U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ABSOLUTE
Molecular Formula C23H30O5
Molecular Weight 386.4813
Optical Activity UNSPECIFIED
Defined Stereocenters 5 / 5
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of ANECORTAVE ACETATE

SMILES

[H][C@@]12CC[C@](O)(C(=O)COC(C)=O)[C@@]1(C)CC=C3[C@@]2([H])CCC4=CC(=O)CC[C@]34C

InChI

InChIKey=YUWPMEXLKGOSBF-GACAOOTBSA-N
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

HIDE SMILES / InChI

Description
Curator's Comment: description was created based on several sources, including http://www.businesswire.com/news/home/20090702005343/en/Alcon-Discontinues-Development-Anecortave-Acetate-Intraocular-Pressure http://www.sec.gov/Archives/edgar/data/1167379/000116737908000065/acl6k0708anaacetateex991.pdf https://www.ncbi.nlm.nih.gov/pubmed/23301619

Anecortave is a novel angiogenesis inhibitor used in the treatment of the exudative (wet) form of age-related macular degeneration. It will be marketed by Alcon as anecortave acetate (AA) for depot suspension under the trade name Retaane. In 2007 they received their letter of approval for Retaane’s indication to treat wet age-related macular degeneration (AMD), but final approval would require the completion of an additional clinical study. As a result, the Anecortave Acetate Risk-Reduction Trial (AART) was continued to be supported by Alcon. This study looked at the efficacy of Retaane to reduce the progression of the dry from of AMD to the wet-form. In 2008, Alcon Inc. announced they were terminating the development of anecortave acetate for the prevention of developing sight-threatening choroidal neovascularization secondary to age-related macular degeneration. In 2009, Alcon Inc. announced they would terminate the development of the drug for the reducing intraocular pressure associated with glaucoma. Currently, anecortave acetate is not on the market or being made for therapeutic use by Alcon Inc.[7] This could be due to the lack of efficacy of clinical trials with anecortave acetate or because of newer more efficacious products that are currently on the market. 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. 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. Recently was discovered, that phosphodiesterase 6-delta (PDE6D) was a molecular binding partner of AA and this provided insight into the role of this drug candidate in treating glaucoma.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Secondary
Retaane

Approved Use

Unknown

Launch Date

2004
PubMed

PubMed

TitleDatePubMed
Anecortave acetate in the treatment of age-related macular degeneration.
2006
A preliminary benefit-risk assessment of verteporfin in age-related macular degeneration.
2006
An update of treatment options for neovascular age-related macular degeneration.
2007 Dec
Anecortave may help choroidal neovascularization regression in serpiginous choroiditis.
2007 Feb
Surgical implantation of steroids with antiangiogenic characteristics for treating neovascular age-related macular degeneration.
2007 Oct 17
Triamcinolone acetonide and anecortave acetate do not stimulate uveal melanoma cell growth.
2008 Sep 24
Anecortave acetate for fibrotic lesions with presence of residual peripheral activity in age-related macular degeneration.
2008 Spring
Anterior juxtascleral delivery of anecortave acetate in eyes with primary open-angle glaucoma: a pilot investigation.
2009 Jan
Suppression and reduction of corticosteroid-induced ocular hypertension by anecortave in sheep.
2010 Mar
Suppression of corticosteroid-induced ocular hypertension in sheep by anecortave.
2010 Mar
Patents

Sample Use Guides

injection of three doses of anecortave acetate (24 mg, 48 mg and 60 mg)
Route of Administration: Other
A murine uveal melanoma cell line (99E1) was transplanted intracamerally into athymic nude BALB/c mice. Mice were treated topically three times per day beginning on the day of tumor transplantation and continuing through day 28. Groups included (a) 1% anecortave acetate. Intraocular tumor weights were determined on days 10, 14, 21, and 28. The effect of the test agents on tumor cell proliferation was examined in vitro by [3H]thymidine incorporation.
Name Type Language
ANECORTAVE ACETATE
JAN   MI   USAN  
JAN   USAN  
Official Name English
ANECORTAVE ACETATE [MI]
Common Name English
17-HYDROXY-3,20-DIOXOPREGNA-4,9(11)-DIEN-21-YL ACETATE
Common Name English
ANECORTAVE ACETATE [JAN]
Common Name English
anecortave [INN]
Common Name English
17,21-Dihydroxypregna-4,9(11)-diene-3,20-dione 21-acetate
Systematic Name English
ANECORTAVE [MART.]
Common Name English
NSC-15475
Code English
21-(ACETYLOXY)-17-HYDROXYPREGNA-4,9(11)-DIENE-3,20-DIONE
Systematic Name English
AL3789
Code English
AL-3789
Code English
ANECORTAVE ACETATE [USAN]
Common Name English
HYDROCORTISONE ACETATE IMPURITY E [EP IMPURITY]
Common Name English
NSC-24345
Code English
Classification Tree Code System Code
WHO-ATC S01LA02
Created by admin on Sat Dec 16 05:14:20 GMT 2023 , Edited by admin on Sat Dec 16 05:14:20 GMT 2023
Code System Code Type Description
USAN
II-98
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PRIMARY
INN
7747
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EVMPD
SUB126328
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SMS_ID
100000151904
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EPA CompTox
DTXSID5046805
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ChEMBL
CHEMBL2106613
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ECHA (EC/EINECS)
231-812-5
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FDA UNII
Y0PC411K4T
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CAS
7753-60-8
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DRUG BANK
DB05288
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PUBCHEM
111332
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WIKIPEDIA
ANECORTAVE ACETATE
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MERCK INDEX
m1904
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PRIMARY Merck Index
NSC
24345
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NCI_THESAURUS
C171908
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NSC
15475
Created by admin on Sat Dec 16 05:14:20 GMT 2023 , Edited by admin on Sat Dec 16 05:14:20 GMT 2023
PRIMARY