This drug entry is a stub and has not been fully annotated. It is scheduled to be annotated soon.

Identification

Name
Fluprednisolone
Accession Number
DB09378
Type
Small Molecule
Groups
Approved
Description

A synthetic glucocorticoid with anti-inflammatory properties.

Structure
Thumb
Synonyms
  • 6alpha-Fluoroprednisolone
  • Fluprednisolonum
External IDs
FI 6150 / NSC-47439 / U 7800 / U-7800
International/Other Brands
Alphadrol
Categories
UNII
9H05937G3X
CAS number
53-34-9
Weight
Average: 378.44
Monoisotopic: 378.184252132
Chemical Formula
C21H27FO5
InChI Key
MYYIMZRZXIQBGI-HVIRSNARSA-N
InChI
InChI=1S/C21H27FO5/c1-19-5-3-11(24)7-14(19)15(22)8-12-13-4-6-21(27,17(26)10-23)20(13,2)9-16(25)18(12)19/h3,5,7,12-13,15-16,18,23,25,27H,4,6,8-10H2,1-2H3/t12-,13-,15-,16-,18+,19-,20-,21-/m0/s1
IUPAC Name
(1R,3aS,3bS,5S,9aR,9bS,10S,11aS)-5-fluoro-1,10-dihydroxy-1-(2-hydroxyacetyl)-9a,11a-dimethyl-1H,2H,3H,3aH,3bH,4H,5H,7H,9aH,9bH,10H,11H,11aH-cyclopenta[a]phenanthren-7-one
SMILES
[H][C@@]12CC[C@](O)(C(=O)CO)[C@@]1(C)C[C@H](O)[C@@]1([H])[C@@]2([H])C[C@H](F)C2=CC(=O)C=C[C@]12C

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
DrugInteraction
(R)-warfarinThe therapeutic efficacy of (R)-warfarin can be increased when used in combination with Fluprednisolone.
(S)-WarfarinThe therapeutic efficacy of (S)-Warfarin can be increased when used in combination with Fluprednisolone.
1-TestosteroneThe risk or severity of edema formation can be increased when 1-Testosterone is combined with Fluprednisolone.
1,10-PhenanthrolineThe therapeutic efficacy of 1,10-Phenanthroline can be decreased when used in combination with Fluprednisolone.
16-BromoepiandrosteroneThe risk or severity of edema formation can be increased when 16-Bromoepiandrosterone is combined with Fluprednisolone.
19-norandrostenedioneThe risk or severity of edema formation can be increased when 19-norandrostenedione is combined with Fluprednisolone.
1alpha-Hydroxyvitamin D5The therapeutic efficacy of 1alpha-Hydroxyvitamin D5 can be decreased when used in combination with Fluprednisolone.
2-MethoxyethanolThe risk or severity of adverse effects can be increased when 2-Methoxyethanol is combined with Fluprednisolone.
3,5-diiodothyropropionic acidThe metabolism of 3,5-diiodothyropropionic acid can be decreased when combined with Fluprednisolone.
4-hydroxycoumarinThe metabolism of 4-hydroxycoumarin can be decreased when combined with Fluprednisolone.
Food Interactions
Not Available

References

General References
  1. Naggar VF, Gouda MW, Khalil SA: In vitro adsorption of some corticosteroids on antacids. Pharmazie. 1977 Dec;32(12):778-81. [PubMed:613316]
External Links
KEGG Drug
D04227
KEGG Compound
C14618
ChemSpider
5665
ChEBI
34474
ChEMBL
CHEMBL1200774
Wikipedia
Fluprednisolone

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
Not Available
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.261 mg/mLALOGPS
logP1.3ALOGPS
logP0.93ChemAxon
logS-3.2ALOGPS
pKa (Strongest Acidic)12.58ChemAxon
pKa (Strongest Basic)-2.9ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area94.83 Å2ChemAxon
Rotatable Bond Count2ChemAxon
Refractivity98.32 m3·mol-1ChemAxon
Polarizability38.9 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 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 / 11-beta-hydroxysteroids / 17-hydroxysteroids / 3-oxo delta-1,4-steroids / Halogenated steroids / Delta-1,4-steroids / Tertiary alcohols / Alpha-hydroxy ketones / Secondary alcohols
show 7 more
Substituents
21-hydroxysteroid / Progestogin-skeleton / 20-oxosteroid / Pregnane-skeleton / Halo-steroid / 3-oxo-delta-1,4-steroid / 6-halo-steroid / 3-oxosteroid / Oxosteroid / 11-beta-hydroxysteroid
show 21 more
Molecular Framework
Aliphatic homopolycyclic compounds
External Descriptors
fluorinated steroid (CHEBI:34474)

Enzymes

Kind
Protein
Organism
Human
Pharmacological action
No
Actions
Substrate
General Function
Vitamin d3 25-hydroxylase activity
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation react...
Gene Name
CYP3A4
Uniprot ID
P08684
Uniprot Name
Cytochrome P450 3A4
Molecular Weight
57342.67 Da
References
  1. NCI/NIH [Link]

Drug created on November 30, 2015 12:10 / Updated on November 02, 2018 07:02