From August 18th 2026, GtoPdb will require users to register to use the website. Please see our blog post for more information.

flumethasone pivalate   Click here for help

GtoPdb Ligand ID: 7075

Synonyms: Locorten®
Approved drug Immunopharmacology Ligand
flumethasone pivalate is an approved drug
Compound class: Synthetic organic
Comment: Flumethasone pivalate is a corticosteroid.
IUPHAR Pharmacology Education Project (PEP) logo

View more information in the IUPHAR Pharmacology Education Project: flumetasone

flumethasone pivalate is commercially available from our sponsors

2D Structure
Click here for help

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.

✖
Click here for structure editor
Physico-chemical Properties
Click here for help

Physico-chemical Properties

Calculated molecular properties are available for small molecules and natural products (not peptides). Properties were generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/). 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.

✖
Hydrogen bond acceptors 6
Hydrogen bond donors 2
Rotatable bonds 5
Topological polar surface area 100.9
Molecular weight 494.25
XLogP 2.13
No. Lipinski's rules broken 0

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
SMILES / InChI / InChIKey
Click here for help

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.

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)

✖
Canonical SMILES O=C1C=CC2(C(=C1)C(F)CC1C2(F)C(O)CC2(C1CC(C2(O)C(=O)COC(=O)C(C)(C)C)C)C)C
Isomeric SMILES O=C1C=C[C@]2(C(=C1)[C@@H](F)C[C@@H]1[C@]2(F)[C@@H](O)C[C@]2([C@H]1C[C@H]([C@]2(O)C(=O)COC(=O)C(C)(C)C)C)C)C
InChI InChI=1S/C27H36F2O6/c1-14-9-16-17-11-19(28)18-10-15(30)7-8-24(18,5)26(17,29)20(31)12-25(16,6)27(14,34)21(32)13-35-22(33)23(2,3)4/h7-8,10,14,16-17,19-20,31,34H,9,11-13H2,1-6H3/t14-,16+,17+,19+,20+,24+,25+,26+,27+/m1/s1
InChI Key JWRMHDSINXPDHB-OJAGFMMFSA-N

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
No information available.
Summary of Clinical Use Click here for help
Used to reduce skin inflammation caused by allergic reactions, eczema and psoriasis. However, there is no information regarding approval for clinical use of this drug on the US FDA website. Other national approval agencies may have granted marketing authorisation.
Mechanism Of Action and Pharmacodynamic Effects Click here for help
As an agonist of the glucocorticoid receptor, flumethasone pivalate modulates expression of genes containing the glucocorticoid response element (GRE). Although complex, the response appears to include inhibition of the biosynthesis of pro-inflammatory prostaglandins and leukotrienes. However, we have been unable to find affinity data for this drug to substantiate its MMOA.