| Identification | Back Directory | [Name]
Anecortave Acetate | [CAS]
7753-60-8 | [Synonyms]
H6
Retaane
Al 3789
NSC 15475
NSC 24345
Anecortave
Anacorta acetate
Anechota acetate
anecortave acetate
Anecortave Acetate[H6]
Hydrocortisone Acetate EP Impurity E
ANECORTAVE ACETATE (200 MG)F0E2980.997MG/MG(AI)
Pregna-4,9(11)-diene-17-ol-3,20-dione-21-acetate
21-Acetoxypregna-
4,9(11)-dien-17α-ol-3,20-dione
3,20-Dioxopregna-4,9(11)-diene-17,21-diol 21-acetate
21-Acetoxy-17-hydroxypregna-4,9(11)-diene-3,20-dione
17-Hydroxypregna-4,9(11)-diene-3,20-dione-21-acetate
21-Acetoxy-17α-hydroxypregna-4,9(11)-diene-3,20-dione
3,20-Dioxopregna-4,9(11)-diene-17α,21-diol 21-acetate
Pregna-4,9(11)-diene-17α,21-diol-3,20-dione 21-acetate
delta-9(11)-Hydrocortisone Acetate (Anecortave Acetate)
21-(Acetyloxy)-17-hydroxypregna-4,9(11)-diene-3,20-dione
17-α,21-dihydroxypregna-4,9(11)-diene-3,20-dione 21-acetate
Pregna-4,9(11)-diene-3,20-dione, 21-(acetyloxy)-17-hydroxy-
17-α,21-dihydroxypregna-4,9(11)-diene-3,20-dione 21-acetate
17-ALPHA-HYDROXY-3,20-DIOXOPREGNA-4,9(11)-DIENE-21-YL ACETATE
17-alpha,21-dihydroxypregna-4,9(11)-diene-3,20-dione21-acetate
[2-[(8S,10S,13S,14S,17R)-17-hydroxy-10,13-dimethyl-3-oxo-2,6,7,8,12,14,15,16-octahydro-1H-cyclopenta[a]phenanthren-17-yl]-2-oxoethyl] acetate | [EINECS(EC#)]
231-812-5 | [Molecular Formula]
C23H30O5 | [MDL Number]
MFCD00921393 | [MOL File]
7753-60-8.mol | [Molecular Weight]
386.48 |
| Chemical Properties | Back Directory | [Melting point ]
230-234°C | [alpha ]
D +117° (c = 1.0 in CHCl3); D22 +124° (c = 1.04 in CHCl3). | [Boiling point ]
551.8±50.0 °C(Predicted) | [density ]
1.23±0.1 g/cm3(Predicted) | [storage temp. ]
-20°C Freezer | [solubility ]
Chloroform (Slightly), Methanol (Slightly) | [form ]
Solid | [pka]
12.47±0.60(Predicted) | [color ]
Off-White to Beige |
| Hazard Information | Back Directory | [Description]
Anecortave acetate, an angiogenesis inhibitor, was launched
in Australia by Alcon for the treatment of age-related
macular degeneration (AMD). AMD is the leading cause of
untreatable blindness among people aged 65 to 74 years in
the U.S. Worldwide, approximately 20 to 25 million people suffer from AMD, a disease that until recently was untreatable.
Anecortave, an angiostatic steroid, down-regulates the
expression MMP-2 and -9 to exert its antiangiogenic effects. | [Chemical Properties]
Off-White Solid | [Uses]
As an angiostatic steroid, Anecortave Acetate can be used in treatment of macular degeneration.
| [Definition]
ChEBI: Anecortave acetate is an organic molecular entity. | [Synthesis]
Anecortave has been synthesized by several different
routes, and Pharmacia process patents are cited here.
The synthesis is depicted in the scheme. Compound 1 was
condensed with 2-chlorovinyl ethyl ether with n-BuLi in
THF at low temperature to give a mixture of two isomeric
aldehydes 2 in 91% yield. The mixture 2 was treated with
acetic anhydride and anhydrous potassium acetate in DMF at
106??C to give acetate 3 which was reacted with RhCl(PPh3)3
and triethylsilane in methylene chloride at 45??C for 4 hours
to yield the corresponding triethylsilane ether 4 as a solid
after crystallization in hexane. Finally, compound 4 was oxidized
with 40% peracetic acid in toluene at low temperature,
and the reaction was quenched with SO2 in methanol (2M),
and treated with TEA to give anecortave acetate
. | [Enzyme inhibitor]
This novel angiogenesis pro-drug (FW = 386.48 g/mol; CAS 7753-60-8) is taken up and metabolically de-esterified to form the aqnecortave, a synthetic steroid that suppresses the development and elongation of neovascular sprouts and tip cell motility in a VEGF-treated retinal explant model in a dose-dependent manner. Whether used as monotherapy or in combination with sub-therapeutic doses of cisplatin, anecortave acetate significantly controlled tumor burden in a murine retinoblastoma model. |
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