Methotrexate (injection): Difference between revisions

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{{Redirect3|Amethopterin|Not to be confused with [[aminopterin]]}}
{{DrugProjectFormSinglePage
{{Drugbox|
|authorTag=
| image = Methotrexate.png
 
| width = 250
 
| IUPAC_name = (''S'')-2-(4-(((2,4-diaminopteridin-6-yl)<br />[[methyl]])methylamino)benzamido)<br />pentanedioic acid
<!--Overview-->
| ATC_prefix=L01
 
| ATC_suffix=BA01
|genericName=
| ATC_supplemental={{ATC|L04|AX03}}
 
| PubChem=126941
 
| DrugBank=APRD00353
 
| CAS_number = 59-05-2
|aOrAn=
| C=20 | H=22 | N=8 | O=5
 
| molecular_weight = 454.44 g/mol
a
| bioavailability = 17–90%
 
| metabolism = [[hepatic]]
|drugClass=
| elimination_half-life = 3–15 hours (dose dependent)
 
| excretion = [[renal]] 48–100%
 
| pregnancy_AU = D
 
| pregnancy_US = X
|indication=
| pregnancy_category =  
 
| legal_AU = S4
 
| legal_UK =POM
 
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| routes_of_administration = [[Wiktionary:oral|oral]], [[intravenous|IV]], [[intramuscular|IM]], [[subcutaneous|SC]], [[intrathecal]]
 
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=====Condition1=====
 
* Developed by:
 
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* Strength of Evidence:
 
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=====Condition1=====
 
* Dosing Information
 
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There is limited information regarding <i>Off-Label Non–Guideline-Supported Use</i> of {{PAGENAME}} in adult patients.
 
<!--Pediatric Indications and Dosage-->
 
<!--FDA-Labeled Indications and Dosage (Pediatric)-->
 
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=====Condition1=====
 
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<!--Guideline-Supported Use (Pediatric)-->
 
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=====Condition1=====
 
* Developed by:
 
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<!--Non–Guideline-Supported Use (Pediatric)-->
 
|offLabelPedNoGuideSupport=
 
=====Condition1=====
 
* Dosing Information
 
:* Dosage
 
=====Condition2=====
 
There is limited information regarding <i>Off-Label Non–Guideline-Supported Use</i> of {{PAGENAME}} in pediatric patients.
 
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=====Cardiovascular=====
 
 
 
=====Digestive=====
 
 
 
=====Endocrine=====
 
 
 
=====Hematologic and Lymphatic=====
 
 
 
=====Metabolic and Nutritional=====
 
 
 
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=====Neurologic=====
 
 
 
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There is no FDA guidance one the use of {{PAGENAME}} in patients who are immunocompromised.
 
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* Oral
 
* Intravenous
 
|monitoring=
 
There is limited information regarding <i>Monitoring</i> of {{PAGENAME}} in the drug label.
 
* Description
 
<!--IV Compatibility-->
 
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There is limited information regarding <i>IV Compatibility</i> of {{PAGENAME}} in the drug label.
 
<!--Overdosage-->
 
|overdose=
 
===Acute Overdose===
 
====Signs and Symptoms====
 
* Description
 
====Management====
 
* Description
 
===Chronic Overdose===
 
There is limited information regarding <i>Chronic Overdose</i> of {{PAGENAME}} in the drug label.
 
<!--Pharmacology-->
 
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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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|PK=
 
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.
 
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==Overview==
<!--How Supplied-->
'''Methotrexate''' ([[International Nonproprietary Name|rINN]]) ([[International Phonetic Alphabet|IPA]]: {{IPA|[mɛθəˈtrɛkseɪt]}}), abbreviated '''MTX''' and formerly known as '''amethopterin''', is an [[antimetabolite]] and antifolate drug used in treatment of [[cancer]] and [[autoimmune disease]]s. It acts by inhibiting the metabolism of [[folic acid]]. Methotrexate replaced the more powerful and toxic antifolate [[aminopterin]], and the two should not be confused with each other.
==History==
Methotrexate originated in the 1940s when [[Sidney Farber]] at [[Children's Hospital Boston]] was testing the effects of [[folic acid]] on cancer. This inspired chemists at the drug company Lederle to start looking for antimetabolites resembling folate. The result was methotrexate, which was developed in 1948 by [[Yellapragada Subbarao]] from Lederle. Methotrexate gained [[Food and Drug Administration]] (FDA) approval as an oncology drug in 1953.


==Uses==
|howSupplied=
===In chemotherapy===
Methotrexate was originally used, as part of combination chemotherapy regimens, to treat many kinds of [[cancer]]s. It is still the mainstay for the treatment of many [[neoplasm|neoplastic]] disorders including [[acute lymphoblastic leukemia]].


===Other uses===
*
More recently it has come into use as a treatment for some [[autoimmune diseases]], including [[ankylosing spondylitis]], [[Crohn's disease]], [[psoriasis]], [[psoriatic arthritis]], and [[rheumatoid arthritis]] (see [[disease-modifying antirheumatic drug]]s). A parallel use with [[Tumor necrosis factor-alpha|TNFα]] blockers as [[infliximab]] or [[etanercept]] has been shown to markedly improve symptoms.<ref>{{cite journal | author=Klareskog L, van der Heijde D, de Jager JP, Gough A, Kalden J, Malaise M, Martin Mola E, Pavelka K, Sany J, Settas L, Wajdula J, Pedersen R, Fatenejad S, Sanda M | title=Therapeutic effect of the combination of etanercept and methotrexate compared with each treatment alone in patients with rheumatoid arthritis: double-blind randomised controlled trial | journal=Lancet | year=2004 | pages=675-81 | volume=363 | issue=9410 | id=PMID 15001324}}</ref>


Although not indicated for this use, methotrexate is also sometimes used (generally in combination with [[misoprostol]]) to terminate early [[pregnancy|pregnancies]], particularly [[ectopic pregnancy|ectopic pregnancies]].
<!--Patient Counseling Information-->


==Pharmacokinetics==
|fdaPatientInfo=
Methotrexate is a weak dicarboxylic acid with [[Acid dissociation constant|pKa]] 4.8 and 5.5, and thus it is mostly [[Ionization|ionized]] at physiologic pH.  Oral absorption is saturatable and thus dose-dependent, with doses less than 40mg/M2 having 42% bioavailability and doses greater than 40mg/M2 only 18%.  Mean oral bioavailability is 33% (13-76% range), and there is no clear benefit to subdividing an oral dose.  Mean intramuscular bioavailability is 76%.


Methotrexate is metabolized by intestinal bacteria to the inactive metabolite 4-amino-4-deoxy-N-methylpteroic acid (DAMPA) and accounts for less than 5% loss of the oral dose.
There is limited information regarding <i>Patient Counseling Information</i> of {{PAGENAME}} in the drug label.


Factors that decrease absorption include food, oral non-absorbable antibiotics (e.g. vancomycin, neomycin, and bacitracin), and more rapid transit through the Gastrointestinal (GI) tract such as diarrhea, while slower transit time in the GI tract from constipation will increase absorption.
<!--Precautions with Alcohol-->


==Administration==
|alcohol=
It can be taken orally or administered by injection (subcutaneous, [[intramuscular]], [[intravenous]] or [[intrathecal]]). Although daily preparations are occasionally used, most patients take weekly doses, which decreases the risk of certain side-effects.


==Adverse effects==
* Alcohol-{{PAGENAME}} interaction has not been established. Talk to your doctor about the effects of taking alcohol with this medication.


Possible side effects can include [[anemia]], [[neutropenia]], increased risk of [[bruising]], [[nausea]] and [[vomiting]], [[dermatitis]] and [[diarrhea]].  A small percentage of patients develop [[hepatitis]], and there is an increased risk of [[pulmonary fibrosis]].
<!--Brand Names-->


The higher doses of methotrexate often used in cancer chemotherapy can cause toxic effects to the rapidly-dividing cells of [[bone marrow]] and [[gastrointestinal]] [[mucosa]]. The resulting myelosuppression and [[mucositis]] are often prevented (termed methotrexate "rescue") by using [[folinic acid]] supplements (not to be confused with [[folic acid]]).
|brandNames=


Methotrexate is a highly [[teratogenic]] drug and categorized in [[Pregnancy category|Pregnancy Category X]] by the FDA. Women must not take the drug during pregnancy, if there is a risk of becoming pregnant, or if they are breastfeeding. Men who are trying to get their partner pregnant must also not take the drug. To engage in any of these activities (after discontinuing the drug), women must wait until the end of a full ovulation cycle and men must wait three months.
* ®<ref>{{Cite web | title =  | url =  }}</ref>


There is a risk of a severe adverse reaction if [[penicillin]] is prescribed alongside methotrexate.
<!--Look-Alike Drug Names-->


Interestingly, there have also been some reports of central nervous system reactions to methotrexate especially when given via the intrathecal route which include myelopathies and leucoencephalopathies.
|lookAlike=


==Mode of action==
* A® — B®<ref name="www.ismp.org">{{Cite web  | last = | first = | title = http://www.ismp.org | url = http://www.ismp.org | publisher =  | date = }}</ref>
Methotrexate competitively and reversibly inhibits [[dihydrofolate reductase]] (DHFR), an [[enzyme]] that is part of the [[folate]] synthesis metabolic pathway. The affinity of methotrexate for DHFR is about one thousand-fold that of folate for DHFR. Dihydrofolate reductase catalyses the conversion of [[dihydrofolate]] to the active [[tetrahydrofolate]]. Folic acid is needed for the ''de novo'' synthesis of the [[nucleoside]] [[thymidine]], required for [[DNA synthesis]]. Also, folate is needed for purine base synthesis, so all purine synthesis will be inhibited.  Methotrexate, therefore, inhibits the synthesis of [[DNA]], [[RNA]], thymidylates, and [[protein]]s.


Methotrexate acts specifically during DNA and RNA synthesis, and thus it is cytotoxic during the S-phase of the [[cell cycle]].  Logically, it therefore has a greater toxic effect on rapidly dividing cells (such as [[malignant]] and [[myeloid]] cells, and GI & oral mucosa), which replicate their DNA more frequently, and thus inhibits the growth and proliferation of these non-cancerous cells as well causing side effects listed above.
<!--Drug Shortage Status-->


Lower doses of methotrexate have been shown to be very effective for the management of [[rheumatoid arthritis]] and [[psoriasis]]. In these cases inhibition of [[dihydrofolate reductase]] (DHFR) is not thought to be the main mechanism, rather the inhibition of [[enzyme]]s involved in purine metabolism, leading to accumulation of [[adenosine]], or the inhibition of [[T cell]] activation and suppression of [[intercellular adhesion molecule]] expression by [[T cell]]s.<ref>{{cite journal | author=Johnston A, Gudjonsson JE, Sigmundsdottir H, Ludviksson BR, Valdimarsson H; | title=The anti-inflammatory action of methotrexate is not mediated by lymphocyte apoptosis, but by the suppression of activation and adhesion molecules | journal=Clin Immunol. | volume=114 | issue=Feb.  | year=2005 | pages=154-163 | id=PMID 15639649}}</ref>
|drugShortage=
}}


==References==
<!--Pill Image-->
{{reflist|2}}


{{Chemotherapeutic agents}}
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[[Category:Drugs]]
{{LabelImage
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[[Category:Dihydrofolate reductase inhibitors]]
 
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[[de:Methotrexat]]
<!--Category-->
[[es:Metotrexato]]
[[fr:Méthotrexate]]
[[hu:Metotrexát]]
[[nl:Methotrexaat]]
[[ja:メトトレキサート]]
[[pl:Metotreksat]]
[[ru:Метотрексат]]
[[zh-yue:甲氨喋呤]]


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Revision as of 16:37, 27 October 2014

Methotrexate (injection)
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];

Disclaimer

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Black Box Warning

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

Overview

Methotrexate (injection) 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 Methotrexate (injection) in adult patients.

Non–Guideline-Supported Use

Condition1
  • Dosing Information
  • Dosage
Condition2

There is limited information regarding Off-Label Non–Guideline-Supported Use of Methotrexate (injection) 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 Methotrexate (injection) 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 Methotrexate (injection) in pediatric patients.

Non–Guideline-Supported Use

Condition1
  • Dosing Information
  • Dosage
Condition2

There is limited information regarding Off-Label Non–Guideline-Supported Use of Methotrexate (injection) 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 Methotrexate (injection) 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 Methotrexate (injection) 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 Methotrexate (injection) in women who are pregnant.

Labor and Delivery

There is no FDA guidance on use of Methotrexate (injection) during labor and delivery.

Nursing Mothers

There is no FDA guidance on the use of Methotrexate (injection) with respect to nursing mothers.

Pediatric Use

There is no FDA guidance on the use of Methotrexate (injection) with respect to pediatric patients.

Geriatic Use

There is no FDA guidance on the use of Methotrexate (injection) with respect to geriatric patients.

Gender

There is no FDA guidance on the use of Methotrexate (injection) with respect to specific gender populations.

Race

There is no FDA guidance on the use of Methotrexate (injection) with respect to specific racial populations.

Renal Impairment

There is no FDA guidance on the use of Methotrexate (injection) in patients with renal impairment.

Hepatic Impairment

There is no FDA guidance on the use of Methotrexate (injection) in patients with hepatic impairment.

Females of Reproductive Potential and Males

There is no FDA guidance on the use of Methotrexate (injection) in women of reproductive potentials and males.

Immunocompromised Patients

There is no FDA guidance one the use of Methotrexate (injection) in patients who are immunocompromised.

Administration and Monitoring

Administration

  • Oral
  • Intravenous

Monitoring

There is limited information regarding Monitoring of Methotrexate (injection) in the drug label.

  • Description

IV Compatibility

There is limited information regarding IV Compatibility of Methotrexate (injection) in the drug label.

Overdosage

Acute Overdose

Signs and Symptoms

  • Description

Management

  • Description

Chronic Overdose

There is limited information regarding Chronic Overdose of Methotrexate (injection) in the drug label.

Pharmacology

There is limited information regarding Methotrexate (injection) Pharmacology in the drug label.

Mechanism of Action

Structure

File:Methotrexate (injection)01.png
This image is provided by the National Library of Medicine.

Pharmacodynamics

There is limited information regarding Pharmacodynamics of Methotrexate (injection) in the drug label.

Pharmacokinetics

There is limited information regarding Pharmacokinetics of Methotrexate (injection) in the drug label.

Nonclinical Toxicology

There is limited information regarding Nonclinical Toxicology of Methotrexate (injection) in the drug label.

Clinical Studies

There is limited information regarding Clinical Studies of Methotrexate (injection) in the drug label.

How Supplied

Storage

There is limited information regarding Methotrexate (injection) Storage in the drug label.

Images

Drug Images

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Package and Label Display Panel

{{#ask: Label Page::Methotrexate (injection) |?Label Name |format=template |template=DrugLabelImages |mainlabel=- |sort=Label Page }}

Patient Counseling Information

There is limited information regarding Patient Counseling Information of Methotrexate (injection) in the drug label.

Precautions with Alcohol

  • Alcohol-Methotrexate (injection) 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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