Details of the Active Pharmaceutical Ingredient (API)

General Information of API (ID: D01089)
Name
Fluocinolone acetonide
Synonyms    Click to Show/Hide the Synonyms of This API
FLUOCINOLONE ACETONIDE; 67-73-2; Synalar; Flucinar; Synandone; Fluonid; Jellin; Synamol; Synemol; Coriphate; Fluovitif; Flupollon; Percutina; Synandrone; Dermalar; Localyn; Omniderm; Radiocin; Sinalar; Synotic; Tefunote; Synsac; Fluotrex; Retisert; Synalar-HP; Fluocet; Localyn Syntex; Derma-smoothe/fs; Cortiplastol; Prodermin; Fluocinolonacetonidum; Flucort; Fluocinolone 16,17-acetonide; Iluvien; Capex; 6alpha-Fluorotriamcinolone acetonide; Fluocinolone acetonide [DCIT]; Fluocinoloni acetonidum; RS-1401 AT; Fluocinoloni acetonidum [INN-Latin]; Acetonide de fluocinolone; C24H30F2O6; component of Neo-Synalar; Fluocinolone (Acetonide); UNII-0CD5FD6S2M; Dermatin (steroid); 6alpha,9alpha-Difluoro-16alpha-hydroxyprednisolone 16,17-acetonide; MFCD00010525; NSC-92339; 0CD5FD6S2M; MLS000028545; CHEBI:31623; Fluocinolone acetonide (Flucort-N); Fs Shampoo; NSC92339; flucinolone; SMR000058329; DSSTox_CID_20674; DSSTox_RID_79533; DSSTox_GSID_40674; Acetonida de fluocinolona; RS 1401AT; Flucort-N; 6.alpha.-Fluorotriamcinolone acetonide; CAS-67-73-2; Retisert (TN); (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; (6alpha,11beta,16alpha)-6,9-Difluoro-11,21-dihydroxy-16,17-[(1-methylethylidene)bis(oxy)]pregna-1,4-diene-3,20-dione; Fluocet (TN); Synalar (TN); Acetonide de fluocinolone [INN-French]; Acetonida de fluocinolona [INN-Spanish]; CCRIS 3250; HSDB 3083; 6.Alpha.,9-Difluoro; EINECS 200-668-5; NSC 92339; Dermatin; Fluzon [Steroid]; NCGC00021301-04; 6-alpha,9-alpha-Difluoro-16-alpha-hydroxyprednisolone 16,17-acetonide; Fluocinoloneacetonide; fluocinolone-acetonide; 6alpha,9-Difluoro-11beta,16alpha,17,21-tetrahydroxypregna-1,4-diene-3,20-dione, cyclic 16,17-acetal with acetone; Pregna-1,4-diene-3,20-dione, 6,9-difluoro-11,21-dihydroxy-16,17-((1-methylethylidene)bis(oxy))-, (6alpha,11beta,16alpha)-; Pregna-1,4-diene-3,20-dione, 6alpha,9-difluoro-11beta,16alpha,17,21-tetrahydroxy-, cyclic 16,17-acetal with acetone; Fluocinolone acetonide intravitreal implant; acetonido de fluocinolona; 6.alpha.,17-acetonide; Opera_ID_1295; F0657; Fluocinolone acetonide [USAN:USP:INN:JAN]; CHEMBL989; SCHEMBL4795; 6alpha,9alpha-Difluoro-11beta,16alpha,17alpha,21-tetrahydroxy-1,4-pregnadiene-3,20-dione 16,17-Acetonide; MLS001076276; ARONIS24561; GTPL7077; DTXSID0040674; EBD4852; HMS2090I14; HMS2230D13; HMS3259G12; HMS3715J11; HY-B0415; ZINC3977981; Tox21_110869; Tox21_302364; AC-429; s2470; AKOS015963144; Tox21_110869_1; ACN-043362; CCG-221165; DB00591; NC00562; Fluocinolone acetonide (JP17/USP/INN); NCGC00021301-06; NCGC00255654-01; (4aS,4bR,5S,6aS,6bS,9aR,10aS,10bS,12S)-4b,12-difluoro-5-hydroxy-6b-(hydroxyacetyl)-4a,6a,8,8-tetramethyl-4a,4b,5,6,6a,6b,9a,10,10a,10b,11,12-dodecahydro-2H-naphtho[2',1':4,5]indeno[1,2-d][1,3]dioxol-2-one; (4aS,4bR,5S,6aS,6bS,9aR,10aS,10bS,12S)-4b,12-difluoro-6b-glycoloyl-5-hydroxy-4a,6a,8,8-tetramethyl-4a,4b,5,6,6a,6b,9a,10,10a,10b,11,12-dodecahydro-2H-naphtho[2',1':4,5]indeno[1,2-d][1,3]dioxol-2-one; 4b,12-Difluoro-6b-glycoloyl-5-hydroxy-4a,6a,8,8-tetramethyl-4a,4b,5,6,6a,6b,9a,10,10a,10b,11,12-dodecahydro-2H-naphtho[2',1':4,5]indeno[1,2-d][1,3]dioxol-2-one; AS-13690; NCI60_042042; Pregna-1,4-diene-3,20-dione, 6alpha,9-difluoro-11beta,16alpha,17,21-tetrahydroxy-, cyclic 16,17-acetal with acetone (8CI); Fluocinolone acetonide, analytical standard; D01825; J10113; AB00383017-10; AB00383017_11; 010F525; Q924467; SR-01000000109; SR-01000000109-2; W-104704; BRD-K94353609-001-21-6; difluoro-hydroxy-(2-hydroxyacetyl)-tetramethyl-[?]one; 6.alpha., 9.alpha.-Difluoro-16.alpha.-hydroxyprednisolone 16,17-acetonide; Fluocinolone acetonide, European Pharmacopoeia (EP) Reference Standard; Fluocinolone acetonide, United States Pharmacopeia (USP) Reference Standard; Fluocinolone acetonide for system suitability, European Pharmacopoeia (EP) Reference Standard; Fluocinolone Acetonide, Pharmaceutical Secondary Standard; Certified Reference Material; WLN: T F5 E5 B666 GO IO RV AHTTTT&J A BF CQ E FVIQ H H OF -A&BHO -B&ACEF; (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; (2S,6aS,6bR,7S,8aS,8bS,11aR,12aS,12bS)-2,6b-difluoro-7-hydroxy-8b-(2-hydroxyacetyl)-6a,8a,10,10-tetramethyl-6a,6b,7,8,8a,8b,11a,12,12a,12b-decahydro-1H-naphtho[2',1':4,5]indeno[1,2-d][1,3]dioxol-4(2H)-one; 6.alpha.,16.alpha.,17,21-tetrahydroxypregna-1,4-diene-3,20-dione, cyclic 16,17-acetal with acetone; 6alpha,9alpha-difluoro-11beta,21-dihydroxy-16alpha-17alpha-isopropylidenedioxypregna-1,4-diene-3,20-dione;; Fluocinolone acetonide for peak identification, European Pharmacopoeia (EP) Reference Standard; Pregna-1,20-dione, 6,9-difluoro-11,12-dihydroxy-16,17-[(1-methylethylidene)bis(oxy)]-, (6.alpha.,11.beta.,16.alpha.)-; Pregna-1,20-dione, 6,9-difluoro-11,21-dihydroxy-16,17-[(1-methylethylidene)bis(oxy)-, (6.alpha.,11.beta.,16.alpha.)-; Pregna-1,20-dione, 6,9-difluoro-11,21-dihydroxy-16,17-[(1-methylethylidene)bis(oxy)]-, (6.alpha.,11.beta.,16.alpha.)-; Pregna-1,20-dione, 6.alpha.,9-difluoro-11.beta.,16.alpha.,17,21-tetrahydroxy-, cyclic 16,17-acetal with acetone
Clinical Status
Approved
PubChem CID
6215
Formula
C24H30F2O6
Canonical SMILES
C[C@]12C[C@@H]([C@]3([C@H]([C@@H]1C[C@@H]4[C@]2(OC(O4)(C)C)C(=O)CO)C[C@@H](C5=CC(=O)C=C[C@@]53C)F)F)O
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
InChIKey
FEBLZLNTKCEFIT-VSXGLTOVSA-N
   Click to Show/Hide the Molecular Data (Structure/Property) of This API
Structure
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3D MOL 2D MOL
Physicochemical Properties Molecular Weight 452.5 Topological Polar Surface Area 93.1
XlogP 2.5 Complexity 960
Heavy Atom Count 32 Rotatable Bond Count 2
Hydrogen Bond Donor Count 2 Hydrogen Bond Acceptor Count 8
Full List of Drug Formulations (DFMs) Containing This API
          Fluocinolone Acetonide 0.01% ointment Click to Show/Hide the Full List of Formulation(s):          1 Formulation(s)
             Drug Formulation 1 DFM Info click to show the detail info of this DFM
                   All DIGs    Click to Show/Hide the Full List of DIGs in This DFM
Mineral Oil; Lanolin Alcohols; Isopropyl Palmitate; Propylene Glycol Stearate; Cetyl Alcohol; Sorbitan Monostearate; Polysorbate 60; Sorbic Acid; Polyoxyl 40 Stearate; Water; Propylene Glycol; Propylparaben; Methylparaben
                   Dosage Form Ointment
                   Company Cosette Pharmaceuticals
                   DIG(s) with
                   Biological Activity
DIG Name DIG Info Representative Biological Activity of This DIG REF
methylparaben DIG Info Carbonic anhydrase VII (Ki = 780 nM) [1]
Isopropyl palmitate DIG Info Acylsphingosine deacylase NAAA (IC50 = 19000 nM) [2]
Propylparaben sodium DIG Info Estrogen receptor alpha (EC50 = 38200 nM) [3]
Cetyl alcohol DIG Info Breast cancer FM3A cells (EC50 = 1600 nM) [4]
Propylene glycol DIG Info Albendazole monooxygenase (Inhibition ratio < 20 %) [5]
Polyoxyl 40 stearate DIG Info Mephenytoin 4-hydroxylase (IC50 = 20.6 uM) [6]
Propylene glycol monostearate DIG Info Multidrug resistance protein 1 (Inhibition ratio = 25 %) [7]
          Fluocinolone Acetonide 0.01% oil Click to Show/Hide the Full List of Formulation(s):          1 Formulation(s)
             Drug Formulation 1 DFM Info click to show the detail info of this DFM
                   All DIGs    Click to Show/Hide the Full List of DIGs in This DFM
Isopropyl Alcohol; Isopropyl Myristate; Light Mineral Oil; Oleth-2; Peanut Oil
                   Dosage Form Oil
                   Company Seton Pharmaceuticals
                   DIG(s) with
                   Biological Activity
DIG Name DIG Info Representative Biological Activity of This DIG REF
Oleth-2 DIG Info Cannabinoid CB1 receptor (EC50 = 39810.72 nM) [8]
Glyceryl monooleate DIG Info Diacylglycerol kinase alpha (Ki = 91000 nM) [9]
Isopropyl alcohol DIG Info Lymphoma P388/ADR cells (IC50 = 0.22 uM) [10]
References
1 Mono-/dihydroxybenzoic acid esters and phenol pyridinium derivatives as inhibitors of the mammalian carbonic anhydrase isoforms I, II, VII, IX, XII and XIV. Bioorg Med Chem. 2013 Mar 15; 21(6):1564-9.
2 The endocannabinoid system: drug targets, lead compounds, and potential therapeutic applications. J Med Chem. 2005 Aug 11; 48(16):5059-87.
3 Discovery of natural estrogen receptor modulators with structure-based virtual screening. Bioorg Med Chem Lett. 2013 Jun 1; 23(11):3329-33.
4 Synthesis and notable antimalarial activity of acyclic peroxides, L-(alkyldioxy)-L-(methyldioxy)cyclododecanes. J Med Chem. 2002 Mar 14; 45(6):1374-8.
5 Pharmaceutical excipients inhibit cytochrome P450 activity in cell free systems and after systemic administration. Eur J Pharm Biopharm. 2008 Sep;70(1):279-88.
6 Effects of polyoxyethylene (40) stearate on the activity of P-glycoprotein and cytochrome P450. Eur J Pharm Sci. 2009 Jul 12;37(5):573-80.
7 Modulation of intestinal P-glycoprotein function by polyethylene glycols and their derivatives by in vitro transport and in situ absorption studies. Int J Pharm. 2006 Apr 26;313(1-2):49-56.
8 3D-QSAR studies on cannabinoid CB1 receptor agonists: G-protein activation as biological data. J Med Chem. 2006 Jan 26; 49(2):554-66.
9 Identification of a novel DGKalpha inhibitor for XLP-1 therapy by virtual screening. Eur J Med Chem. 2019; 164:378-390.
10 Synthesis and evaluation of dihydropyrroloquinolines that selectively antagonize P-glycoprotein. J Med Chem. 2004 Mar 11; 47(6):1413-22.

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