ruxolitinib (CED0002329)

Record Information

Version

1.0

Creation Date

2016-06-03 13:33:58 UTC

Update Date

2026-05-14 19:00:21 UTC

SynCED ID

CED0002329

Secondary Accession Numbers

CHEM045664

Identification

Common Name

ruxolitinib

Class

Small Molecule

Description

Ruxolitinib is an organic compound with the formula C17H18N6 and an average molecular weight of 306.37 g/mol. It is classified as an organoheterocyclic compound. Specifically, ruxolitinib belongs to the pyrrolo[2,3-d]pyrimidines, a subclass of pyrrolopyrimidines within the organic compounds. The compound is found in or released from two recorded sources: healthcare, pharmaceuticals, and veterinary products, specifically as antineoplastic agents and dermatological preparations. Recorded routes of exposure include oral and topical administration. Ruxolitinib acts on five recorded protein targets, serving as an inhibitor of Tyrosine-protein kinase JAK1, Tyrosine-protein kinase JAK2, Tyrosine-protein kinase JAK3, and Non-receptor tyrosine-protein kinase TYK2, in addition to one other protein.

Contaminant Type

Not Available

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Not Available

Chemical Formula

C₁₇H₁₈N₆

Average Molecular Mass

306.373 g/mol

Monoisotopic Mass

306.159 g/mol

CAS Registry Number

941678-49-5

IUPAC Name

3-cyclopentyl-3-(4-{1H-pyrrolo[2,3-d]pyrimidin-4-yl}-1H-pyrazol-1-yl)propanenitrile

Traditional Name

3-cyclopentyl-3-(4-{1H-pyrrolo[2,3-d]pyrimidin-4-yl}pyrazol-1-yl)propanenitrile

SMILES

N#CCC(C1CCCC1)N1C=C(C=N1)C1=C2C=CN=C2NC=N1

InChI Identifier

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)

InChI Key

HFNKQEVNSGCOJV-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as pyrrolo[2,3-d]pyrimidines. These are aromatic heteropolycyclic compounds containing a pyrrolo[2,3-d]pyrimidine ring system, which is an pyrrolopyrimidine isomers having the 3 ring nitrogen atoms at the 1-, 5-, and 7-positions.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Pyrrolopyrimidines

Sub Class

Pyrrolo[2,3-d]pyrimidines

Direct Parent

Pyrrolo[2,3-d]pyrimidines

Alternative Parents

Substituents

Pyrrolo[2,3-d]pyrimidine
Pyrimidine
Heteroaromatic compound
Pyrrole
Pyrazole
Azole
Azacycle
Nitrile
Carbonitrile
Organic nitrogen compound
Organopnictogen compound
Hydrocarbon derivative
Organonitrogen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Biological Properties

Status

Detected and Not Quantified

Origin

Not Available

Cellular Locations

Not Available

Biofluid Locations

Not Available

Tissue Locations

Not Available

Applications

Not Available

Biological Roles

Not Available

Chemical Roles

Not Available

Organoleptic Effects

Not Available

Physical Properties

State

Not Available

Appearance

Not Available

Experimental Properties

Property	Value
Melting Point	Not Available
Boiling Point	Not Available
Solubility	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	0.26 g/L	ALOGPS
logP	2.1	ALOGPS
logP	1.99	ChemAxon
logS	-3.1	ALOGPS
pKa (Strongest Acidic)	7.69	ChemAxon
pKa (Strongest Basic)	2.54	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	83.18 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	97.38 m³·mol⁻¹	ChemAxon
Polarizability	33.1 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
Predicted GC-MS	Predicted GC-MS Spectrum	splash10-016r-6490000000-f32e582dec057388a9a7	Not Available	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum	Not Available	Not Available	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum	Not Available	Not Available	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum	Not Available	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0a4i-0049000000-d015643f3c527963b6fe	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0a4i-0931000000-0163e9c9fd1906e3f508	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0006-7910000000-5f2edb2a7381ccd203ba	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0a4i-0119000000-79098e8dad52259f4c4d	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0a4i-0933000000-7baff41b4f39eb645835	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-001i-1930000000-c02fc35a0ca25af7c4d4	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0a4i-0009000000-693aebf8643ec3a388c2	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0a4i-0298000000-a2101da4bab9091da0d0	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-001i-1920000000-3d702e83269c9262778b	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0a4i-0109000000-6923f182bfd184e659d8	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-115i-0498000000-d5fbc17da73f987444ee	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0ue9-0924000000-4b5c388e58853f017c58	Not Available	View Spectrum

Toxicity Profile

Toxicity Values

Toxicity Value	Organism	Dose Descriptor	Route of Exposure	Predicted or Experimental	Toxicity Rating	Reference
556.0 Log mg/kg [310:990]	Rat	LD50	oral	predicted	Not Available	Not Available

Toxicity / Toxin Class

Not Available

Mechanism of Toxicity

Not Available

Carcinogenicity (IARC Classification)

Not Available

Minimum Risk Level

Not Available

Symptoms

Not Available

Treatment

Not Available

Health Effects

Health Effect	Relationship	Direction	Description	Reference

Exposure Sources

Source ID	Source	Sector	Reference
CEDs000233	Brushes?Brushes used in personal care and cosmetics can be a source of synthetic chemical contamination due to the materials and coatings used in their manufacturing.	Personal care & cosmetics	PubChem
CEDs000315	Dermatological preparations?Dermatological preparations encompass a wide range of topical products, including creams, ointments, gels, and lotions, designed for the treatment of skin conditions.	Healthcare, pharmaceuticals & veterinary products	Not Available
CEDs000358	Antineoplastic agents?Antineoplastic agents are a class of synthetic chemicals used primarily in the treatment of cancer.	Healthcare, pharmaceuticals & veterinary products	Not Available

Pathways

2 pathwaysPathway Source: PathBank

Ruxolitinib Mechanism of Action Action Pathway

Ruxolitinib Drug Metabolism Action Pathway

Targets

Structure	Protein	UniProt ID	Organism	Relationship	Details
Click to view 3D structure	Tyrosine-protein kinase JAK1	P23458	Humans	Predicted (SEA)	Prediction Confidence Score 0.473 Applicability Domain 0.594 Statistical Significance 0.004 Supporting Reference Compounds 368 E-value 31.2175
Click to view 3D structure	Tyrosine-protein kinase JAK2	O60674	Humans	Predicted (SEA)	Prediction Confidence Score 0.438 Applicability Domain 0.594 Statistical Significance 0.0159 Supporting Reference Compounds 1022 E-value 123.469
Click to view 3D structure	Tyrosine-protein kinase JAK3	P52333	Humans	Predicted (SEA)	Prediction Confidence Score 0.438 Applicability Domain 0.594 Statistical Significance 0.0153 Supporting Reference Compounds 961 E-value 119.343
Click to view 3D structure	Tyrosine-protein kinase receptor TYRO3	Q06418	Humans	Predicted (SEA)	Prediction Confidence Score 0.423 Applicability Domain 0.594 Statistical Significance 0.0087 Supporting Reference Compounds 543 E-value 68.1181
Click to view 3D structure	Vascular endothelial growth factor receptor 2	P35968	Humans	Predicted (SEA)	Prediction Confidence Score 0.42 Applicability Domain 0.594 Statistical Significance 0.0282 Supporting Reference Compounds 1660 E-value 219.846
Click to view 3D structure	Glycogen synthase kinase-3 beta	P49841	Humans	Predicted (SEA)	Prediction Confidence Score 0.419 Applicability Domain 0.594 Statistical Significance 0.0156 Supporting Reference Compounds 1157 E-value 121.523
Click to view 3D structure	Tyrosine-protein kinase ABL1	P00519	Humans	Predicted (SEA)	Prediction Confidence Score 0.417 Applicability Domain 0.594 Statistical Significance 0.0172 Supporting Reference Compounds 927 E-value 133.823
Click to view 3D structure	Aurora kinase B	Q96GD4	Humans	Predicted (SEA)	Prediction Confidence Score 0.417 Applicability Domain 0.594 Statistical Significance 0.0164 Supporting Reference Compounds 1017 E-value 127.828
Click to view 3D structure	Rho-associated protein kinase 1	Q13464	Humans	Predicted (SEA)	Prediction Confidence Score 0.383 Applicability Domain 0.594 Statistical Significance 0.0178 Supporting Reference Compounds 834 E-value 138.805
Click to view 3D structure	Proto-oncogene tyrosine-protein kinase receptor Ret	P07949	Humans	Predicted (SEA)	Prediction Confidence Score 0.38 Applicability Domain 0.594 Statistical Significance 0.0267 Supporting Reference Compounds 764 E-value 208.247
Click to view 3D structure	cAMP-dependent protein kinase catalytic subunit alpha	P17612	Humans	Predicted (SEA)	Prediction Confidence Score 0.379 Applicability Domain 0.594 Statistical Significance 0.0177 Supporting Reference Compounds 735 E-value 137.949
Click to view 3D structure	Receptor-type tyrosine-protein kinase FLT3	P36888	Humans	Predicted (SEA)	Prediction Confidence Score 0.375 Applicability Domain 0.594 Statistical Significance 0.0403 Supporting Reference Compounds 1274 E-value 313.421
Click to view 3D structure	Non-receptor tyrosine-protein kinase TYK2	P29597	Humans	Predicted (SEA)	Prediction Confidence Score 0.368 Applicability Domain 0.594 Statistical Significance 0.0265 Supporting Reference Compounds 657 E-value 206.456
Click to view 3D structure	Fibroblast growth factor receptor 1	P11362	Humans	Predicted (SEA)	Prediction Confidence Score 0.367 Applicability Domain 0.594 Statistical Significance 0.0351 Supporting Reference Compounds 1010 E-value 273.64
Click to view 3D structure	5'-AMP-activated protein kinase catalytic subunit alpha-1	Q13131	Humans	Predicted (SEA)	Prediction Confidence Score 0.366 Applicability Domain 0.594 Statistical Significance 0.0199 Supporting Reference Compounds 596 E-value 155.309
Click to view 3D structure	Protein kinase C theta type	Q04759	Humans	Predicted (SEA)	Prediction Confidence Score 0.365 Applicability Domain 0.594 Statistical Significance 0.0124 Supporting Reference Compounds 356 E-value 96.533
Click to view 3D structure	Vascular endothelial growth factor receptor 1	P17948	Humans	Predicted (SEA)	Prediction Confidence Score 0.365 Applicability Domain 0.594 Statistical Significance 0.0272 Supporting Reference Compounds 711 E-value 211.672
Click to view 3D structure	Platelet-derived growth factor receptor alpha	P16234	Humans	Predicted (SEA)	Prediction Confidence Score 0.365 Applicability Domain 0.594 Statistical Significance 0.0214 Supporting Reference Compounds 519 E-value 166.753
Click to view 3D structure	Serine/threonine-protein kinase D3	O94806	Humans	Predicted (SEA)	Prediction Confidence Score 0.365 Applicability Domain 0.594 Statistical Significance 0.0216 Supporting Reference Compounds 628 E-value 168.232
Click to view 3D structure	Dual specificity protein kinase CLK4	Q9HAZ1	Humans	Predicted (SEA)	Prediction Confidence Score 0.365 Applicability Domain 0.594 Statistical Significance 0.0224 Supporting Reference Compounds 742 E-value 174.149
Click to view 3D structure	Mitogen-activated protein kinase 8	P45983	Humans	Predicted (SEA)	Prediction Confidence Score 0.364 Applicability Domain 0.594 Statistical Significance 0.0263 Supporting Reference Compounds 782 E-value 204.51
Click to view 3D structure	Tyrosine-protein kinase Lck	P06239	Humans	Predicted (SEA)	Prediction Confidence Score 0.364 Applicability Domain 0.594 Statistical Significance 0.0445 Supporting Reference Compounds 1130 E-value 346.195
Click to view 3D structure	Aurora kinase A	O14965	Humans	Predicted (SEA)	Prediction Confidence Score 0.361 Applicability Domain 0.594 Statistical Significance 0.0377 Supporting Reference Compounds 996 E-value 293.803
Click to view 3D structure	High affinity nerve growth factor receptor	P04629	Humans	Predicted (SEA)	Prediction Confidence Score 0.361 Applicability Domain 0.594 Statistical Significance 0.0331 Supporting Reference Compounds 869 E-value 257.759
Click to view 3D structure	Mitogen-activated protein kinase 9	P45984	Humans	Predicted (SEA)	Prediction Confidence Score 0.361 Applicability Domain 0.594 Statistical Significance 0.0267 Supporting Reference Compounds 758 E-value 208.091