dexamethasone   Click here for help

GtoPdb Ligand ID: 2768

Synonyms: Decadron® | desametasone | fluormethylprednisolone
Approved drug PDB Ligand Immunopharmacology Ligand
dexamethasone is an approved drug (FDA (1958), EMA (2010))
Compound class: Synthetic organic
Comment: Dexamethasone is a glucocorticoid receptor agonist with anti-inflammatory action.
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 5
Hydrogen bond donors 3
Rotatable bonds 2
Topological polar surface area 94.83
Molecular weight 392.2
XLogP 1.14
No. Lipinski's rules broken 0
SMILES / InChI / InChIKey
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Canonical SMILES OCC(=O)C1(O)C(C)CC2C1(C)CC(O)C1(C2CCC2=CC(=O)C=CC12C)F
Isomeric SMILES OCC(=O)[C@@]1(O)[C@H](C)C[C@@H]2[C@]1(C)C[C@H](O)[C@]1([C@H]2CCC2=CC(=O)C=C[C@]12C)F
InChI InChI=1S/C22H29FO5/c1-12-8-16-15-5-4-13-9-14(25)6-7-19(13,2)21(15,23)17(26)10-20(16,3)22(12,28)18(27)11-24/h6-7,9,12,15-17,24,26,28H,4-5,8,10-11H2,1-3H3/t12-,15+,16+,17+,19+,20+,21+,22+/m1/s1
InChI Key UREBDLICKHMUKA-CXSFZGCWSA-N
Classification Click here for help
Compound class Synthetic organic
Approved drug? Yes (FDA (1958), EMA (2010))
WHO Essential Medicine WHO Model List of Essential Medicines (21st List, 2019). Access PDF version.
IUPAC Name Click here for help
(8S,9R,10S,11S,13S,14S,16R,17R)-9-fluoro-11,17-dihydroxy-17-(2-hydroxyacetyl)-10,13,16-trimethyl-6,7,8,11,12,14,15,16-octahydrocyclopenta[a]phenanthren-3-one
International Nonproprietary Names Click here for help
INN number INN
816 dexamethasone
Synonyms Click here for help
Decadron® | desametasone | fluormethylprednisolone
Database Links Click here for help
BindingDB Ligand 18207
CAS Registry No. 50-02-2
ChEMBL Ligand CHEMBL384467
DrugBank Ligand DB01234
DrugCentral Ligand 824
GtoPdb PubChem SID 135651471
Immunopaedia Search dexamethasone
PubChem CID 5743
RCSB PDB Ligand DEX
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SynPHARM 6570 (in complex with Glucocorticoid receptor)
6583 (in complex with Mineralocorticoid receptor)
Wikipedia Dexamethasone