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{{Short description|Chemical compound}}
{{cs1 config|name-list-style=vanc}}
{{Drugbox {{Drugbox
| Verifiedfields = changed
| verifiedrevid = 443939999 | verifiedrevid = 457130466
| IUPAC_name = phenanthren-17-yl]-<br />2-oxo-ethyl] acetate | IUPAC_name = phenanthren-17-yl]-<br />2-oxo-ethyl] acetate
| image = Anecortave acetate.svg
| width = 200 | width = 200


<!--Clinical data--> <!--Clinical data-->
| tradename = | tradename =
| Drugs.com = {{drugs.com|international|anecortave}} | Drugs.com = {{drugs.com|international|anecortave}}
| pregnancy_category = ? | pregnancy_category =
| legal_status = Schedule 4 (]) | legal_status =
| legal_AU = Schedule 4
| routes_of_administration = ] ] | routes_of_administration = ] ]


<!--Pharmacokinetic data--> <!--Pharmacokinetic data-->
| bioavailability = ? | bioavailability =
| metabolism = ? | metabolism =
| elimination_half-life = ? | elimination_half-life =
| excretion = ? | excretion =


<!--Identifiers--> <!--Identifiers-->
| CAS_number_Ref = {{cascite|changed|??}}
| CAS_number = <!-- blanked - oldvalue: 7753-60-8 --> | CAS_number = 7753-60-8
| ATC_prefix = S01 | ATC_prefix = S01
| ATC_suffix = LA02 | ATC_suffix = LA02
| PubChem = 111332 | PubChem = 111332
| PubChemSubstance = 175426966
⚫ | DrugBank_Ref = {{drugbankcite|correct|drugbank}}
| ChEBI = 31215
| DrugBank = <!-- blanked - oldvalue: ? -->
| ChEMBL_Ref = {{ebicite|changed|EBI}}
| ChEMBL = 2106613
⚫ | DrugBank_Ref = {{drugbankcite|changed|drugbank}}
| DrugBank = DB05288
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 99892 | ChemSpiderID = 99892
| KEGG = D01733
| UNII_Ref = {{fdacite|correct|FDA}} | UNII_Ref = {{fdacite|correct|FDA}}
| UNII = Y0PC411K4T | UNII = Y0PC411K4T
| synonyms = δ<sup>9(11)</sup>-11-Deoxycortisol 21-acetate; 17α,21-Dihydroxy-δ<sup>9(11)</sup>-progesterone 21-acetate; 17α,21-Dihydroxypregna-4,9(11)-diene-3,20-dione 21-acetate


<!--Chemical data--> <!--Chemical data-->
| C=23 | H=30 | O=5 | C=23 | H=30 | O=5
| molecular_weight = 386.48
| smiles = O=C(OCC(=O)1(O)CC24/C(=C\C12C)3(/C(=C\C(=O)CC3)CC4)C)C | smiles = O=C(OCC(=O)1(O)CC24/C(=C\C12C)3(/C(=C\C(=O)CC3)CC4)C)C
| InChI = 1/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
| InChIKey = YUWPMEXLKGOSBF-GACAOOTBBL
| StdInChI_Ref = {{stdinchicite|correct|chemspider}} | StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 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 | StdInChI = 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
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}} }}


'''Anecortave''' (]) ({{IPAc-en|icon|æ|n|ə|ˈ|k|ɔr|t|eɪ|v}}) is a novel ] used in the treatment of the exudative (wet) form of age-related ]. Although based on a ] nucleus, it possesses little ] activity. It will be marketed by ] as '''anecortave acetate''' for depot suspension under the trade name '''Retaane'''. '''Anecortave''' (]) {{IPAc-en|æ|n|ə|ˈ|k|ɔr|t|eɪ|v}} is a novel ] used in the treatment of the exudative (wet) form of age-related ]. Although similar in ] to the ] ], it possesses no ] activity.<ref name="AdisInsight"> {{dead link|date=March 2022}}</ref> If it is approved, it will be marketed by ] as '''anecortave acetate''' for depot suspension under the trade name '''Retaane'''. No development has been reported since 2010.<ref name="AdisInsight" />

==Potential applications==
In addition to treating ] age-related macular degeneration - aka. ], it has also been evaluated as a potential therapy for dry-form age related macular degeneration, as well as for reducing the intraocular pressure in eyes with ocular steroid injection-related glaucoma.<ref name="pmid19204235">{{cite journal | vauthors = Robin AL, Suan EP, Sjaarda RN, Callanan DG, Defaller J | title = Reduction of intraocular pressure with anecortave acetate in eyes with ocular steroid injection-related glaucoma | journal = Arch. Ophthalmol. | volume = 127 | issue = 2 | pages = 173–8 |date=February 2009 | pmid = 19204235 | doi = 10.1001/archophthalmol.2008.595 | doi-access = free }}</ref>


==Synthesis== ==Synthesis==
Anecortave can be synthesized from a 17-oxosteroid:<ref>{{cite journal | doi = 10.1016/S0040-4039(00)97440-9 | author = J.G. Reid, T. Debiak-Krook | title = Corticoids from 17-oxosteroids | journal = Tetrahedron Lett. | volume = 31 | pages = 3669 | year = 1990}}</ref> Anecortave can be synthesized from a 17-oxosteroid:<ref>{{cite journal | doi = 10.1016/S0040-4039(00)97440-9 | vauthors = Reid JG, Debiak-Krook T | title = Corticoids from 17-oxosteroids | journal = Tetrahedron Lett. | volume = 31 | issue = 26 | pages = 3669–3672 | year = 1990}}</ref>
] ]


In addition to being synthesized from a 17-oxosteroid, anecortave acetate can be derived from cortisol by reducing the 11-beta hydroxyl on cortisol to a double bond between carbons 9 and 11 and the addition of an acetate group to carbon 21. This results in a molecule with no glucocorticoid or mineralocorticoid activity.<ref name="pmid19204235"/>
⚫ ==References==
{{reflist}}


==FDA application history==
Retaane (15&nbsp;mg anecortave acetate depot suspension) which is manufactured by Alcon, Inc., was a fast track designated product which was also a drug in FDA’s Pilot Continuous Marketing Application (CMA) program which often enrolls drugs which are being brought to the market and have an indication for a significant unmet medical need. This allowed Retaane to file with the FDA using a “rolling” New Drug Application, which allows specific units, Chemistry, Manufacturing, and Controls (CMC), pre-clinical, and the clinical unit, of the NDA to be reviewed as they are completed instead of as one large document. This allows the FDA to review each unit within six months of the submission. Alcon first filed the CMC unit in 2003, the Pre-clinical and Clinical units in 2004. In 2005 Alcon, Inc. announced it received the approval letter for the NDA for Retaane.{{Citation needed|date=January 2021}}


In 2007, Alcon got its 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, it supported the Anecortave Acetate Risk-Reduction Trial (AART). This study looked at the efficacy of Retaane to reduce the progression of the dry form of AMD to the wet form. It ended in 2008.<ref>{{Cite journal|url=http://clinicaltrials.gov/ct2/show/study/NCT00333216|title = Efficacy and Safety of Posterior Juxtascleral Administrations of Anecortave Acetate for Depot Suspension (15 mg or 30 mg) Versus Sham Administration in Singaporean Patients at Risk for Progressing to Exudative Age-Related Macular Degeneration (AMD)|website=Clinicaltrials.gov|date = 27 November 2012}}</ref><ref name="urlAlcon Receives FDA Decision on Retaane Suspension for Wet AMD">{{cite web | url = https://www.drugs.com/nda/retaane_070925.html | title = Alcon Receives FDA Decision on Retaane Suspension for Wet AMD | date = 2007-09-24 | website= Drugs.com }}</ref>
{{Pharma-stub}}


In 2008, Alcon announced it was terminating the development of anecortave acetate for the prevention of developing sight-threatening choroidal neovascularization secondary to age-related macular degeneration.<ref>{{cite web|url=https://www.sec.gov/Archives/edgar/data/1167379/000116737908000065/acl6k0708anaacetateex991.pdf|title=Alcon Terminates the Development of Anecortave Acetate in Age-Related Macular Degeneration|website=Sec.gov|access-date=16 March 2022}}</ref> In 2009, Alcon announced the end of the drug's development for reducing intraocular pressure associated with glaucoma.<ref>{{Cite press release|url=https://www.businesswire.com/news/home/20090702005343/en/Alcon-Discontinues-Development-Anecortave-Acetate-Intraocular-Pressure|title=News|website=Businesswire.com|access-date=16 March 2022}}</ref>{{Better source needed|date=January 2021}} Currently, anecortave acetate is not on the market or being made for therapeutic use.<ref>{{Cite web|url=https://www.alcon.com/node/4026|title=Alcon Official Site: Developing Innovative Eye Care Treatments|website=Alcon.com|access-date=16 March 2022}}</ref> {{Better source needed|date=January 2021}}

==Delivery==
Retaane depot is delivered via posterior juxtascleral depot (PJD) that delivers the drug onto the sclera near the macula. This delivery method allows for a decreased risk of intraocular infection as well as decreased risk for detachment of the retina. Not only is the delivery method advantageous, but Retaane compared to other angiogenesis inhibitors used for similar indications, only has to be delivered once every six months compared to nine to twelve times a year. This allows for increased patient compliance.<ref name="pmid17240258">{{cite journal | vauthors = Kaiser PK, Goldberg MF, Davis AA | title = Posterior juxtascleral depot administration of anecortave acetate | journal = Surv Ophthalmol | volume = 52 | pages = S62–9 |date=January 2007 | issue = Suppl 1 | pmid = 17240258 | doi = 10.1016/j.survophthal.2006.10.015 }}</ref>

==See also==
* ]

⚫ ==References==
{{Reflist}}


{{Ocular vascular disorder agents}} {{Ocular vascular disorder agents}}


]
] ]
] ]
]
]
]

Latest revision as of 02:41, 4 January 2025

Chemical compound

Pharmaceutical compound
Anecortave acetate
Clinical data
Other namesδ-11-Deoxycortisol 21-acetate; 17α,21-Dihydroxy-δ-progesterone 21-acetate; 17α,21-Dihydroxypregna-4,9(11)-diene-3,20-dione 21-acetate
AHFS/Drugs.comInternational Drug Names
Routes of
administration		intravitreal depot injection
ATC code
Legal status
Legal status
  • AU: S4 (Prescription only)
Identifiers
IUPAC name
  • phenanthren-17-yl]-
    2-oxo-ethyl] acetate
CAS Number
PubChem CID
PubChem SID
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.028.920 Edit this at Wikidata
Chemical and physical data
FormulaC23H30O5
Molar mass386.488 g·mol
3D model (JSmol)
SMILES
  • O=C(OCC(=O)1(O)CC24/C(=C\C12C)3(/C(=C\C(=O)CC3)CC4)C)C
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
  • Key:YUWPMEXLKGOSBF-GACAOOTBSA-N
  (what is this?)  (verify)

Anecortave (rINN) /ænəˈkɔːrteɪv/ is a novel angiogenesis inhibitor used in the treatment of the exudative (wet) form of age-related macular degeneration. Although similar in chemical structure to the corticosteroid hydrocortisone acetate, it possesses no glucocorticoid activity. If it is approved, it will be marketed by Alcon as anecortave acetate for depot suspension under the trade name Retaane. No development has been reported since 2010.

Potential applications

In addition to treating wet-form age-related macular degeneration - aka. neovascular age-related macular degeneration, it has also been evaluated as a potential therapy for dry-form age related macular degeneration, as well as for reducing the intraocular pressure in eyes with ocular steroid injection-related glaucoma.

Synthesis

Anecortave can be synthesized from a 17-oxosteroid:

In addition to being synthesized from a 17-oxosteroid, anecortave acetate can be derived from cortisol by reducing the 11-beta hydroxyl on cortisol to a double bond between carbons 9 and 11 and the addition of an acetate group to carbon 21. This results in a molecule with no glucocorticoid or mineralocorticoid activity.

FDA application history

Retaane (15 mg anecortave acetate depot suspension) which is manufactured by Alcon, Inc., was a fast track designated product which was also a drug in FDA’s Pilot Continuous Marketing Application (CMA) program which often enrolls drugs which are being brought to the market and have an indication for a significant unmet medical need. This allowed Retaane to file with the FDA using a “rolling” New Drug Application, which allows specific units, Chemistry, Manufacturing, and Controls (CMC), pre-clinical, and the clinical unit, of the NDA to be reviewed as they are completed instead of as one large document. This allows the FDA to review each unit within six months of the submission. Alcon first filed the CMC unit in 2003, the Pre-clinical and Clinical units in 2004. In 2005 Alcon, Inc. announced it received the approval letter for the NDA for Retaane.

In 2007, Alcon got its 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, it supported the Anecortave Acetate Risk-Reduction Trial (AART). This study looked at the efficacy of Retaane to reduce the progression of the dry form of AMD to the wet form. It ended in 2008.

In 2008, Alcon announced it was terminating the development of anecortave acetate for the prevention of developing sight-threatening choroidal neovascularization secondary to age-related macular degeneration. In 2009, Alcon announced the end of the drug's development for reducing intraocular pressure associated with glaucoma. Currently, anecortave acetate is not on the market or being made for therapeutic use.

Delivery

Retaane depot is delivered via posterior juxtascleral depot (PJD) that delivers the drug onto the sclera near the macula. This delivery method allows for a decreased risk of intraocular infection as well as decreased risk for detachment of the retina. Not only is the delivery method advantageous, but Retaane compared to other angiogenesis inhibitors used for similar indications, only has to be delivered once every six months compared to nine to twelve times a year. This allows for increased patient compliance.

See also

References

  1. ^
  2. ^ Robin AL, Suan EP, Sjaarda RN, Callanan DG, Defaller J (February 2009). "Reduction of intraocular pressure with anecortave acetate in eyes with ocular steroid injection-related glaucoma". Arch. Ophthalmol. 127 (2): 173–8. doi:10.1001/archophthalmol.2008.595. PMID 19204235.
  3. Reid JG, Debiak-Krook T (1990). "Corticoids from 17-oxosteroids". Tetrahedron Lett. 31 (26): 3669–3672. doi:10.1016/S0040-4039(00)97440-9.
  4. "Efficacy and Safety of Posterior Juxtascleral Administrations of Anecortave Acetate for Depot Suspension (15 mg or 30 mg) Versus Sham Administration in Singaporean Patients at Risk for Progressing to Exudative Age-Related Macular Degeneration (AMD)". Clinicaltrials.gov. 27 November 2012.
  5. "Alcon Receives FDA Decision on Retaane Suspension for Wet AMD". Drugs.com. 2007-09-24.
  6. "Alcon Terminates the Development of Anecortave Acetate in Age-Related Macular Degeneration" (PDF). Sec.gov. Retrieved 16 March 2022.
  7. "News". Businesswire.com (Press release). Retrieved 16 March 2022.
  8. "Alcon Official Site: Developing Innovative Eye Care Treatments". Alcon.com. Retrieved 16 March 2022.
  9. Kaiser PK, Goldberg MF, Davis AA (January 2007). "Posterior juxtascleral depot administration of anecortave acetate". Surv Ophthalmol. 52 (Suppl 1): S62–9. doi:10.1016/j.survophthal.2006.10.015. PMID 17240258.
Ophthalmologicals: ocular vascular disorder agents (S01L)
Antineovascularisation agents
Categories: