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Details

Stereochemistry ABSOLUTE
Molecular Formula C21H28O4
Molecular Weight 344.4446
Optical Activity UNSPECIFIED
Defined Stereocenters 5 / 5
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of ANECORTAVE

SMILES

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

InChI

InChIKey=BCFCRXOJOFDUMZ-ONKRVSLGSA-N
InChI=1S/C21H28O4/c1-19-8-5-14(23)11-13(19)3-4-15-16(19)6-9-20(2)17(15)7-10-21(20,25)18(24)12-22/h6,11,15,17,22,25H,3-5,7-10,12H2,1-2H3/t15-,17+,19+,20+,21+/m1/s1

HIDE SMILES / InChI

Molecular Formula C21H28O4
Molecular Weight 344.4446
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 5 / 5
E/Z Centers 0
Optical Activity UNSPECIFIED

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

1.08855362E12
PubMed

PubMed

TitleDatePubMed
Anecortave (Alcon Laboratories).
2005 Apr
Drug pricing for a novel treatment for wet macular degeneration: using incremental cost-effectiveness ratios to ensure societal value.
2005 Jun
Anecortave acetate in the treatment of 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
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.
Substance Class Chemical
Created
by admin
on Fri Dec 15 19:02:45 UTC 2023
Edited
by admin
on Fri Dec 15 19:02:45 UTC 2023
Record UNII
R5Y8O51589
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
ANECORTAVE
WHO-DD  
Common Name English
ANECORTAVE (USAN)
Common Name English
AL-4940
Code English
17,21-DIHYDROXYPREGNA-4,9(11)-DIENE-3,20-DIONE
Systematic Name English
Anecortave [WHO-DD]
Common Name English
PREGNA-4,9(11)-DIENE-3,20-DIONE, 17,21-DIHYDROXY-
Systematic Name English
Anecortave Desacetate
Common Name English
AL4940
Code English
Classification Tree Code System Code
WHO-VATC QS01LA02
Created by admin on Fri Dec 15 19:02:46 UTC 2023 , Edited by admin on Fri Dec 15 19:02:46 UTC 2023
WHO-ATC S01LA02
Created by admin on Fri Dec 15 19:02:46 UTC 2023 , Edited by admin on Fri Dec 15 19:02:46 UTC 2023
Code System Code Type Description
CAS
10184-70-0
Created by admin on Fri Dec 15 19:02:46 UTC 2023 , Edited by admin on Fri Dec 15 19:02:46 UTC 2023
PRIMARY
DRUG BANK
DB12081
Created by admin on Fri Dec 15 19:02:46 UTC 2023 , Edited by admin on Fri Dec 15 19:02:46 UTC 2023
PRIMARY
DRUG CENTRAL
217
Created by admin on Fri Dec 15 19:02:46 UTC 2023 , Edited by admin on Fri Dec 15 19:02:46 UTC 2023
PRIMARY
SMS_ID
100000180103
Created by admin on Fri Dec 15 19:02:46 UTC 2023 , Edited by admin on Fri Dec 15 19:02:46 UTC 2023
PRIMARY
EPA CompTox
DTXSID70144268
Created by admin on Fri Dec 15 19:02:46 UTC 2023 , Edited by admin on Fri Dec 15 19:02:46 UTC 2023
PRIMARY
FDA UNII
R5Y8O51589
Created by admin on Fri Dec 15 19:02:46 UTC 2023 , Edited by admin on Fri Dec 15 19:02:46 UTC 2023
PRIMARY
PUBCHEM
7074810
Created by admin on Fri Dec 15 19:02:46 UTC 2023 , Edited by admin on Fri Dec 15 19:02:46 UTC 2023
PRIMARY
ChEMBL
CHEMBL2106613
Created by admin on Fri Dec 15 19:02:46 UTC 2023 , Edited by admin on Fri Dec 15 19:02:46 UTC 2023
PRIMARY
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