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

Stem definition	Drug id	CAS RN
tyrosine kinase inhibitors	1423	152459-95-5

Description:

Molecule	Description
Molfile Inchi Smiles Synonyms: imatinib gleevec imatinib mesylate imatinib mesilate CGP-57-148B CGP57148B CGP-57148 CGP57148 STI-571 STI571	A tyrosine kinase inhibitor and ANTINEOPLASTIC AGENT that inhibits the BCR-ABL kinase created by chromosome rearrangements in CHRONIC MYELOID LEUKEMIA and ACUTE LYMPHOBLASTIC LEUKEMIA, as well as PDG-derived tyrosine kinases that are overexpressed in gastrointestinal stromal tumors. Molecular weight: 493.62 Formula: C29H31N7O CLOGP: 4.38 LIPINSKI: 0 HAC: 8 HDO: 2 TPSA: 86.28 ALOGS: -4.53 ROTB: 7 Status: OFP Legend: OFP - off patent OFM - off market ONP - on patent

Molecule

Description

Molfile Inchi Smiles

Synonyms:

imatinib
gleevec
imatinib mesylate
imatinib mesilate
CGP-57-148B
CGP57148B
CGP-57148
CGP57148
STI-571
STI571

A tyrosine kinase inhibitor and ANTINEOPLASTIC AGENT that inhibits the BCR-ABL kinase created by chromosome rearrangements in CHRONIC MYELOID LEUKEMIA and ACUTE LYMPHOBLASTIC LEUKEMIA, as well as PDG-derived tyrosine kinases that are overexpressed in gastrointestinal stromal tumors.

Molecular weight: 493.62
Formula: C29H31N7O
CLOGP: 4.38
LIPINSKI: 0
HAC: 8
HDO: 2
TPSA: 86.28
ALOGS: -4.53
ROTB: 7

Status: OFP

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

Drug dosage:

Dose	Unit	Route
0.40	g	O

ADMET properties:

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Property	Value	Reference
BA (Bioavailability)	98 %	Kim MT, Sedykh A, Chakravarti SK, Saiakhov RD, Zhu H
EoM (Fraction excreted unchanged in urine)	5 %	Benet LZ, Broccatelli F, Oprea TI
Vd (Volume of distribution)	3.90 L/kg	Lombardo F, Berellini G, Obach RS
CL (Clearance)	3.30 mL/min/kg	Lombardo F, Berellini G, Obach RS
t_half (Half-life)	22 hours	Lombardo F, Berellini G, Obach RS
MRTD (Maximum Recommended Therapeutic Daily Dose)	20.26 µM/kg/day	Contrera JF, Matthews EJ, Kruhlak NL, Benz RD
BDDCS (Biopharmaceutical Drug Disposition Classification System)	2	Benet LZ, Broccatelli F, Oprea TI
S (Water solubility)	0.05 mg/mL	Bocci G, Oprea TI, Benet LZ
fu (Fraction unbound in plasma)	0.05 %	Lombardo F, Berellini G, Obach RS

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Approvals:

Date	Agency	Company	Orphan
May 10, 2001	FDA	NOVARTIS
Nov. 7, 2001	EMA	Novartis Europharm Limited

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	1902.81	13.24	1745	41199	372636	63073442
Drug resistance	770.05	13.24	354	42590	22579	63423499
Blast crisis in myelogenous leukaemia	736.69	13.24	148	42796	409	63445669
Cytogenetic analysis abnormal	684.62	13.24	152	42792	768	63445310
Malignant neoplasm progression	490.84	13.24	422	42522	81699	63364379
Second primary malignancy	443.59	13.24	176	42768	7777	63438301
Periorbital oedema	360.17	13.24	138	42806	5546	63440532
Philadelphia chromosome positive	307.14	13.24	68	42876	338	63445740
Gene mutation identification test positive	275.42	13.24	52	42892	90	63445988
Chronic myeloid leukaemia recurrent	271.66	13.24	56	42888	183	63445895

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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	2625.54	12.31	2889	43205	395160	34515677
Drug resistance	1015.02	12.31	550	45544	25377	34885460
Blast crisis in myelogenous leukaemia	791.43	12.31	179	45915	425	34910412
Second primary malignancy	623.72	12.31	271	45823	7615	34903222
Cytogenetic analysis abnormal	566.59	12.31	142	45952	597	34910240
Malignant neoplasm progression	552.79	12.31	629	45465	87417	34823420
Neoplasm malignant	365.36	12.31	261	45833	19644	34891193
Philadelphia chromosome positive	337.45	12.31	82	46012	294	34910543
Drug intolerance	284.45	12.31	371	45723	59199	34851638
Pleural effusion	260.85	12.31	420	45674	81126	34829711

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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
Death	2830.50	12.30	2821	61098	563693	79116776
Drug resistance	1412.58	12.30	685	63234	41528	79638941
Blast crisis in myelogenous leukaemia	983.21	12.30	209	63710	664	79679805
Malignant neoplasm progression	810.70	12.30	751	63168	135239	79545230
Second primary malignancy	803.43	12.30	334	63585	14016	79666453
Cytogenetic analysis abnormal	785.46	12.30	184	63735	1006	79679463
Philadelphia chromosome positive	558.67	12.30	126	63793	564	79679905
Periorbital oedema	385.80	12.30	170	63749	8232	79672237
Pleural effusion	368.40	12.30	515	63404	144747	79535722
Chromosome analysis abnormal	345.18	12.30	71	63848	182	79680287

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FDA Adverse Event Reporting System (Pediatric)

None

Pharmacologic Action:

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Source	Code	Description
ATC	L01EA01	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
CHEBI has role	CHEBI:68495	Type I cell-death inducers
CHEBI has role	CHEBI:149553	anticoronaviral drug
FDA EPC	N0000175605	Kinase Inhibitor
FDA MoA	N0000020009	Bcr-Abl Tyrosine Kinase Inhibitors
FDA MoA	N0000182137	Cytochrome P450 2D6 Inhibitors
FDA MoA	N0000182141	Cytochrome P450 3A4 Inhibitors
MeSH PA	D000970	Antineoplastic Agents

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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
Dermatofibrosarcoma protuberans	indication	276799004
Systemic mast cell disease	indication	397016004	DOID:349
Blastic phase chronic myeloid leukemia	indication	413656006
Chronic eosinophilic leukemia	indication	413836008
Chronic phase chronic myeloid leukemia	indication	413847001
Gastrointestinal stromal tumor	indication	420120006	DOID:9253
Idiopathic hypereosinophilic syndrome	indication	423294001
Philadelphia chromosome-positive acute lymphoblastic leukemia	indication	425688002
Philadelphia Chromosome Positive Chronic Myelocytic Leukemia	indication	449108003
Myelodysplastic/myeloproliferative diseases with re-arrangements of the gene for platelet-derived growth factor receptor (PDGFR)	indication	738527001

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🐶 Veterinary Drug Use

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🐶 Veterinary products

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Acid dissociation constants calculated using MoKa v3.0.0

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Dissociation level	Dissociation constant	Type (acidic/basic)
pKa1	11.96	acidic
pKa2	8.49	Basic
pKa3	4.34	Basic
pKa4	3.73	Basic
pKa5	2.2	Basic

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Orange Book patent data (new drug applications)

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Orange Book exclusivity data (new drug applications)

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Bioactivity Summary:

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Target	Class	Pharos	UniProt	Action	Type	Activity value (-log[M])	Bioact source	MoA source
Platelet-derived growth factor receptor beta	Kinase	P09619	PGFRB_HUMAN	INHIBITOR	Kd	7.85	CHEMBL	CHEMBL
Tyrosine-protein kinase ABL1	Kinase	P00519	ABL1_HUMAN	INHIBITOR	Kd	8.96	CHEMBL	CHEMBL
Mast/stem cell growth factor receptor Kit	Kinase	P10721	KIT_HUMAN	INHIBITOR	Kd	7.89	CHEMBL	CHEMBL
Histamine H2 receptor	GPCR	P25021	HRH2_HUMAN		Ki	5.71	DRUG MATRIX
Carbonic anhydrase 2	Enzyme	P00918	CAH2_HUMAN		Ki	7.52	CHEMBL
Multidrug resistance-associated protein 1	Transporter	P33527	MRP1_HUMAN				WOMBAT-PK
ATP-binding cassette sub-family G member 2	Transporter	Q9UNQ0	ABCG2_HUMAN		IC50	5.47	CHEMBL
Carbonic anhydrase 1	Enzyme	P00915	CAH1_HUMAN		Ki	7.50	CHEMBL
Carbonic anhydrase 4	Enzyme	P22748	CAH4_HUMAN		Ki	5.34	CHEMBL
Ribosyldihydronicotinamide dehydrogenase [quinone]	Enzyme	P16083	NQO2_HUMAN		IC50	6.40	CHEMBL

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External reference:

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ID	Source
STI	PDB_CHEM_ID
009151	NDDF
009152	NDDF
129558005	SNOMEDCT_US
16030	MMSL
220127-57-1	SECONDARY_CAS_RN
238904	MMSL
282386	RXNORM
391634008	SNOMEDCT_US
4021257	VUID

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Pharmaceutical products:

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Product	Category	Ingredients	NDC	Form	Quantity	Route	Marketing	Label
Gleevec	HUMAN PRESCRIPTION DRUG LABEL	1	0078-0401	TABLET	100 mg	ORAL	NDA	32 sections
Gleevec	HUMAN PRESCRIPTION DRUG LABEL	1	0078-0401	TABLET	100 mg	ORAL	NDA	32 sections
Gleevec	HUMAN PRESCRIPTION DRUG LABEL	1	0078-0401	TABLET	100 mg	ORAL	NDA	32 sections
Gleevec	HUMAN PRESCRIPTION DRUG LABEL	1	0078-0401	TABLET	100 mg	ORAL	NDA	32 sections
Gleevec	HUMAN PRESCRIPTION DRUG LABEL	1	0078-0649	TABLET	400 mg	ORAL	NDA	32 sections
Gleevec	HUMAN PRESCRIPTION DRUG LABEL	1	0078-0649	TABLET	400 mg	ORAL	NDA	32 sections
Gleevec	HUMAN PRESCRIPTION DRUG LABEL	1	0078-0649	TABLET	400 mg	ORAL	NDA	32 sections
Gleevec	HUMAN PRESCRIPTION DRUG LABEL	1	0078-0649	TABLET	400 mg	ORAL	NDA	32 sections
Imatinib Mesylate	HUMAN PRESCRIPTION DRUG LABEL	1	0054-0248	TABLET, FILM COATED	100 mg	ORAL	ANDA	26 sections
Imatinib Mesylate	HUMAN PRESCRIPTION DRUG LABEL	1	0054-0248	TABLET, FILM COATED	100 mg	ORAL	ANDA	26 sections

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