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tofacitinib 🐶 Veterinary Use | Indications/Contra | FAERs-F | FAERs-M | Orange Bk | BioActivity |

Stem definition	Drug id	CAS RN
Janus kinase inhibitors, antineoplastics	4713	477600-75-2

Description:

Molecule	Description
Molfile Inchi Smiles Synonyms: tasocitinib xeljanz CP 690550 tofacitinib citrate tofacitinib CP-690550	Tofacitinib is a Janus kinase (JAK) inhibitor. JAKs are intracellular enzymes which transmit signals arising from cytokine or growth factor-receptor interactions on the cellular membrane to influence cellular processes of hematopoiesis and immune cell function. Within the signaling pathway, JAKs phosphorylate and activate Signal Transducers and Activators of Transcription (STATs) which modulate intracellular activity including gene expression. Tofacitinib modulates the signaling pathway at the point of JAKs, preventing the phosphorylation and activation of STATs. Molecular weight: 312.38 Formula: C16H20N6O CLOGP: 2.03 LIPINSKI: 0 HAC: 7 HDO: 1 TPSA: 88.91 ALOGS: -3.02 ROTB: 3 Status: OFP Legend: OFP - off patent OFM - off market ONP - on patent

Molecule

Description

Molfile Inchi Smiles

Synonyms:

tasocitinib
xeljanz
CP 690550
tofacitinib citrate
tofacitinib
CP-690550

Tofacitinib is a Janus kinase (JAK) inhibitor. JAKs are intracellular enzymes which transmit signals arising from cytokine or growth factor-receptor interactions on the cellular membrane to influence cellular processes of hematopoiesis and immune cell function. Within the signaling pathway, JAKs phosphorylate and activate Signal Transducers and Activators of Transcription (STATs) which modulate intracellular activity including gene expression. Tofacitinib modulates the signaling pathway at the point of JAKs, preventing the phosphorylation and activation of STATs.

Molecular weight: 312.38
Formula: C16H20N6O
CLOGP: 2.03
LIPINSKI: 0
HAC: 7
HDO: 1
TPSA: 88.91
ALOGS: -3.02
ROTB: 3

Status: OFP

Legend:
OFP - off patent
OFM - off market
ONP - on patent

Drug dosage:

Dose	Unit	Route
10	mg	O

ADMET properties:

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Property	Value	Reference
CL (Clearance)	5.88 mL/min/kg	Lombardo F, Berellini G, Obach RS
Vd (Volume of distribution)	1.24 L/kg	Lombardo F, Berellini G, Obach RS
fu (Fraction unbound in plasma)	0.60 %	Lombardo F, Berellini G, Obach RS

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Approvals:

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Date	Agency	Company
March 22, 2017	EMA	PFIZER EUROPE MA EEIG
March 25, 2013	PMDA	Pfizer Japan Inc.
Nov. 6, 2012	FDA	PF PRISM CV

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FDA Adverse Event Reporting System (Female)

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MedDRA adverse event term	Likelihood ratio	Likelihood ratio threshold	Patients taking drug having adverse event	Patients taking drug not having adverse event	Patients not taking drug having adverse event	Patients not taking drug not having adverse event
Drug ineffective	8011.25	16.79	20352	423291	1024413	62020966
Condition aggravated	3236.14	16.79	8025	435618	394192	62651187
Joint swelling	3173.66	16.79	7032	436611	320634	62724745
Arthralgia	2884.30	16.79	9619	434024	560091	62485288
Drug intolerance	2749.27	16.79	6410	437233	302251	62743128
Synovitis	2745.16	16.79	4783	438860	182135	62863244
Therapeutic product effect incomplete	2347.84	16.79	3578	440065	121478	62923901
Musculoskeletal stiffness	2344.03	16.79	4436	439207	180182	62865197
Treatment failure	2327.66	16.79	4619	439024	194424	62850955
Pain	2249.01	16.79	10655	432988	729973	62315406

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FDA Adverse Event Reporting System (Male)

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MedDRA adverse event term	Likelihood ratio	Likelihood ratio threshold	Patients taking drug having adverse event	Patients taking drug not having adverse event	Patients not taking drug having adverse event	Patients not taking drug not having adverse event
Drug ineffective	3523.45	20.11	4294	62265	452457	34437915
Joint swelling	1500.95	20.11	1094	65465	58796	34831576
Therapeutic product effect incomplete	1320.06	20.11	947	65612	49594	34840778
Arthralgia	1303.87	20.11	1607	64952	168434	34721938
Musculoskeletal stiffness	1126.35	20.11	834	65725	45846	34844526
Condition aggravated	1106.72	20.11	1579	64980	190617	34699755
Product dose omission in error	1074.92	20.11	323	66236	1951	34888421
Pain	1030.72	20.11	1579	64980	203096	34687276
Rheumatoid arthritis	890.32	20.11	669	65890	37569	34852803
Therapeutic product effect decreased	756.10	20.11	584	65975	34159	34856213

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FDA Adverse Event Reporting System (Geriatric)

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MedDRA adverse event term	Likelihood ratio	Likelihood ratio threshold	Patients taking drug having adverse event	Patients taking drug not having adverse event	Patients not taking drug having adverse event	Patients not taking drug not having adverse event
Drug ineffective	8728.44	16.91	17805	390330	1063108	78273145
Condition aggravated	4236.21	16.91	8453	399682	492671	78843582
Joint swelling	3793.73	16.91	5916	402219	282730	79053523
Pain	3765.61	16.91	9905	398230	693897	78642356
Arthralgia	3547.65	16.91	8518	399617	563285	78772968
Product dose omission in error	3185.05	16.91	1275	406860	6513	79329740
Drug intolerance	2961.13	16.91	5040	403095	259079	79077174
Therapeutic product effect incomplete	2909.28	16.91	3603	404532	138042	79198211
Synovitis	2898.64	16.91	3710	404425	147024	79189229
Product dose omission issue	2506.53	16.91	4518	403617	243019	79093234

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FDA Adverse Event Reporting System (Pediatric)

None

Pharmacologic Action:

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Source	Code	Description
ATC	L04AA29	ANTINEOPLASTIC AND IMMUNOMODULATING AGENTS IMMUNOSUPPRESSANTS IMMUNOSUPPRESSANTS Selective immunosuppressants
CHEBI has role	CHEBI:35842	anti-rheumatic drugs
CHEBI has role	CHEBI:76617	BTK inhibitor
FDA EPC	N0000190858	Janus Kinase Inhibitor
FDA MoA	N0000190857	Janus Kinase Inhibitors
MeSH PA	D004791	Enzyme Inhibitors
MeSH PA	D000075242	Janus Kinase Inhibitors
MeSH PA	D047428	Protein Kinase Inhibitors

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Drug Use | Suggest Off label Use Form| |View source of the data|

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Disease	Relation	SNOMED_ID	DOID
Ulcerative colitis	indication	64766004	DOID:8577
Rheumatoid arthritis	indication	69896004	DOID:7148
Psoriatic arthritis	indication	156370009	DOID:9008
Juvenile psoriatic arthritis	indication	239802003
Juvenile idiopathic arthritis, extended oligoarthritis	indication	410800006
Polyarticular juvenile idiopathic arthritis	indication	16044800000000000

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🐶 Veterinary Drug Use

None

🐶 Veterinary products

None

Acid dissociation constants calculated using MoKa v3.0.0

Dissociation level	Dissociation constant	Type (acidic/basic)
pKa1	11.27	acidic
pKa2	6.48	Basic
pKa3	0.91	Basic

Orange Book patent data (new drug applications)

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Formulation strength	Trade name	Applicant	Application number	Approval date	Type	Dose form	Route	Patent number	Patent expiration date	Patent use
EQ 11MG BASE	XELJANZ XR	PFIZER	N208246	Feb. 23, 2016	RX	TABLET, EXTENDED RELEASE	ORAL	11253523	March 14, 2034	A METHOD OF TREATING ANKYLOSING SPONDYLITIS BY ADMINISTERING THE FORMULATION OF TOFACITINIB OF CLAIMS 1, 8, 15-20, 27-31, 34-43, 45, 47, 49, 50, 54, 59, 63, 68-71, 73, 77, 82-84, AND 87-98
EQ 11MG BASE	XELJANZ XR	PFIZER	N208246	Feb. 23, 2016	RX	TABLET, EXTENDED RELEASE	ORAL	11253523	March 14, 2034	A METHOD OF TREATING PSORIATIC ARTHRITIS BY ADMINISTERING THE FORMULATION OF TOFACITINIB OF CLAIMS 1, 8, 15-20, 27-31, 34-44, 46, 48, 50, 53, 59, 62, 68-71, 73, 76, 82-84, AND 87-98
EQ 11MG BASE	XELJANZ XR	PFIZER	N208246	Feb. 23, 2016	RX	TABLET, EXTENDED RELEASE	ORAL	11253523	March 14, 2034	A METHOD OF TREATING RHEUMATOID ARTHRITIS BY ADMINISTERING THE FORMULATION OF TOFACITINIB OF CLAIMS 1, 2, 8, 9, 15-21, 27-31, 34-43, 50, 51, 59, 60, 68-71, 73, 74, 82-84 AND 87-98
EQ 11MG BASE	XELJANZ XR	PFIZER	N208246	Feb. 23, 2016	RX	TABLET, EXTENDED RELEASE	ORAL	11253523	March 14, 2034	A METHOD OF TREATING ULCERATIVE COLITIS, BY ADMINISTERING THE FORMULATION OF TOFACITINIB OF CLAIMS 1, 3, 8, 10, 15-20, 22, 27-31, 34-43, 50, 52, 59, 61, 68-71, 73, 75, 82-84 AND 87-98
EQ 22MG BASE	XELJANZ XR	PFIZER	N208246	Dec. 12, 2019	RX	TABLET, EXTENDED RELEASE	ORAL	11253523	March 14, 2034	A METHOD OF TREATING ANKYLOSING SPONDYLITIS BY ADMINISTERING THE FORMULATION OF TOFACITINIB OF CLAIMS 1, 8, 15-20, 27-31, 34-43, 45, 47, 49, 50, 54, 59, 63, 68-71, 73, 77, 82-84, AND 87-98
EQ 22MG BASE	XELJANZ XR	PFIZER	N208246	Dec. 12, 2019	RX	TABLET, EXTENDED RELEASE	ORAL	11253523	March 14, 2034	A METHOD OF TREATING PSORIATIC ARTHRITIS BY ADMINISTERING THE FORMULATION OF TOFACITINIB OF CLAIMS 1, 8, 15-20, 27-31, 34-44, 46, 48, 50, 53, 59, 62, 68-71, 73, 76, 82-84, AND 87-98
EQ 22MG BASE	XELJANZ XR	PFIZER	N208246	Dec. 12, 2019	RX	TABLET, EXTENDED RELEASE	ORAL	11253523	March 14, 2034	A METHOD OF TREATING RHEUMATOID ARTHRITIS BY ADMINISTERING THE FORMULATION OF TOFACITINIB OF CLAIMS 1, 2, 8, 9, 15-21, 27-31, 34-43, 50, 51, 59, 60, 68-71, 73, 74, 82-84 AND 87-98
EQ 22MG BASE	XELJANZ XR	PFIZER	N208246	Dec. 12, 2019	RX	TABLET, EXTENDED RELEASE	ORAL	11253523	March 14, 2034	A METHOD OF TREATING ULCERATIVE COLITIS, BY ADMINISTERING THE FORMULATION OF TOFACITINIB OF CLAIMS 1, 3, 8, 10, 15-20, 22, 27-31, 34-43, 50, 52, 59, 61, 68-71, 73, 75, 82-84 AND 87-98

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Orange Book exclusivity data (new drug applications)

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Formulation strength	Trade name	Applicant	Application number	Approval date	Type	Dose form	Route	Exclusivity date	Description
EQ 10MG BASE	XELJANZ	PF PRISM CV	N203214	May 30, 2018	RX	TABLET	ORAL	Dec. 14, 2024	TREATMENT OF ADULT PATIENTS WITH ACTIVE ANKYLOSING SPONDYLITIS WHO HAVE HAD AN INADEQUATE RESPONSE OR INTOLERANCE TO ONE OR MORE TNF BLOCKERS, TO THE PRESCRIBING INFORMATION
EQ 11MG BASE	XELJANZ XR	PFIZER	N208246	Feb. 23, 2016	RX	TABLET, EXTENDED RELEASE	ORAL	Dec. 14, 2024	TREATMENT OF ADULT PATIENTS WITH ACTIVE ANKYLOSING SPONDYLITIS WHO HAVE HAD AN INADEQUATE RESPONSE OR INTOLERANCE TO ONE OR MORE TNF BLOCKERS, TO THE PRESCRIBING INFORMATION
EQ 1MG/ML BASE	XELJANZ	PFIZER	N213082	Sept. 25, 2020	RX	SOLUTION	ORAL	Sept. 25, 2023	NEW PRODUCT
EQ 5MG BASE	XELJANZ	PF PRISM CV	N203214	Nov. 6, 2012	RX	TABLET	ORAL	Sept. 25, 2023	NEW PATIENT POPULATION
EQ 5MG BASE	XELJANZ	PF PRISM CV	N203214	Nov. 6, 2012	RX	TABLET	ORAL	Dec. 14, 2024	TREATMENT OF ADULT PATIENTS WITH ACTIVE ANKYLOSING SPONDYLITIS WHO HAVE HAD AN INADEQUATE RESPONSE OR INTOLERANCE TO ONE OR MORE TNF BLOCKERS, TO THE PRESCRIBING INFORMATION

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Bioactivity Summary:

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Target	Class	Pharos	UniProt	Action	Type	Activity value (-log[M])	Bioact source	MoA source
JAK1/TYK2	Kinase	P23458 P29597	JAK1_HUMAN TYK2_HUMAN	INHIBITOR	IC50	7.46	CHEMBL	CHEMBL
JAK2/TYK2	Kinase	O60674 P29597	JAK2_HUMAN TYK2_HUMAN	INHIBITOR	IC50	6.64	CHEMBL	CHEMBL
JAK2/JAK1	Kinase	O60674 P23458	JAK2_HUMAN JAK1_HUMAN	INHIBITOR	IC50	6.39	DRUG LABEL	DRUG LABEL
JAK3/JAK1	Kinase	P23458 P52333	JAK1_HUMAN JAK3_HUMAN	INHIBITOR	IC50	7.25	DRUG LABEL	DRUG LABEL
Proto-oncogene tyrosine-protein kinase receptor Ret	Kinase	P07949	RET_HUMAN		Kd	5.48	CHEMBL
Calcium/calmodulin-dependent protein kinase type 1	Kinase	Q14012	KCC1A_HUMAN		Kd	5.92	CHEMBL
Rho-associated protein kinase 1	Kinase	Q13464	ROCK1_HUMAN		Kd	6.33	CHEMBL
Tyrosine-protein kinase JAK1	Kinase	P23458	JAK1_HUMAN	INHIBITOR	Ki	9.17	CHEMBL
Protein kinase C delta type	Kinase	Q05655	KPCD_HUMAN		Kd	5.70	CHEMBL
Tyrosine-protein kinase JAK2	Kinase	O60674	JAK2_HUMAN	INHIBITOR	Kd	9.24	CHEMBL

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External reference:

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ID	Source
014743	NDDF
014744	NDDF
1357536	RXNORM
194456	MMSL
28976	MMSL
31571	MMSL
4031786	VUID
4031786	VANDF
540737-29-9	SECONDARY_CAS_RN
5677	IUPHAR_LIGAND_ID

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Pharmaceutical products:

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Product	Category	Ingredients	NDC	Form	Quantity	Route	Marketing	Label
XELJANZ	HUMAN PRESCRIPTION DRUG LABEL	1	0069-1001	TABLET, FILM COATED	5 mg	ORAL	NDA	35 sections
XELJANZ	HUMAN PRESCRIPTION DRUG LABEL	1	0069-1001	TABLET, FILM COATED	5 mg	ORAL	NDA	35 sections
XELJANZ	HUMAN PRESCRIPTION DRUG LABEL	1	0069-1001	TABLET, FILM COATED	5 mg	ORAL	NDA	35 sections
XELJANZ	HUMAN PRESCRIPTION DRUG LABEL	1	0069-1002	TABLET, FILM COATED	10 mg	ORAL	NDA	35 sections
XELJANZ	HUMAN PRESCRIPTION DRUG LABEL	1	0069-1002	TABLET, FILM COATED	10 mg	ORAL	NDA	35 sections
XELJANZ	HUMAN PRESCRIPTION DRUG LABEL	1	0069-1002	TABLET, FILM COATED	10 mg	ORAL	NDA	35 sections
XELJANZ	HUMAN PRESCRIPTION DRUG LABEL	1	0069-1029	SOLUTION	1 mg	ORAL	NDA	35 sections
XELJANZ	HUMAN PRESCRIPTION DRUG LABEL	1	0069-1029	SOLUTION	1 mg	ORAL	NDA	35 sections
XELJANZ	HUMAN PRESCRIPTION DRUG LABEL	1	0069-1029	SOLUTION	1 mg	ORAL	NDA	35 sections
XELJANZ	HUMAN PRESCRIPTION DRUG LABEL	1	63539-012	TABLET, FILM COATED	5 mg	ORAL	NDA	35 sections

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