Structure via PubChem · Public domain (PubChem)
hydroxyprogesterone caproate
Sign in to saveAlso known as Makena, Delalutin, Hydroxyprogesterone hexanoate, 17α-hydroxyprogesterone caproate, 17alpha-Caproyloxypregn-4-ene-3,20-dione, Hydroxyprogesterone, Oxiprogesterone Caproate
chemical compound
Chemical data
- Formula
- C27H40O4
- Molecular weight
- 428.6 g/mol
- 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
- SMILES
- CCCCCC(=O)O[C@@]1(CC[C@@H]2[C@@]1(CC[C@H]3[C@H]2CCC4=CC(=O)CC[C@]34C)C)C(=O)C
- InChIKey
- DOMWKUIIPQCAJU-LJHIYBGHSA-N
- XLogP
- 5.7
- Polar surface area
- 60.4 Ų
- H-bond donors
- 0
- H-bond acceptors
- 4
- Formal charge
- 0
via PubChem
Drug data · ChEMBL
Withdrawn- Max clinical phase
- Approved
- Molecule type
- Small molecule
- First approval
- 1975
- Admin. routes
- parenteral
- Indications
- premature birth, pregnancy
via ChEMBL · EBI
Research
762 papers- 17α-Hydroxyprogesterone Caproate and the Risk of Glucose Intolerance in Pregnancy: A Systematic Review and Meta-analysis.Obstetrics and gynecology · 2019
- Adjuvant 17-hydroxyprogesterone caproate in women withultrasound-indicated cerclage: a systematic review and meta-analysis.The journal of maternal-fetal & neonatal medicine : the official journal of the European Association of Perinatal Medicine, the Federation of Asia and Oceania Perinatal Societies, the International Society of Perinatal Obstetricians · 2020
- 17-alpha hydroxyprogesterone caproate for preterm birth prevention: Where have we been, how did we get here, and where are we going?Seminars in perinatology · 2017
- Adjuvant 17-hydroxyprogesterone caproate in women with history-indicated cerclage: A systematic review and meta-analysis.Acta obstetricia et gynecologica Scandinavica · 2019
- 17 Alpha-hydroxyprogesterone caproate use in a rural state.The journal of maternal-fetal & neonatal medicine : the official journal of the European Association of Perinatal Medicine, the Federation of Asia and Oceania Perinatal Societies, the International Society of Perinatal Obstetricians · 2022
via PubMed
Wikidata facts
- Subclass of
- chemical compound
- Mass
- 428.29266
- Has use
- medication
Show 4 more facts
- chemical formula
- C₂₇H₄₀O₄
- canonical SMILES
- CCCCCC(=O)OC1(CCC2C1(CCC3C2CCC4=CC(=O)CCC34C)C)C(=O)C
- isomeric SMILES
- CCCCCC(=O)O[C@@]1(CC[C@@H]2[C@@]1(CC[C@H]3[C@H]2CCC4=CC(=O)CC[C@]34C)C)C(=O)C
- Commons category
- Hydroxyprogesterone caproate
Sources (2)
via Wikidata · CC0
Available in 7 languages
via Wikidata sitelinks · CC0