Hydroxyprogesterone caproate
Hydroxyprogesterone caproate, sold under the brand names Proluton and Makena among others, is a medication used to reduce the risk of preterm birth in women pregnant with one baby who have a history of spontaneous preterm birth. In March 2023, the manufacturer, Covis Pharma, agreed to withdraw the drug from the US market. The approvals of Makena and its generics were withdrawn by the US Food and Drug Administration (FDA) in April 2023.
| Clinical data | |
|---|---|
| Trade names | Delalutin, Proluton, Makena, others |
| Other names | OHPC; Hydroxyprogesterone capronate; Hydroxyprogesterone hexanoate; 17α-Hydroxyprogesterone caproate; 17α-OHPC; 17-Hydroxyprogesterone caproate; 17-OHPC; 17-HPC; 17α-HPC; HPC; LPCN-1107; 17α-Hydroxypregn-4-ene-3,20-dione 17α-hexanoate |
| Routes of administration | Intramuscular injection, subcutaneous autoinjection |
| Drug class | Progestogen; Progestin; Progestogen ester; Antigonadotropin |
| ATC code | |
| Legal status | |
| Legal status |
|
| 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) |
| Elimination half-life | Non-pregnant: 7.8 days Singlet: 16–17 days Twins: 10 days |
| Excretion | Feces: 50% Urine: 30% |
| Identifiers | |
| |
| CAS Number | |
| PubChem CID | |
| DrugBank | |
| ChemSpider | |
| UNII | |
| KEGG | |
| ChEBI | |
| ChEMBL | |
| CompTox Dashboard (EPA) | |
| ECHA InfoCard | 100.010.127 |
| Chemical and physical data | |
| Formula | C27H40O4 |
| Molar mass | 428.613 g·mol−1 |
| 3D model (JSmol) | |
| |
| |
| (verify) | |
Hydroxyprogesterone caproate is a progestin medication which was used to prevent preterm birth in pregnant women with a history of the condition and to treat gynecological disorders. It has also been formulated in combination with estrogens for various indications (brand names Gravibinon and Primosiston) and as a form of long-lasting injectable birth control (brand name Chinese Injectable No. 1). It is not used by mouth and is instead given by injection into muscle or fat, typically once per week to once per month depending on the indication.
Hydroxyprogesterone caproate is generally well tolerated and produces few side effects. Injection site reactions such as pain and swelling are the most common side effect of hydroxyprogesterone caproate. The medication may increase the risk of gestational diabetes when used in pregnant women. Hydroxyprogesterone caproate 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.
Hydroxyprogesterone caproate was discovered in 1953 and was introduced for medical use in 1954 or 1955. It was marketed in the United States under the brand name Delalutin and throughout Europe under the brand name Proluton. The medication was discontinued in the United States in 1999. However, hydroxyprogesterone caproate was subsequently reintroduced in the United States under the brand name Makena for the treatment of preterm birth in 2011.