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

Stem definition	Drug id	CAS RN
tyrosine kinase inhibitors	4359	380843-75-4

Description:

Molecule	Description
Molfile Inchi Smiles Synonyms: WAY-173606 bosutinib bosulif bosutinib monohydrate bosutinib hydrate SKI-606 SKI 606	a 4-anilino-3-quinolinecarbonitrile dual inhibitor of Src and Abl kinases Molecular weight: 530.45 Formula: C26H29Cl2N5O3 CLOGP: 4.94 LIPINSKI: 1 HAC: 8 HDO: 1 TPSA: 82.88 ALOGS: -4.75 ROTB: 9 Status: ONP Legend: OFP - off patent OFM - off market ONP - on patent

Molecule

Description

Molfile Inchi Smiles

Synonyms:

WAY-173606
bosutinib
bosulif
bosutinib monohydrate
bosutinib hydrate
SKI-606
SKI 606

a 4-anilino-3-quinolinecarbonitrile dual inhibitor of Src and Abl kinases

Molecular weight: 530.45
Formula: C26H29Cl2N5O3
CLOGP: 4.94
LIPINSKI: 1
HAC: 8
HDO: 1
TPSA: 82.88
ALOGS: -4.75
ROTB: 9

Status: ONP

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

Drug dosage:

Dose	Unit	Route
0.40	g	O

ADMET properties:

None

Approvals:

Date	Agency	Company	Orphan
Sept. 26, 2014	PMDA	Pfizer Japan Inc
Sept. 4, 2012	FDA	WYETH PHARMS INC

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
Diarrhoea	779.50	24.81	602	5695	714764	62767961
Nausea	232.51	24.81	347	5950	854124	62628601
Neoplasm progression	178.12	24.81	82	6215	36346	63446379
Pleural effusion	131.50	24.81	93	6204	93117	63389608
Cytogenetic analysis abnormal	115.47	24.81	25	6272	895	63481830
Vomiting	100.77	24.81	190	6107	559427	62923298
Drug resistance	88.76	24.81	44	6253	22889	63459836
Philadelphia chromosome positive	85.84	24.81	17	6280	389	63482336
Rash	69.89	24.81	164	6133	560707	62922018
Blast crisis in myelogenous leukaemia	52.64	24.81	12	6285	545	63482180

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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
Diarrhoea	561.16	26.10	478	5279	389434	34561740
Neoplasm progression	257.22	26.10	108	5649	23192	34927982
Pleural effusion	236.85	26.10	154	5603	81392	34869782
Drug intolerance	135.73	26.10	97	5660	59473	34891701
Cytogenetic analysis abnormal	129.92	26.10	29	5728	710	34950464
Nausea	98.51	26.10	189	5568	339719	34611455
Drug resistance	77.47	26.10	50	5707	25877	34925297
Fatigue	71.50	26.10	175	5582	370478	34580696
Second primary malignancy	59.34	26.10	28	5729	7858	34943316
Abdominal discomfort	58.46	26.10	60	5697	59775	34891399

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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
Diarrhoea	1174.33	23.05	950	9845	879539	78854054
Neoplasm progression	361.48	23.05	164	10631	51518	79682075
Nausea	277.28	23.05	475	10320	956721	78776872
Pleural effusion	266.56	23.05	192	10603	145070	79588523
Cytogenetic analysis abnormal	175.32	23.05	39	10756	1151	79732442
Fatigue	110.08	23.05	324	10471	929403	78804190
Vomiting	105.86	23.05	259	10536	665569	79068024
Philadelphia chromosome positive	103.76	23.05	23	10772	667	79732926
Rash	93.97	23.05	227	10568	578131	79155462
Second primary malignancy	74.04	23.05	37	10758	14313	79719280

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FDA Adverse Event Reporting System (Pediatric)

None

Pharmacologic Action:

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Source	Code	Description
ATC	L01EA04	ANTINEOPLASTIC AND IMMUNOMODULATING AGENTS ANTINEOPLASTIC AGENTS PROTEIN KINASE INHIBITORS BCR-ABL tyrosine kinase inhibitors
CHEBI has role	CHEBI:35610	antineoplastic agents
CHEBI has role	CHEBI:38637	tyrosine kinase inhibitors
FDA EPC	N0000175605	Kinase Inhibitor
FDA MoA	N0000020009	Bcr-Abl Tyrosine 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
Blastic phase chronic myeloid leukemia	indication	413656006
Chronic Myelocytic Leukemia Accelerated Phase	indication

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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	8.74	Basic
pKa2	6.69	Basic
pKa3	4.74	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 100MG BASE	BOSULIF	PF PRISM CV	N203341	Sept. 4, 2012	RX	TABLET	ORAL	7417148	Dec. 11, 2025	A METHOD OF TREATING CHRONIC MYELOGENOUS LEUKEMIA
EQ 100MG BASE	BOSULIF	PF PRISM CV	N203341	Sept. 4, 2012	RX	TABLET	ORAL	11103497	Feb. 28, 2034	A METHOD FOR TREATING A BCRABL POSITIVE LEUKEMIA IN A SUBJECT THAT IS RESISTANT TO IMATINIB COMPRISING ADMINISTERING TO THE SUBJECT A THERAPEUTICALLY EFFECTIVE AMOUNT OF BOSUTINIB, WHEREIN THE SUBJECT HAS A MUTATION IN THE BCRABL PROTEIN AT 949T>C
EQ 100MG BASE	BOSULIF	PF PRISM CV	N203341	Sept. 4, 2012	RX	TABLET	ORAL	11103497	Feb. 28, 2034	A METHOD FOR TREATING A BCRABL POSITIVE LEUKEMIA IN A SUBJECT THAT IS RESISTANT TO IMATINIB COMPRISING ADMINISTERING TO THE SUBJECT A THERAPEUTICALLY EFFECTIVE AMOUNT OF BOSUTINIB, WHEREIN THE SUBJECT HAS A MUTATION IN THE BCRABL PROTEIN AT F317L
EQ 400MG BASE	BOSULIF	PF PRISM CV	N203341	Oct. 27, 2017	RX	TABLET	ORAL	7417148	Dec. 11, 2025	A METHOD OF TREATING CHRONIC MYELOGENOUS LEUKEMIA
EQ 400MG BASE	BOSULIF	PF PRISM CV	N203341	Oct. 27, 2017	RX	TABLET	ORAL	11103497	Feb. 28, 2034	A METHOD FOR TREATING A BCRABL POSITIVE LEUKEMIA IN A SUBJECT THAT IS RESISTANT TO IMATINIB COMPRISING ADMINISTERING TO THE SUBJECT A THERAPEUTICALLY EFFECTIVE AMOUNT OF BOSUTINIB, WHEREIN THE SUBJECT HAS A MUTATION IN THE BCRABL PROTEIN AT 949T>C
EQ 400MG BASE	BOSULIF	PF PRISM CV	N203341	Oct. 27, 2017	RX	TABLET	ORAL	11103497	Feb. 28, 2034	A METHOD FOR TREATING A BCRABL POSITIVE LEUKEMIA IN A SUBJECT THAT IS RESISTANT TO IMATINIB COMPRISING ADMINISTERING TO THE SUBJECT A THERAPEUTICALLY EFFECTIVE AMOUNT OF BOSUTINIB, WHEREIN THE SUBJECT HAS A MUTATION IN THE BCRABL PROTEIN AT F317L
EQ 500MG BASE	BOSULIF	PF PRISM CV	N203341	Sept. 4, 2012	RX	TABLET	ORAL	7417148	Dec. 11, 2025	A METHOD OF TREATING CHRONIC MYELOGENOUS LEUKEMIA
EQ 500MG BASE	BOSULIF	PF PRISM CV	N203341	Sept. 4, 2012	RX	TABLET	ORAL	11103497	Feb. 28, 2034	A METHOD FOR TREATING A BCRABL POSITIVE LEUKEMIA IN A SUBJECT THAT IS RESISTANT TO IMATINIB COMPRISING ADMINISTERING TO THE SUBJECT A THERAPEUTICALLY EFFECTIVE AMOUNT OF BOSUTINIB, WHEREIN THE SUBJECT HAS A MUTATION IN THE BCRABL PROTEIN AT 949T>C
EQ 500MG BASE	BOSULIF	PF PRISM CV	N203341	Sept. 4, 2012	RX	TABLET	ORAL	11103497	Feb. 28, 2034	A METHOD FOR TREATING A BCRABL POSITIVE LEUKEMIA IN A SUBJECT THAT IS RESISTANT TO IMATINIB COMPRISING ADMINISTERING TO THE SUBJECT A THERAPEUTICALLY EFFECTIVE AMOUNT OF BOSUTINIB, WHEREIN THE SUBJECT HAS A MUTATION IN THE BCRABL PROTEIN AT F317L

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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 100MG BASE	BOSULIF	PF PRISM CV	N203341	Sept. 4, 2012	RX	TABLET	ORAL	Dec. 19, 2024	TREATMENT OF ADULT PATIENTS WITH NEWLY-DIAGNOSED CHRONIC PHASE (CP) PHILADELPHIA CHROMOSOME-POSITIVE CHRONIC MYELOGENOUS LEUKEMIA (PH+ CML)
EQ 400MG BASE	BOSULIF	PF PRISM CV	N203341	Oct. 27, 2017	RX	TABLET	ORAL	Dec. 19, 2024	TREATMENT OF ADULT PATIENTS WITH NEWLY-DIAGNOSED CHRONIC PHASE (CP) PHILADELPHIA CHROMOSOME-POSITIVE CHRONIC MYELOGENOUS LEUKEMIA (PH+ CML)
EQ 500MG BASE	BOSULIF	PF PRISM CV	N203341	Sept. 4, 2012	RX	TABLET	ORAL	Dec. 19, 2024	TREATMENT OF ADULT PATIENTS WITH NEWLY-DIAGNOSED CHRONIC PHASE (CP) PHILADELPHIA CHROMOSOME-POSITIVE CHRONIC MYELOGENOUS LEUKEMIA (PH+ CML)

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Bioactivity Summary:

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Target	Class	Pharos	UniProt	Action	Type	Activity value (-log[M])	Bioact source	MoA source
Tyrosine-protein kinase Lyn	Kinase	P07948	LYN_HUMAN	INHIBITOR	Kd	8.38	CHEMBL	CHEMBL
Proto-oncogene tyrosine-protein kinase Src	Kinase	P12931	SRC_HUMAN	INHIBITOR	Kd	9	CHEMBL	CHEMBL
Tyrosine-protein kinase HCK	Kinase	P08631	HCK_HUMAN	INHIBITOR	Kd	8.47	CHEMBL	CHEMBL
Tyrosine-protein kinase ABL1	Kinase	P00519	ABL1_HUMAN	INHIBITOR	Kd	10.54	CHEMBL	CHEMBL
Mast/stem cell growth factor receptor Kit	Kinase	P10721	KIT_HUMAN		Kd	7.14	CHEMBL
Epidermal growth factor receptor	Kinase	P00533	EGFR_HUMAN		Kd	7.74	CHEMBL
Tyrosine-protein kinase Lck	Kinase	P06239	LCK_HUMAN		Kd	9.23	CHEMBL
Tyrosine-protein kinase Yes	Kinase	P07947	YES_HUMAN		Kd	8.40	CHEMBL
Tyrosine-protein kinase Fyn	Kinase	P06241	FYN_HUMAN		Kd	7.96	CHEMBL
Ephrin type-A receptor 2	Kinase	P29317	EPHA2_HUMAN		Kd	7.74	CHEMBL

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External reference:

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ID	Source
DB8	PDB_CHEM_ID
014636	NDDF
1307619	RXNORM
192772	MMSL
28803	MMSL
4031718	VUID
4031718	VANDF
5018V4AEZ0	UNII
5328940	PUBCHEM_CID
5710	IUPHAR_LIGAND_ID

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Pharmaceutical products:

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Product	Category	Ingredients	NDC	Form	Quantity	Route	Marketing	Label
BOSULIF	HUMAN PRESCRIPTION DRUG LABEL	1	0069-0135	TABLET, FILM COATED	100 mg	ORAL	NDA	33 sections
BOSULIF	HUMAN PRESCRIPTION DRUG LABEL	1	0069-0135	TABLET, FILM COATED	100 mg	ORAL	NDA	33 sections
BOSULIF	HUMAN PRESCRIPTION DRUG LABEL	1	0069-0136	TABLET, FILM COATED	500 mg	ORAL	NDA	33 sections
BOSULIF	HUMAN PRESCRIPTION DRUG LABEL	1	0069-0136	TABLET, FILM COATED	500 mg	ORAL	NDA	33 sections
BOSULIF	HUMAN PRESCRIPTION DRUG LABEL	1	0069-0193	TABLET, FILM COATED	400 mg	ORAL	NDA	33 sections
BOSULIF	HUMAN PRESCRIPTION DRUG LABEL	1	0069-0193	TABLET, FILM COATED	400 mg	ORAL	NDA	33 sections
BOSULIF	HUMAN PRESCRIPTION DRUG LABEL	1	63539-117	TABLET, FILM COATED	100 mg	ORAL	NDA	35 sections
BOSULIF	HUMAN PRESCRIPTION DRUG LABEL	1	63539-117	TABLET, FILM COATED	100 mg	ORAL	NDA	35 sections
BOSULIF	HUMAN PRESCRIPTION DRUG LABEL	1	63539-193	TABLET, FILM COATED	400 mg	ORAL	NDA	35 sections

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