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Compound Report Card

Compound Name and Classification

Compound ID CHEMBL221959
CHEMBL221959
Compound Name TOFACITINIB
ChEMBL Synonyms TOFACITINIB | TOFACITINIB CITRATE | CP-690550-10 | TASOCITINIB | TASOCITINIB CITRATE | 550 | CP-690 | CP-690550 | XELJANZ | XELJANZ XR
Max Phase 4 (Approved)
Trade Names XELJANZ XR | XELJANZ
Molecular Formula C16H20N6O

Additional synonyms for CHEMBL221959 found using NCI Chemical Identifier Resolver

Compound Representations

Molfile Download MolFile
Canonical SMILES C[C@@H]1CCN(C[C@@H]1N(C)c2ncnc3[nH]ccc23)C(=O)CC#N
Standard InChI InChI=1S/C16H20N6O/c1-11-5-8-22(14(23)3-6-17)9-13(11)21(2)16 ...
Download InChI
Standard InChI Key UJLAWZDWDVHWOW-YPMHNXCESA-N

Sources

  • British National Formulary
  • Orange Book
  • PubChem BioAssays
  • Scientific Literature
  • USP Dictionary of USAN and International Drug Names
  • WHO Anatomical Therapeutic Chemical Classification

Alternate Forms of Compound in ChEMBL


CHEMBL221959

Molecule Features

CHEMBL221959 compound icon
Drug Type:Synthetic Small Molecule Rule of Five:Y First In Class:N Chirality:Single Stereoisomer Prodrug:N Oral:Y Parenteral:N Topical:N Black Box:Y Availability Type:Prescription-only

Mechanism of Action

Mechanism of Action ChEMBL Target References
Janus Kinase (JAK) inhibitor Janus Kinase (JAK) Expert

Indications

MESH Heading MESH ID EFO ID EFO Term Max phase for indication References
Arthritis, JuvenileD001171EFO:0002609chronic childhood arthritis3ClinicalTrials
Arthritis, RheumatoidD001172EFO:0000685rheumatoid arthritis4ClinicalTrials
DailyMed
DailyMed
Renal Insufficiency, ChronicD051436EFO:0003884chronic kidney disease1ClinicalTrials
Crohn DiseaseD003424EFO:0000384Crohn's disease2ClinicalTrials
DermatomyositisD003882EFO:0000398dermatomyositis1ClinicalTrials
Lupus Erythematosus, SystemicD008180EFO:0002690systemic lupus erythematosus1ClinicalTrials
ClinicalTrials
Immune System DiseasesD007154EFO:0000540immune system disease4ATC
Spondylitis, AnkylosingD013167EFO:0003898ankylosing spondylitis2ClinicalTrials
Colitis, UlcerativeD003093EFO:0000729ulcerative colitis3ClinicalTrials
Dry Eye SyndromesD015352EFO:1000906dry eye syndrome2ClinicalTrials
Alopecia AreataD000506EFO:0004192alopecia areata2ClinicalTrials
Arthritis, PsoriaticD015535EFO:0003778psoriatic arthritis3ClinicalTrials
Dermatitis, AtopicD003876EFO:0000274atopic eczema2ClinicalTrials
Keratoconjunctivitis SiccaD007638EFO:1001001keratoconjunctivitis sicca2ClinicalTrials
PsoriasisD011565EFO:0000676psoriasis3ClinicalTrials
Scleroderma, SystemicD012595EFO:0000717systemic scleroderma1ClinicalTrials

Clinical Data

ClinicalTrials.gov TOFACITINIB
The Cochrane Collaboration TOFACITINIB

Compound Bioactivity Summary

Compound Assay Summary

Compound Target Summary

Target Predictions

The two tables below display ChEMBL single-protein targets which are predicted to interact with CHEMBL221959. A 1uM and 10 uM cut-off have been applied to ChEMBL bioactivity data used to generate the respective models and the yellow coloured rows correspond to genuine predictions, i.e. targets not included in the original training set for this compound.


1uM


ChEMBL_ID Target Name Organism Score
CHEMBL2148 Tyrosine-protein kinase JAK3 Homo sapiens 1.000
CHEMBL2835 Tyrosine-protein kinase JAK1 Homo sapiens 1.000
CHEMBL2971 Tyrosine-protein kinase JAK2 Homo sapiens 1.000
CHEMBL3553 Tyrosine-protein kinase TYK2 Homo sapiens 1.000
CHEMBL1075104 Leucine-rich repeat serine/threonine-protein kinase 2 Homo sapiens 0.259

10uM


ChEMBL_ID Target Name Organism Score
CHEMBL2148 Tyrosine-protein kinase JAK3 Homo sapiens 1.000
CHEMBL2835 Tyrosine-protein kinase JAK1 Homo sapiens 1.000
CHEMBL2971 Tyrosine-protein kinase JAK2 Homo sapiens 1.000
CHEMBL3553 Tyrosine-protein kinase TYK2 Homo sapiens 1.000
CHEMBL4708 Serine/threonine-protein kinase MST2 Homo sapiens 1.000
CHEMBL5330 Mitogen-activated protein kinase kinase kinase kinase 2 Homo sapiens 0.999
CHEMBL4924 Ribosomal protein S6 kinase alpha 6 Homo sapiens 0.999
CHEMBL5698 NUAK family SNF1-like kinase 2 Homo sapiens 0.999
CHEMBL4852 Mitogen-activated protein kinase kinase kinase kinase 5 Homo sapiens 0.984
CHEMBL3032 Protein kinase N2 Homo sapiens 0.979
CHEMBL1908385 Serine/threonine-protein kinase pknB Mycobacterium tuberculosis 0.979
CHEMBL5432 Mitogen-activated protein kinase kinase kinase kinase 3 Homo sapiens 0.957
CHEMBL3384 Protein kinase N1 Homo sapiens 0.919
CHEMBL1841 Tyrosine-protein kinase FYN Homo sapiens 0.665
CHEMBL1075104 Leucine-rich repeat serine/threonine-protein kinase 2 Homo sapiens 0.461

Calculated Compound Parent Properties

Mol. Weight Mol. Weight Monoisotopic ALogP #Rotatable Bonds Polar Surface Area Molecular Species
312.4 312.1699 1.54 3 88.91 ACID


HBA HBD #Ro5 Violations HBA (Lipinski) HBD (Lipinski) #Ro5 Violations (Lipinski)
5 1 0 7 1 0


ACD Acidic pKa ACD Basic pKa ACD LogP ACD LogD pH7.4 Aromatic Rings Heavy Atoms QED Weighted
6.04 6.61 1.76 .04 2 23 0.93

Structural Alerts

There are no structural alerts for CHEMBL221959

Compound Cross References

ATC L - ANTINEOPLASTIC AND IMMUNOMODULATING AGENTS
L04 - IMMUNOSUPPRESSANTS
L04A - IMMUNOSUPPRESSANTS
L04AA - Selective immunosuppressants
L04AA29 - tofacitinib

ChemSpider ChemSpider:UJLAWZDWDVHWOW-YPMHNXCESA-N
DailyMed tofacitinib citrate
PubChem SID: 124939204 SID: 50100095
Wikipedia Tofacitinib

UniChem Cross References

View the UniChem Connectivity matches for CHEMBL221959



BindingDB 50193995
Brenda 154591 155478 27073 77457
ChEBI 71200
DrugBank DB08895
DrugCentral 4713
eMolecules 28294753
EPA CompTox Dashboard DTXSID90197271
FDA SRS 87LA6FU830
Guide to Pharmacology 5677
IBM Patent System C6655A3CAD2A83668913500139638CB6 01A0D2F56FB10E73168B671BB7DE0881
LINCS LSM-1227
MolPort MolPort-006-393-346
Nikkaji J2.740.060D
PDBe MI1
PubChem 9926791
PubChem: Thomson Pharma 16573063 14898931
Selleck tofacitinib-cp-690550
SureChEMBL SCHEMBL322753
ZINC ZINC000003818808

UniChem REST Service Call:
https://www.ebi.ac.uk/unichem/rest/verbose_inchikey/UJLAWZDWDVHWOW-YPMHNXCESA-N spacer
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