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Compound Detail

CHEMBL989

FLUOCINOLONE ACETONIDE
💊 Approved Drug
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💊 Approved Drug
CC1(C)O[C@@H]2C[C@H]3[C@@H]4C[C@H](F)C5=CC(=O)C=C[C@]5(C)[C@@]4(F)[C@@H](O)C[C@]3(C)[C@]2(C(=O)CO)O1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL989
Name FLUOCINOLONE ACETONIDE
Phase Approved
Structure Type MOL
InChI Key FEBLZLNTKCEFIT-VSXGLTOVSA-N
Therapeutic ✓ Yes

Known Names

Acetonide de fluocinolone Acetonido de fluocinolona Capex Derma-smoothe/fs Dermotic Flucinolone acetonide Fluocet Fluocinolide (acetate) Fluocinolone Fluocinolone acetonide Fluocinolone acetonide component of iluvien Fluocinolone acetonide component of neo-synalar +16 more
2
Targets
4
Activities
2
Assay Types
0
PK Parameters
20
Publications
28
Known Names
17
Indications
1
Mechanisms

Molecular Properties

452.5
MW (Da)
2.37
ALogP
6
HBA
2
HBD
93.1
PSA (Ų)
0.67
QED
0
Ro5 Violations
2
Rot. Bonds

Drug Information

Molecule Type Small molecule
First Approval 1963
Availability Prescription
Chirality Single Enantiomer

Routes of Administration

Parenteral Topical
USAN Stem -olone; -onide
USAN Year 1962

Extended Properties

Molecular Formula C24H30F2O6
MW 452.49
Aromatic Rings 0
Heavy Atoms 32
NP-Likeness 2.05

Mechanism of Action

Mechanism Action Type Target Direct Efficacy
Glucocorticoid receptor agonist AGONIST Glucocorticoid receptor ✓ ✓

Indications

Dermatitis, Atopic Dermatitis, Seborrheic Eye Diseases Hemorrhoids Infections Macular Edema Melanosis Psoriasis Skin Diseases Uveitis Uveitis, Anterior Uveitis, Intermediate Uveitis, Posterior Macular Degeneration Macular Degeneration Retinal Diseases Glaucoma

ATC Classification

C05AA10
fluocinolone acetonide
Level 1: CARDIOVASCULAR SYSTEM
Level 2: VASOPROTECTIVES
D07AC04
fluocinolone acetonide
Level 1: DERMATOLOGICALS
Level 2: CORTICOSTEROIDS, DERMATOLOGICAL PREPARATIONS
S01BA15
fluocinolone acetonide
Level 1: SENSORY ORGANS
Level 2: OPHTHALMOLOGICALS
S02BA08
fluocinolone acetonide
Level 1: SENSORY ORGANS
Level 2: OTOLOGICALS

Activity Summary

IC50 2 meas. best 8.5
Ki 2 meas. best 8.85

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Glucocorticoid receptor
CHEMBL2034
 Ki 8.85 8.85 1.4 1
Glucocorticoid receptor
CHEMBL2034
 IC50 8.5 8.5 3.1 1
Progesterone receptor
CHEMBL1909044
 Ki 8.47 8.47 3.3 1
Progesterone receptor
CHEMBL1909044
 IC50 7.58 7.58 26.0 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Glucocorticoid receptor Ki = 1.423 nM 8.85 DRUGMATRIX: Glucocorticoid radioligand binding (ligand: [3H] Dexamethasone) -
Glucocorticoid receptor IC50 = 3.131 nM 8.5 DRUGMATRIX: Glucocorticoid radioligand binding (ligand: [3H] Dexamethasone) -
Progesterone receptor Ki = 3.346 nM 8.47 DRUGMATRIX: Progesterone radioligand binding (ligand: [3H] R-5020) -
Progesterone receptor IC50 = 26.0 nM 7.58 DRUGMATRIX: Progesterone radioligand binding (ligand: [3H] R-5020) -

Literature References

PubMed DOI Target Context # Activities
- 10.6019/CHEMBL3885881 Rattus norvegicus 298
22194678 10.1371/journal.pcbi.1002310 Hepatotoxicity 14
7966132 10.1021/jm00048a008 Mus musculus 2
836493 10.1021/jm00212a006 Rattus norvegicus 2
37468498 10.1038/s41467-023-40064-9 Prostaglandin G/H synthase 1 2
37468498 10.1038/s41467-023-40064-9 Alpha-1A adrenergic receptor 2
- 10.6019/CHEMBL4651402 SARS-CoV-2 2
37468498 10.1038/s41467-023-40064-9 Thromboxane A2 receptor 2
- 10.6019/CHEMBL4495565 SARS-CoV-2 2
18834112 10.1021/jm800656v Amine oxidase [flavin-containing] B 2
18834112 10.1021/jm800656v Amine oxidase [flavin-containing] A 2
7966132 10.1021/jm00048a008 Rattus norvegicus 2
37468498 10.1038/s41467-023-40064-9 Muscarinic acetylcholine receptor M1 2
20185316 10.1016/j.bmc.2010.01.068 Trypanosoma brucei rhodesiense 1
20185316 10.1016/j.bmc.2010.01.068 Trypanosoma brucei brucei 1
20185316 10.1016/j.bmc.2010.01.068 Trypanosoma brucei 1
20185316 10.1016/j.bmc.2010.01.068 Trichomonas vaginalis 1
38318365 10.1016/j.isci.2024.108907 Deoxynucleoside triphosphate triphosphohydrolase SAMHD1 1
3783574 10.1021/jm00161a001 Homo sapiens 1
6827553 10.1021/jm00357a003 Rattus norvegicus 1

Data from ChEMBL 36 via Core Engine