ruxolitinib   Click here for help

GtoPdb Ligand ID: 5688

Synonyms: (R)-ruxolitinib | INC424 | INCB 18424 | INCB018424 | Jakafi® | Jakavi®
Approved drug PDB Ligand Immunopharmacology Ligand
ruxolitinib is an approved drug (FDA (2011), EMA (2012))
Compound class: Synthetic organic
Comment: Ruxolitinib is a Type-1 kinase inhibitor and was first approved by the US FDA in 2011. Ruxolitinib has high potency against Janus kinases 1 and 2 (JAK1, JAK2), as well as against the related family member, tyrosine kinase 2 (TYK2) [3]. Inhibitory activity against JAK3 is only slightly reduced compared to the other three family kinases.
Marketed formulations may contain ruxolitinib phosphate (PubChem CID 25127112).
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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: ruxolitinib

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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 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 4
Hydrogen bond donors 1
Rotatable bonds 4
Topological polar surface area 83.18
Molecular weight 306.16
XLogP 2.7
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 N#CCC(n1ncc(c1)c1ncnc2c1cc[nH]2)C1CCCC1
Isomeric SMILES N#CC[C@@H](n1ncc(c1)c1ncnc2c1cc[nH]2)C1CCCC1
InChI InChI=1S/C17H18N6/c18-7-5-15(12-3-1-2-4-12)23-10-13(9-22-23)16-14-6-8-19-17(14)21-11-20-16/h6,8-12,15H,1-5H2,(H,19,20,21)/t15-/m1/s1
InChI Key HFNKQEVNSGCOJV-OAHLLOKOSA-N
Classification Click here for help
Compound class Synthetic organic
Approved drug? Yes (FDA (2011), EMA (2012))
IUPAC Name Click here for help
(3R)-3-cyclopentyl-3-(4-{7H-pyrrolo[2,3-d]pyrimidin-4-yl}-1H-pyrazol-1-yl)propanenitrile
International Nonproprietary Names Click here for help
INN number INN
9287 ruxolitinib
Synonyms Click here for help
(R)-ruxolitinib | INC424 | INCB 18424 | INCB018424 | Jakafi® | Jakavi®
Database Links Click here for help
Specialist databases
Reactome Drug Reactome logo R-ALL-9678786
Reactome Reaction Reactome logo R-HSA-9678935, R-HSA-9678561, R-HSA-9679028, R-HSA-9678737
Other databases
CAS Registry No. 941685-37-6
ChEMBL Ligand CHEMBL1789941
DrugCentral Ligand 4190
GtoPdb PubChem SID 178102315
PubChem CID 25126798
RCSB PDB Ligand RXT
Search Google for chemical match using the InChIKey HFNKQEVNSGCOJV-OAHLLOKOSA-N
Search Google for chemicals with the same backbone HFNKQEVNSGCOJV
Search PubMed clinical trials ruxolitinib
Search PubMed titles ruxolitinib
Search PubMed titles/abstracts ruxolitinib
UniChem Compound Search for chemical match using the InChIKey HFNKQEVNSGCOJV-OAHLLOKOSA-N
UniChem Connectivity Search for chemical match using the InChIKey HFNKQEVNSGCOJV-OAHLLOKOSA-N
Wikipedia Ruxolitinib

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Tocris
Ruxolitinib (links to external site)
Cat. No. 7064