17-Hydroxyprogesterone caproate

Hydroxyprogesterone caproate

Clinical data
Trade names	Delalutin, Proluton, Proluton Depot, Makena, others
Synonyms	OHPC; Hydroxyprogesterone hexanoate; 17α-Hydroxyprogesterone caproate; 17α-OHPC; 17-Hydroxyprogesterone caproate; 17-OHPC; 17-HPC; 17α-HPC; HPC; 17α-Hydroxypregn-4-ene-3,20-dione 17α-hexanoate
Pregnancy category	US: B (No risk in non-human studies)
Routes of administration	• Intramuscular injection • Subcutaneous injection
Drug class	Progestin; Progestogen; Progestogen ester; Antigonadotropin
ATC code	G03DA03 (WHO) G03FA02 (WHO)
Pharmacokinetic data
Bioavailability	Oral: Very low (~3% in rats) Intramuscular: 100% (in rats)
Protein binding	Extensive (to albumin, not to CBG or (likely) SHBG)
Metabolism	Reduction and hydroxylation (via CYP3A4, CYP3A5, CYP3A7) and conjugation (glucuronidation, sulfation, acetylation)
Biological half-life	Non-pregnant: 7.8 days Singlet: 16–17 days Twins: 10 days
Excretion	Feces: 50% Urine: 30%
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 Y
PubChem CID	169870
ChemSpider	148552 Y
UNII	276F2O42F5
ECHA InfoCard	100.010.127
Chemical and physical data
Formula	C27H40O4
Molar mass	428.604 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

Hydroxyprogesterone caproate (OHPC), sold under the brand names Proluton and Makena among others, is a progestin medication which is used to prevent preterm birth in pregnant women with a history of the condition and to treat gynecological disorders. It is also used in combination with an estrogen as a form of long-lasting injectable birth control. It is not effective by mouth and must be given by injection into muscle, typically once per week.

OHPC is generally well-tolerated and produces few side effects.Injection site reactions such as pain and swelling are the most common side effect of OHPC. The medication may increase the risk of gestational diabetes when used in pregnant women. OHPC is a progestin, or a synthetic progestogen, and hence is an agonist of the progesterone receptor, the biological target of progestogens like progesterone. It has some antimineralocorticoid activity and no other important hormonal activity. The medication shows a number of differences from natural progesterone.