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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

Molecular Formula C23H30O5
Molecular Weight 386.4813
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 acetate in the treatment of age-related macular degeneration.
2006
A preliminary benefit-risk assessment of verteporfin in age-related macular degeneration.
2006
Surgical implantation of steroids with antiangiogenic characteristics for treating neovascular age-related macular degeneration.
2007 Oct 17
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 Sat Dec 16 05:14:20 UTC 2023
Edited
by admin
on Sat Dec 16 05:14:20 UTC 2023
Record UNII
Y0PC411K4T
Record Status Validated (UNII)
Record Version
  • Download
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 UTC 2023 , Edited by admin on Sat Dec 16 05:14:20 UTC 2023
Code System Code Type Description
USAN
II-98
Created by admin on Sat Dec 16 05:14:20 UTC 2023 , Edited by admin on Sat Dec 16 05:14:20 UTC 2023
PRIMARY
INN
7747
Created by admin on Sat Dec 16 05:14:20 UTC 2023 , Edited by admin on Sat Dec 16 05:14:20 UTC 2023
PRIMARY
EVMPD
SUB126328
Created by admin on Sat Dec 16 05:14:20 UTC 2023 , Edited by admin on Sat Dec 16 05:14:20 UTC 2023
PRIMARY
SMS_ID
100000151904
Created by admin on Sat Dec 16 05:14:20 UTC 2023 , Edited by admin on Sat Dec 16 05:14:20 UTC 2023
PRIMARY
EPA CompTox
DTXSID5046805
Created by admin on Sat Dec 16 05:14:20 UTC 2023 , Edited by admin on Sat Dec 16 05:14:20 UTC 2023
PRIMARY
ChEMBL
CHEMBL2106613
Created by admin on Sat Dec 16 05:14:20 UTC 2023 , Edited by admin on Sat Dec 16 05:14:20 UTC 2023
PRIMARY
ECHA (EC/EINECS)
231-812-5
Created by admin on Sat Dec 16 05:14:20 UTC 2023 , Edited by admin on Sat Dec 16 05:14:20 UTC 2023
PRIMARY
FDA UNII
Y0PC411K4T
Created by admin on Sat Dec 16 05:14:20 UTC 2023 , Edited by admin on Sat Dec 16 05:14:20 UTC 2023
PRIMARY
CAS
7753-60-8
Created by admin on Sat Dec 16 05:14:20 UTC 2023 , Edited by admin on Sat Dec 16 05:14:20 UTC 2023
PRIMARY
DRUG BANK
DB05288
Created by admin on Sat Dec 16 05:14:20 UTC 2023 , Edited by admin on Sat Dec 16 05:14:20 UTC 2023
PRIMARY
PUBCHEM
111332
Created by admin on Sat Dec 16 05:14:20 UTC 2023 , Edited by admin on Sat Dec 16 05:14:20 UTC 2023
PRIMARY
WIKIPEDIA
ANECORTAVE ACETATE
Created by admin on Sat Dec 16 05:14:20 UTC 2023 , Edited by admin on Sat Dec 16 05:14:20 UTC 2023
PRIMARY
MERCK INDEX
m1904
Created by admin on Sat Dec 16 05:14:20 UTC 2023 , Edited by admin on Sat Dec 16 05:14:20 UTC 2023
PRIMARY Merck Index
NSC
24345
Created by admin on Sat Dec 16 05:14:20 UTC 2023 , Edited by admin on Sat Dec 16 05:14:20 UTC 2023
PRIMARY
NCI_THESAURUS
C171908
Created by admin on Sat Dec 16 05:14:20 UTC 2023 , Edited by admin on Sat Dec 16 05:14:20 UTC 2023
PRIMARY
NSC
15475
Created by admin on Sat Dec 16 05:14:20 UTC 2023 , Edited by admin on Sat Dec 16 05:14:20 UTC 2023
PRIMARY
Related Record Type Details
METABOLITE ACTIVE -> PRODRUG
Related Record Type Details
PARENT -> IMPURITY
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
Related Record Type Details
ACTIVE MOIETY