Compound Detail

CHEMBL2103743

TOFACITINIB CITRATE

💊 Approved Drug

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💊 Approved Drug

C[C@@H]1CCN(C(=O)CC#N)C[C@@H]1N(C)c1ncnc2[nH]ccc12.O=C(O)CC(O)(CC(=O)O)C(=O)O

ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID	CHEMBL2103743
Name	TOFACITINIB CITRATE
Phase	Approved
Structure Type	MOL
InChI Key	SYIKUFDOYJFGBQ-YLAFAASESA-N
Therapeutic	✓ Yes
Parent Compound	CHEMBL221959
Active Moiety	CHEMBL221959

Known Names

CP-690,550-10 Cp-690550 citrate CP-690550-10 Tasocitinib monocitrate Tofacitinib citrate Tofacitinib monocitrate Xeljanz Xeljanz xr

Targets

155

Activities

Assay Types

PK Parameters

Publications

Known Names

Indications

Mechanisms

Molecular Properties

312.4

MW (Da)

1.54

ALogP

HBA

HBD

88.9

PSA (Å²)

0.93

QED

Ro5 Violations

Rot. Bonds

Drug Information

Molecule Type	Small molecule
First Approval	2012
Availability	Prescription
Chirality	Single Enantiomer

Routes of Administration

Oral

Flags

Black Box Warning

USAN Stem	-tinib
USAN Year	2010

Extended Properties

Molecular Formula	C22H28N6O8
MW	504.50
Aromatic Rings	2
Heavy Atoms	23
NP-Likeness	-1.14

Mechanism of Action

Mechanism	Action Type	Target	Direct	Efficacy
Janus Kinase (JAK) inhibitor	INHIBITOR	Janus Kinase (JAK)	✓	✓

Indications

Arthritis, Psoriatic Arthritis, Rheumatoid Spondylitis, Ankylosing Dermatitis, Atopic Lupus Erythematosus, Discoid Lupus Erythematosus, Systemic

Drug Warnings

Black Box Warning

carcinogenicity

Country: United States

Black Box Warning

vascular toxicity

Country: United States

Black Box Warning

infectious disease

Country: United States

Activity Summary

IC50 105 meas. best 8.8

Kd 46 meas. best 9.7

Ki 4 meas. best 9.62

Target Activity Profile

Target	Type	Best pChEMBL	Mean pChEMBL	Best (nM)	# Data
Tyrosine-protein kinase JAK3 CHEMBL2148	Kd	9.7	9.18	0.2	2
Tyrosine-protein kinase JAK3 CHEMBL2148	Ki	9.62	9.62	0.2	1
Tyrosine-protein kinase JAK2 CHEMBL2971	Kd	9.22	8.76	0.6	2
Tyrosine-protein kinase JAK1 CHEMBL2835	Ki	9.17	9.17	0.7	1
Tyrosine-protein kinase JAK2 CHEMBL2971	Ki	9.0	9.0	1.0	1
Tyrosine-protein kinase JAK3 CHEMBL2148	IC50	8.8	6.7965	1.6	26
Tyrosine-protein kinase JAK1 CHEMBL2835	Kd	8.8	8.8	1.6	1
Tyrosine-protein kinase JAK1 CHEMBL2835	IC50	8.49	6.76	3.2	26
Tyrosine-protein kinase JAK2 CHEMBL2971	IC50	8.39	6.7731	4.1	26
Non-receptor tyrosine-protein kinase TYK2 CHEMBL3553	Ki	8.36	8.36	4.4	1
Serine/threonine-protein kinase DCLK3 CHEMBL6123	Kd	8.35	8.135	4.5	2
Non-receptor tyrosine-protein kinase TYK2 CHEMBL3553	Kd	8.32	7.265	4.8	2
Non-receptor tyrosine-protein kinase TYK2 CHEMBL3553	IC50	7.96	6.7208	11.0	26
Non-receptor tyrosine-protein kinase TNK1 CHEMBL5334	Kd	6.92	6.92	120.0	1
Serine/threonine-protein kinase N1 CHEMBL3384	Kd	6.77	6.735	170.0	2
NUAK family SNF1-like kinase 2 CHEMBL5698	Kd	6.62	6.5	240.0	2
Rho-associated protein kinase 2 CHEMBL2973	Kd	6.38	6.38	420.0	1
Tyrosine-protein kinase Lck CHEMBL258	Kd	6.34	6.045	460.0	2
Rho-associated protein kinase 1 CHEMBL3231	Kd	6.33	6.33	470.0	1
Ribosomal protein S6 kinase alpha-6 CHEMBL4924	Kd	6.27	6.095	540.0	2
Leucine-rich repeat serine/threonine-protein kinase 2 CHEMBL1075104	Kd	6.26	6.075	550.0	2
Ribosomal protein S6 kinase alpha-2 CHEMBL3906	Kd	6.22	6.035	600.0	2
Tyrosine-protein kinase Fyn CHEMBL1841	Kd	5.96	5.96	1100.0	1
Serine/threonine-protein kinase N2 CHEMBL3032	Kd	5.92	5.92	1200.0	1
Myotonin-protein kinase CHEMBL5320	Kd	5.92	5.92	1200.0	1
Calcium/calmodulin-dependent protein kinase type 1 CHEMBL2493	Kd	5.92	5.61	1200.0	2
Ribosomal protein S6 kinase alpha-1 CHEMBL2553	Kd	5.85	5.85	1400.0	1
Calcium/calmodulin-dependent protein kinase type 1D CHEMBL5073	Kd	5.8	5.8	1600.0	1
MAP kinase-interacting serine/threonine-protein kinase 2 CHEMBL4204	Kd	5.8	5.8	1600.0	1
Unchecked CHEMBL612545	Kd	5.7	5.7	2000.0	1
Protein kinase C delta type CHEMBL2996	Kd	5.7	5.7	2000.0	1
Tyrosine-protein kinase ABL1 CHEMBL1862	Kd	5.66	5.3933	2200.0	3
Calcium/calmodulin-dependent protein kinase type II subunit delta CHEMBL2801	Kd	5.57	5.57	2700.0	1
Proto-oncogene tyrosine-protein kinase receptor Ret CHEMBL2041	Kd	5.48	5.48	3300.0	1
Calcium/calmodulin-dependent protein kinase type II subunit alpha CHEMBL4147	Kd	5.46	5.46	3500.0	1
Serine/threonine-protein kinase 3 CHEMBL4708	Kd	5.37	5.37	4300.0	1
Rhodopsin kinase GRK7 CHEMBL1075133	Kd	5.37	5.37	4300.0	1
Mitogen-activated protein kinase kinase kinase kinase 2 CHEMBL5330	Kd	5.32	5.32	4800.0	1
Serine/threonine-protein kinase ULK3 CHEMBL5047	Kd	5.19	5.19	6400.0	1
Serine/threonine-protein kinase DCLK1 CHEMBL5683	Kd	5.17	5.17	6700.0	1
BMP-2-inducible protein kinase CHEMBL4522	Kd	5.15	5.15	7100.0	1
Serine/threonine-protein kinase DCLK3 CHEMBL6123	IC50	4.64	4.64	22960.0	1

Pharmacokinetic Data

Parameter	Value	Units	Species
AUC	22072.77	ng.hr.mL-1	Rattus norvegicus
AUC	2217.9	ng.hr.mL-1	Mus musculus
AUC	20929.46	ng.hr.mL-1	Mus musculus
AUC	13432.34	ng.hr.mL-1	Mus musculus
AUC	15712.71	ng.hr.mL-1	Mus musculus
AUC	52073.75	ng.hr.mL-1	Mus musculus
Cmax	54870.0	nM	Rattus norvegicus
T1/2	3.94	hr	Rattus norvegicus
Tmax	0.42	hr	Rattus norvegicus

Activity Data Samples

Top measurements by pChEMBL value

Target	Type	Rel.	Value	Units	pChEMBL	Assay	PubMed
Tyrosine-protein kinase JAK3	Kd	=	0.2	nM	9.7	Selectivity interaction (Competition-binding assay (DiscoverX)) EUB0000286bCit J...	-
Tyrosine-protein kinase JAK3	Ki	=	0.24	nM	9.62	Selectivity interaction (Peptide mobility shift assay) EUB0000286bCit JAK3	-
Tyrosine-protein kinase JAK2	Kd	=	0.6	nM	9.22	Selectivity interaction (Competition-binding assay (DiscoverX)) EUB0000286bCit J...	-
Tyrosine-protein kinase JAK1	Ki	=	0.68	nM	9.17	Selectivity interaction (Peptide mobility shift assay) EUB0000286bCit JAK1	-
Tyrosine-protein kinase JAK2	Ki	=	0.99	nM	9.0	Selectivity interaction (Peptide mobility shift assay) EUB0000286bCit JAK2	-
Tyrosine-protein kinase JAK3	IC50	=	1.6	nM	8.8	Affinity Biochemical interaction: (Peptide mobility shift assay (phosphorylation...	-
Tyrosine-protein kinase JAK1	Kd	=	1.6	nM	8.8	Selectivity interaction (Competition-binding assay (DiscoverX)) EUB0000286bCit J...	-
Tyrosine-protein kinase JAK3	Kd	=	2.2	nM	8.66	Selectivity interaction (Competition binding assay with immobilized ligands) EUB...	-
Tyrosine-protein kinase JAK1	IC50	=	3.2	nM	8.49	Affinity Biochemical interaction: (Peptide mobility shift assay (phosphorylation...	-
Tyrosine-protein kinase JAK2	IC50	=	4.1	nM	8.39	Affinity Biochemical interaction: (Peptide mobility shift assay (phosphorylation...	-
Non-receptor tyrosine-protein kinase TYK2	Ki	=	4.39	nM	8.36	Selectivity interaction (Peptide mobility shift assay) EUB0000286bCit TYK2	-
Serine/threonine-protein kinase DCLK3	Kd	=	4.5	nM	8.35	Selectivity interaction (Competition binding assay with immobilized ligands) EUB...	-
Non-receptor tyrosine-protein kinase TYK2	Kd	=	4.8	nM	8.32	Selectivity interaction (KinomeScan (competition-binding assay, DiscoverX)) EUB0...	-
Tyrosine-protein kinase JAK2	Kd	=	5.0	nM	8.3	Selectivity interaction (Competition binding assay with immobilized ligands) EUB...	-
Tyrosine-protein kinase JAK1	IC50	=	11.0	nM	7.96	Affinity Phenotypic Cellular interaction: (IL-2 induced T cell blast proliferati...	-
Non-receptor tyrosine-protein kinase TYK2	IC50	=	11.0	nM	7.96	Affinity Phenotypic Cellular interaction: (IL-2 induced T cell blast proliferati...	-
Tyrosine-protein kinase JAK3	IC50	=	11.0	nM	7.96	Affinity Phenotypic Cellular interaction: (IL-2 induced T cell blast proliferati...	-
Tyrosine-protein kinase JAK2	IC50	=	11.0	nM	7.96	Affinity Phenotypic Cellular interaction: (IL-2 induced T cell blast proliferati...	-
Serine/threonine-protein kinase DCLK3	Kd	=	12.0	nM	7.92	Selectivity interaction (Competition-binding assay (DiscoverX)) EUB0000286bCit D...	-
Non-receptor tyrosine-protein kinase TYK2	IC50	=	25.0	nM	7.6	Affinity Phenotypic Cellular interaction: (Whole blood STAT phosphorylation assa...	-

Literature References

PubMed	DOI	Target Context	# Activities
-	10.6019/CHEMBL5444388	Tyrosine-protein kinase JAK1	24
-	10.6019/CHEMBL5444388	Tyrosine-protein kinase JAK2	24
-	10.6019/CHEMBL5444388	Tyrosine-protein kinase JAK3	24
-	10.6019/CHEMBL5444388	Non-receptor tyrosine-protein kinase TYK2	24
35275619	10.1021/acs.jmedchem.1c02166	Mus musculus	13
-	10.6019/CHEMBL5724558	Colon cancer organoid	12
-	10.6019/CHEMBL5674860	Colon cancer organoid	12
-	10.6019/CHEMBL4689842	U2OS	10
35275619	10.1021/acs.jmedchem.1c02166	ADMET	9
-	10.6019/CHEMBL4689842	HEK-293T	8
-	10.6019/CHEMBL4689842	Fibroblast	7
-	10.6019/CHEMBL5608141	Colon cancer organoid	6
33691794	10.1186/s13148-021-01037-1	A549	4
-	10.6019/CHEMBL5465560	Tyrosine-protein kinase ABL1	3
-	10.6019/CHEMBL5465560	Tyrosine-protein kinase JAK3	3
-	10.6019/CHEMBL5465560	Tyrosine-protein kinase JAK2	3
-	10.6019/CHEMBL5465560	Non-receptor tyrosine-protein kinase TYK2	3
-	10.6019/CHEMBL5465560	Tyrosine-protein kinase Lck	2
-	10.6019/CHEMBL5465560	Serine/threonine-protein kinase DCLK3	2
-	10.6019/CHEMBL5465560	Tyrosine-protein kinase JAK1	2

Data from ChEMBL 36 via Core Engine