Details of the Drug

General Information of Drug (ID: DMG2KI4)

Drug Name

Fluocinolone Acetonide

Synonyms

Coriphate; Cortiplastol; Dermalar; Flucinar; Flucinolone; Flucort; Fluocet; Fluocinolonacetonidum; Fluonid; Fluotrex; Fluovitif; Flupollon; Jellin; Localyn; Medidur; Omniderm; Percutina; Prodermin; Radiocin; Retisert; Sinalar; Synalar; Synamol; Synandone; Synandrone; Synemol; Synotic; Synsac; Tefunote;Acetonida de fluocinolona; Acetonide de fluocinolone; Fluocinolone acetonide [DCIT]; Fluocinoloni acetonidum; Fluortriamcinolone Acetonide; Fs Shampoo; Localyn Syntex; F0657; RS 1401AT; Acetonida de fluocinolona [INN-Spanish]; Acetonide de fluocinolone [INN-French]; Component of Neo-Synalar; Dermatin (steroid); Fluocet (TN); Fluocinoloni acetonidum [INN-Latin]; Neo-Synalar; RS-1401 AT; Retisert (TN); Synalar (TN); Synalar-HP; Derma-smoothe/fs; Flucort-N (TN); Fluocinolone 16,17-acetonide; Fluocinolone acetonide [USAN:INN:JAN]; Ydroxyprednisolone 16,17-acetonide; Fluocinolone acetonide (JP15/USP/INN); Pregna-1,4-diene-3,20-dione, 6alpha,9-difluoro-11beta,16alpha,17,21-tetrahydroxy-, cyclic 16,17-acetal with acetone; Pregna-1,4-diene-3,20-dione, 6alpha,9-difluoro-11beta,16alpha,17,21-tetrahydroxy-, cyclic 16,17-acetal with acetone (8CI); Pregna-1,4-diene-3,20-dione, 6.alpha.,9-difluoro-11.beta.,16.alpha.,17,21-tetrahydroxy-, cyclic 16,17-acetal with acetone; (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; 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; 6-alpha,9-alpha-Difluoro-16-alpha-hydroxyprednisolone 16,17-acetonide; 6.Alpha., 9.alpha.-Difluoro-16.alpha.-h; 6.Alpha.,9-Difluoro; 6.alpha.,9-Difluoro-11.beta.,16.alpha.,17,21-tetrahydroxypregna-1,4-diene-3,20-dione, cyclic 16,17-acetal with acetone; 6.alpha.,9.alpha.-Difluoro-16.alpha.-hydroxyprednisolone 16,17-acetonide; 6.alpha.-Fluorotriamcinolone acetonide; 6a,9a-difluoro-16a-hydroxyprednisolone 16,17-acetonide; 6alpha,9-Difluoro-11beta,16alpha,17,21-tetrahydroxypregna-1,4-diene-3,20-dione, cyclic 16,17-acetal with acetone; 6alpha,9alpha-Difluoro-11beta,16alpha,17alpha,21-tetrahydroxy-1,4-pregnadiene-3,20-dione; 6alpha,9alpha-Difluoro-11beta,16alpha,17alpha,21-tetrahydroxy-1,4-pregnadiene-3,20-dione 16,17-Acetonide; 6alpha,9alpha-Difluoro-16alpha-hydroxyprednisolone 16,17-acetonide; 6alpha-Fluorotriamcinolone acetonide

Indication

Disease Entry	ICD 11	Status	REF
Choroiditis	N.A.	Approved	[1]
Exanthem	N.A.	Approved	[1]
Granuloma annulare	N.A.	Approved	[1]
Inflammation	1A00-CA43.1	Approved	[2]
Melasma	ED60.1	Approved	[1]
Pityriasis simplex	N.A.	Approved	[1]
Primary cutaneous T-cell lymphoma	N.A.	Approved	[1]
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Therapeutic Class

Antiinflammatory Agents

Drug Type

Small molecular drug

Structure

3D MOL

2D MOL

#Ro5 Violations (Lipinski): 0

Molecular Weight (mw)

452.5

Logarithm of the Partition Coefficient (xlogp)

2.5

Rotatable Bond Count (rotbonds)

Hydrogen Bond Donor Count (hbonddonor)

Hydrogen Bond Acceptor Count (hbondacc)

ADMET Property

Half-life: The concentration or amount of drug in body reduced by one-half in 1.3 - 1.7 hours [3]
Metabolism: The drug is metabolized via the hepatic []

Chemical Identifiers

Formula: C24H30F2O6
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
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: 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

Cross-matching ID

PubChem CID: 6215
ChEBI ID: CHEBI:31623
CAS Number: 67-73-2
DrugBank ID: DB00591
TTD ID: D02QJH
INTEDE ID: DR0713
ACDINA ID: D01089

Combinatorial Drugs (CBD)

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Repurposed Drugs (RPD)

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Molecular Interaction Atlas of This Drug

Drug Therapeutic Target (DTT)

DTT Name	DTT ID	UniProt ID	MOA	REF
Glucocorticoid receptor (NR3C1)	TTYRL6O	GCR_HUMAN	Modulator	[4]

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Drug-Metabolizing Enzyme (DME)

DME Name	DME ID	UniProt ID	MOA	REF
Cytochrome P450 3A4 (CYP3A4)_{Main DME}	DE4LYSA	CP3A4_HUMAN	Substrate	[5]

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Molecular Interaction Atlas (MIA)

MIA Detail

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Molecular Expression Atlas of This Drug

The Studied Disease

Choroiditis

ICD Disease Classification

Molecule Name	Molecule Type	Gene Name	p-value	Fold-Change	Z-score
Cytochrome P450 3A4 (CYP3A4)	DME	CYP3A4	9.85E-01	2.24E-02	7.33E-02

Molecular Expression Atlas (MEA)

MEA Detail

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Drug Inactive Ingredient(s) (DIG) and Formulation(s) of This Drug

DIG

DIG Name	DIG ID	PubChem CID	Functional Classification
Cetyl alcohol	E00061	2682	Coating agent; Emollient; Emulsifying agent; Stiffening agent
Glyceryl monooleate	E00473	5283468	Bioadhesive material; Emollient; Emulsifying agent; Emulsion stabilizing agent; Gelling agent; Modified-release agent; Surfactant
Isopropyl alcohol	E00070	3776	Antimicrobial preservative; Solvent
methylparaben	E00149	7456	Antimicrobial preservative
Propylparaben sodium	E00567	23679044	Antimicrobial preservative
Isopropyl palmitate	E00193	8907	Emollient; Oleaginous vehicle; Penetration agent; Solvent
Oleth-2	E00515	13387455	Emulsifying agent; Surfactant
Polyoxyl 40 stearate	E00663	Not Available	Emulsifying agent; Surfactant
Propylene glycol	E00040	1030	Antimicrobial preservative; Humectant; Plasticizing agent; Solvent
Propylene glycol monostearate	E00239	14878	Emollient; Emulsifying agent; Surfactant
Sorbic acid	E00441	643460	Antimicrobial preservative
Water	E00035	962	Solvent
Isopropyl myristate	E00161	8042	Emollient; Oleaginous vehicle; Penetration agent; Solvent
Sorbitan monostearate	E00524	16218600	Dispersing agent; Emulsifying agent; Solubilizing agent; Surfactant; Suspending agent; Vaccine adjuvant
Polysorbate 60	E00715	Not Available	Dispersing agent; Emollient; Emulsifying agent; Surfactant; Plasticizing agent; Solubilizing agent; Suspending agent
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Pharmaceutical Formulation

Formulation Name	Drug Dosage	Dosage Form	Route
Fluocinolone Acetonide 0.01% ointment	0.01%	Ointment	Topical
Fluocinolone Acetonide 0.01% oil	0.01%	Oil	Topical

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References

1	Fluocinolone acetonide FDA Label
2	URL: http://www.guidetopharmacology.org Nucleic Acids Res. 2015 Oct 12. pii: gkv1037. The IUPHAR/BPS Guide to PHARMACOLOGY in 2016: towards curated quantitative interactions between 1300 protein targets and 6000 ligands. (Ligand id: 7077).
3	Pharmacokinetics of fluocinolone acetonide in patch versus cream formulations. Int J Clin Pharmacol Res. 1991;11(1):17-21.
4	Drugs@FDA. U.S. Food and Drug Administration. U.S. Department of Health & Human Services.
5	Metabolic pathways of inhaled glucocorticoids by the CYP3A enzymes. Drug Metab Dispos. 2013 Feb;41(2):379-89.