Eltanolone (CHEM018931)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-22 05:40:55 UTC
Update Date2016-11-09 01:15:53 UTC
Accession NumberCHEM018931
Identification
Common NameEltanolone
ClassSmall Molecule
DescriptionAs of March 2019, brexanolone - developed and made available commercially by Sage Therapeutics Inc. as the brand name product Allopregnanolone - is the first drug to have ever been approved by the US FDA specifically for the treatment of postpartum depression (PPD) in adult females . Since PPD, like various other types of depression, is characterized by feelings of sadness, worthlessness or guilt, cognitive impairment, and/or possibly suicidal ideation, it is considered a life-threatening condition . Studies have consequently found that PPD can genuinely have profound negative effects on the maternal-infant bond and later infant development . The development and availability of brexanolone for the treatment of PPD in adult females subsequently provides a new and promising therapy where few existed before . In particular, the use of brexanolone in treating PPD is surrounded with promise because it acts in part as a synthetic supplement for possible deficiencies in endogenous brexanolone (allopregnanolone) in postpartum women susceptible to PPD whereas many commonly used anti-depressive medications elicit actions that may modulate the presence and activity of substances like serotonin, norepinephrine, and/or monoamine oxidase but do not mediate activities directly associated with PPD like natural fluctuations in the levels of endogenous neuroactive steroids like allopregnanolone . And finally, although brexanolone may also be undergoing clinical trials to investigate its abilities to treat super-refractory status epilepticus, it appears that some such studies have failed to meet primary endpoints that compare success in the weaning of third-line agents and resolution of potentially life-threatening status epilepticus with brexanolone vs. placebo when added to standard-of-care .
Contaminant Sources
  • FooDB Chemicals
  • ToxCast & Tox21 Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
(3alpha,5alpha)-3-Hydroxypregnan-20-oneChEBI
3alpha,5alpha-TetrahydroprogesteroneChEBI
3alpha,5alpha-THPChEBI
3alpha-Hydroxy-5alpha-dihydroprogesteroneChEBI
3alpha-Hydroxy-5alpha-pregnan-20-oneChEBI
3alpha-OH DHPChEBI
5alpha-Pregnan-3alpha-ol-20-oneChEBI
Allopregnan-3alpha-ol-20-oneChEBI
AllotetrahydroprogesteroneChEBI
BrexanolonaChEBI
BrexanolonumChEBI
SAGE-547ChEBI
SGE-102ChEBI
ZulressoChEBI
(3a,5a)-3-Hydroxypregnan-20-oneGenerator
(3Α,5α)-3-hydroxypregnan-20-oneGenerator
3a,5a-TetrahydroprogesteroneGenerator
3Α,5α-tetrahydroprogesteroneGenerator
3a,5a-THPGenerator
3Α,5α-THPGenerator
3a-Hydroxy-5a-dihydroprogesteroneGenerator
3Α-hydroxy-5α-dihydroprogesteroneGenerator
3a-Hydroxy-5a-pregnan-20-oneGenerator
3Α-hydroxy-5α-pregnan-20-oneGenerator
3a-OH DHPGenerator
3Α-OH DHPGenerator
5a-Pregnan-3a-ol-20-oneGenerator
5Α-pregnan-3α-ol-20-oneGenerator
Allopregnan-3a-ol-20-oneGenerator
Allopregnan-3α-ol-20-oneGenerator
(+)-3a-Hydroxy-5a-pregnan-20-oneHMDB
(3a)-AllopregnanoloneHMDB
3-a-TetrahydroprogesteroneHMDB
3-alpha-TetrahydroprogesteroneHMDB
3a,5a-PregnanoloneHMDB
3a-Hydroxy-5a-pregnane-20-oneHMDB
5a-Pregnane-3a-ol-20-oneHMDB
3-Hydroxypregnan-20-oneHMDB
alpha-Hydroxy-5 alpha-pregnan-20-one, 3HMDB
Pregnan-3alpha-ol-20-oneHMDB
Pregnanolone, (3alpha)-isomerHMDB
3 Hydroxypregnan 20 oneHMDB
3 alpha Hydroxy 5 alpha pregnan 20 oneHMDB
3 alpha-Hydroxy-5 alpha-pregnan-20-oneHMDB
Pregnan 3alpha ol 20 oneHMDB
alpha-Pregnan-20-one, 3 alpha-hydroxy-5HMDB
(+)-3alpha-Hydroxy-5alpha-pregnan-20-oneHMDB
(+)-3Α-hydroxy-5α-pregnan-20-oneHMDB
(3alpha)-AllopregnanoloneHMDB
(3Α)-allopregnanoloneHMDB
3alpha,5alpha-PregnanoloneHMDB
3alpha-Hydroxy-5alpha-pregnane-20-oneHMDB
3Α,5α-pregnanoloneHMDB
3Α-hydroxy-5α-pregnane-20-oneHMDB
5alpha-Pregnane-3alpha-ol-20-oneHMDB
5Α-pregnane-3α-ol-20-oneHMDB
AllopregnanoloneMeSH, ChEBI
Chemical FormulaC21H34O2
Average Molecular Mass318.494 g/mol
Monoisotopic Mass318.256 g/mol
CAS Registry Number128-20-1
IUPAC Name1-[(1S,2S,5R,7S,10R,11S,14S,15S)-5-hydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl]ethan-1-one
Traditional Name1-[(1S,2S,5R,7S,10R,11S,14S,15S)-5-hydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl]ethanone
SMILES[H][C@@]12CC[C@H](C(C)=O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CC[C@@]2([H])C[C@H](O)CC[C@]12C
InChI IdentifierInChI=1S/C21H34O2/c1-13(22)17-6-7-18-16-5-4-14-12-15(23)8-10-20(14,2)19(16)9-11-21(17,18)3/h14-19,23H,4-12H2,1-3H3/t14-,15+,16-,17+,18-,19-,20-,21+/m0/s1
InChI KeyAURFZBICLPNKBZ-SYBPFIFISA-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
  • 20-oxosteroid
  • 3-hydroxysteroid
  • Hydroxysteroid
  • 3-alpha-hydroxysteroid
  • Oxosteroid
  • Cyclic alcohol
  • Ketone
  • Secondary alcohol
  • Organooxygen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Organic oxygen compound
  • Carbonyl group
  • Alcohol
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External Descriptors
  • 3-hydroxy-5alpha-pregnan-20-one (CHEBI:50169 )
  • C21 steroids (gluco/mineralocorticoids, progestogins) and derivatives (LMST02030156 )
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.0014 g/LALOGPS
logP4.28ALOGPS
logP3.99ChemAxon
logS-5.4ALOGPS
pKa (Strongest Acidic)18.3ChemAxon
pKa (Strongest Basic)-1.4ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area37.3 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity92.91 m³·mol⁻¹ChemAxon
Polarizability38.52 ųChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - GC-MS (1 MEOX; 1 TMS)splash10-0udi-6910000000-837b37f206729753b640Spectrum
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-0udi-6910000000-837b37f206729753b640Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-1174-0292000000-fb2c0f3a1cfddb10cb08Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-004i-2139000000-ab8a6de8f5a129af086eSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0uxr-0129000000-90e5fcb36022dd1ba688Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0uxr-0396000000-4c39fe7ccd8e0c86e179Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-2490000000-7ac55935cc0d4da95860Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0029000000-fa09e69c9c0b6736d2e7Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014i-0069000000-d1d57e3e1a99da4ed11fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0zg0-1193000000-44d1597a59ac11f16a41Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0gb9-0019000000-5b53b3ba37ccafca449fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0lgi-1797000000-c11629ffa10cac4be118Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4m-8910000000-2813a600e98ff5997275Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0009000000-bbaa566ea695ae62f84eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014i-0029000000-ac1c6a15538469151b6cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00ks-0093000000-db70f670eb2440b743f9Spectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDDB11859
HMDB IDHMDB0001449
FooDB IDFDB022630
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkAllopregnanolone
Chemspider ID83760
ChEBI ID50169
PubChem Compound ID92786
Kegg Compound IDC13712
YMDB IDNot Available
ECMDB IDM2MDB005177
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. Wiebe, J. P.; Deline, C.; Buckingham, K. D.; Dave, Vinod; Stothers, J. B. Synthesis of the allylic gonadal steroids, 3a-hydroxy-4-pregnen-20-one and 3a-hydroxy-4-androsten-17-one, and of 3a-hydroxy-5a-pregnan-20-one. Steroids (1985), 45(1), 39-51.
2. Wiebe, J. P.; Deline, C.; Buckingham, K. D.; Dave, Vinod; Stothers, J. B. Synthesis of the allylic gonadal steroids, 3a-hydroxy-4-pregnen-20-one and 3a-hydroxy-4-androsten-17-one, and of 3a-hydroxy-5a-pregnan-20-one. Steroids (1985), 45(1), 39-51.
3. Kim YS, Zhang H, Kim HY: Profiling neurosteroids in cerebrospinal fluids and plasma by gas chromatography/electron capture negative chemical ionization mass spectrometry. Anal Biochem. 2000 Jan 15;277(2):187-95.
4. Uzunova V, Sheline Y, Davis JM, Rasmusson A, Uzunov DP, Costa E, Guidotti A: Increase in the cerebrospinal fluid content of neurosteroids in patients with unipolar major depression who are receiving fluoxetine or fluvoxamine. Proc Natl Acad Sci U S A. 1998 Mar 17;95(6):3239-44.
5. Pearson Murphy BE, Steinberg SI, Hu FY, Allison CM: Neuroactive ring A-reduced metabolites of progesterone in human plasma during pregnancy: elevated levels of 5 alpha-dihydroprogesterone in depressed patients during the latter half of pregnancy. J Clin Endocrinol Metab. 2001 Dec;86(12):5981-7.
6. https://www.ncbi.nlm.nih.gov/pubmed/?term=10625505
7. https://www.ncbi.nlm.nih.gov/pubmed/?term=11739473
8. https://www.ncbi.nlm.nih.gov/pubmed/?term=19290593
9. https://www.ncbi.nlm.nih.gov/pubmed/?term=28370307
10. https://www.ncbi.nlm.nih.gov/pubmed/?term=28619476
11. https://www.ncbi.nlm.nih.gov/pubmed/?term=28666923
12. https://www.ncbi.nlm.nih.gov/pubmed/?term=28779545
13. https://www.ncbi.nlm.nih.gov/pubmed/?term=29453777
14. https://www.ncbi.nlm.nih.gov/pubmed/?term=29636114
15. https://www.ncbi.nlm.nih.gov/pubmed/?term=30177236
16. https://www.ncbi.nlm.nih.gov/pubmed/?term=30362283
17. https://www.ncbi.nlm.nih.gov/pubmed/?term=30481569
18. https://www.ncbi.nlm.nih.gov/pubmed/?term=30701996
19. https://www.ncbi.nlm.nih.gov/pubmed/?term=9501247