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

Stem definition	Drug id	CAS RN
tyrosine kinase inhibitors	4810	936563-96-1

Description:

Molecule	Description
Molfile Inchi Smiles Synonyms: imbruvica PCI-32765 CRA-032765 PCI-32765-00 ibrutinib	Ibrutinib is a small-molecule inhibitor of BTK. Ibrutinib forms a covalent bond with a cysteine residue in the BTK active site, leading to inhibition of BTK enzymatic activity. BTK is a signaling molecule of the B-cell antigen receptor (BCR) and cytokine receptor pathways. BTK's role in signaling through the B-cell surface receptors results in activation of pathways necessary for B-cell trafficking, chemotaxis, and adhesion. Nonclinical studies show that ibrutinib inhibits malignant B-cell proliferation and survival in vivo as well as cell migration and substrate adhesion in vitro. Molecular weight: 440.51 Formula: C25H24N6O2 CLOGP: 4.04 LIPINSKI: 0 HAC: 8 HDO: 1 TPSA: 99.16 ALOGS: -4.34 ROTB: 5 Status: ONP Legend: OFP - off patent OFM - off market ONP - on patent

Molecule

Description

Molfile Inchi Smiles

Synonyms:

imbruvica
PCI-32765
CRA-032765
PCI-32765-00
ibrutinib

Ibrutinib is a small-molecule inhibitor of BTK. Ibrutinib forms a covalent bond with a cysteine residue in the BTK active site, leading to inhibition of BTK enzymatic activity. BTK is a signaling molecule of the B-cell antigen receptor (BCR) and cytokine receptor pathways. BTK's role in signaling through the B-cell surface receptors results in activation of pathways necessary for B-cell trafficking, chemotaxis, and adhesion. Nonclinical studies show that ibrutinib inhibits malignant B-cell proliferation and survival in vivo as well as cell migration and substrate adhesion in vitro.

Molecular weight: 440.51
Formula: C25H24N6O2
CLOGP: 4.04
LIPINSKI: 0
HAC: 8
HDO: 1
TPSA: 99.16
ALOGS: -4.34
ROTB: 5

Status: ONP

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

Drug dosage:

Dose	Unit	Route
0.42	g	O

ADMET properties:

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Property	Value	Reference
Vd (Volume of distribution)	9.75 L/kg	Lombardo F, Berellini G, Obach RS
t_half (Half-life)	5 hours	Lombardo F, Berellini G, Obach RS
CL (Clearance)	16.40 mL/min/kg	Lombardo F, Berellini G, Obach RS
fu (Fraction unbound in plasma)	0.03 %	Lombardo F, Berellini G, Obach RS

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Approvals:

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Date	Agency	Company
March 28, 2016	PMDA	Janssen Pharmaceutical
Nov. 13, 2013	FDA	PHARMACYCLICS INC
Oct. 21, 2014	EMA

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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
Death	818.80	16.63	805	20751	373576	63093890
Atrial fibrillation	400.62	16.63	325	21231	116311	63351155
Incorrect dose administered	275.77	16.63	199	21357	59769	63407697
Off label use	254.95	16.63	644	20912	673818	62793648
Disease progression	231.60	16.63	245	21311	122513	63344953
Contusion	144.71	16.63	214	21342	149830	63317636
Petechiae	142.85	16.63	77	21479	13820	63453646
Lymphadenopathy	133.45	16.63	108	21448	38350	63429116
Hospice care	132.10	16.63	61	21495	7871	63459595
White blood cell count increased	123.14	16.63	114	21442	48447	63419019

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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
Death	839.81	13.73	1583	39149	396466	34519733
Atrial fibrillation	759.09	13.73	818	39914	121575	34794624
Incorrect dose administered	363.80	13.73	332	40400	40183	34876016
Off label use	278.25	13.73	1091	39641	418433	34497766
Disease progression	276.38	13.73	470	40262	107607	34808592
Lymphocytosis	229.38	13.73	93	40639	2484	34913715
Contusion	226.04	13.73	244	40488	36120	34880079
Lymphocyte count increased	208.66	13.73	94	40638	3271	34912928
Haemorrhage	191.13	13.73	266	40466	51104	34865095
Lymphadenopathy	180.39	13.73	193	40539	28270	34887929

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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
Atrial fibrillation	1111.54	13.60	963	50841	196923	79495661
Death	640.48	13.60	1239	50565	565275	79127309
Incorrect dose administered	598.70	13.60	453	51351	76177	79616407
Off label use	355.56	13.60	1340	50464	905875	78786709
Disease progression	317.20	13.60	487	51317	183875	79508709
Lymphocytosis	280.44	13.60	108	51696	4585	79687999
Platelet count decreased	262.84	13.60	461	51343	194203	79498381
Lymphadenopathy	256.02	13.60	238	51566	53009	79639575
White blood cell count increased	247.78	13.60	273	51531	74360	79618224
Pleural effusion	243.10	13.60	379	51425	144883	79547701

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FDA Adverse Event Reporting System (Pediatric)

None

Pharmacologic Action:

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Source	Code	Description
ATC	L01EL01	ANTINEOPLASTIC AND IMMUNOMODULATING AGENTS ANTINEOPLASTIC AGENTS PROTEIN KINASE INHIBITORS Bruton's tyrosine kinase (BTK) inhibitors
CHEBI has role	CHEBI:35610	antineoplastic agents
CHEBI has role	CHEBI:76617	BTK inhibitor
FDA EPC	N0000175605	Kinase Inhibitor
FDA MoA	N0000175076	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
Chronic lymphoid leukemia, disease	indication	92814006
Waldenström macroglobulinemia	indication	190818004	DOID:0050747
Malignant lymphoma - small lymphocytic	indication	302841002
M lymphoplasmacytic	indication	307623001
Chronic graft-versus-host disease	indication	402356004
Mantle cell lymphoma	indication	443487006
Marginal zone lymphoma	indication	447100004
Pregnancy, function	contraindication	289908002

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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	4.7	Basic
pKa2	0.18	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
140MG	IMBRUVICA	PHARMACYCLICS LLC	N205552	Nov. 13, 2013	RX	CAPSULE	ORAL	8476284	Dec. 28, 2026	TREATMENT OF MANTLE CELL LYMPHOMA
140MG	IMBRUVICA	PHARMACYCLICS LLC	N205552	Nov. 13, 2013	RX	CAPSULE	ORAL	8476284	Dec. 28, 2026	TREATMENT OF MARGINAL ZONE LYMPHOMA
140MG	IMBRUVICA	PHARMACYCLICS LLC	N205552	Nov. 13, 2013	RX	CAPSULE	ORAL	8476284	Dec. 28, 2026	TREATMENT OF SMALL LYMPHOCYTIC LYMPHOMA
140MG	IMBRUVICA	PHARMACYCLICS LLC	N205552	Nov. 13, 2013	RX	CAPSULE	ORAL	8476284	Dec. 28, 2026	TREATMENT OF WALDENSTROMS MACROGLOBULINEMIA
140MG	IMBRUVICA	PHARMACYCLICS LLC	N205552	Nov. 13, 2013	RX	CAPSULE	ORAL	8497277	Dec. 28, 2026	TREATMENT OF CHRONIC LYMPHOCYTIC LEUKEMIA
140MG	IMBRUVICA	PHARMACYCLICS LLC	N205552	Nov. 13, 2013	RX	CAPSULE	ORAL	8497277	Dec. 28, 2026	TREATMENT OF CHRONIC LYMPHOCYTIC LEUKEMIA WITH 17P DELETION
140MG	IMBRUVICA	PHARMACYCLICS LLC	N205552	Nov. 13, 2013	RX	CAPSULE	ORAL	8497277	Dec. 28, 2026	TREATMENT OF MANTLE CELL LYMPHOMA
140MG	IMBRUVICA	PHARMACYCLICS LLC	N205552	Nov. 13, 2013	RX	CAPSULE	ORAL	8497277	Dec. 28, 2026	TREATMENT OF MARGINAL ZONE LYMPHOMA
140MG	IMBRUVICA	PHARMACYCLICS LLC	N205552	Nov. 13, 2013	RX	CAPSULE	ORAL	8497277	Dec. 28, 2026	TREATMENT OF PEDIATRIC PATIENTS AGE 1 YEAR AND OLDER WITH CHRONIC GRAFT-VERSUS-HOST DISEASE (CGVHD) AFTER FAILURE OF ONE OR MORE LINES OF SYSTEMIC THERAPY
140MG	IMBRUVICA	PHARMACYCLICS LLC	N205552	Nov. 13, 2013	RX	CAPSULE	ORAL	8497277	Dec. 28, 2026	TREATMENT OF SMALL LYMPHOCYTIC LYMPHOMA

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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
140MG	IMBRUVICA	PHARMACYCLICS LLC	N205552	Nov. 13, 2013	RX	CAPSULE	ORAL	March 4, 2023	INDICATED FOR THE TREATMENT OF PATIENTS WITH CHRONIC LYMPHOCYTIC LEUKEMIA WITHOUT 17P DELETION WHO HAVE NOT RECEIVED AT LEAST ONE PRIOR THERAPY (FIRST LINE THERAPY)
140MG	IMBRUVICA	PHARMACYCLICS LLC	N210563	Feb. 16, 2018	RX	TABLET	ORAL	March 4, 2023	FDA HAS NOT RECOGNIZED ORPHAN-DRUG EXCLUSIVITY (ODE) FOR THIS DRUG, BUT IT CONTAINS THE SAME ACTIVE MOIETY OR MOIETIES AS ANOTHER DRUG(S) THAT WAS ELIGIBLE FOR ODE, AND ALSO SHARES ODE-PROTECTED USE(S) OR INDICATION(S) WITH THAT DRUG(S). AN APPLICATION SEEKING APPROVAL FOR THE SAME ACTIVE MOIETY OR MOIETIES, INCLUDING AN ANDA THAT CITES THIS NDA AS ITS BASIS OF SUBMISSION, MAY NOT BE APPROVED FOR SUCH ODE-PROTECTED USE(S) AND INDICATION(S)
140MG	IMBRUVICA	PHARMACYCLICS LLC	N205552	Nov. 13, 2013	RX	CAPSULE	ORAL	May 6, 2023	FOR TREATMENT OF PATIENTS WITH SMALL LYMPHOCYTIC LYMPHOMA (SLL)
140MG	IMBRUVICA	PHARMACYCLICS LLC	N210563	Feb. 16, 2018	RX	TABLET	ORAL	May 6, 2023	FDA HAS NOT RECOGNIZED ORPHAN-DRUG EXCLUSIVITY (ODE) FOR THIS DRUG, BUT IT CONTAINS THE SAME ACTIVE MOIETY OR MOIETIES AS ANOTHER DRUG(S) THAT WAS ELIGIBLE FOR ODE, AND ALSO SHARES ODE-PROTECTED USE(S) OR INDICATION(S) WITH THAT DRUG(S). AN APPLICATION SEEKING APPROVAL FOR THE SAME ACTIVE MOIETY OR MOIETIES, INCLUDING AN ANDA THAT CITES THIS NDA AS ITS BASIS OF SUBMISSION, MAY NOT BE APPROVED FOR SUCH ODE-PROTECTED USE(S) AND INDICATION(S)
140MG	IMBRUVICA	PHARMACYCLICS LLC	N205552	Nov. 13, 2013	RX	CAPSULE	ORAL	Aug. 2, 2024	TREATMENT OF ADULT PATIENTS WITH CHRONIC GRAFT VERSUS HOST DISEASE (CGVHD)
140MG	IMBRUVICA	PHARMACYCLICS LLC	N210563	Feb. 16, 2018	RX	TABLET	ORAL	Aug. 2, 2024	FDA HAS NOT RECOGNIZED ORPHAN-DRUG EXCLUSIVITY (ODE) FOR THIS DRUG, BUT IT CONTAINS THE SAME ACTIVE MOIETY OR MOIETIES AS ANOTHER DRUG(S) THAT WAS ELIGIBLE FOR ODE, AND ALSO SHARES ODE-PROTECTED USE(S) OR INDICATION(S) WITH THAT DRUG(S). AN APPLICATION SEEKING APPROVAL FOR THE SAME ACTIVE MOIETY OR MOIETIES, INCLUDING AN ANDA THAT CITES THIS NDA AS ITS BASIS OF SUBMISSION, MAY NOT BE APPROVED FOR SUCH ODE-PROTECTED USE(S) AND INDICATION(S)
140MG	IMBRUVICA	PHARMACYCLICS LLC	N205552	Nov. 13, 2013	RX	CAPSULE	ORAL	Feb. 2, 2025	PEDIATRIC EXCLUSIVITY
140MG	IMBRUVICA	PHARMACYCLICS LLC	N205552	Nov. 13, 2013	RX	CAPSULE	ORAL	Aug. 24, 2025	NEW PATIENT POPULATION
140MG	IMBRUVICA	PHARMACYCLICS LLC	N210563	Feb. 16, 2018	RX	TABLET	ORAL	Aug. 24, 2025	NEW PATIENT POPULATION
140MG	IMBRUVICA	PHARMACYCLICS LLC	N205552	Nov. 13, 2013	RX	CAPSULE	ORAL	Feb. 24, 2026	PEDIATRIC EXCLUSIVITY

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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 BTK	Kinase	Q06187	BTK_HUMAN	INHIBITOR	Ki	9.14	SCIENTIFIC LITERATURE	SCIENTIFIC LITERATURE
Tyrosine-protein kinase ABL1	Kinase	P00519	ABL1_HUMAN		IC50	7.07	CHEMBL
Epidermal growth factor receptor	Kinase	P00533	EGFR_HUMAN		IC50	8.25	CHEMBL
Breakpoint cluster region protein	Kinase	P11274	BCR_HUMAN		Kd	5.84	CHEMBL
Receptor-type tyrosine-protein kinase FLT3	Kinase	P36888	FLT3_HUMAN		Kd	5.80	CHEMBL
Proto-oncogene tyrosine-protein kinase receptor Ret	Kinase	P07949	RET_HUMAN		IC50	7.43	CHEMBL
Macrophage colony-stimulating factor 1 receptor	Kinase	P07333	CSF1R_HUMAN		IC50	5.26	CHEMBL
Tyrosine-protein kinase CSK	Kinase	P41240	CSK_HUMAN		IC50	8.66	CHEMBL
Cytoplasmic tyrosine-protein kinase BMX	Kinase	P51813	BMX_HUMAN		IC50	9.10	CHEMBL
LIM domain kinase 1	Kinase	P53667	LIMK1_HUMAN		Kd	4.68	CHEMBL

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External reference:

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ID	Source
1E8	PDB_CHEM_ID
015287	NDDF
1442981	RXNORM
1X70OSD4VX	UNII
207254	MMSL
24821094	PUBCHEM_CID
29840	MMSL
4032872	VANDF
6912	IUPHAR_LIGAND_ID
710228002	SNOMEDCT_US

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Pharmaceutical products:

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Product	Category	Ingredients	NDC	Form	Quantity	Route	Marketing	Label
Imbruvica	HUMAN PRESCRIPTION DRUG LABEL	1	57962-007	SUSPENSION	70 mg	ORAL	NDA	32 sections
Imbruvica	HUMAN PRESCRIPTION DRUG LABEL	1	57962-007	SUSPENSION	70 mg	ORAL	NDA	32 sections
Imbruvica	HUMAN PRESCRIPTION DRUG LABEL	1	57962-007	SUSPENSION	70 mg	ORAL	NDA	32 sections
Imbruvica	HUMAN PRESCRIPTION DRUG LABEL	1	57962-014	TABLET, FILM COATED	140 mg	ORAL	NDA	32 sections
Imbruvica	HUMAN PRESCRIPTION DRUG LABEL	1	57962-014	TABLET, FILM COATED	140 mg	ORAL	NDA	32 sections
Imbruvica	HUMAN PRESCRIPTION DRUG LABEL	1	57962-014	TABLET, FILM COATED	140 mg	ORAL	NDA	32 sections
Imbruvica	HUMAN PRESCRIPTION DRUG LABEL	1	57962-014	TABLET, FILM COATED	140 mg	ORAL	NDA	32 sections
Imbruvica	HUMAN PRESCRIPTION DRUG LABEL	1	57962-070	CAPSULE	70 mg	ORAL	NDA	32 sections
Imbruvica	HUMAN PRESCRIPTION DRUG LABEL	1	57962-070	CAPSULE	70 mg	ORAL	NDA	32 sections
Imbruvica	HUMAN PRESCRIPTION DRUG LABEL	1	57962-070	CAPSULE	70 mg	ORAL	NDA	32 sections

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