Basic information
- CAS
630-56-8- Standard SMILES
CCCCCC(=O)O[C@]1(C(C)=O)CC[C@H]2[C@@H]3CCC4=CC(=O)CC[C@]4(C)[C@H]3CC[C@@]21C- InChIKey
DOMWKUIIPQCAJU-LJHIYBGHSA-N- Molecular formula
- C27H40O4
- Average molar mass
- 428.6 g/mol
- Monoisotopic mass
- 428.29265976
Overview
Hydroxyprogesterone caproate is a corticosteroid hormone.
Names & identifiers
- Preferred name
- Hydroxyprogesterone Caproate
- IUPAC
- [(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
- English name
- Hydroxyprogesterone caproate
- Molecular formula
- C27H40O4
- Molecular weight
- 428.6
Names & synonyms
HYDROXYPROGESTERONE CAPROATE630-56-8DelalutinPrimolut DepotHydroxyprogesterone hexanoateHormofortSyngynonProluton DepotDepo-ProlutonTeralutilHylutinMakena
Show more names
17a-hydroxyprogesterone caproate17α-Hydroxyprogesterone CaproateProgeLutateSquibbHyroxonRelutinLutopronNeolutin
Pharlon17alpha-Hydroxyprogesterone caproateProcyte depoNSC-1759217-alpha-hydroxy-progesterone caproate17-OHPC17alpha-Caproyloxypregn-4-ene-3,20-dione17-((1-Oxohexyl)oxy)pregn-4-ene-3,20-dione
Database identifiers
- CAS
630-56-8- PubChem CID
- 169870
- DTXSID
DTXSID6043915- ChEMBL
CHEMBL1200848- ChEBI
CHEBI:5812
Properties
Computed structural properties
- XLogP
- 5.7
- Topological polar surface area
- 60.4 Ų
- Hydrogen bond donors
- 0
- Hydrogen bond acceptors
- 4
- Rotatable bonds
- 7
- Heavy atoms
- 31
- Formal charge
- 0
- Complexity
- 797
Experimental & physicochemical properties
Drugs
Pharmaceuticals -> Listed in ZINC15
Pharmaceutical
Human Drugs
FDA approved drugs -> Active ingredient
FDA approved drugs -> Active ingredient
Animal DrugsPharmaceuticals -> Animal Drugs -> Approved in Taiwan
Endocrine DisruptorsPotential endocrine disrupting compound
Melting Point119-121
Collision Cross Section225.6 Ų [M+Na]+ [CCS Type: DT; Buffer gas: N2; Ionization: ESI+; Dataset: TOXCAST; Source Identifier: DTXSID6043915]
Physicochemical properties
- Melting point
- 119 °C · 119°C
- Boiling point
- 463.43 °C · 463.43°C (rough estimate)
- alpha
- 44 · +44~+50°(D/20℃)(c=1,CH3OH)
- Density
- 1.0148 · 1.0148 (rough estimate)
Safety & regulation
GHS classification
GHS Classification
Danger
H360 (93.2%): May damage fertility or the unborn child [Danger Reproductive toxicity]
P203, P280, P318, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 44 reports by companies from 7 notifications to the ECHA C&L Inventory.
Hazard information
Regulatory InformationHydroxyprogesterone caproate: Does not have an individual approval but may be used as a component in a product covered by a group standard. It is not approved for use as a chemical in its own right.
Other Safety InformationIMAP assessments - Pregn-4-ene-3,20-dione, 17-[(1-oxohexyl)oxy]-: Environment tier I assessment
Hazard Classes and CategoriesRepr. 1B (93.2%)
Toxicology
Carcinogen Classification2B, possibly carcinogenic to humans. (L135)
Drug Induced Liver Injury
Drug Induced Liver Injury Rank (DILIrank 2.0)
Hydroxyprogesterone caproate
Ambiguous-DILI-concern
2
Warnings & precautions
DOI:10.1016/j.drudis.2016.02.015
Safety data
- wgk
- 3
- rtecs
- TU5085000
- hs_code
- 2937230000
- risk_code
- 61
- Signal word
- Danger
Chemistry & industry
Pharmacology
Protein BindingHydroxyprogesterone caproate is extensively protein bound in the plasma.
PharmacodynamicsNo specific pharmacodynamic studies have been performed to assess hydroxyprogesterone caproate injections. However, the mechanism of action is likely related to increased interaction between progesterone and progesterone receptors.
Mechanism of Action
The mechanism by which progesterone prevents preterm birth is not well understood, but many pathways are likely involved. Progesterone plays a vital role in regulation of the female reproductive system and is important for successful implantation of the embryo and maintenance of pregnancy. It acts by binding to progesterone receptors in the uterus, ovaries, breasts and in the central nervous system. These receptors exist in 2 isoforms, PR-A and PR-B. Progesterone binding to these receptors ultimately leads to regulation of gene transcription. This results in an anti-inflammatory effect which blunts the proinflammatory state that occurs with initiation of labor, and maintains uterine queiscence by stabilizing progesterone acting on the myometrium.
Biological Half-LifeHalf-life = 16 days (±6 days).
Metabolism/MetabolitesThe main enzymes involved in metabolism of hydroxyprogesterone caproate are cytochrome P450 (CYP) 3A4 and to a lesser extent CYP3A5.
FDA Pharmacological Classification
HYDROXYPROGESTERONE CAPROATE
Progesterone Congeners [CS]; Progestin [EPC]
MeSH Pharmacological Classification
Compounds which inhibit or antagonize the action or biosynthesis of estrogenic compounds.
Compounds that interact with PROGESTERONE RECEPTORS in target tissues to bring about the effects similar to those of PROGESTERONE. Primary actions of progestins, including natural and synthetic steroids, are on the UTERUS and the MAMMARY GLAND in preparation for and in maintenance of PREGNANCY.
Related reactions
1 records
Compound notes
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