rabeximod   Click here for help

GtoPdb Ligand ID: 9856

Synonyms: Rob-803 | Rob803
Immunopharmacology Ligand
Compound class: Synthetic organic
Comment: Rabeximod is an orally active immunomodulator. It has potent anti-rheumatic effects in animal models and is being evaluated as a potential drug for rheumatoid arthritis patients. The structure was originally claimed in patent WO2005123741A1 (Compound E) for anti-inflammatory potential [1], and later for antiviral potential in patent WO2014140321A1 (example 2). The molecular mechanism of action of this compound vis its anti-inflammatory activity remains unclear.
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 CDK toolkit. 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 5
Hydrogen bond donors 1
Rotatable bonds 6
Topological polar surface area 63.05
Molecular weight 409.17
XLogP 4.11
No. Lipinski's rules broken 0
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.

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Canonical SMILES CN(CCNC(=O)Cn1c2ccc(cc2c2c1nc1cc(C)c(cc1n2)C)Cl)C
Isomeric SMILES CN(CCNC(=O)Cn1c2ccc(cc2c2c1nc1cc(C)c(cc1n2)C)Cl)C
InChI InChI=1S/C22H24ClN5O/c1-13-9-17-18(10-14(13)2)26-22-21(25-17)16-11-15(23)5-6-19(16)28(22)12-20(29)24-7-8-27(3)4/h5-6,9-11H,7-8,12H2,1-4H3,(H,24,29)
InChI Key PDNNUMNEXITLCZ-UHFFFAOYSA-N
Classification Click here for help
Compound class Synthetic organic
IUPAC Name Click here for help
2-(9-chloro-2,3-dimethylindolo[3,2-b]quinoxalin-6-yl)-N-[2-(dimethylamino)ethyl]acetamide
International Nonproprietary Names Click here for help
INN number INN
8866 rabeximod
Synonyms Click here for help
Rob-803 | Rob803
Database Links Click here for help
CAS Registry No. 872178-65-9 (source: WHO INN record)
DrugBank Ligand DB05772
GtoPdb PubChem SID 363894150
PubChem CID 56841552
Search Google for chemical match using the InChIKey PDNNUMNEXITLCZ-UHFFFAOYSA-N
Search Google for chemicals with the same backbone PDNNUMNEXITLCZ
Search PubMed clinical trials rabeximod
Search PubMed titles rabeximod
Search PubMed titles/abstracts rabeximod
UniChem Compound Search for chemical match using the InChIKey PDNNUMNEXITLCZ-UHFFFAOYSA-N
UniChem Connectivity Search for chemical match using the InChIKey PDNNUMNEXITLCZ-UHFFFAOYSA-N