Identification
- Generic Name
- Anecortave acetate
- DrugBank Accession Number
- DB05288
- Background
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.
- Type
- Small Molecule
- Groups
- Investigational
- Structure
Structure for Anecortave acetate (DB05288)
- Weight
- Average: 386.4813
Monoisotopic: 386.20932407 - Chemical Formula
- C23H30O5
- Synonyms
- Anecortave acetate
- External IDs
- AL 3789
- AL-3789
Pharmacology
- Indication
Investigated for use/treatment in glaucoma and macular degeneration.
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Avoid life-threatening adverse drug eventsImprove clinical decision support with information on contraindications & blackbox warnings, population restrictions, harmful risks, & more.Avoid life-threatening adverse drug events & improve clinical decision support.- 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
- Adverse Effects
Improve decision support & research outcomesWith structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates.Improve decision support & research outcomes with our structured adverse effects data.- 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.
Drug Interaction Integrate drug-drug
interactions in your softwareAlendronic acid The risk or severity of jaw osteonecrosis and anti-angiogenesis can be increased when Anecortave acetate is combined with Alendronic acid. Clodronic acid The risk or severity of jaw osteonecrosis and anti-angiogenesis can be increased when Anecortave acetate is combined with Clodronic acid. Etidronic acid The risk or severity of jaw osteonecrosis and anti-angiogenesis can be increased when Anecortave acetate is combined with Etidronic acid. Ibandronate The risk or severity of jaw osteonecrosis and anti-angiogenesis can be increased when Anecortave acetate is combined with Ibandronate. Pamidronic acid The risk or severity of jaw osteonecrosis and anti-angiogenesis can be increased when Anecortave acetate is combined with Pamidronic acid. Risedronic acid The risk or severity of jaw osteonecrosis and anti-angiogenesis can be increased when Anecortave acetate is combined with Risedronic acid. Tiludronic acid The risk or severity of jaw osteonecrosis and anti-angiogenesis can be increased when Anecortave acetate is combined with Tiludronic acid. Zoledronic acid The risk or severity of jaw osteonecrosis and anti-angiogenesis can be increased when Anecortave acetate is combined with Zoledronic acid. 
Identify potential medication risksEasily compare up to 40 drugs with our drug interaction checker.Get severity rating, description, and management advice.Learn more - Food Interactions
- Not Available
Products
Drug product information from 10+ global regionsOur datasets provide approved product information including:dosage, form, labeller, route of administration, and marketing period.Access drug product information from over 10 global regions.- Active Moieties
Name Kind UNII CAS InChI Key Anecortave prodrug R5Y8O51589 10184-70-0 BCFCRXOJOFDUMZ-ONKRVSLGSA-N - International/Other Brands
- Retaane
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 / 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
- 17-hydroxysteroid / 20-oxosteroid / 3-oxosteroid / Alcohol / Aliphatic homopolycyclic compound / Alpha-acyloxy ketone / Alpha-hydroxy ketone / Carbonyl group / Carboxylic acid derivative / Carboxylic acid ester show 13 more
- Molecular Framework
- Aliphatic homopolycyclic compounds
- External Descriptors
- Not Available
- Affected organisms
- Not Available
Chemical Identifiers
- UNII
- Y0PC411K4T
- CAS number
- 7753-60-8
- 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-[(1R,3aS,3bS,9aS,11aS)-1-hydroxy-9a,11a-dimethyl-7-oxo-1H,2H,3H,3aH,3bH,4H,5H,7H,8H,9H,9aH,11H,11aH-cyclopenta[a]phenanthren-1-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
References
- General References
- Augustin A: Anecortave acetate in the treatment of age-related macular degeneration. Clin Interv Aging. 2006;1(3):237-46. [Article]
- External Links
- KEGG Drug
- D01733
- PubChem Compound
- 111332
- PubChem Substance
- 175426966
- ChemSpider
- 99892
- ChEBI
- 31215
- ChEMBL
- CHEMBL2106613
- ZINC
- ZINC000003931050
- Wikipedia
- Anecortave
Clinical Trials
- Clinical Trials
Phase Status Purpose Conditions Count 3 Completed Treatment Macular Degeneration 2 3 Completed Treatment Macular Degeneration / Maculopathy, Age Related 2 3 Terminated Prevention AMD 2 3 Terminated Treatment Dry AMD 1 3 Terminated Treatment Macular Degeneration 1 2 Completed Treatment Age - Related Macular Degeneration (AMD) / Subfoveal Neovascularization 1 2 Completed Treatment AMD 2 2 Completed Treatment Eye Diseases 1 2 Completed Treatment Eye Diseases / Pseudovitellium Detachment 1 2 Completed Treatment Idiopathic Perifoveal Telangiectasia 1
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
Property Value Source Water Solubility 0.0113 mg/mL ALOGPS logP 3.33 ALOGPS logP 2.62 Chemaxon logS -4.5 ALOGPS pKa (Strongest Acidic) 12.61 Chemaxon pKa (Strongest Basic) -3.8 Chemaxon Physiological Charge 0 Chemaxon Hydrogen Acceptor Count 4 Chemaxon Hydrogen Donor Count 1 Chemaxon Polar Surface Area 80.67 Å2 Chemaxon Rotatable Bond Count 4 Chemaxon Refractivity 105.81 m3·mol-1 Chemaxon Polarizability 42.64 Å3 Chemaxon Number of Rings 4 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter Yes Chemaxon Veber's Rule No Chemaxon MDDR-like Rule No Chemaxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption + 0.983 Blood Brain Barrier + 0.9851 Caco-2 permeable - 0.6606 P-glycoprotein substrate Substrate 0.7382 P-glycoprotein inhibitor I Inhibitor 0.7341 P-glycoprotein inhibitor II Inhibitor 0.5925 Renal organic cation transporter Non-inhibitor 0.7452 CYP450 2C9 substrate Non-substrate 0.8551 CYP450 2D6 substrate Non-substrate 0.9294 CYP450 3A4 substrate Substrate 0.7841 CYP450 1A2 substrate Non-inhibitor 0.9045 CYP450 2C9 inhibitor Non-inhibitor 0.9071 CYP450 2D6 inhibitor Non-inhibitor 0.9556 CYP450 2C19 inhibitor Non-inhibitor 0.9026 CYP450 3A4 inhibitor Non-inhibitor 0.8588 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.9246 Ames test Non AMES toxic 0.9409 Carcinogenicity Non-carcinogens 0.9551 Biodegradation Not ready biodegradable 0.9354 Rat acute toxicity 2.1280 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.9599 hERG inhibition (predictor II) Non-inhibitor 0.6638
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS Not Available
Drug created at November 18, 2007 18:23 / Updated at February 21, 2021 18:51