Anecortave acetate

Identification

Name
Anecortave acetate
Accession Number
DB05288
Type
Small Molecule
Groups
Investigational
Description

Anecortave acetate (Retaane) is an analog of cortisol acetate; among the modifications to the steroid are the removal of the 11ß hydroxyl OH group and an addition of a 21-acetate group. As a result of these modifications, anecortave acetate lacks the typical antiinflammatory and immunosuppressive properties of glucocorticoids.Alcon Inc. is developing and marketing Retaane.

Structure
Thumb
Synonyms
Not Available
External IDs
AL 3789 / AL-3789
Active Moieties
NameKindUNIICASInChI Key
AnecortaveprodrugR5Y8O5158910184-70-0BCFCRXOJOFDUMZ-ONKRVSLGSA-N
International/Other Brands
Retaane
Categories
UNII
Y0PC411K4T
CAS number
7753-60-8
Weight
Average: 386.4813
Monoisotopic: 386.20932407
Chemical Formula
C23H30O5
InChI Key
YUWPMEXLKGOSBF-GACAOOTBSA-N
InChI
InChI=1S/C23H30O5/c1-14(24)28-13-20(26)23(27)11-8-19-17-5-4-15-12-16(25)6-9-21(15,2)18(17)7-10-22(19,23)3/h7,12,17,19,27H,4-6,8-11,13H2,1-3H3/t17-,19+,21+,22+,23+/m1/s1
IUPAC Name
2-[(2S,10S,11S,14R,15S)-14-hydroxy-2,15-dimethyl-5-oxotetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadeca-1(17),6-dien-14-yl]-2-oxoethyl acetate
SMILES
[H][C@@]12CC[C@](O)(C(=O)COC(C)=O)[C@@]1(C)CC=C1[C@@]2([H])CCC2=CC(=O)CC[C@]12C

Pharmacology

Indication

Investigated for use/treatment in glaucoma and macular degeneration.

Pharmacodynamics
Not Available
Mechanism of action

Anecortave acetate functions as an antiangiogenic agent, inhibiting blood vessel growth by decreasing extracellular protease expression and inhibiting endothelial cell migration. Its angiostatic activity does not seem to be mediated through any of the commonly known pharmacological receptors. (Ophthalmology 2004;111:2316-7) RETAANE blocks signals from multiple growth factors because it acts downstream and independent of the initiating angiogenic stimuli and inhibits angiogenesis subsequent to the angiogenic stimulation.

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 anecortave acetate.
1,10-PhenanthrolineThe risk or severity of adverse effects can be increased when anecortave acetate is combined with 1,10-Phenanthroline.
AceclofenacThe risk or severity of adverse effects can be increased when Aceclofenac is combined with anecortave acetate.
AcemetacinThe risk or severity of adverse effects can be increased when Acemetacin is combined with anecortave acetate.
AlclofenacThe risk or severity of adverse effects can be increased when Alclofenac is combined with anecortave acetate.
AlmasilateThe bioavailability of anecortave acetate can be decreased when combined with Almasilate.
AlminoprofenThe risk or severity of adverse effects can be increased when Alminoprofen is combined with anecortave acetate.
AloglutamolThe bioavailability of anecortave acetate can be decreased when combined with Aloglutamol.
AloxiprinThe risk or severity of adverse effects can be increased when Aloxiprin is combined with anecortave acetate.
AluminiumThe bioavailability of anecortave acetate can be decreased when combined with Aluminium.
Food Interactions
Not Available

References

General References
  1. Augustin A: Anecortave acetate in the treatment of age-related macular degeneration. Clin Interv Aging. 2006;1(3):237-46. [PubMed:18046876]
External Links
KEGG Drug
D01733
PubChem Compound
111332
PubChem Substance
175426966
ChemSpider
99892
ChEBI
31215
ChEMBL
CHEMBL2106613
Wikipedia
Anecortave

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
1CompletedPreventionDiffuse posterior uveitis / Glaucoma1
1CompletedTreatmentMaculopathies, Age-Related1
1, 2CompletedTreatmentChronic Central Serous Chorioretinopathy1
2CompletedTreatmentAMD2
2CompletedTreatmentAge-Related Macular Degenerations / Subfoveal Neovascularization1
2CompletedTreatmentCoat's Disease1
2CompletedTreatmentEye Diseases1
2CompletedTreatmentIdiopathic Perifoveal Telangiectasia1
2CompletedTreatmentOpen-angle Glaucoma (OAG)2
2TerminatedTreatmentCentral Retinal Vein Occlusion (CRVO) / Chronic Inflammation / Infectious Diseases / Severe Diabetic Retinopathy1
2TerminatedTreatmentEye Injuries1
2WithdrawnTreatmentRetinal Vein Occlusions(RVO)1
2, 3CompletedTreatmentOpen-angle Glaucoma (OAG) / Oular Hypertension1
2, 3WithdrawnTreatmentOpen-angle Glaucoma (OAG)1
3CompletedTreatmentMacular Degeneration / Maculopathies, Age-Related2
3TerminatedPreventionAMD2
3TerminatedTreatmentDry AMD1
3TerminatedTreatmentMacular Degeneration1
Not AvailableNo Longer AvailableNot AvailableMacular Degeneration1
Not AvailableTerminatedTreatmentIntraocular Pressure / Transplanted1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.0113 mg/mLALOGPS
logP3.33ALOGPS
logP2.62ChemAxon
logS-4.5ALOGPS
pKa (Strongest Acidic)12.61ChemAxon
pKa (Strongest Basic)-3.8ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area80.67 Å2ChemAxon
Rotatable Bond Count4ChemAxon
Refractivity105.81 m3·mol-1ChemAxon
Polarizability42.44 Å3ChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.983
Blood Brain Barrier+0.9851
Caco-2 permeable-0.6606
P-glycoprotein substrateSubstrate0.7382
P-glycoprotein inhibitor IInhibitor0.7341
P-glycoprotein inhibitor IIInhibitor0.5925
Renal organic cation transporterNon-inhibitor0.7452
CYP450 2C9 substrateNon-substrate0.8551
CYP450 2D6 substrateNon-substrate0.9294
CYP450 3A4 substrateSubstrate0.7841
CYP450 1A2 substrateNon-inhibitor0.9045
CYP450 2C9 inhibitorNon-inhibitor0.9071
CYP450 2D6 inhibitorNon-inhibitor0.9556
CYP450 2C19 inhibitorNon-inhibitor0.9026
CYP450 3A4 inhibitorNon-inhibitor0.8588
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9246
Ames testNon AMES toxic0.9409
CarcinogenicityNon-carcinogens0.9551
BiodegradationNot ready biodegradable0.9354
Rat acute toxicity2.1280 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9599
hERG inhibition (predictor II)Non-inhibitor0.6638
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

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 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 / 3-oxosteroids / 17-hydroxysteroids / Cyclohexenones / Alpha-acyloxy ketones / Tertiary alcohols / Alpha-hydroxy ketones / Cyclic alcohols and derivatives / Carboxylic acid esters / Monocarboxylic acids and derivatives
show 2 more
Substituents
Progestogin-skeleton / 20-oxosteroid / 3-oxosteroid / 17-hydroxysteroid / Oxosteroid / Hydroxysteroid / Cyclohexenone / Alpha-acyloxy ketone / Alpha-hydroxy ketone / Tertiary alcohol
show 13 more
Molecular Framework
Aliphatic homopolycyclic compounds
External Descriptors
Not Available

Drug created on November 18, 2007 11:23 / Updated on September 07, 2018 03:21