cromoglicic acid   Click here for help

GtoPdb Ligand ID: 7608

Synonyms: cromoglycate | cromolyn | cromolyn sodium | FPL-670 | Intal® | Opticrom® | sodium cromoglicate
Approved drug Immunopharmacology Ligand
cromoglicic acid is an approved drug (FDA (1984))
Compound class: Synthetic organic
Comment: Cromoglicic acid (cromolyn) is regarded as a mast cell stabilising drug, although its exact mechanism of action appears to be much more complicated.
Recent reports suggest that cromolyn inhibits glycogen synthase kinase 3β and may therefore have potential to treat diabetes and obesity [3] and may prove effective in treating insulin-induced lipoatrophy [4]. It also has reported potential anti-fibrotic action through agonism of GPR35 [1,5].
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Ligand Activity Visualisation Charts

These are box plot that provide a unique visualisation, summarising all the activity data for a ligand taken from ChEMBL and GtoPdb across multiple targets and species. Click on a plot to see the median, interquartile range, low and high data points. A value of zero indicates that no data are available. A separate chart is created for each target, and where possible the algorithm tries to merge ChEMBL and GtoPdb targets by matching them on name and UniProt accession, for each available species. However, please note that inconsistency in naming of targets may lead to data for the same target being reported across multiple charts.

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View interactive charts of activity data across species

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View more information in the IUPHAR Pharmacology Education Project: cromoglicic acid

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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 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.

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Hydrogen bond acceptors 7
Hydrogen bond donors 3
Rotatable bonds 8
Topological polar surface area 173.71
Molecular weight 468.07
XLogP 3.48
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
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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.

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/)

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Canonical SMILES OC(COc1cccc2c1c(=O)cc(o2)C(=O)O)COc1cccc2c1c(=O)cc(o2)C(=O)O
Isomeric SMILES OC(COc1cccc2c1c(=O)cc(o2)C(=O)O)COc1cccc2c1c(=O)cc(o2)C(=O)O
InChI InChI=1S/C23H16O11/c24-11(9-31-14-3-1-5-16-20(14)12(25)7-18(33-16)22(27)28)10-32-15-4-2-6-17-21(15)13(26)8-19(34-17)23(29)30/h1-8,11,24H,9-10H2,(H,27,28)(H,29,30)
InChI Key IMZMKUWMOSJXDT-UHFFFAOYSA-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
Cromoglicic acid is available in different formulations; nasal spray is used to treat allergic rhinitis, nebulizer solution to treat asthma, eye drops to treat allergic conjunctivitis and an oral form to treat mastocytosis, dermatographic urticaria and ulcerative colitis. Clinical use in asthma has largely been replaced by the more convenient leukotriene receptor antagonists.
Mechanism Of Action and Pharmacodynamic Effects Click here for help
Cromoglicic acid is considered to predominantly stabilise mast cells and inhibit their degranulation. This action supresses the release of histamine and tryptase, thus reducing the synthesis of pro-inflammatory prostaglandins and leukotrienes. The drug also inhibits the activity of other types of inflammatory cells (eg eosinophils, neutrophils, macrophages, monocytes, and platelets) which are associated with asthma. As mast cell stabilisation is not sufficient on its own to explain the anti-asthmatic activity of this chromone type drug, other as yet incompletely resolved mechanisms must be involved.
External links Click here for help
For extended ADME data see the following:

Electronic Medicines Compendium (eMC)
Drugs.com