17α-hydroxyprogesterone caproate

Hydroxyprogesterone caproate

Clinical data
Trade names	Proluton, Proluton Depot, Makena, others
Synonyms	OHPC; Hydroxyprogesterone hexanoate; 17α-Hydroxyprogesterone caproate; 17α-OHPC; 17-Hydroxyprogesterone caproate; 17-OHPC; 17-HPC; 17α-HPC; HPC
Pregnancy category	B
Routes of administration	Intramuscular injection
ATC code	G03DA03 (WHO)
Pharmacokinetic data
Bioavailability	Oral: Very low (~3% in rats) Intramuscular: 100% (in rats)
Biological half-life	Non-pregnant: 7.8 days Singlet: 16 days Twins: 10 days
Identifiers
IUPAC name [(8R,9S,10R,13S,14S,17R)-17-acetyl-10,13-dimethyl-3-oxo-2,6,7,8,9,11,12,14,15,16-decahydro-1H-cyclopenta[a]phenanthren-17-yl] hexanoate
CAS Number	630-56-8 N
PubChem CID	169870
ChemSpider	148552 Y
UNII	276F2O42F5
ECHA InfoCard	100.010.127
Chemical and physical data
Formula	C27H40O4
Molar mass	428.6041 g/mol
3D model (JSmol)	Interactive image
SMILES O=C4\C=C2/[C@]([C@H]1CC[C@@]3([C@@](OC(=O)CCCCC)(C(=O)C)CC[C@H]3[C@@H]1CC2)C)(C)CC4
InChI InChI=1S/C27H40O4/c1-5-6-7-8-24(30)31-27(18(2)28)16-13-23-21-10-9-19-17-20(29)11-14-25(19,3)22(21)12-15-26(23,27)4/h17,21-23H,5-16H2,1-4H3/t21-,22+,23+,25+,26+,27+/m1/s1 Y Key:DOMWKUIIPQCAJU-LJHIYBGHSA-N Y
NY (what is this?)

Hydroxyprogesterone caproate (OHPC), sold under the brand names Proluton, Proluton Depot, and Makena among others, is a progestin which is used in the treatment of a variety of gynecological disorders and for specific obstetric indications. It was previously marketed under the trade name Delalutin by Squibb, which was approved by the United States (U.S.) Food and Drug Administration (FDA) in 1956 and withdrawn from marketing in 1999. It is also sold as Proluton throughout Europe. The U.S. FDA approved Makena from KV Pharmaceutical on February 4, 2011 for prevention of preterm delivery in women with a history of preterm delivery, sparking a pricing controversy. OHPC is not active by mouth and must be administered by injection into muscle.

OHPC is used in the treatment of threatened miscarriage, gynecological disorders such as dysmenorrhea, premenstrual syndrome, fibrocystic breast disease, adenosis, and breast pain, and endometrial cancer. It was used widely in the 1950s through the 1970s for these indications, but OHPC more recently has received the most attention in the prevention of preterm birth.