Fluocinolone acetonide

Fluocinolone acetonide
Clinical data
AHFS/Drugs.com	Monograph; Monograph
Pregnancy; category	AU: C; C;
Routes of; administration	Topical, ophthalmic intravitreal injection
ATC code	C05AA10 (WHO) D07AC04 (WHO) S01BA15 (WHO) S02BA08 (WHO);
Legal status
Legal status	AU: S4 (Prescription only) ; US: ℞-only ; In general: ℞ (Prescription only);
Pharmacokinetic data
Metabolism	Hepatic, CYP3A4-mediated
Elimination half-life	1.3 to 1.7 hours
Identifiers
	IUPAC name (1S,2S,4R,8S,9S,11S,12R,13S,19S)-12,19-difluoro-11-hydroxy-8-(2-hydroxyacetyl)-6,6,9,13-tetramethyl-5,7-dioxapentacyclo[10.8.0.02,9.04,8.013,18]icosa-14,17-dien-16-one;
CAS Number	67-73-2 ;
PubChem CID	6215;
IUPHAR/BPS	7077;
DrugBank	DB00591 ;
ChemSpider	5980 ;
UNII	0CD5FD6S2M;
KEGG	D01825 ;
ChEBI	CHEBI:31623 ;
ChEMBL	ChEMBL989 ;
CompTox Dashboard (EPA)	DTXSID0040674 ;
ECHA InfoCard	100.000.607
Chemical and physical data
Formula	C24H30F2O6
Molar mass	452.495 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES O=C\1\C=C5/[C@@](/C=C/1)(C)[C@]2(F)[C@H]([C@H]3[C@](C[C@@H]2O)([C@@]4(OC(O[C@@H]4C3)(C)C)C(=O)CO)C)C[C@@H]5F;
	InChI InChI=1S/C24H30F2O6/c1-20(2)31-19-9-13-14-8-16(25)15-7-12(28)5-6-21(15,3)23(14,26)17(29)10-22(13,4)24(19,32-20)18(30)11-27/h5-7,13-14,16-17,19,27,29H,8-11H2,1-4H3/t13-,14-,16-,17-,19+,21-,22-,23-,24+/m0/s1 ; Key:FEBLZLNTKCEFIT-VSXGLTOVSA-N ;
	(verify)

Fluocinolone acetonide is a corticosteroid primarily used in dermatology to reduce skin inflammation and relieve itching. It is a synthetic hydrocortisone derivative. The fluorine substitution at position 9 in the steroid nucleus greatly enhances its activity. It was first synthesized in 1959 in the Research Department of Syntex Laboratories S.A. Mexico City.^[1] Preparations containing it were first marketed under the name Synalar. A typical dosage strength used in dermatology is 0.01–0.025%. One such cream is sold under the brand name Flucort-N and includes the antibiotic neomycin.

Fluocinolone acetonide was also found to strongly potentiate TGF-β-associated chondrogenesis of bone marrow mesenchymal stem/progenitor cells, by increasing the levels of collagen type II by more than 100 fold compared to the widely used dexamethasone.^[2]

Fluocinolone acetonide intravitreal implants have been used to treat non-infectious uveitis. A systematic review could not determine whether fluocinolone acetonide implants are superior to standard of care treatment for uveitis.^[3] A fluocinolone acetonide intravitreal implant with the brand name ILUVIEN is sold by biopharmaceutical company Alimera Sciences to treat diabetic macular edema (DME).^[4]

It was patented in 1958 and approved for medical use in 1961.^[5]

Classification

Fluocinolone is a group V (0.025%) or group VI (0.01%) corticosteroid under US classification.

References

^ J S Mills, A. Bowers, Carl Djerassi and H.J. Ringold, Steroids CXXXVII. Synthesis of a New Class of Potent Cortical Hormones. 6α,9α-Difluoro-16α-Hydroxyprednisolone and its Acetonide, Journal of the American Chemical Society, 80, 3399-3404 (1960)
^ Hara ES, Ono M, Pham HT, Sonoyama W, Kubota S, Takigawa M, Matsumoto T, Young MF, Olsen BR, Kuboki T. Fluocinolone Acetonide is a Potent Synergistic Factor of TGF-β3-Associated Chondrogenesis of Bone Marrow-Derived Mesenchymal Stem Cells for Articular Surface Regeneration. J Bone Miner Res. 2015. http://onlinelibrary.wiley.com/doi/10.1002/jbmr.2502/abstract
^ Brady CJ, Villanti AC, Law HA, Rahimy E, Reddy R, Sieving PC, Garg SJ, Tang J (2016). "Corticosteroid implants for chronic non-infectious uveitis". Cochrane Database Syst Rev. 2: CD010469. doi:10.1002/14651858.CD010469.pub2. PMC 5038923. PMID 26866343.
^ "Real-world study shows long-term safety, efficacy of Iluvien in DME". Healio. 2020-07-02. Retrieved 2020-10-28.
^ Fischer, Jnos; Ganellin, C. Robin (2006). Analogue-based Drug Discovery. John Wiley & Sons. p. 485. ISBN 9783527607495.

External links

"Fluocinolone acetonide". Drug Information Portal. U.S. National Library of Medicine.

[1] J S Mills, A. Bowers, Carl Djerassi and H.J. Ringold, Steroids CXXXVII. Synthesis of a New Class of Potent Cortical Hormones. 6α,9α-Difluoro-16α-Hydroxyprednisolone and its Acetonide, Journal of the American Chemical Society, 80, 3399-3404 (1960)

[2] Hara ES, Ono M, Pham HT, Sonoyama W, Kubota S, Takigawa M, Matsumoto T, Young MF, Olsen BR, Kuboki T. Fluocinolone Acetonide is a Potent Synergistic Factor of TGF-β3-Associated Chondrogenesis of Bone Marrow-Derived Mesenchymal Stem Cells for Articular Surface Regeneration. J Bone Miner Res. 2015. http://onlinelibrary.wiley.com/doi/10.1002/jbmr.2502/abstract

[Brady-3] Brady CJ, Villanti AC, Law HA, Rahimy E, Reddy R, Sieving PC, Garg SJ, Tang J (2016). "Corticosteroid implants for chronic non-infectious uveitis". Cochrane Database Syst Rev. 2: CD010469. doi:10.1002/14651858.CD010469.pub2. PMC 5038923. PMID 26866343.

[4] "Real-world study shows long-term safety, efficacy of Iluvien in DME". Healio. 2020-07-02. Retrieved 2020-10-28.

[Fis2006-5] Fischer, Jnos; Ganellin, C. Robin (2006). Analogue-based Drug Discovery. John Wiley & Sons. p. 485. ISBN 9783527607495.

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Clinical data


AHFS/Drugs.com	Monograph Monograph
Pregnancy category	AU: C C
Routes of administration	Topical, ophthalmic intravitreal injection
ATC code	C05AA10 (WHO) D07AC04 (WHO) S01BA15 (WHO) S02BA08 (WHO)
Legal status
Legal status	AU: S4 (Prescription only) US: ℞-only In general: ℞ (Prescription only)
Pharmacokinetic data
Metabolism	Hepatic, CYP3A4-mediated
Elimination half-life	1.3 to 1.7 hours
Identifiers
IUPAC name (1S,2S,4R,8S,9S,11S,12R,13S,19S)-12,19-difluoro-11-hydroxy-8-(2-hydroxyacetyl)-6,6,9,13-tetramethyl-5,7-dioxapentacyclo[10.8.0.0^2,9.0^4,8.0^13,18]icosa-14,17-dien-16-one
CAS Number	67-73-2
PubChem CID	6215
IUPHAR/BPS	7077
DrugBank	DB00591
ChemSpider	5980
UNII	0CD5FD6S2M
KEGG	D01825
ChEBI	CHEBI:31623
ChEMBL	ChEMBL989
CompTox Dashboard (EPA)	DTXSID0040674
ECHA InfoCard	100.000.607
Chemical and physical data
Formula	C₂₄H₃₀F₂O₆
Molar mass	452.495 g·mol⁻¹
3D model (JSmol)	Interactive image
SMILES O=C\1\C=C5/[C@@](/C=C/1)(C)[C@]2(F)[C@H]([C@H]3[C@](C[C@@H]2O)([C@@]4(OC(O[C@@H]4C3)(C)C)C(=O)CO)C)C[C@@H]5F
InChI InChI=1S/C24H30F2O6/c1-20(2)31-19-9-13-14-8-16(25)15-7-12(28)5-6-21(15,3)23(14,26)17(29)10-22(13,4)24(19,32-20)18(30)11-27/h5-7,13-14,16-17,19,27,29H,8-11H2,1-4H3/t13-,14-,16-,17-,19+,21-,22-,23-,24+/m0/s1 Key:FEBLZLNTKCEFIT-VSXGLTOVSA-N
(verify)

Fluocinolone acetonide

Classification

See also

References

External links