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
Inflammation 1A00-CA43.1 Approved [1], [2]
Therapeutic Class
Antiinflammatory Agents
Drug Type
Small molecular drug
Structure
3D MOL 2D MOL
#Ro5 Violations (Lipinski): 0 Molecular Weight (mw) 452.5
Topological Polar Surface Area (xlogp) 2.5
Rotatable Bond Count (rotbonds) 2
Hydrogen Bond Donor Count (hbonddonor) 2
Hydrogen Bond Acceptor Count (hbondacc) 8
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 [4]
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

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 [5]

Drug-Metabolizing Enzyme (DME)
DME Name DME ID UniProt ID MOA REF
Cytochrome P450 3A4 (CYP3A4)
Main DME
DE4LYSA CP3A4_HUMAN Substrate [6]
Molecular Interaction Atlas (MIA) Jump to Detail Molecular Interaction Atlas of This Drug

Molecular Expression Atlas of This Drug

The Studied Disease Inflammation
ICD Disease Classification 1A00-CA43.1
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) Jump to Detail Molecular Expression Atlas of This Drug

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
⏷ Show the Full List of 15 Pharmaceutical Excipients of This Drug
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
Jump to Detail Pharmaceutical Formulation Page of This Drug

References

1 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).
2 FDA Approved Drug Products from FDA Official Website. 2009. Application Number: (NDA) 019452.
3 Pharmacokinetics of fluocinolone acetonide in patch versus cream formulations. Int J Clin Pharmacol Res. 1991;11(1):17-21.
4 FDA approval: ado-trastuzumab emtansine for the treatment of patients with HER2-positive metastatic breast cancer. Clin Cancer Res. 2014 Sep 1;20(17):4436-41.
5 Drugs@FDA. U.S. Food and Drug Administration. U.S. Department of Health & Human Services.
6 Metabolic pathways of inhaled glucocorticoids by the CYP3A enzymes. Drug Metab Dispos. 2013 Feb;41(2):379-89.
7 Expression levels and activation of a PXR variant are directly related to drug resistance in osteosarcoma cell lines. Cancer. 2007 Mar 1;109(5):957-65.
8 Contribution of human hepatic cytochrome P450 isoforms to regioselective hydroxylation of steroid hormones. Xenobiotica. 1998 Jun;28(6):539-47.
9 Comprehensive evaluation of tamoxifen sequential biotransformation by the human cytochrome P450 system in vitro: prominent roles for CYP3A and CYP2D6. J Pharmacol Exp Ther. 2004 Sep;310(3):1062-75.
10 Isoform-specific regulation of cytochromes P450 expression by estradiol and progesterone. Drug Metab Dispos. 2013 Feb;41(2):263-9.
11 Metabolic interactions between acetaminophen (paracetamol) and two flavonoids, luteolin and quercetin, through in-vitro inhibition studies. J Pharm Pharmacol. 2017 Dec;69(12):1762-1772.
12 Potent mechanism-based inhibition of CYP3A4 by imatinib explains its liability to interact with CYP3A4 substrates. Br J Pharmacol. 2012 Apr;165(8):2787-98.
13 Effects of morin on the pharmacokinetics of etoposide in rats. Biopharm Drug Dispos. 2007 Apr;28(3):151-6.
14 The metabolism of zidovudine by human liver microsomes in vitro: formation of 3'-amino-3'-deoxythymidine. Biochem Pharmacol. 1994 Jul 19;48(2):267-76.
15 Substrates, inducers, inhibitors and structure-activity relationships of human Cytochrome P450 2C9 and implications in drug development. Curr Med Chem. 2009;16(27):3480-675.
16 Interaction between the glucocorticoid and erythropoietin receptors in human erythroid cells. Exp Hematol. 2009 May;37(5):559-72.
17 Aldosterone (mineralocorticoid) equivalent to prednisolone (glucocorticoid) in reversing hearing loss in MRL/MpJ-Fas1pr autoimmune mice. Laryngoscope. 2000 Nov;110(11):1902-6.
18 Fluticasone furoate nasal spray in allergic rhinitis. Drugs Today (Barc). 2008 Apr;44(4):251-60.
19 Cytochromes P450 (CYP) in the Poeciliopsis lucida hepatocellular carcinoma cell line (PLHC-1): dose- and time-dependent glucocorticoid potentiation of CYP1A induction without induction of CYP3A. ArchBiochem Biophys. 1996 May 1;329(1):113-22.
20 PXR-mediated induction of human CYP3A4 and mouse Cyp3a11 by the glucocorticoid budesonide. Eur J Pharm Sci. 2009 Mar 2;36(4-5):565-71.
21 The glucocorticoid agonist activities of mifepristone (RU486) and progesterone are dependent on glucocorticoid receptor levels but not on EC50 values. Steroids. 2007 Jun;72(6-7):600-8.