Identification

Name
Fluocortolone
Accession Number
DB08971
Type
Small Molecule
Groups
Approved, Withdrawn
Description

Fluocortolone is a glucocorticoid with anti-inflammatory activity used topically for various skin disorders.

Structure
Thumb
Synonyms
Not Available
External IDs
SH 742
Categories
UNII
65VXC1MH0J
CAS number
152-97-6
Weight
Average: 376.4617
Monoisotopic: 376.204987621
Chemical Formula
C22H29FO4
InChI Key
GAKMQHDJQHZUTJ-ULHLPKEOSA-N
InChI
InChI=1S/C22H29FO4/c1-11-6-14-13-8-16(23)15-7-12(25)4-5-21(15,2)20(13)17(26)9-22(14,3)19(11)18(27)10-24/h4-5,7,11,13-14,16-17,19-20,24,26H,6,8-10H2,1-3H3/t11-,13+,14+,16+,17+,19-,20-,21+,22+/m1/s1
IUPAC Name
(1S,2R,8S,10S,11S,13R,14S,15S,17S)-8-fluoro-17-hydroxy-14-(2-hydroxyacetyl)-2,13,15-trimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadeca-3,6-dien-5-one
SMILES
[H][C@@]1(C)C[C@@]2([H])[C@]3([H])C[C@]([H])(F)C4=CC(=O)C=C[C@]4(C)[C@@]3([H])[C@@]([H])(O)C[C@]2(C)[C@@]1([H])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
DrugInteraction
(4R)-limoneneThe risk or severity of adverse effects can be increased when (4R)-limonene is combined with Fluocortolone.
1,10-PhenanthrolineThe risk or severity of adverse effects can be increased when Fluocortolone is combined with 1,10-Phenanthroline.
AceclofenacThe risk or severity of adverse effects can be increased when Aceclofenac is combined with Fluocortolone.
AcemetacinThe risk or severity of adverse effects can be increased when Acemetacin is combined with Fluocortolone.
AcetazolamideThe metabolism of Fluocortolone can be decreased when combined with Acetazolamide.
Acetylsalicylic acidThe risk or severity of adverse effects can be increased when Acetylsalicylic acid is combined with Fluocortolone.
AdalimumabThe risk or severity of adverse effects can be increased when Adalimumab is combined with Fluocortolone.
AlbendazoleThe metabolism of Fluocortolone can be decreased when combined with Albendazole.
AlclofenacThe risk or severity of adverse effects can be increased when Alclofenac is combined with Fluocortolone.
AlclometasoneThe risk or severity of adverse effects can be increased when Alclometasone is combined with Fluocortolone.
Food Interactions
Not Available

References

Synthesis Reference

U.S. Patent 3,426,128.

General References
Not Available
External Links
PubChem Compound
9053
PubChem Substance
310264934
ChemSpider
8701
ChEBI
135581
ChEMBL
CHEMBL251634
Wikipedia
Fluocortolone
ATC Codes
D07BC03 — Fluocortolone and antisepticsD07AC05 — FluocortoloneH02AB03 — FluocortoloneD07CC06 — Fluocortolone and antibioticsD07XC05 — FluocortoloneS01CA04 — Fluocortolone and antiinfectivesC05AA08 — Fluocortolone

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)180-182U.S. Patent 3,426,128.
Predicted Properties
PropertyValueSource
Water Solubility0.0339 mg/mLALOGPS
logP2.09ALOGPS
logP1.97ChemAxon
logS-4ALOGPS
pKa (Strongest Acidic)13.84ChemAxon
pKa (Strongest Basic)-0.23ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area74.6 Å2ChemAxon
Rotatable Bond Count2ChemAxon
Refractivity101.47 m3·mol-1ChemAxon
Polarizability40.07 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 / Halogenated steroids / 3-oxo delta-1,4-steroids / 11-beta-hydroxysteroids / Delta-1,4-steroids / Alpha-hydroxy ketones / Secondary alcohols / Cyclic ketones / Cyclic alcohols and derivatives
show 5 more
Substituents
Progestogin-skeleton / 21-hydroxysteroid / Pregnane-skeleton / 20-oxosteroid / 3-oxo-delta-1,4-steroid / 3-oxosteroid / 11-hydroxysteroid / 11-beta-hydroxysteroid / Oxosteroid / 6-halo-steroid
show 19 more
Molecular Framework
Aliphatic homopolycyclic compounds
External Descriptors
Not Available

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. Grayson L., Crowe S., Hope W., McCarthy J., Mills J., Mouton J., Paterson D., Paterson D. and Pfaller M. (2010). Kucers' the use of antibiotics (6th ed.). Taylor and Francis Group. [ISBN:978-1-4441-4752-0]

Drug created on June 09, 2014 10:27 / Updated on October 01, 2018 14:44