Wikipedia:WikiProject Chemicals/Chembox validation/VerifiedDataSandbox and Ifosfamide: Difference between pages

{{short description|Chemotherapy medication}}

| Watchedfields = changed

| verifiedrevid = 461936381

| IUPAC_name = ''N'',3-Bis(2-chloroethyl)-1,3,2-oxazaphosphinan-2-amide 2-oxide

| image = (R,S)-ifosfamide.svg

| width = 275

| image2 = Ifosfamide-3D-balls.png

| width2 = 220

| caption = (''R'')-(+)- and (''S'')-(−)-ifosfamide (top),<br /> (''S'')-(−)-ifosfamide (bottom)

| pronounce = {{IPAc-en|aɪ|ˈ|f|ɒ|s|f|ə|m|aɪ|d}}

| tradename = Ifex, others

| legal_AU = S4

| legal_CA = Rx-only

| legal_NZ_comment = Prescription medicine

| legal_UK = POM

| legal_US = Rx-only

| pregnancy_AU = D

| pregnancy_US = D

| elimination_half-life = 60–80% in 72 hours

| IUPHAR_ligand = 7201

| C=7 | H=15 | Cl=2 | N=2 | O=2 | P=1

| SMILES = O=P1(OCCCN1CCCl)NCCCl

<!-- Definitio and medical uses -->

'''Ifosfamide''' ('''IFO'''), sold under the brand name '''Ifex''' among others, is a [[chemotherapy medication]] used to treat a number of types of cancer.<ref name=AHFS2016/> This includes [[testicular cancer]], [[soft tissue sarcoma]], [[osteosarcoma]], [[bladder cancer]], [[small cell lung cancer]], [[cervical cancer]], and [[ovarian cancer]].<ref name=AHFS2016/> It is administered by [[intravenous|injection into a vein]].<ref name=AHFS2016>{{cite web|title=Ifosfamide|url=https://www.drugs.com/monograph/ifosfamide.html|publisher=The American Society of Health-System Pharmacists|access-date=8 December 2016|url-status=live|archive-url=https://web.archive.org/web/20170507031629/https://www.drugs.com/monograph/ifosfamide.html|archive-date=7 May 2017}}</ref>

<!-- Side effect and mechanisms -->

Common side effects include hair loss, vomiting, [[hematuria|blood in the urine]], infections, and [[kidney problems]].<ref name=AHFS2016/> Other severe side effects include [[bone marrow suppression]] and [[decreased level of consciousness]].<ref name=AHFS2016/> Use during [[pregnancy]] will likely result in harm to the baby.<ref name=AHFS2016/> Ifosfamide is in the [[alkylating antineoplastic agent|alkylating agent]] and [[nitrogen mustard]] family of medications.<ref name=AHFS2016/><ref>{{cite book| vauthors = Dowd FJ, Johnson B, Mariotti A |title=Pharmacology and Therapeutics for Dentistry|date=2016|publisher=Elsevier Health Sciences|isbn=9780323445955|page=533|edition=7th |url=https://books.google.com/books?id=6xT7DAAAQBAJ&pg=PA533|language=en|url-status=live|archive-url=https://web.archive.org/web/20170911002643/https://books.google.ca/books?id=6xT7DAAAQBAJ&pg=PA533|archive-date=2017-09-11}}</ref> It works by disrupting the duplication of [[DNA]] and the creation of [[RNA]].<ref name=AHFS2016/>

<!-- History, society and culture -->

Ifosfamide was approved for medical use in the United States in 1987.<ref name=AHFS2016/> It is on the [[WHO Model List of Essential Medicines|World Health Organization's List of Essential Medicines]].<ref name="WHO21st">{{cite book | vauthors = ((World Health Organization)) | title = World Health Organization model list of essential medicines: 21st list 2019 | year = 2019 | hdl = 10665/325771 | author-link = World Health Organization | publisher = World Health Organization | location = Geneva | id = WHO/MVP/EMP/IAU/2019.06. License: CC BY-NC-SA 3.0 IGO | hdl-access=free }}</ref>

==Medical uses==

It is given as a treatment for a variety of [[cancer]]s, including:

* [[Testicular cancer]]

* [[Breast cancer]]

* [[Lymphoma]] (Hodgkin and non-Hodgkin)

* [[Soft tissue sarcoma]]

* [[Osteosarcoma]] or [[bone tumor]]

* [[Lung cancer]]

* [[Cervical cancer]]

* [[Ovarian cancer]]

===Administration===

It is a white [[Powder (substance)|powder]] which, when prepared for use in [[chemotherapy]], becomes a clear, colorless fluid. The delivery is [[intravenous]].

Ifosfamide is often used in conjunction with [[mesna]] to avoid [[internal bleeding]] in the patient, in particular [[hemorrhagic cystitis]].

Ifosfamide is given quickly, and in some cases can be given as quickly as an hour.

==Side effects==

Hemorrhagic cystitis is rare when ifosfamide is given with [[mesna]]. A common and dose-limiting side effect is [[encephalopathy]] (brain dysfunction).<ref name=Ajithkumar/> It occurs in some form in up to 50% of people receiving the agent. The reaction is probably mediated by [[chloroacetaldehyde]], one of the breakdown products of the ifosfamide molecule, which has chemical properties similar to [[acetaldehyde]] and [[chloral hydrate]]. The symptoms of ifosfamide encephalopathy can range from mild (difficulty concentrating, fatigue), to moderate ([[delirium]], [[psychosis]]), to severe ([[Status epilepticus#Nonconvulsive|nonconvulsive status epilepticus]] or [[coma]]). In children, this can interfere with neurological development. Apart from the brain, ifosfamide can also affect peripheral nerves. The severity of the reaction can be classified according to either the [[National Cancer Institute]] or the Meanwell criteria (grade I–IV). Previous brain problems and low levels of [[albumin]] in the blood increase the likelihood of ifosfamide encephalopathy. In most cases, the reaction resolves spontaneously within 72 hours. If it develops during an infusion of the drug, discontinuing the infusion is advised. The most effective treatment for severe (grade III–IV) encephalopathy is an intravenous solution of [[methylene blue]], which appears to shorten the duration of encephalopathy; the exact mechanism of action of methylene blue is unclear. In some cases, methylene blue may be used as a prophylaxis before further doses of ifosfamide are administered. Other treatments include albumin and [[thiamine]], and [[Kidney dialysis|dialysis]] as a rescue modality.<ref name=Ajithkumar>{{cite journal | vauthors = Ajithkumar T, Parkinson C, Shamshad F, Murray P | title = Ifosfamide encephalopathy | journal = Clinical Oncology | volume = 19 | issue = 2 | pages = 108–114 | date = March 2007 | pmid = 17355105 | doi = 10.1016/j.clon.2006.11.003 }}</ref>

Ifosfamide may also cause a [[normal anion gap acidosis]], specifically [[renal tubular acidosis]] type 2.<ref>{{cite book|title=The Washington Manual of Therapeutics|year=2010|publisher=Wolters Kluwer {{!}} Lippincott Williams & Wilkins|pages=407|edition=33| veditors = Foster C }}</ref>

== References ==

{{Reflist}}

== External links ==

* [https://web.archive.org/web/20060602101647/http://www.cancer.org/docroot/CDG/content/CDG_ifosfamide.asp ACS Drug Guide: Ifosfamide]

* [http://www.bidmc.harvard.edu/display.asp?node_id=4535 Harvard Medical School Health Information on Ifosfamide]

* [https://web.archive.org/web/20150314044442/http://www.bccancer.bc.ca/HPI/DrugDatabase/DrugIndexPro/Ifosfamide.htm BC Cancer Agency Ifosamide Information] (Professional)

* [https://web.archive.org/web/20020217134834/http://www.rxlist.com/cgi/generic2/ifosfamide.htm RxList Online Drug Index Ifosamide Listing]

* {{cite web | url = https://druginfo.nlm.nih.gov/drugportal/name/ifosfamide | publisher = U.S. National Library of Medicine | work = Drug Information Portal | title = Ifosfamide }}

{{Chemotherapeutic agents}}

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[[Category:Oxazaphosphinans]]

[[Category:Organochlorides]]

[[Category:Nitrogen mustards]]

[[Category:Phosphorodiamidates]]

[[Category:Chloroethyl compounds]]

[[Category:World Health Organization essential medicines]]

[[Category:Wikipedia medicine articles ready to translate]]