Hydroxydione

Identification

Name
Hydroxydione
Accession Number
DB08956
Type
Small Molecule
Groups
Investigational, Withdrawn
Description

Hydroxydione (Viadril) is a neuroactive steroid used as a general anesthetic.

Structure
Thumb
Synonyms
  • 21-hydroxy-5β-pregnane-3,20-dione
  • 5beta-dihydrodeoxycorticosterone
  • 5β-dihydrodeoxycorticosterone
External IDs
NSC-86000
Product Ingredients
IngredientUNIICASInChI Key
Hydroxydione sodium53J8I8O5EW53-10-1BFQDICGJHAONBN-OOFWROCWSA-M
International/Other Brands
Viadril (Pfizer)
Categories
UNII
B7VFN88375
CAS number
303-01-5
Weight
Average: 332.477
Monoisotopic: 332.23514489
Chemical Formula
C21H32O3
InChI Key
USPYDUPOCUYHQL-VEVMSBRDSA-N
InChI
InChI=1S/C21H32O3/c1-20-9-7-14(23)11-13(20)3-4-15-16-5-6-18(19(24)12-22)21(16,2)10-8-17(15)20/h13,15-18,22H,3-12H2,1-2H3/t13-,15+,16+,17+,18-,20+,21+/m1/s1
IUPAC Name
(1S,2S,7R,10R,11S,14S,15S)-14-(2-hydroxyacetyl)-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-5-one
SMILES
[H][C@@]1(CC[C@@]2([H])[C@]3([H])CC[C@]4([H])CC(=O)CC[C@]4(C)[C@@]3([H])CC[C@]12C)C(=O)CO

Pharmacology

Indication
Not Available
Pharmacodynamics
Not Available
Mechanism of action
Not Available
Absorption
Not Available
Volume of distribution
Not Available
Protein binding
Not Available
Metabolism
Not Available
Route of elimination
Not Available
Half life
Not Available
Clearance
Not Available
Toxicity
Not Available
Affected organisms
Not Available
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
Not Available
Food Interactions
Not Available

References

Synthesis Reference

U.S. Patent 2,708,651.

General References
  1. LERMAN LH: Viadril: a new steroid anaesthetic; preliminary communication. Br Med J. 1956 Jul 21;2(4985):129-32. [PubMed:13329402]
External Links
Human Metabolome Database
HMDB0062609
PubChem Compound
257630
PubChem Substance
310264921
ChemSpider
226020
ChEBI
86384
Wikipedia
Hydroxydione

Clinical Trials

Clinical Trials
Not Available

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)200U.S. Patent 2,708,651.
Predicted Properties
PropertyValueSource
Water Solubility0.0156 mg/mLALOGPS
logP3.43ALOGPS
logP3.38ChemAxon
logS-4.3ALOGPS
pKa (Strongest Acidic)13.86ChemAxon
pKa (Strongest Basic)-3.3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area54.37 Å2ChemAxon
Rotatable Bond Count2ChemAxon
Refractivity93.58 m3·mol-1ChemAxon
Polarizability38.61 Å3ChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
Not Available

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available

Taxonomy

Description
This compound belongs to the class of organic compounds known as 21-hydroxysteroids. These are steroids carrying a hydroxyl group at the 21-position of the steroid backbone.
Kingdom
Organic compounds
Super Class
Lipids and lipid-like molecules
Class
Steroids and steroid derivatives
Sub Class
Hydroxysteroids
Direct Parent
21-hydroxysteroids
Alternative Parents
Gluco/mineralocorticoids, progestogins and derivatives / 20-oxosteroids / 3-oxo-5-beta-steroids / Alpha-hydroxy ketones / Cyclic ketones / Primary alcohols / Organic oxides / Hydrocarbon derivatives
Substituents
Progestogin-skeleton / 21-hydroxysteroid / Pregnane-skeleton / 20-oxosteroid / 3-oxosteroid / 3-oxo-5-beta-steroid / Oxosteroid / Alpha-hydroxy ketone / Cyclic ketone / Ketone
Molecular Framework
Aliphatic homopolycyclic compounds
External Descriptors
3-oxo steroid, 20-oxo steroid, 21-hydroxy steroid (CHEBI:86384)

Drug created on May 28, 2014 13:40 / Updated on November 02, 2018 08:46