NAV

Isoflupredone

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

Identification

Generic Name
Isoflupredone
DrugBank Accession Number
DB11522
Background

Not Available

Type
Small Molecule
Groups
Vet approved
Structure
3D
Similar Structures
Weight
Average: 378.44
Monoisotopic: 378.184252132
Chemical Formula
C21H27FO5
Synonyms
  • 9-fluoroprednisolone
  • delta-Fluorocortisone
  • Isoflupredona
  • Isoflupredone
  • Isoflupredonum
External IDs
  • NSC-12174
Poor quality drug data slowing you down?
Unlock 38% more drug discovery time and eliminate decision-making doubts with this one-stop guide to quality drug data.
Download eBook
Poor quality drug data slowing you down?
Download eBook

Pharmacology

Indication

Not Available

Reduce drug development failure rates
Build, train, & validate machine-learning models
with evidence-based and structured datasets.
See how
Build, train, & validate predictive machine-learning models with structured datasets.
See how
Contraindications & Blackbox Warnings
Prevent Adverse Drug Events Today
Tap into our Clinical API for life-saving information on contraindications & blackbox warnings, population restrictions, harmful risks, & more.
Learn more
Avoid life-threatening adverse drug events with our Clinical API
Learn more
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
Improve decision support & research outcomes
With structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates. View sample adverse effects data in our new Data Library!
See the data
Improve decision support & research outcomes with our structured adverse effects data.
See a data sample
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

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 / 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 8 more
Substituents
11-beta-hydroxysteroid / 11-hydroxysteroid / 17-hydroxysteroid / 20-oxosteroid / 21-hydroxysteroid / 3-oxo-delta-1,4-steroid / 3-oxosteroid / 9-halo-steroid / Alcohol / Aliphatic homopolycyclic compound
show 23 more
Molecular Framework
Aliphatic homopolycyclic compounds
External Descriptors
21-hydroxy steroid (CHEBI:34511)
Affected organisms
Not Available

Chemical Identifiers

UNII
HYS0B45Z2S
CAS number
338-95-4
InChI Key
WAIJIHDWAKJCBX-BULBTXNYSA-N
InChI
InChI=1S/C21H27FO5/c1-18-7-5-13(24)9-12(18)3-4-15-14-6-8-20(27,17(26)11-23)19(14,2)10-16(25)21(15,18)22/h5,7,9,14-16,23,25,27H,3-4,6,8,10-11H2,1-2H3/t14-,15-,16-,18-,19-,20-,21-/m0/s1
IUPAC Name
(1R,3aS,3bS,9aS,9bR,10S,11aS)-9b-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(F)[C@@]2([H])CCC2=CC(=O)C=C[C@]12C

References

General References
  1. Mohammedsadegh M: Effect of isoflupredone acetate on pregnancy in cattle. Vet Rec. 1994 Apr 23;134(17):453. [Article]
  2. Wagner SA, Apley MD: Pharmacodynamics of isoflupredone acetate in an endotoxin-induced mastitis model. J Dairy Sci. 2003 Mar;86(3):792-8. [Article]
  3. Hewson J, Viel L, Caswell JL, Shewen PE, Buchanan-Smith JG: Impact of isoflupredone acetate treatment on clinical signs and weight gain in weanling heifers with experimentally induced Mannheimia haemolytica bronchopneumonia. Am J Vet Res. 2011 Dec;72(12):1613-21. doi: 10.2460/ajvr.72.12.1613. [Article]
  4. Lillich JD, Bertone AL, Schmall LM, Ruggles AJ, Sams RA: Plasma, urine, and synovial fluid disposition of methylprednisolone acetate and isoflupredone acetate after intra-articular administration in horses. Am J Vet Res. 1996 Feb;57(2):187-92. [Article]
  5. Coffer NJ, Frank N, Elliott SB, Young CD, van Amstel SR: Effects of dexamethasone and isoflupredone acetate on plasma potassium concentrations and other biochemical measurements in dairy cows in early lactation. Am J Vet Res. 2006 Jul;67(7):1244-51. [Article]
  6. Picandet V, Leguillette R, Lavoie JP: Comparison of efficacy and tolerability of isoflupredone and dexamethasone in the treatment of horses affected with recurrent airway obstruction ('heaves'). Equine Vet J. 2003 Jun;35(4):419-24. [Article]
  7. Seifi HA, LeBlanc SJ, Vernooy E, Leslie KE, Duffield TF: Effect of isoflupredone acetate with or without insulin on energy metabolism, reproduction, milk production, and health in dairy cows in early lactation. J Dairy Sci. 2007 Sep;90(9):4181-91. [Article]
  8. Bate LA, Ireland W, Connell BJ, Grimmelt B: Development of the small intestine of piglets in response to prenatal elevation of glucocorticoids. Histol Histopathol. 1991 Apr;6(2):207-16. [Article]
  9. Sattler N, Fecteau G, Girard C, Couture Y: Description of 14 cases of bovine hypokalaemia syndrome. Vet Rec. 1998 Oct 31;143(18):503-7. [Article]
  10. Shaw MC, Vanderwielen AJ: Liquid chromatographic assay for diflorasone diacetate in cream and ointment formulations. J Pharm Sci. 1984 Nov;73(11):1606-8. [Article]
KEGG Compound
C14484
ChemSpider
113134
RxNav
1546449
ChEBI
34511
ZINC
ZINC000003876095
Wikipedia
Isoflupredone

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount

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 Solubility0.0811 mg/mLALOGPS
logP1.57ALOGPS
logP1.32Chemaxon
logS-3.7ALOGPS
pKa (Strongest Acidic)12.55Chemaxon
pKa (Strongest Basic)-3.3Chemaxon
Physiological Charge0Chemaxon
Hydrogen Acceptor Count5Chemaxon
Hydrogen Donor Count3Chemaxon
Polar Surface Area94.83 Å2Chemaxon
Rotatable Bond Count2Chemaxon
Refractivity98.02 m3·mol-1Chemaxon
Polarizability38.88 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/MSsplash10-0006-0009000000-d45eead46fc601a58996
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-0002-0009000000-b3636d76ee0b1f4ddef8
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-002b-1009000000-2dc4726814599c2f47d3
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-01t9-0669000000-5958474c7f4128bcb170
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-01c0-1945000000-7d9c74ed3574fbb051e2
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-056r-1290000000-3e433dca8f004c1c2fa8
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]-188.19205
predicted
DeepCCS 1.0 (2019)
[M+H]+190.08746
predicted
DeepCCS 1.0 (2019)
[M+Na]+196.17227
predicted
DeepCCS 1.0 (2019)

Drug created at February 26, 2016 17:33 / Updated at February 21, 2021 18:53