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Revision as of 11:23, 21 November 2011 editBeetstra (talk | contribs)Edit filter managers, Administrators172,031 edits Saving copy of the {{drugbox}} taken from revid 461468732 of page Pralatrexate for the Chem/Drugbox validation project (updated: 'ChEMBL', 'CAS_number').  Latest revision as of 02:54, 29 May 2023 edit Citation bot (talk | contribs)Bots5,420,519 edits Add: date. | Use this bot. Report bugs. | Suggested by Whywhenwhohow | #UCB_webform 388/534 
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{{Short description|Chemical compound}}
{{ambox | text = This page contains a copy of the infobox ({{tl|drugbox}}) taken from revid of page ] with values updated to verified values.}}
{{Drugbox {{Drugbox
| Verifiedfields = changed | Verifiedfields = changed
| verifiedrevid = 400859808 | verifiedrevid = 461750802
⚫ | IUPAC_name = ''N''-(4-{1-but-3-yn-1-yl}benzoyl)-<small>L</small>-glutamic acid
| image = Pralatrexate.png | image = Pralatrexate.png
| width = 300
| image2 = Pralatrexate ball-and-stick.png
| width2 = 300


<!--Clinical data--> <!--Clinical data-->
| tradename = | tradename = Folotyn
| Drugs.com = {{drugs.com|monograph|pralatrexate}} | Drugs.com = {{drugs.com|monograph|pralatrexate}}
| licence_US = Pralatrexate | licence_US = Pralatrexate
| pregnancy_AU = <!-- A / B1 / B2 / B3 / C / D / X --> | pregnancy_AU = <!-- A / B1 / B2 / B3 / C / D / X -->
⚫ | pregnancy_category =
| pregnancy_US = <!-- A / B / C / D / X -->
⚫ | routes_of_administration = ]
⚫ | pregnancy_category = D
⚫ | ATC_prefix = L01
| legal_AU = <!-- Unscheduled / S2 / S3 / S4 / S5 / S6 / S7 / S8 / S9 -->
⚫ | ATC_suffix = BA05
| legal_CA = <!-- / Schedule I, II, III, IV, V, VI, VII, VIII -->

| legal_AU = S4
| legal_AU_comment = <ref>{{cite web | title=Prescription medicines: registration of new chemical entities in Australia, 2015 | website=Therapeutic Goods Administration (TGA) | date=21 June 2022 | url=https://www.tga.gov.au/prescription-medicines-registration-new-chemical-entities-australia-2015 | access-date=10 April 2023}}</ref>
| legal_CA = Rx-only
| legal_CA_comment = <ref>{{cite web | title=Summary Basis of Decision (SBD) for Folotyn | website=] | date=23 October 2014 | url=https://hpr-rps.hres.ca/reg-content/summary-basis-decision-detailTwo.php?linkID=SBD00427&lang=en | access-date=29 May 2022}}</ref>
| legal_UK = <!-- GSL / P / POM / CD / Class A, B, C --> | legal_UK = <!-- GSL / P / POM / CD / Class A, B, C -->
| legal_US = Rx-only | legal_US = Rx-only
| legal_status = | legal_status =
⚫ | routes_of_administration = ]


<!--Pharmacokinetic data--> <!--Pharmacokinetic data-->
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| metabolism = | metabolism =
| elimination_half-life = | elimination_half-life =
| excretion = | excretion =


<!--Identifiers--> <!--Identifiers-->
| CAS_number_Ref = {{cascite|correct|??}} | CAS_number_Ref = {{cascite|changed|??}}
| CAS_number = <!-- blanked - oldvalue: 146464-95-1 --> | CAS_number = 146464-95-1
⚫ | ATC_prefix = L01
⚫ | ATC_suffix = BA05
| PubChem = 148121 | PubChem = 148121
| IUPHAR_ligand = 6840
| DrugBank_Ref = {{drugbankcite|correct|drugbank}} | DrugBank_Ref = {{drugbankcite|correct|drugbank}}
| DrugBank = | DrugBank = DB06813
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 130578 | ChemSpiderID = 130578
| UNII_Ref = {{fdacite|changed|FDA}} | UNII_Ref = {{fdacite|correct|FDA}}
| UNII = A8Q8I19Q20 | UNII = A8Q8I19Q20
| KEGG_Ref =
| KEGG = D05589
| ChEBI_Ref = {{ebicite|changed|EBI}}
| ChEBI = 71223
| ChEMBL_Ref = {{ebicite|changed|EBI}} | ChEMBL_Ref = {{ebicite|changed|EBI}}
| ChEMBL = <!-- blanked - oldvalue: 1201746 --> | ChEMBL = 1201746

<!--Chemical data-->
⚫ | IUPAC_name = ''N''-(4-<nowiki/>{1-but-3-yn-1-yl}benzoyl)-<small>L</small>-glutamic acid
| C=23 | H=23 | N=7 | O=5 | C=23 | H=23 | N=7 | O=5
| molecular_weight = 477.47 g/mol
| smiles = O=C(O)(NC(=O)c1ccc(cc1)C(CC#C)Cc2nc3c(nc2)nc(nc3N)N)CCC(=O)O | smiles = O=C(O)(NC(=O)c1ccc(cc1)C(CC#C)Cc2nc3c(nc2)nc(nc3N)N)CCC(=O)O
| InChI = 1/C23H23N7O5/c1-2-3-14(10-15-11-26-20-18(27-15)19(24)29-23(25)30-20)12-4-6-13(7-5-12)21(33)28-16(22(34)35)8-9-17(31)32/h1,4-7,11,14,16H,3,8-10H2,(H,28,33)(H,31,32)(H,34,35)(H4,24,25,26,29,30)/t14?,16-/m0/s1
| InChIKey = OGSBUKJUDHAQEA-WMCAAGNKBV
| StdInChI_Ref = {{stdinchicite|correct|chemspider}} | StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 1S/C23H23N7O5/c1-2-3-14(10-15-11-26-20-18(27-15)19(24)29-23(25)30-20)12-4-6-13(7-5-12)21(33)28-16(22(34)35)8-9-17(31)32/h1,4-7,11,14,16H,3,8-10H2,(H,28,33)(H,31,32)(H,34,35)(H4,24,25,26,29,30)/t14?,16-/m0/s1 | StdInChI = 1S/C23H23N7O5/c1-2-3-14(10-15-11-26-20-18(27-15)19(24)29-23(25)30-20)12-4-6-13(7-5-12)21(33)28-16(22(34)35)8-9-17(31)32/h1,4-7,11,14,16H,3,8-10H2,(H,28,33)(H,31,32)(H,34,35)(H4,24,25,26,29,30)/t14?,16-/m0/s1
Line 51: Line 60:
| StdInChIKey = OGSBUKJUDHAQEA-WMCAAGNKSA-N | StdInChIKey = OGSBUKJUDHAQEA-WMCAAGNKSA-N
}} }}

'''Pralatrexate''', sold under the brand name '''Folotyn''', is a medication used for the treatment of relapsed or refractory ] (PTCL).<ref name="Folotyn FDA label">{{cite web | title=Folotyn- pralatrexate injection | website=DailyMed | date=28 May 2020 | url=https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=9f3d9c4d-9386-4451-b712-0fbdc5478d8f | access-date=21 October 2020}}</ref><ref name="FDA PR" />

Pralatrexate was approved for medical use in the United States in September 2009, as the first treatment for Peripheral T-cell Lymphoma (PTCL), an often aggressive type of ].<ref name="FDA PR" /><ref name="FDA approval package" />

== Medical uses ==
Pralatrexate is ] for the treatment of people with relapsed or refractory peripheral T-cell lymphoma (PTCL).<ref name="Folotyn FDA label" />

==Mechanism==
Pralatrexate is a dihydrofolate reductase inhibitor.<ref name="Folotyn FDA label" />

==Discovery==
Research on this class of drugs began in the 1950s at ], where scientists were focused on developing new ] and antifolates that would be effective against ].<ref name="PR">{{cite web |url=http://ir.allos.com/phoenix.zhtml?c=125475&p=irol-newsArticle&ID=1277828&highlight |title=Allos Therapeutics: News |access-date=2010-09-20 |url-status=dead |archive-url=https://archive.today/20130117035243/http://ir.allos.com/phoenix.zhtml?c=125475&p=irol-newsArticle&ID=1277828&highlight |archive-date=2013-01-17 }}, Allos Therapeutics Press Release, "Allos Therapeutics' Pralatrexate Demonstrates Anticancer Activity in Multiple Cancer Cell Lines".</ref>

In the late 1970s, researchers at Memorial Sloan Kettering Cancer Center discovered that cancerous cells take in natural folate through a protein identified as plasma membrane transporter (now referred to as "reduced folate carrier type 1" or "RFC-1"). Further research showed that when normal cells evolve into cancerous cells they often overproduce RFC-1 to ensure they get enough folate.<ref name="PR6">, Memorial Sloan Kettering Cancer Center Press Release, "FDA Approves Lymphoma Drug Developed at Memorial Sloan Kettering".</ref>

A subsequent scientific collaboration was ultimately formed among SRI International, Memorial Sloan Kettering Cancer Center, and the Southern Research Institute with the intention of developing an antifolate with greater therapeutic selectivity – an agent that could be more effectively internalized into tumors (transported into the cells through RFC-1) and would be more toxic to cancer cells than normal cells.<ref name="PR6"/>

This collaboration, supported by the National Cancer Institute,<ref>{{cite journal | title=The NExT Steps in Drug Development at NCI | journal=NCI Cancer Bulletin | date=20 October 2009 | archive-date=5 October 2014 | url=http://www.cancer.gov/ncicancerbulletin/archive/2009/102009/page4 | archive-url=https://web.archive.org/web/20141005215902/http://www.cancer.gov/ncicancerbulletin/archive/2009/102009/page4 | url-status=dead | access-date=21 October 2020 }}</ref> led to the identification of pralatrexate in the mid-1990s. Pralatrexate was later licensed to Allos Therapeutics in 2002 for further development.<ref name="PR7">{{cite press release|url=http://www.sri.com/newsroom/press-releases/fda-approves-pralatrexate|title=FDA Approves Pralatrexate for Treatment of Peripheral T-Cell Lymphoma|publisher=]|date=2009-09-25|access-date=2013-07-10|archive-date=2013-07-03|archive-url=https://web.archive.org/web/20130703050331/http://www.sri.com/newsroom/press-releases/fda-approves-pralatrexate|url-status=dead}}</ref> Allos Therapeutics, Inc. was acquired by Spectrum Pharmaceuticals, Inc. on September 5, 2012. Allos is a wholly owned subsidiary of Spectrum.<ref>{{cite news|url=https://www.bizjournals.com/denver/news/2012/09/05/purchase-of-allos-therapeutics-is.html |title=Purchase of Allos Therapeutics is completed | vauthors = Avery G |work=]|date=2012-09-07|access-date=2013-07-10}}</ref>

== Society and culture ==

=== Legal status ===
Pralatrexate was approved for medical use in the United States in September 2009.<ref name="FDA approval package">{{cite web | title=Drug Approval Package: Folotyn (Pralatrexate) Injection NDA #022468 | website=U.S. ] (FDA) | date=23 November 2009 | url=https://www.accessdata.fda.gov/drugsatfda_docs/nda/2009/022468s000TOC.cfm | access-date=21 October 2020}}</ref><ref name="FDA PR">{{cite press release | title=FDA Approves First Drug for Treatment of Peripheral T-cell Lymphoma | website=U.S. ] (FDA) | date=25 September 2009 | url=http://www.fda.gov/NewsEvents/Newsroom/PressAnnouncements/ucm183799.htm | archive-url=https://web.archive.org/web/20091001053043/http://www.fda.gov/NewsEvents/Newsroom/PressAnnouncements/ucm183799.htm | archive-date=1 October 2009 | url-status=dead | access-date=21 October 2020}} {{PD-notice}}</ref>

=== Economics ===
Some oncologists, patient groups, and insurance companies criticized the cost of $30,000 a month or more, which could reach a total of $126,000 during a course of treatment.<ref name="questioning">{{cite news |url=https://www.nytimes.com/2009/12/05/health/05drug.html?_r=1&?8dpc |title=Questioning a Cancer Drug That Costs $30,000 a Month |work=] |date=December 4, 2009 | vauthors = Pollack A |quote=The price of the new drug, called Folotyn, is at least triple that of other drugs that critics have said are too expensive for the benefits they offer to patients.|access-date=2009-12-05}}</ref>

==References==
{{reflist}}

== External links ==
* {{cite web | url = https://druginfo.nlm.nih.gov/drugportal/name/pralatrexate | publisher = U.S. National Library of Medicine | work = Drug Information Portal | title = Pralatrexate }}
* {{cite web | title=Pralatrexate | work=NCI Drug Dictionary | publisher=National Cancer Institute | url=https://www.cancer.gov/publications/dictionaries/cancer-drug/def/pralatrexate }}
* {{cite web | title=Pralatrexate | website=National Cancer Institute | date=29 October 2009 | url=https://www.cancer.gov/about-cancer/treatment/drugs/pralatrexate }}

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