NAV

Hydroxydione

Identification

Generic Name
Hydroxydione
DrugBank Accession Number
DB08956
Background

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

Type
Small Molecule
Groups
Investigational, Withdrawn
Structure
3D
Similar Structures
Weight
Average: 332.477
Monoisotopic: 332.23514489
Chemical Formula
C21H32O3
Synonyms
  • 21-hydroxy-5β-pregnane-3,20-dione
  • 5beta-dihydrodeoxycorticosterone
  • 5β-dihydrodeoxycorticosterone
External IDs
  • NSC-86000
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Pharmacology

Indication

Not Available

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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

Adverse Effects
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Toxicity

Not Available

Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
Not Available
Food Interactions
Not Available

Products

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Product Ingredients
IngredientUNIICASInChI Key
Hydroxydione sodium53J8I8O5EW53-10-1BFQDICGJHAONBN-OOFWROCWSA-M
International/Other Brands
Viadril (Pfizer)

Categories

Drug Categories
Chemical TaxonomyProvided by Classyfire
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
20-oxosteroid / 21-hydroxysteroid / 3-oxo-5-beta-steroid / 3-oxosteroid / Alcohol / Aliphatic homopolycyclic compound / Alpha-hydroxy ketone / Carbonyl group / Cyclic ketone / Hydrocarbon derivative
Molecular Framework
Aliphatic homopolycyclic compounds
External Descriptors
3-oxo steroid, 20-oxo steroid, 21-hydroxy steroid (CHEBI:86384)
Affected organisms
Not Available

Chemical Identifiers

UNII
B7VFN88375
CAS number
303-01-5
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,3aS,3bR,5aR,9aS,9bS,11aS)-1-(2-hydroxyacetyl)-9a,11a-dimethyl-hexadecahydro-1H-cyclopenta[a]phenanthren-7-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

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. [Article]
Human Metabolome Database
HMDB0062609
PubChem Compound
257630
PubChem Substance
310264921
ChemSpider
226020
ChEBI
86384
ZINC
ZINC000004900230
Wikipedia
Hydroxydione

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount

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-MSsplash10-107m-0293000000-19151626690502ed9eee
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-00lr-0239000000-d7f5fe4880dd2128aabe
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-001i-0009000000-5dc8f60357a828b18026
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-001j-0049000000-a9714e1a6661bb8ba96e
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-02tj-0895000000-1b21bd15d04fc4c6f201
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-0gx0-0059000000-8584c88643a284b518f2
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-0ab9-0920000000-787917c69412d3dd3323
Predicted 1H NMR Spectrum1D NMRNot Applicable
Predicted 13C NMR Spectrum1D NMRNot Applicable
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-193.7864187
predicted
DarkChem Lite v0.1.0
[M-H]-179.48363
predicted
DeepCCS 1.0 (2019)
[M+H]+194.0527187
predicted
DarkChem Lite v0.1.0
[M+H]+181.37903
predicted
DeepCCS 1.0 (2019)
[M+Na]+193.3049187
predicted
DarkChem Lite v0.1.0
[M+Na]+187.14632
predicted
DeepCCS 1.0 (2019)

Drug created at May 28, 2014 19:40 / Updated at December 02, 2023 07:01