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{{drugbox
{{DrugProjectFormSinglePage
| IUPAC_name = 4-[(4-methylpiperazin-1-yl)methyl]-''N''-[4-methyl-3-<br>[(4-pyridin-3-ylpyrimidin-2-yl)amino]-phenyl]-<br>benzamide
|authorTag=
| image = Imatinib_mesylate.png
 
| CAS_number = 152459-95-5
{{VP}}
| CAS_supplemental = {{CAS|220127-57-1}}(mesilate)
 
| ATC_prefix = L01
<!--Overview-->
| ATC_suffix = XE01
 
| ATC_supplemental =  
|genericName=
| PubChem = 5291
 
| DrugBank = APRD01028
 
| C=29 | H=31 | N=7 | O=1
 
| molecular_weight = 493.603 g/mol<br>589.7 g/mol (mesilate)
|aOrAn=
| bioavailability = 98%
 
| protein_bound = 95%
a
| metabolism = [[Liver|Hepatic]] (mainly [[CYP3A4]]-mediated)
 
| elimination_half-life = 18 hours (imatinib)<br>40 hours (active metabolite)
|drugClass=
| excretion = Fecal (68%) and [[Kidney|renal]] (13%)
 
| pregnancy_AU = D
 
| pregnancy_US = D
 
| legal_AU = <!-- Unscheduled / S2 / S4 / S8 -->
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| legal_UK = POM
 
| legal_US = Rx-only
 
| routes_of_administration = Oral
 
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There is limited information regarding <i>Off-Label Guideline-Supported Use</i> of {{PAGENAME}} in adult patients.
 
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===Acute Overdose===
 
====Signs and Symptoms====
 
* Description
 
====Management====
 
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There is limited information regarding <i>Chronic Overdose</i> of {{PAGENAME}} in the drug label.
 
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: [[File:{{PAGENAME}}01.png|thumb|none|600px|This image is provided by the National Library of Medicine.]]
 
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There is limited information regarding <i>Pharmacodynamics</i> of {{PAGENAME}} in the drug label.
 
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There is limited information regarding <i>Pharmacokinetics</i> of {{PAGENAME}} in the drug label.
 
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There is limited information regarding <i>Nonclinical Toxicology</i> of {{PAGENAME}} in the drug label.


<!--Clinical Studies-->


==Overview==
|clinicalStudies=


'''Imatinib''' is a [[medication|drug]] used to treat certain types of [[cancer]]. It is currently marketed by [[Novartis]] as '''Gleevec''' ([[USA]]) or '''Glivec''' ([[Europe]]/[[Australia]]) as its [[mesylate]] salt, '''imatinib mesilate''' ([[International Nonproprietary Name|INN]]). It is occasionally referred to as CGP57148B or STI571 (especially in older publications). It is used in treating [[chronic myelogenous leukemia]] (CML), [[gastrointestinal stromal tumor]]s (GISTs) and a number of other [[malignancy|malignancies]].  
There is limited information regarding <i>Clinical Studies</i> of {{PAGENAME}} in the drug label.


It is the first member of a new class of agents that act by inhibiting particular [[tyrosine kinase]] [[enzyme]]s, instead of non-specifically inhibiting rapidly dividing cells.
<!--How Supplied-->


==Molecular biology==
|howSupplied=
Imatinib is a 2-[[phenyl]][[amino]][[pyrimidine]] derivative that functions as a specific inhibitor of a number of tyrosine kinase enzymes. It occupies the ''TK'' active site, leading to a decrease in activity.


There are a large number of ''TK'' enzymes in the body, including the [[insulin receptor]]. Imatinib is specific for the ''TK'' domain in ''[[Philadelphia chromosome|abl]]'' (the Abelson proto-oncogene), [[c-kit]] and [[PDGF-R]] ([[platelet-derived growth factor]] receptor).
*


In [[chronic myelogenous leukemia]], the [[Philadelphia chromosome]] leads to a fusion protein of ''abl'' with ''bcr'' (''breakpoint cluster region''), termed ''bcr-abl''. As this is now a continuously active [[tyrosine kinase]], imatinib is used to decrease ''bcr-abl'' activity.
<!--Patient Counseling Information-->


[[Image:Mechanism imatinib.jpg||left|Mechanism of action of imatinib]]
|fdaPatientInfo=
The [[active site]]s of tyrosine kinases each have a [[binding site]] for [[adenosine triphosphate|ATP]]. The enzymatic activity [[Catalysis|catalyzed]] by a tyrosine kinase is the transfer of the terminal [[phosphate]] from ATP to [[tyrosine]] residues on its [[Substrate (biochemistry)|substrates]], a process known as protein tyrosine [[phosphorylation]].  Imatinib works by binding to the ATP binding site of ''bcr-abl'' and inhibiting the enzyme activity of the protein [[enzyme inhibitor|competitively]]. Imatinib is quite selective for ''bcr-abl'' &ndash; it does also inhibit other targets mentioned above (c-kit and PDGF-R), but no other known  [[tyrosine kinase]]s. Imatinib also inhibits the ''abl'' protein of non-cancer cells but cells normally have additional redundant tyrosine kinases which allow them to continue to function even if ''abl'' tyrosine kinase is inhibited. Some [[Cancer cell|tumour cells]], however, have a dependence on ''bcr-abl''.<ref name="DeiningerDruker">Deininger M, Druker BJ. Specific Targeted Therapy of Chronic Myelogenous Leukemia with Imatinib. Pharmacol Rev 2003;55:401-423. PMID 12869662.</ref> Inhibition of the ''bcr-abl'' tyrosine kinase also stimulates its entry in to the nucleus, where it is unable to perform any of its normal anti-[[apoptosis|apoptopic]] functions.<ref>Vigneri P, Wang JY. Induction of apoptosis in chronic myelogenous leukemia cells through nuclear entrapment of BCR-ABL tyrosine kinase. Nat Med 2001:7:228-234. PMID 11175855</ref>


==Uses==
There is limited information regarding <i>Patient Counseling Information</i> of {{PAGENAME}} in the drug label.
[[Image:Glivec 400mg.jpg|thumb|left|Glivec / Gleevec]]
Imatinib is used in  [[chronic myelogenous leukemia]] (CML), [[gastrointestinal stromal tumor]]s (GISTs) and a number of other [[malignancy|malignancies]].  One study demonstrated that Imatinib mesylate was effective in patients with systemic [[mastocytosis]], including those who had the D816V mutation in c-Kit.<ref>Droogendijk HJ, Kluin-Nelemans HJ, van Doormaal JJ, Oranje AP, van de Loosdrecht AA, van Daele PL. Imatinib mesylate in the treatment of systemic mastocytosis: a phase II trial.  Cancer. 2006 Jul 15;107(2):345-51. PMID 16779792</ref> Experience has shown, however, that imatinib is much less effective in patients with this mutation, and patients with the mutation comprise nearly 90% of cases of mastocytosis.  Early clinical trials also show its potential for treatment of hypereosinophilic syndrome and [[dermatofibrosarcoma protuberans]].


In [[laboratory]] settings, imatinib is being used as an experimental agent to suppress [[platelet-derived growth factor]] (PDGF) by inhibiting its receptor (PDGF-Rβ). One of its effects is delaying [[atherosclerosis]] in [[mouse|mice]] with [[diabetes mellitus|diabetes]].<ref>Lassila M, Allen TJ, Cao Z, Thallas V, Jandeleit-Dahm KA, Candido R, Cooper ME. Imatinib attenuates diabetes-associated atherosclerosis. Arterioscler Thromb Vasc Biol 2004;24:935-42. PMID 14988091</ref>
<!--Precautions with Alcohol-->


Recent mouse animal studies at [[Emory University]] in Atlanta have suggested that imatinib and related drugs may be useful in treating [[smallpox]], should an outbreak ever occur.<ref>Reeves P, Bommarius B, Lebeis S, McNulty S, Christensen J, Swimm A, Chahroudi A, Chavan R, Feinberg M, Veach D, Bornmann W, Sherman M, Kalman D (2005). Disabling poxvirus pathogenesis by inhibition of Abl-family tyrosine kinases. Nat Med 11 (7): 731-9. PMID 15980865</ref>
|alcohol=


Gleevec is also being used in the treatment of certain brain tumors to include high grade glioblastoma.
* Alcohol-{{PAGENAME}} interaction has not been established. Talk to your doctor about the effects of taking alcohol with this medication.


==Tolerability and side effects==
<!--Brand Names-->
[[Image:Bcr abl STI 1IEP.png|left|thumb|<em style="color:green;font-style:normal">bcr-abl kinase</em>, which causes [[Chronic myelogenous leukemia|CML]], inhibited by <em style="color:red;font-style:normal">imatinib</em> (small molecule).]]
In the [[United States]], the [[Food and Drug Administration]] has approved imatinib as first-line treatment for CML.<ref name="DeiningerDruker"> </ref> Imatinib has passed through Phase III trials for CML, and has been shown to be more effective than the previous standard treatment of [[interferon|α-interferon]] and [[cytarabine]]. Although the long-term [[Adverse effect (medicine)|side effects]] of imatinib have not yet been ascertained, research suggests that it is generally very well tolerated (eg. liver toxicity was much less than predicted). Broadly, side effects such as [[edema]], [[nausea]], [[rash]] and musculoskeletal pain are common but mild.


Severe [[congestive cardiac failure]] is an uncommon but recognised side effect of imatinib and mice treated with large doses of imatinib show toxic damage to their myocardium.<ref>{{cite journal | title=Cardiotoxicity of the cancer therapeutic agent imatinib mesylate | author=Risto Kerkelä, Luanda Grazette, Rinat Yacobi, ''et al.'' | journal=Nature Med | volume=12 | pages=908&ndash;16 }}</ref>
|brandNames=


== Metabolism ==
* ®<ref>{{Cite web | title = | url = }}</ref>
Metabolism of imatinib occurs in the liver and the main metabolite, ''N''-demethylated [[piperazine]] derivative, is also active. The major route of elimination is in the bile, only a small portion is excreted in the urine. Most of imatinib is eliminated as metabolites, only 25% is eliminated unchanged. The [[half-life|half-lives]] of imatinib and its main metabolite are 18 and 40 hours, respectively.


==History==
<!--Look-Alike Drug Names-->
Imatinib was identified in the late [[1990s]] by Novartis chemists.  Dr Brian J. Druker led many of the key clinical trials confirming the efficacy of imatinib in [[chronic myelogenous leukemia|CML]]. Its development is the template for [[rational drug design]]. Soon after identification of the ''bcr-abl'' target, the search for an inhibitor began. Chemists used a [[High-throughput screening|high-throughput screen]] of chemical libraries to identify the molecule 2-phenylaminopyrimidine. This lead compound was then tested and modified by the introduction of methyl and benzamide groups to give it enhanced binding properties, resulting in imatinib.<ref>Druker BJ, Lydon NB. Lessons learned from the development of an Abl tyrosine kinase inhibitor for chronic myelogenous leukemia. [http://www.jci.org/cgi/content/full/105/1/3 J Clin Invest 2000;105:3-7]. PMID 10619854</ref>


Gleevec received FDA approval in May 2001. On the same month it made the cover of ''[[Time (magazine)|TIME]]'' magazine as the "magic bullet" to cure cancer.
|lookAlike=


Gleevec, which costs $32,000 per year for a 400 mg/day dose, is often cited as an example of pharmaceutical industry innovation that justifies the high cost of drugs. [[Marcia Angell]] and Arnold S. Relman argue that Gleevec is actually an example of the contribution of taxpayer-supported research and of industry inaction. Novartis patented several tyrosine kinase inhibitors, and lost interest, they write. Drucker tested several, and imatinib was the most potent, and unusually, had almost no effect on normal cells. Novartis had "little corporate enthusiasm," they write, but Drucker persisted<ref>[http://www.commercialalert.org/relmanangell.pdf]How the drug industry distorts medicine and politics: America’s Other Drug Problem, By Arnold S. Relman and Marcia Angell, New Republic, December 16, 2002</ref>.
* A® — B®<ref name="www.ismp.org">{{Cite web  | last =  | first =  | title = http://www.ismp.org | url = http://www.ismp.org | publisher =  | date =  }}</ref>


In [[2007]], imatinib became a [[test case]] through which Novartis challenged [[India|India's]] patent laws. This would make it harder for Indian companies to produce generic versions of drugs still manufactured under patent elsewhere in the world. Organisations such as [[Médecins Sans Frontières]] argue that a change in law would make it impossible for Indian companies to produce cheap antiretrovirals (anti-AIDS medication), endangering access to these drugs in Third World countries.<ref>[[Médecins Sans Frontières]]. ''[http://www.doctorswithoutborders.org/pr/2006/09-26-2006_1.cfm "As Novartis Challenges India's Patent Law, MSF Warns Access to Medicines Is Under Threat"]'', [[2006-09-26]]. Accessed [[2006-02-10]].</ref>
<!--Drug Shortage Status-->


==References==
|drugShortage=
{{Reflist|2}}
}}


==See also==
<!--Pill Image-->
*[[History of cancer chemotherapy]]


== External link ==
{{PillImage
* [http://www.gleevec.com Glivec commercial website (Novartis)]
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{{Chemotherapeutic agents}}
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[[Category:Cancer treatments]]
{{LabelImage
[[Category:Tyrosine kinase inhibitors]]
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[[de:Imatinib]]
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Revision as of 18:57, 1 August 2014

Imatinib
Black Box Warning
Adult Indications & Dosage
Pediatric Indications & Dosage
Contraindications
Warnings & Precautions
Adverse Reactions
Drug Interactions
Use in Specific Populations
Administration & Monitoring
Overdosage
Pharmacology
Clinical Studies
How Supplied
Images
Patient Counseling Information
Precautions with Alcohol
Brand Names
Look-Alike Names

Editor-In-Chief: C. Michael Gibson, M.S., M.D. [1]; Associate Editor(s)-in-Chief: Vignesh Ponnusamy, M.B.B.S. [2]

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Black Box Warning

Title
See full prescribing information for complete Boxed Warning.
ConditionName:
  • Content

Overview

Imatinib is a that is FDA approved for the {{{indicationType}}} of . There is a Black Box Warning for this drug as shown here. Common adverse reactions include .

Adult Indications and Dosage

FDA-Labeled Indications and Dosage (Adult)

Condition1
  • Dosing Information
  • Dosage
Condition2
  • Dosing Information
  • Dosage
Condition3
  • Dosing Information
  • Dosage
Condition4
  • Dosing Information
  • Dosage

Off-Label Use and Dosage (Adult)

Guideline-Supported Use

Condition1
  • Developed by:
  • Class of Recommendation:
  • Strength of Evidence:
  • Dosing Information
  • Dosage
Condition2

There is limited information regarding Off-Label Guideline-Supported Use of Imatinib in adult patients.

Non–Guideline-Supported Use

Condition1
  • Dosing Information
  • Dosage
Condition2

There is limited information regarding Off-Label Non–Guideline-Supported Use of Imatinib in adult patients.

Pediatric Indications and Dosage

FDA-Labeled Indications and Dosage (Pediatric)

Condition1
  • Dosing Information
  • Dosage
Condition2

There is limited information regarding FDA-Labeled Use of Imatinib in pediatric patients.

Off-Label Use and Dosage (Pediatric)

Guideline-Supported Use

Condition1
  • Developed by:
  • Class of Recommendation:
  • Strength of Evidence:
  • Dosing Information
  • Dosage
Condition2

There is limited information regarding Off-Label Guideline-Supported Use of Imatinib in pediatric patients.

Non–Guideline-Supported Use

Condition1
  • Dosing Information
  • Dosage
Condition2

There is limited information regarding Off-Label Non–Guideline-Supported Use of Imatinib in pediatric patients.

Contraindications

  • Condition1

Warnings

Title
See full prescribing information for complete Boxed Warning.
ConditionName:
  • Content
  • Description

Precautions

  • Description

Adverse Reactions

Clinical Trials Experience

There is limited information regarding Clinical Trial Experience of Imatinib in the drug label.

Body as a Whole
Cardiovascular
Digestive
Endocrine
Hematologic and Lymphatic
Metabolic and Nutritional
Musculoskeletal
Neurologic
Respiratory
Skin and Hypersensitivy Reactions
Special Senses
Urogenital
Miscellaneous

Postmarketing Experience

There is limited information regarding Postmarketing Experience of Imatinib in the drug label.

Body as a Whole
Cardiovascular
Digestive
Endocrine
Hematologic and Lymphatic
Metabolic and Nutritional
Musculoskeletal
Neurologic
Respiratory
Skin and Hypersensitivy Reactions
Special Senses
Urogenital
Miscellaneous

Drug Interactions

  • Drug
  • Description

Use in Specific Populations

Pregnancy

Pregnancy Category (FDA):

  • Pregnancy Category


Pregnancy Category (AUS):

  • Australian Drug Evaluation Committee (ADEC) Pregnancy Category

There is no Australian Drug Evaluation Committee (ADEC) guidance on usage of Imatinib in women who are pregnant.

Labor and Delivery

There is no FDA guidance on use of Imatinib during labor and delivery.

Nursing Mothers

There is no FDA guidance on the use of Imatinib with respect to nursing mothers.

Pediatric Use

There is no FDA guidance on the use of Imatinib with respect to pediatric patients.

Geriatic Use

There is no FDA guidance on the use of Imatinib with respect to geriatric patients.

Gender

There is no FDA guidance on the use of Imatinib with respect to specific gender populations.

Race

There is no FDA guidance on the use of Imatinib with respect to specific racial populations.

Renal Impairment

There is no FDA guidance on the use of Imatinib in patients with renal impairment.

Hepatic Impairment

There is no FDA guidance on the use of Imatinib in patients with hepatic impairment.

Females of Reproductive Potential and Males

There is no FDA guidance on the use of Imatinib in women of reproductive potentials and males.

Immunocompromised Patients

There is no FDA guidance one the use of Imatinib in patients who are immunocompromised.

Administration and Monitoring

Administration

  • Oral
  • Intravenous

Monitoring

There is limited information regarding Monitoring of Imatinib in the drug label.

  • Description

IV Compatibility

There is limited information regarding IV Compatibility of Imatinib in the drug label.

Overdosage

Acute Overdose

Signs and Symptoms

  • Description

Management

  • Description

Chronic Overdose

There is limited information regarding Chronic Overdose of Imatinib in the drug label.

Pharmacology

There is limited information regarding Imatinib Pharmacology in the drug label.

Mechanism of Action

Structure

This image is provided by the National Library of Medicine.

Pharmacodynamics

There is limited information regarding Pharmacodynamics of Imatinib in the drug label.

Pharmacokinetics

There is limited information regarding Pharmacokinetics of Imatinib in the drug label.

Nonclinical Toxicology

There is limited information regarding Nonclinical Toxicology of Imatinib in the drug label.

Clinical Studies

There is limited information regarding Clinical Studies of Imatinib in the drug label.

How Supplied

Storage

There is limited information regarding Imatinib Storage in the drug label.

Images

Drug Images

{{#ask: Page Name::Imatinib |?Pill Name |?Drug Name |?Pill Ingred |?Pill Imprint |?Pill Dosage |?Pill Color |?Pill Shape |?Pill Size (mm) |?Pill Scoring |?NDC |?Drug Author |format=template |template=DrugPageImages |mainlabel=- |sort=Pill Name }}

Package and Label Display Panel

{{#ask: Label Page::Imatinib |?Label Name |format=template |template=DrugLabelImages |mainlabel=- |sort=Label Page }}

Patient Counseling Information

There is limited information regarding Patient Counseling Information of Imatinib in the drug label.

Precautions with Alcohol

  • Alcohol-Imatinib interaction has not been established. Talk to your doctor about the effects of taking alcohol with this medication.

Brand Names

Look-Alike Drug Names

Drug Shortage Status

Price

References

The contents of this FDA label are provided by the National Library of Medicine.

  1. ↑ Empty citation (help)
  2. ↑ "http://www.ismp.org". External link in |title= (help)


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