NAV

Isoflupredone acetate

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

Identification

Generic Name
Isoflupredone acetate
DrugBank Accession Number
DB14640
Background

Not Available

Type
Small Molecule
Groups
Vet approved
Structure
3D
Similar Structures
Weight
Average: 420.477
Monoisotopic: 420.194816817
Chemical Formula
C23H29FO6
Synonyms
  • Isoflupredone 21-acetate
  • Isoflupredone acetate
External IDs
  • U-6013
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Pharmacology

Indication

Not Available

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Contraindications & Blackbox Warnings
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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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Active Moieties
NameKindUNIICASInChI Key
IsoflupredoneprodrugHYS0B45Z2S338-95-4WAIJIHDWAKJCBX-BULBTXNYSA-N

Categories

Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as gluco/mineralocorticoids, progestogins and derivatives. These are steroids with a structure based on a hydroxylated prostane moiety.
Kingdom
Organic compounds
Super Class
Lipids and lipid-like molecules
Class
Steroids and steroid derivatives
Sub Class
Pregnane steroids
Direct Parent
Gluco/mineralocorticoids, progestogins and derivatives
Alternative Parents
20-oxosteroids / 11-beta-hydroxysteroids / 17-hydroxysteroids / Halogenated steroids / 3-oxo delta-1,4-steroids / Delta-1,4-steroids / Alpha-acyloxy ketones / Tertiary alcohols / Alpha-hydroxy ketones / Secondary alcohols
show 9 more
Substituents
11-beta-hydroxysteroid / 11-hydroxysteroid / 17-hydroxysteroid / 20-oxosteroid / 3-oxo-delta-1,4-steroid / 3-oxosteroid / 9-halo-steroid / Alcohol / Aliphatic homopolycyclic compound / Alkyl fluoride
show 25 more
Molecular Framework
Aliphatic homopolycyclic compounds
External Descriptors
corticosteroid hormone (CHEBI:34517)
Affected organisms
Not Available

Chemical Identifiers

UNII
55P9TUL75S
CAS number
338-98-7
InChI Key
ZOCUOMKMBMEYQV-GSLJADNHSA-N
InChI
InChI=1S/C23H29FO6/c1-13(25)30-12-19(28)22(29)9-7-16-17-5-4-14-10-15(26)6-8-20(14,2)23(17,24)18(27)11-21(16,22)3/h6,8,10,16-18,27,29H,4-5,7,9,11-12H2,1-3H3/t16-,17-,18-,20-,21-,22-,23-/m0/s1
IUPAC Name
2-[(1R,3aS,3bS,9aS,9bR,10S,11aS)-9b-fluoro-1,10-dihydroxy-9a,11a-dimethyl-7-oxo-1H,2H,3H,3aH,3bH,4H,5H,7H,9aH,9bH,10H,11H,11aH-cyclopenta[a]phenanthren-1-yl]-2-oxoethyl acetate
SMILES
[H][C@@]12CC[C@](O)(C(=O)COC(C)=O)[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 Drug
D04627
KEGG Compound
C14636
ChemSpider
194836
ChEBI
34517
ChEMBL
CHEMBL1608183
ZINC
ZINC000004213604

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 Solubility0.025 mg/mLALOGPS
logP2.23ALOGPS
logP1.76Chemaxon
logS-4.2ALOGPS
pKa (Strongest Acidic)12.58Chemaxon
pKa (Strongest Basic)-3.4Chemaxon
Physiological Charge0Chemaxon
Hydrogen Acceptor Count5Chemaxon
Hydrogen Donor Count2Chemaxon
Polar Surface Area100.9 Å2Chemaxon
Rotatable Bond Count4Chemaxon
Refractivity107.17 m3·mol-1Chemaxon
Polarizability42.89 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
LC-MS/MS Spectrum - LC-ESI-qTof , PositiveLC-MS/MSsplash10-00dr-3980000000-9fe7b7d7abc41f2978e5
MS/MS Spectrum - , positiveLC-MS/MSsplash10-00dr-3980000000-9fe7b7d7abc41f2978e5
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-0udl-0009600000-34d8e60d0e4d5f98fd17
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-0a4i-9105400000-155d30ee6abe5e8ccd5d
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-0ukj-1669600000-7c2db7c55f9145d913cd
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-0a4i-9008100000-35ecb8881a366cc3357c
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-066r-6009000000-f2eaf8b99f9f54ff765a
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-074i-0592000000-264faf66ebc0116c3bba
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]-200.80563
predicted
DeepCCS 1.0 (2019)
[M+H]+202.70103
predicted
DeepCCS 1.0 (2019)
[M+Na]+208.70866
predicted
DeepCCS 1.0 (2019)

Drug created at September 01, 2018 18:47 / Updated at February 21, 2021 18:54