17-Hydroxyprogesterone caproate (CHEM003749)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesTargets (7)XML
Record Information
Version1.0
Creation Date2014-09-11 05:16:53 UTC
Update Date2016-11-09 01:09:13 UTC
Accession NumberCHEM003749
Identification
Common Name17-Hydroxyprogesterone caproate
ClassSmall Molecule
Description17α-Hydroxyprogesterone caproate is a synthetic steroid hormone that is similar to medroxyprogesterone acetate and megestrol acetate. It is an ester derivative of 17α-hydroxyprogesterone formed from caproic acid (hexanoic acid). 17α-Hydroxyprogesterone caproate was previously marketed under the trade name Delalutin by Squibb, which was approved by the U.S. Food and Drug Administration (FDA) in 1956 and withdrawn from marketing in 1999. Cytyc is seeking FDA approval to market 17α-hydroxyprogesterone caproate under the trade name Gestiva for prevention of preterm delivery in women with a history of preterm delivery. [Wikipedia]
Contaminant Sources
  • IARC Carcinogens Group 2B
  • T3DB toxins
  • ToxCast & Tox21 Chemicals
Contaminant Type
  • Drug
  • Food Toxin
  • Synthetic Compound
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
Primolut depotKegg
17alpha-Caproyloxypregn-4-ene-3,20-dioneKegg
DelalutinKegg
HylutinKegg
MakenaKegg
17a-Caproyloxypregn-4-ene-3,20-dioneGenerator
17Α-caproyloxypregn-4-ene-3,20-dioneGenerator
Hydroxyprogesterone caproic acidGenerator
17-Hydroxyprogesterone caproic acidGenerator
17 alpha-Oxyprogesterone capronateMeSH
17 alpha-Hydroxyprogesterone capronateMeSH
Hydroxyprogesterone hexanoateMeSH
17-alpha-Hydroxy-progesterone caproateMeSH
Oxyprogesterone caproateMeSH
17 alpha-Hydroxyprogesterone caproateMeSH
17-Hydroxyprogesterone capronateMeSH
NeolutinMeSH
Prolutin depotMeSH
Proluton depotMeSH
Caproate, 17-alpha-hydroxy-progesteroneMeSH
17 alpha Hydroxy progesterone caproateMeSH
17 alpha Hydroxyprogesterone caproateMeSH
17 alpha Oxyprogesterone capronateMeSH
17 Hydroxyprogesterone capronateMeSH
Chemical FormulaC27H40O4
Average Molecular Mass428.604 g/mol
Monoisotopic Mass428.293 g/mol
CAS Registry Number630-56-8
IUPAC Name(1S,2R,10R,11S,14R,15S)-14-acetyl-2,15-dimethyl-5-oxotetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-6-en-14-yl hexanoate
Traditional Nameproge
SMILES[H][C@@]12CC[C@](OC(=O)CCCCC)(C(C)=O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CCC2=CC(=O)CC[C@]12C
InChI IdentifierInChI=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
InChI KeyDOMWKUIIPQCAJU-LJHIYBGHSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as gluco/mineralocorticoids, progestogins and derivatives. These are steroids with a structure based on a hydroxylated prostane moiety.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassSteroids and steroid derivatives
Sub ClassPregnane steroids
Direct ParentGluco/mineralocorticoids, progestogins and derivatives
Alternative Parents
Substituents
  • Progestogin-skeleton
  • Steroid ester
  • 20-oxosteroid
  • 3-oxo-delta-4-steroid
  • 3-oxosteroid
  • Oxosteroid
  • Delta-4-steroid
  • Cyclohexenone
  • Alpha-acyloxy ketone
  • Carboxylic acid ester
  • Cyclic ketone
  • Ketone
  • Carboxylic acid derivative
  • Monocarboxylic acid or derivatives
  • Organic oxide
  • Hydrocarbon derivative
  • Organic oxygen compound
  • Carbonyl group
  • Organooxygen compound
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginExogenous
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateSolid
AppearanceWhite powder.
Experimental Properties
PropertyValue
Melting Point119-121°C
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.00087 g/LALOGPS
logP4.81ALOGPS
logP5.88ChemAxon
logS-5.7ALOGPS
pKa (Strongest Acidic)17.81ChemAxon
pKa (Strongest Basic)-4.8ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area60.44 ŲChemAxon
Rotatable Bond Count7ChemAxon
Refractivity121.69 m³·mol⁻¹ChemAxon
Polarizability50.09 ųChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-qTof , Positivesplash10-004i-2950000000-2239a8a809fdd9396eafSpectrum
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-0aba-3940000000-835c32531e48d578d8eeSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-01ta-5016900000-d55ac0fcfd38f6b1e0c8Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-06sj-9066100000-0190e2cb3e354ad5855bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-2190000000-6cb10f57437638e6f339Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-1204900000-5176dc1a9b613d11298aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004r-3139200000-a319c246dda8baaad8dbSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-01rl-9178000000-78a905d5e4c60c4ab5f6Spectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)2B, possibly carcinogenic to humans. (1)
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDDB06789
HMDB IDNot Available
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkHydroxyprogesterone caproate
Chemspider IDNot Available
ChEBI IDNot Available
PubChem Compound ID169870
Kegg Compound IDC08148
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General ReferencesNot Available