PREDNISONE

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Search structure


Trade Names	CORTAN DELTA-DOME DELTASONE FERNISONE LIQUID PRED METICORTEN ORASONE PARACORT PREDNICEN-M PREDNISONE PREDNISONE INTENSOL RAYOS SERVISONE
Synonyms	3en3hg4wsw Cortan Cortancyl Decortin Decortisyl Dehydrocortisone Delta-dome Deltasone Fernisone Liquid pred Lodotra Metacortandracin Meticorten NSC-10023 Orasone Paracort Prednicen-m Prednisone Prednisone anhydrous Prednisone intensol Prednisone tablets Rayos Servisone Sterapred Supercortil
Status
Molecule Category	Free-form
ATC	A07EA03 H02AB07
UNII	VB0R961HZT
EPA CompTox	DTXSID4021185


Active Pharmaceutical Ingredients Bioactive chemicals	Exact Similarity SubStructure	Threshold (%) >= 70

Structure


InChI Key	XOFYZVNMUHMLCC-ZPOLXVRWSA-N
Smiles	C[C@]12C=CC(=O)C=C1CC[C@@H]1[C@@H]2C(=O)C[C@@]2(C)[C@H]1CC[C@]2(O)C(=O)CO
InChI	InChI=1S/C21H26O5/c1-19-7-5-13(23)9-12(19)3-4-14-15-6-8-21(26,17(25)11-22)20(15,2)10-16(24)18(14)19/h5,7,9,14-15,18,22,26H,3-4,6,8,10-11H2,1-2H3/t14-,15-,18+,19-,20-,21-/m0/s1

Physicochemical Descriptors

Property Name	Value
Molecular Formula	C21H26O5
Molecular Weight	358.43
AlogP	1.77
Hydrogen Bond Acceptor	5.0
Hydrogen Bond Donor	2.0
Number of Rotational Bond	2.0
Polar Surface Area	91.67
Molecular species	NEUTRAL
Aromatic Rings	0.0
Heavy Atoms	26.0

Metabolites Network

visNetwork

Bioactivity

Mechanism of Action	Action	Reference
Glucocorticoid receptor agonist	AGONIST	ISBN PubMed Wikipedia


Protein: Glucocorticoid receptor Description: Glucocorticoid receptor Organism : Homo sapiens P04150 ENSG00000113580

Targets	EC50(nM)	IC50(nM)	Kd(nM)	Ki(nM)	Inhibition(%)
Transcription factor Nuclear receptor Nuclear hormone receptor subfamily 3 Nuclear hormone receptor subfamily 3 group C Nuclear hormone receptor subfamily 3 group C member 1	-	-	29	-	-
Transporter Electrochemical transporter SLC superfamily of solute carriers SLC21/SLCO family of organic anion transporting polypeptides	-	-	-	-	10-70
Transporter Electrochemical transporter SLC superfamily of solute carriers SLC22 family of organic cation and anion transporters	-	-	-	-	23

Assay Description	Organism	Bioactivity	Reference
Inhibition of 4-(4-(dimethylamino)styryl)-N-methylpyridinium uptake at human OCT1 expressed in HEK293 cells at 100 uM by confocal microscopy	Homo sapiens	23.3 %
DRUGMATRIX: Glucocorticoid radioligand binding (ligand: [3H] Dexamethasone)	None	521.0 nM
Inhibition of sodium fluorescein uptake in OATP1B1-transfected CHO cells at an equimolar substrate-inhibitor concentration of 10 uM	Cricetulus griseus	69.78 %
Inhibition of sodium fluorescein uptake in OATP1B3-transfected CHO cells at an equimolar substrate-inhibitor concentration of 10 uM	Cricetulus griseus	92.1 %
Inhibition of human OATP1B1-mediated [3H]estrone 3-sulfate at 100 uM after 5 mins relative to control	Homo sapiens	9.8 %
Inhibition of human OATP1B3-mediated [3H]CCK-8 at 100 uM after 5 mins relative to control	Homo sapiens	12.5 %
Antibacterial activity against Staphylococcus aureus MRSA ATCC 43300 (CO-ADD:GP_020); MIC in CAMBH media, using NBS plates, by OD(600)	Staphylococcus aureus subsp. aureus	12.15 %
Antibacterial activity against Escherichia coli ATCC 25922 (CO-ADD:GN_001); MIC in CAMBH media using NBS plates, by OD(600)	Escherichia coli	4.61 %
Antibacterial activity against Klebsiella pneumoniae MDR ATCC 70063 (CO-ADD:GN_003); MIC in CAMBH media using NBS plates, by OD(600)	Klebsiella pneumoniae	18.73 %
Antibacterial activity against Pseudomonas aeruginosa ATCC 27853 (CO-ADD:GN_042); MIC in CAMBH media using NBS plates, by OD(600)	Pseudomonas aeruginosa	17.68 %
Antibacterial activity against Acinetobacter baumannii ATCC 19606 (CO-ADD:GN_034); MIC in CAMBH media using NBS plates, by OD600	Acinetobacter baumannii	30.84 %
Antifungal activity against Candida albicans ATCC 90028 (CO-ADD:FG_001); MIC in YNB media using NBS plates, by OD630	Candida albicans	1.91 %
Antifungal activity against Cryptococcus neoformans H99 ATCC 208821 (CO-ADD:FG_002); MIC in YNB media using NBS plates, by Resazurin OD(600-570)	Cryptococcus neoformans	-7.34 %
Antiviral activity determined as inhibition of SARS-CoV-2 induced cytotoxicity of Caco-2 cells at 10 uM after 48 hours by high content imaging	Homo sapiens	10.71 %
SARS-CoV-2 3CL-Pro protease inhibition percentage at 20µM by FRET kind of response from peptide substrate	Severe acute respiratory syndrome coronavirus 2	10.5 %
Antiviral activity determined as inhibition of SARS-CoV-2 induced cytotoxicity of VERO-6 cells at 10 uM after 48 hours exposure to 0.01 MOI SARS CoV-2 virus by high content imaging	Chlorocebus sabaeus	0.04 %		Antiviral activity determined as inhibition of SARS-CoV-2 induced cytotoxicity of VERO-6 cells at 10 uM after 48 hours exposure to 0.01 MOI SARS CoV-2 virus by high content imaging	Chlorocebus sabaeus	0.04 %
Induction of translocation of human glucocorticoid receptor expressed in HEK293T cells transduced with lentiviral vector expressing H2B-mCherry and GFP-GR assessed as effective dissociation constant measured every 130 sec for 22 mins by fluorescence imaging analysis	Homo sapiens	29.0 nM
Cytotoxicity against human REH cells overexpressing GR assessed as reduction in cell viability measured after 3 days by resazurin based assay	Homo sapiens	29.0 nM

Related Entries

Cross References

Resources	Reference
ChEBI	8382
ChEMBL	CHEMBL635
DrugBank	DB00635
DrugCentral	2253
FDA SRS	VB0R961HZT
Human Metabolome Database	HMDB0014773
Guide to Pharmacology	7096
KEGG	C07370
PharmGKB	PA451100
PubChem	5865
SureChEMBL	SCHEMBL3288
ZINC	ZINC000003875357

CONTENTS

PREMIER has received funding from the Innovative Medicines Initiative 2 Joint Undertaking (JU) under grant agreement No 875508. The JU receives support from the EU’s Horizon 2020 research and innovation programme and the European Federation of Pharmaceutical Industries and Associations (EFPIA). The views reflect only the authors’ perspective and the JU is not responsible for any use that may be made of the information this manuscript contains.

Elements of the website have been developed under projects PREMIER and the Biocenter Finland Drug Discovery and Chemical Biology network. CSC-IT is thanked for providing computational resources. Content of the website is provided without guarantee for correctness. Data has been collected and integrated from multiple public sources, for the largest: FDA, HUGO Gene Nomenclature Committee, ChEMBL, IUPHAR/BPS guide to pharmacology, Reactome, UniProt, and Ensembl. Credit is given to Ensembl for collecting species images (provided under public domain licences such as Wikimedia and NHGRI).