(C)CC4
InChI InChI=1S/C23H32O4/c1-14(24)23(27-15(2)25)12-9-20-18-6-5-16-13-17(26)7-10-21(16,3)19(18)8-11-22(20,23)4/h13,18-20H,5-12H2,1-4H3/t18-,19+,20+,21+,22+,23+/m1/s1 Key:VTHUYJIXSMGYOQ-KOORYGTMSA-N

Hydroxyprogesterone acetate (OHPA) (INN) (brand name Prodox), or 17α-hydroxyprogesterone acetate, also known as 17α-acetoxyprogesterone or simply acetoxyprogesterone, is an orally active steroidal progestin related to hydroxyprogesterone caproate (OHPC) which was discovered in 1953 and was first marketed by Upjohn in the United States in 1957. It is a derivative of progesterone and the acetate ester of 17α-hydroxyprogesterone, as well as the parent compound of a number of progestins including chlormadinone acetate, cyproterone acetate, medroxyprogesterone acetate, and megestrol acetate.

OHPA is a progestogen and acts as an agonist of the progesterone receptor (PR), both PR_A and PR_B isoforms (IC₅₀ = 16.8 nM and 12.6 nM, respectively). It has far (>50-fold) higher affinity for the PR isoforms than 17α-hydroxyprogesterone, a little less than half the affinity of progesterone, and slightly higher affinity than OHPC.