BETAMETHASONE

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Search structure


Trade Names	CELESTONE
Synonyms	Alphatrex BETA-VAL Betamethasone Betasolan Betatrex Betnelan Celestone Dermabet Flubenisolone Lotrisone NSC-39470 SCH 4831 SCH-4831 Taclonex Uticort VISUBETA
Status
Molecule Category	Free-form
ATC	A07EA04 C05AA05 D07AC01 D07XC01 H02AB01 R01AD06 R03BA04 S01BA06 S01CB04 S02BA07 S03BA03
UNII	9842X06Q6M
EPA CompTox	DTXSID3022667


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

Structure


InChI Key	UREBDLICKHMUKA-DVTGEIKXSA-N
Smiles	C[C@H]1C[C@H]2[C@@H]3CCC4=CC(=O)C=C[C@]4(C)[C@@]3(F)[C@@H](O)C[C@]2(C)[C@@]1(O)C(=O)CO
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-/m0/s1

Physicochemical Descriptors

Property Name	Value
Molecular Formula	C22H29FO5
Molecular Weight	392.47
AlogP	1.9
Hydrogen Bond Acceptor	5.0
Hydrogen Bond Donor	3.0
Number of Rotational Bond	2.0
Polar Surface Area	94.83
Molecular species	NEUTRAL
Aromatic Rings	0.0
Heavy Atoms	28.0

Pharmacology

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


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

Targets	EC50(nM)	IC50(nM)	Kd(nM)	Ki(nM)	Inhibition(%)
Transporter Electrochemical transporter SLC superfamily of solute carriers SLC21/SLCO family of organic anion transporting polypeptides	-	-	-	-	103

Assay Description	Organism	Bioactivity	Reference
Antiinflammatory activity in rat assessed as inhibition of carrageenan-induced paw edema at 0.125 mg/kg, po	Rattus norvegicus	63.0 %
DRUGMATRIX: Glucocorticoid radioligand binding (ligand: [3H] Dexamethasone)	None	7.735 nM		DRUGMATRIX: Glucocorticoid radioligand binding (ligand: [3H] Dexamethasone)	None	3.516 nM
Anti-inflammatory activity in Homo sapiens (human) whole blood assessed inhibition of LPS-induced TNF-alpha production at 10 uM treated 30 min before LPS challenge measured after 5 hr	Homo sapiens	87.0 %
Anti-inflammatory activity in Homo sapiens (human) whole blood assessed inhibition of LPS-induced TNF-alpha production at 1 uM treated 30 min before LPS challenge measured after 5 hr	Homo sapiens	72.0 %
Inhibition of sodium fluorescein uptake in OATP1B1-transfected CHO cells at an equimolar substrate-inhibitor concentration of 10 uM	Cricetulus griseus	76.17 %
Inhibition of sodium fluorescein uptake in OATP1B3-transfected CHO cells at an equimolar substrate-inhibitor concentration of 10 uM	Cricetulus griseus	102.69 %
Inhibition of concanavalin A-induced cell proliferation of T cells (unknown origin) at 10 uM after 72 hrs by MTT assay	Not specified	42.6 %
Inhibition of LPS-induced cell proliferation of B cells (unknown origin) at 10 uM after 72 hrs by MTT assay	Not specified	28.1 %
Inhibition of LPS-induced IL6 production in human THP1 cells after 24 hrs	Homo sapiens	22.0 nM
Inhibition of LPS-induced TNFalpha production in human THP1 cells after 24 hrs	Homo sapiens	13.0 nM
Antiarthritic activity in DBA/1J mouse collagen-induced arthritis model assessed as reduction in paw swelling at 5 mg/kg, po administered once daily for 49 days starting from onset of disease	Mus musculus	46.0 %
Cytotoxicity against primary human endothelial keratinocytes assessed as inhibition of cell viability preincubated for 2 hrs followed by cytokine addition measured after 72 hrs by PrestoBlue staining based fluorescence assay	Homo sapiens	300.0 nM
SARS-CoV-2 3CL-Pro protease inhibition percentage at 20µM by FRET kind of response from peptide substrate	Severe acute respiratory syndrome coronavirus 2	7.87 %
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	0.13 %		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	0.13 %

Related Entries

Cross References

Resources	Reference
ChEBI	3077
ChEMBL	CHEMBL632
DrugBank	DB00443
DrugCentral	348
FDA SRS	9842X06Q6M
Human Metabolome Database	HMDB0014586
Guide to Pharmacology	7061
PharmGKB	PA164754818
PubChem	9782
SureChEMBL	SCHEMBL4565
ZINC	ZINC000003876136

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).