TOFACITINIB

Search structure
Trade Names:
Synonyms:
550
Status: Approved (2012)
Entry Type: Small molecule
Molecule Category: Parent
ATC: L04AA29
UNII: 87LA6FU830

Structure
InChI Key UJLAWZDWDVHWOW-YPMHNXCESA-N
Smile C[C@@H]1CCN(C(=O)CC#N)C[C@@H]1N(C)c1ncnc2[nH]ccc12
InChI
InChI=1S/C16H20N6O/c1-11-5-8-22(14(23)3-6-17)9-13(11)21(2)16-12-4-7-18-15(12)19-10-20-16/h4,7,10-11,13H,3,5,8-9H2,1-2H3,(H,18,19,20)/t11-,13+/m1/s1

Physicochemical Descriptors

Property Name Value
Molecular Formula C16H20N6O
Molecular Weight 312.38
AlogP 1.54
Hydrogen Bond Acceptor 5.0
Hydrogen Bond Donor 1.0
Number of Rotational Bond 3.0
Polar Surface Area 88.91
Molecular species NEUTRAL
Aromatic Rings 2.0
Heavy Atoms 23.0

Pharmacology

Primary Target
Janus kinase 1
Janus kinase 2
Janus kinase 3
Targets EC50(nM) IC50(nM) Kd(nM) Ki(nM) Inhibition(%)
Enzyme Kinase Protein Kinase AGC protein kinase group AGC protein kinase DMPK family AGC protein kinase GEK subfamily
- - 1200 - -
Enzyme Kinase Protein Kinase AGC protein kinase group AGC protein kinase DMPK family AGC protein kinase ROCK subfamily
- 3400-3400 420 - -
Enzyme Kinase Protein Kinase AGC protein kinase group AGC protein kinase GRK family AGC protein kinase GRK subfamily
- - 4300 - -
Enzyme Kinase Protein Kinase AGC protein kinase group AGC protein kinase PKC family AGC protein kinase PKC delta subfamily
- - 2000 - -
Enzyme Kinase Protein Kinase AGC protein kinase group AGC protein kinase PKN family
- - 170-200 - -
Enzyme Kinase Protein Kinase AGC protein kinase group AGC protein kinase RSK family AGC protein kinase RSK subfamily
- - 540-1200 - -
Enzyme Kinase Protein Kinase CAMK protein kinase group CAMK protein kinase CAMK1 family CAMK protein kinase NuaK subfamily
- - 240-420 - -
Enzyme Kinase Protein Kinase CAMK protein kinase group CAMK protein kinase CAMK1 family
- - 1200-5000 - -
Enzyme Kinase Protein Kinase CAMK protein kinase group CAMK protein kinase CAMK2 family
- - 2700 - -
Enzyme Kinase Protein Kinase CAMK protein kinase group CAMK protein kinase DCAMK1 family
- - 5-12 - -
Enzyme Kinase Protein Kinase CAMK protein kinase group CAMK protein kinase MAPKAPK family CAMK protein kinase MNK subfamily
- - 1600 - -
Enzyme Kinase Protein Kinase CAMK protein kinase group CAMK protein kinase RSKb family CAMK protein kinase RSKb subfamily
- - 540-1200 - -
Enzyme Kinase Protein Kinase Other protein kinase group Other protein kinase NAK family
- - 7100 - -
Enzyme Kinase Protein Kinase Other protein kinase group Other protein kinase ULK family
- - 6400 - -
Enzyme Kinase Protein Kinase STE protein kinase group STE protein kinase STE20 family STE protein kinase KHS subfamily
- - 4800 - -
Enzyme Kinase Protein Kinase STE protein kinase group STE protein kinase STE20 family STE protein kinase MST subfamily
- - 4300-4300 - -
Enzyme Kinase Protein Kinase TKL protein kinase group TKL protein kinase LRRK family
- - 550-1300 - -
Enzyme Kinase Protein Kinase TK protein kinase group Tyrosine protein kinase Abl family
- - 2200-6700 - -
Enzyme Kinase Protein Kinase TK protein kinase group Tyrosine protein kinase Ack family
- - 120-640 - -
Enzyme Kinase Protein Kinase TK protein kinase group Tyrosine protein kinase JakA family
43-53 1-4724 0-2 0-1 1
Enzyme Kinase Protein Kinase TK protein kinase group Tyrosine protein kinase JakB family
43-53 1-4724 0-2 0-1 1
Enzyme Kinase Protein Kinase TK protein kinase group Tyrosine protein kinase Ret family
- - 3300 - -
Enzyme Kinase Protein Kinase TK protein kinase group Tyrosine protein kinase Src family
- 340-3870 460-1800 - -
Enzyme Kinase Protein Kinase
43-53 1-4724 0-2 0-1 1
Enzyme Transferase
- 1200 - - -

Indications

Mesh Heading Maximum Phase Mesh ID Reference
Spondylitis, Ankylosing 3 D013167 ClinicalTrials
Psoriasis 3 D011565 ClinicalTrials
Colitis, Ulcerative 3 D003093 ClinicalTrials
Arthritis, Rheumatoid 3 D001172 ClinicalTrials
Arthritis, Psoriatic 3 D015535 ClinicalTrials
Psoriasis 3 D011565 ClinicalTrials
Arthritis, Juvenile 3 D001171 ClinicalTrials
Severe Acute Respiratory Syndrome 2 D045169 ClinicalTrials
Alopecia Areata 2 D000506 ClinicalTrials
Dermatitis, Atopic 2 D003876 ClinicalTrials
Crohn Disease 2 D003424 ClinicalTrials
Dry Eye Syndromes 2 D015352 ClinicalTrials
Wounds and Injuries 2 D014947 ClinicalTrials
Pneumonia 2 D011014 ClinicalTrials
Granuloma, Lethal Midline 2 D006103 ClinicalTrials
Pouchitis 2 D019449 ClinicalTrials
Colitis 2 D003092 ClinicalTrials
Polymyalgia Rheumatica 2 D011111 ClinicalTrials
Kidney Diseases 1 D007674 ClinicalTrials
Lupus Erythematosus, Cutaneous 1 D008178 ClinicalTrials
Scleroderma, Systemic 1 D012595 ClinicalTrials
Renal Insufficiency, Chronic 1 D051436 ClinicalTrials
Lupus Erythematosus, Systemic 1 D008180 ClinicalTrials
Sjogren's Syndrome 1 D012859 ClinicalTrials
Dermatomyositis 1 D003882 ClinicalTrials
Sarcoidosis 1 D012507 ClinicalTrials
Myasthenia Gravis 0 D009157 ClinicalTrials

Related Entries

Salt

Side Effects from Label

Cross References

Resources Reference
CAS NUMBER 477600-75-2
ChEBI 71200
ChEMBL CHEMBL221959
DrugBank DB08895
DrugCentral 4713
EPA CompTox DTXSID90197271
FDA SRS 87LA6FU830
Guide to Pharmacology 5677
PDB MI1
PubChem 9926791
SureChEMBL SCHEMBL322753
ZINC ZINC000003818808
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