deflazacort   Click here for help

GtoPdb Ligand ID: 9477

Synonyms: Emflaza® | MDL 458
Approved drug Immunopharmacology Ligand
deflazacort is an approved drug (UK (1994), FDA (2017))
Compound class: Synthetic organic
Comment: Deflazacort is a prednisolone derivative glucocorticoid that is used as an anti-inflammatory and immunosuppressant. It is a prodrug that is metabolised to the active form, 21-desacetyl deflazacort (PubChem CID 97547130) [3].
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View more information in the IUPHAR Pharmacology Education Project: deflazacort

2D Structure
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2D Structure

An image of the ligand's 2D structure. For small molecules with SMILES these are drawn using the NCI/CADD Chemical Identifier Resolver. Click on the image to access the chemical structure search tool with the ligand pre-loaded in the structure editor. For other types of ligands, e.g. longer nucleotides and peptides, a manually drawn representation of the molecule may be provided.

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Physico-chemical Properties
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Physico-chemical Properties

Calculated molecular properties are available for small molecules and natural products (not peptides). Properties were generated using the CDK toolkit. All properties were selected to enable the prediction of the Lipinski Rule-of-Five profile or ‘druglikeness’ for each ligand. For more info on each category see the help pages.

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Hydrogen bond acceptors 7
Hydrogen bond donors 1
Rotatable bonds 4
Topological polar surface area 102.26
Molecular weight 441.22
XLogP 1.92
No. Lipinski's rules broken 0
SMILES / InChI / InChIKey
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SMILES / InChI / InChIKey

SMILES (Simplified Molecular Input Line Entry Specification) A specification for unambiguously describing the structure of chemical molecules using short ASCII strings. Canonical SMILES specify a unique representation of the 2D structure without chiral or isotopic specifications. Isomeric SMILES include chiral specification and isotopes.

Standard InChI (IUPAC International Chemical Identifier) and InChIKey InChI is a non-proprietary, standard, textual identifier for chemical substances designed to facilitate linking of information and database searching. An InChIKey is a simplified version of a full InChI, designed for easier web searching.

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Canonical SMILES CC(=O)OCC(=O)C12N=C(OC1CC1C2(C)CC(O)C2C1CCC1=CC(=O)C=CC21C)C
Isomeric SMILES CC(=O)OCC(=O)[C@@]12N=C(O[C@@H]1C[C@@H]1[C@]2(C)C[C@H](O)[C@H]2[C@H]1CCC1=CC(=O)C=C[C@]21C)C
InChI InChI=1S/C25H31NO6/c1-13-26-25(20(30)12-31-14(2)27)21(32-13)10-18-17-6-5-15-9-16(28)7-8-23(15,3)22(17)19(29)11-24(18,25)4/h7-9,17-19,21-22,29H,5-6,10-12H2,1-4H3/t17-,18-,19-,21+,22+,23-,24-,25+/m0/s1
InChI Key FBHSPRKOSMHSIF-GRMWVWQJSA-N
Immunopharmacology Disease
Disease X-Refs Comment References
Rheumatoid arthritis Disease Ontology: DOID:7148
OMIM: 180300
 Approved corticosteroid that can be prescribed for RA.
Crohn's disease Disease Ontology: DOID:8778
OMIM: 266600
Orphanet: ORPHA206
 Approved corticosteroid that can be prescribed for CD.
Systemic lupus erythematosus Disease Ontology: DOID:9074
OMIM: 152700
Orphanet: ORPHA536
 Approved corticosteroid that can be prescribed for SLE.
Ulcerative colitis Disease Ontology: DOID:8577
OMIM: 266600
Orphanet: ORPHA771
 Approved corticosteroid that can be prescribed for UC.
Juvenile idiopathic arthritis- systemic OMIM: 604302
 Approved corticosteroid that can be prescribed for sJIA.
Sarcoidosis Disease Ontology: DOID:11335
 Approved corticosteroid that can be prescribed for sarcoidosis.
Duchenne muscular dystrophy Disease Ontology: DOID:11723
OMIM: 19518854
 Deflazacort was approved by the US FDA in 2017 as a treatment for DMD.
Autoimmune thrombocytopenic purpura Disease Ontology: DOID:8924
OMIM: 188030
Orphanet: ORPHA3002
 Approved corticosteroid that can be prescribed for ATP.