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Revision as of 09:49, 21 November 2011 editBeetstra (talk | contribs)Edit filter managers, Administrators172,031 edits Saving copy of the {{drugbox}} taken from revid 461640746 of page Nelarabine for the Chem/Drugbox validation project (updated: 'ChEMBL', 'KEGG').  Latest revision as of 01:44, 27 August 2024 edit Whywhenwhohow (talk | contribs)Autopatrolled, Extended confirmed users, Pending changes reviewers49,153 editsm script-assisted date audit and style fixes per MOS:NUM 
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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.}}
{{Use dmy dates|date=August 2024}}
{{Drugbox {{Drugbox
| Verifiedfields = changed | Verifiedfields = changed
| Watchedfields = changed
| verifiedrevid = 402504594 | verifiedrevid = 461742367
| IUPAC_name = (2''R'',3''S'',4''R'',5''R'')-2-(2-amino-6-methoxy-purin-9-yl)-5-(hydroxymethyl)oxolane-3,4-diol
| image = Nelarabine.png | image = Nelarabine structure.svg
| width = 200 | width = 200
| alt =
| image2 = Nelarabine ball-and-stick.png
| alt2 =


<!--Clinical data--> <!--Clinical data-->
| tradename = | tradename = Arranon, Atriance
| Drugs.com = {{drugs.com|monograph|nelarabine}} | Drugs.com = {{drugs.com|monograph|nelarabine}}
| licence_EU = Atriance | MedlinePlus = a607077
| licence_US = Nelarabine | DailyMedID = Nelarabine
| pregnancy_US = D | pregnancy_AU = D
| pregnancy_AU_comment = <ref name="Nelarabine APMDS" />
⚫ | legal_US = Rx-only
| pregnancy_category=
| routes_of_administration = ] | routes_of_administration = ]
⚫ | ATC_prefix = L01
⚫ | ATC_suffix = BB07

<!-- Legal status -->
| legal_AU = S4
| legal_AU_comment = <ref name="Nelarabine APMDS">{{cite web | title=Nelarabine-Reach | website=Therapeutic Goods Administration (TGA) | date=5 June 2024 | url=https://www.tga.gov.au/resources/auspmd/nelarabine-reach | access-date=17 June 2024}}</ref><ref>{{cite web | title=Therapeutic Goods (Poisons Standard—June 2024) Instrument 2024 | website=Federal Register of Legislation | date=30 May 2024 | url=https://www.legislation.gov.au/F2024L00589/asmade/text | access-date=10 June 2024}}</ref>
| legal_BR = <!-- OTC, A1, A2, A3, B1, B2, C1, C2, C3, C4, C5, D1, D2, E, F -->
| legal_BR_comment =
| legal_CA = <!-- OTC, Rx-only, Schedule I, II, III, IV, V, VI, VII, VIII -->
| legal_CA_comment =
| legal_DE = <!-- Anlage I, II, III or Unscheduled -->
| legal_DE_comment =
| legal_NZ = <!-- Class A, B, C -->
| legal_NZ_comment =
| legal_UK = <!-- GSL, P, POM, CD, CD Lic, CD POM, CD No Reg POM, CD (Benz) POM, CD (Anab) POM or CD Inv POM / Class A, B, C -->
| legal_UK_comment =
⚫ | legal_US = Rx-only
| legal_US_comment = <ref name="Arranon FDA label">{{cite web | title=Arranon- nelarabine injection | website=DailyMed | date=11 June 2020 | url=https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=fffa5d75-0dba-4ad7-a252-5f60fa28489a | access-date=4 December 2020}}</ref>
| legal_EU = Rx-only
| legal_EU_comment = <ref name="Atriance EPAR">{{cite web | title=Atriance EPAR | website=] (EMA) | date=20 September 2007 | url=https://www.ema.europa.eu/en/medicines/human/EPAR/atriance | access-date=4 December 2020}}</ref>
| legal_UN = <!-- N I, II, III, IV / P I, II, III, IV -->
| legal_UN_comment =
| legal_status = <!-- For countries not listed above -->


<!--Pharmacokinetic data--> <!--Pharmacokinetic data-->
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| protein_bound = <25% | protein_bound = <25%
| metabolism = By ], to 9-β-<small>D</small>-arabinofuranosylguanine | metabolism = By ], to 9-β-<small>D</small>-arabinofuranosylguanine
| elimination_half-life = 30 minutes (nelarabine)<br>3 hours (ara-G) | elimination_half-life = 30 minutes (nelarabine)<br />3 hours (ara-G)
| excretion = ] | excretion = ]


<!--Identifiers--> <!--Identifiers-->
| CASNo_Ref = {{cascite|correct|CAS}}
| CAS_number_Ref = {{cascite|correct|??}} | CAS_number_Ref = {{cascite|correct|??}}
| CAS_number = 121032-29-9 | CAS_number = 121032-29-9
⚫ | ATC_prefix = L01
⚫ | ATC_suffix = BB07
| PubChem = 3011155 | PubChem = 3011155
| IUPHAR_ligand = 7090
| DrugBank_Ref = {{drugbankcite|changed|drugbank}} | DrugBank_Ref = {{drugbankcite|correct|drugbank}}
| DrugBank = DB01280 | DrugBank = DB01280
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
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| UNII = 60158CV180 | UNII = 60158CV180
| KEGG_Ref = {{keggcite|changed|kegg}} | KEGG_Ref = {{keggcite|changed|kegg}}
| KEGG = <!-- blanked - oldvalue: D05134 --> | KEGG = D05134
| ChEMBL_Ref = {{ebicite|changed|EBI}} | ChEMBL_Ref = {{ebicite|changed|EBI}}
| ChEMBL = <!-- blanked - oldvalue: 1201112 --> | ChEMBL = 1201112
| synonyms = 506U78
⚫ | C=11 | H=15 | N=5 | O=5

| molecular_weight = 297.268 g/mol
<!--Chemical data-->
⚫ | C=11 | H=15 | N=5 | O=5
| smiles = n2c1c(nc(nc1OC)N)n(c2)3O((O)3O)CO | smiles = n2c1c(nc(nc1OC)N)n(c2)3O((O)3O)CO
| InChI = 1/C11H15N5O5/c1-20-9-5-8(14-11(12)15-9)16(3-13-5)10-7(19)6(18)4(2-17)21-10/h3-4,6-7,10,17-19H,2H2,1H3,(H2,12,14,15)/t4-,6-,7+,10-/m1/s1
| InChIKey = IXOXBSCIXZEQEQ-UHTZMRCNBK
| StdInChI_Ref = {{stdinchicite|correct|chemspider}} | StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 1S/C11H15N5O5/c1-20-9-5-8(14-11(12)15-9)16(3-13-5)10-7(19)6(18)4(2-17)21-10/h3-4,6-7,10,17-19H,2H2,1H3,(H2,12,14,15)/t4-,6-,7+,10-/m1/s1 | StdInChI = 1S/C11H15N5O5/c1-20-9-5-8(14-11(12)15-9)16(3-13-5)10-7(19)6(18)4(2-17)21-10/h3-4,6-7,10,17-19H,2H2,1H3,(H2,12,14,15)/t4-,6-,7+,10-/m1/s1
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| StdInChIKey = IXOXBSCIXZEQEQ-UHTZMRCNSA-N | StdInChIKey = IXOXBSCIXZEQEQ-UHTZMRCNSA-N
}} }}

'''Nelarabine''', sold under the brand names '''Arranon''' (US) and '''Atriance''' (EU), is a ] medication used for the treatment of ] (T-ALL) and ] (T-LBL).<ref name="Arranon FDA label" /><ref name="Atriance EPAR" />

Nelarabine is a ] of arabinosylguanine nucleotide triphosphate (araGTP), a type of ] ] analog, which causes inhibition of ] and cytotoxicity.<ref>{{cite web |url= http://www.guidetopharmacology.org/GRAC/LigandDisplayForward?ligandId=7090 |title= Nelarabine|website= Guide to Pharmacology|publisher= IUPHAR/BPS |access-date= 21 August 2015 }}</ref> Pre-clinical studies suggest that T-cells are particularly sensitive to nelarabine. In October 2005, it was approved by the FDA for ] that has not responded to or has relapsed following treatment with at least two chemotherapy regimens.<ref name="Example2006a">{{cite journal | vauthors = Cohen MH, Johnson JR, Justice R, Pazdur R | title = FDA drug approval summary: nelarabine (Arranon) for the treatment of T-cell lymphoblastic leukemia/lymphoma | journal = The Oncologist | volume = 13 | issue = 6 | pages = 709–14 | date = June 2008 | pmid = 18586926 | doi = 10.1634/theoncologist.2006-0017 | s2cid = 23463537 | doi-access = free }}</ref> It was later approved in the European Union in October 2005.<ref name="Atriance EPAR" /> It is available as a ].<ref>{{cite web | title=Competitive Generic Therapy Approvals | website=U.S. ] (FDA) | date=29 June 2023 | url=https://www.fda.gov/drugs/generic-drugs/competitive-generic-therapy-approvals | access-date=29 June 2023 | archive-date=29 June 2023 | archive-url=https://web.archive.org/web/20230629233651/https://www.fda.gov/drugs/generic-drugs/competitive-generic-therapy-approvals | url-status=live }}</ref>

== References ==
{{reflist}}

== External links ==
* {{cite web | title = Nelarabine | work=NCI Dictionary of Cancer Terms | publisher=National Cancer Institute | url=https://www.cancer.gov/publications/dictionaries/cancer-terms/def/nelarabine }}
* {{cite web | title=Nelarabine | website=National Cancer Institute | url=https://www.cancer.gov/about-cancer/treatment/drugs/nelarabin }}{{Dead link|date=August 2023 |bot=InternetArchiveBot |fix-attempted=yes }}

{{Chemotherapeutic agents}}
{{Portal bar | Medicine}}

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{{antineoplastic-drug-stub}}