Nelarabine

Short description: Chemical compound

Nelarabine

Clinical data
Trade names| Arranon, Atriance
Other names| 506U78
AHFS/Drugs.com| Monograph
MedlinePlus| a607077
License data|

* EU EMA: by INN
* US DailyMed: Nelarabine
* US FDA: Nelarabine

Pregnancy
category|

* US: N (Not classified yet)

Routes of
administration| Intravenous
ATC code|

* L01BB07 (WHO)

Legal status
Legal status|

* US: ℞-only [1]
* EU: Rx-only [2]

Pharmacokinetic data
Bioavailability| n/a
Protein binding| <25%
Metabolism| By adenosine deaminase, to 9-β-D-arabinofuranosylguanine
Elimination half-life| 30 minutes (nelarabine)
3 hours (ara-G)
Excretion| Kidney
Identifiers
CAS Number|

* 121032-29-9 Y

PubChem CID|

* 3011155

IUPHAR/BPS|

* 7090

DrugBank|

* DB01280 Y

ChemSpider|

* 2280207 Y

UNII|

* 60158CV180

KEGG|

* D05134 N

ChEMBL|

* ChEMBL1201112 N

Chemical and physical data
Formula| C11H15N5O5
Molar mass| 297.271 g·mol−1
3D model (JSmol)|

* Interactive image

SMILES

* n2c1c(nc(nc1OC)N)n(c2)[C@@H]3O[C@@H]([C@@H](O)[C@@H]3O)CO

InChI

* InChI=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 Y

* Key:IXOXBSCIXZEQEQ-UHTZMRCNSA-N Y

NY (what is this?) (verify)

Nelarabine, sold under the brand names Arranon (US) and Atriance (EU), is a chemotherapy medication used for the treatment of T-cell acute lymphoblastic leukemia (T-ALL) and T-cell lymphoblastic lymphoma (T-LBL).[1][2]

Nelarabine is a prodrug of arabinosylguanine nucleotide triphosphate (araGTP), a type of purine nucleoside analog, which causes inhibition of DNA synthesis and cytotoxicity.[3] Pre-clinical studies suggest that T-cells are particularly sensitive to nelarabine. In October 2005, it was approved by the FDA for acute lymphoblastic leukemia and T-cell lymphoblastic lymphoma that has not responded to or has relapsed following treatment with at least two chemotherapy regimens.[4] It was later approved in the European Union in October 2005.[2] It is available as a generic medication.[5]

## References

1. ↑ 1.0 1.1 "Arranon- nelarabine injection". 11 June 2020. https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=fffa5d75-0dba-4ad7-a252-5f60fa28489a.
2. ↑ 2.0 2.1 2.2 "Atriance EPAR". https://www.ema.europa.eu/en/medicines/human/EPAR/atriance.
3. ↑ "Nelarabine". IUPHAR/BPS. http://www.guidetopharmacology.org/GRAC/LigandDisplayForward?ligandId=7090.
4. ↑ "FDA drug approval summary: nelarabine (Arranon) for the treatment of T-cell lymphoblastic leukemia/lymphoma". The Oncologist 13 (6): 709–14. June 2008. doi:10.1634/theoncologist.2006-0017. PMID 18586926.
5. ↑ "Competitive Generic Therapy Approvals". 29 June 2023. https://www.fda.gov/drugs/generic-drugs/competitive-generic-therapy-approvals.

## External links

* "Nelarabine". Drug Information Portal. U.S. National Library of Medicine. https://druginfo.nlm.nih.gov/drugportal/name/nelarabine.
* "Nelarabine". NCI Dictionary of Cancer Terms. National Cancer Institute. https://www.cancer.gov/publications/dictionaries/cancer-terms/def/nelarabine.

* v
* t
* e

Intracellular chemotherapeutic agents / antineoplastic agents (L01)

SPs/MIs
(M phase)|

| Block microtubule assembly|

* Vinca alkaloids (Vinblastine#
* Vincristine#
* Vinflunine§
* Vindesine
* Vinorelbine#)

|

Block microtubule disassembly|

* Taxanes (Cabazitaxel
* Docetaxel#
* Larotaxel
* Ortataxel†
* Paclitaxel#
* Tesetaxel)
* Epothilones (Ixabepilone)

DNA replication
inhibitor|

| DNA precursors/
antimetabolites
(S phase)|

| Folic acid|

* Dihydrofolate reductase inhibitor (Aminopterin
* Methotrexate#
* Pemetrexed
* Pralatrexate)
* Thymidylate synthase inhibitor (Raltitrexed
* Pemetrexed)

|

Purine|

* Adenosine deaminase inhibitor (Pentostatin)

* Halogenated/ribonucleotide reductase inhibitors (Cladribine
* Clofarabine
* Fludarabine)
* Nelarabine

* Thiopurine (Tioguanine#
* Mercaptopurine#)

Pyrimidine|

* Thymidylate synthase inhibitor (Fluorouracil#
* Capecitabine#
* Doxifluridine
* Tegafur (+gimeracil/oteracil)
* Carmofur
* Floxuridine)

* DNA polymerase inhibitor (Cytarabine#)

* Ribonucleotide reductase inhibitor (Gemcitabine#)

* Hypomethylating agent (Azacitidine
* Decitabine)

Deoxyribonucleotide|

* Ribonucleotide reductase inhibitor (Hydroxycarbamide#)

Topoisomerase inhibitors
(S phase)|

| I|

* Camptotheca (Camptothecin
* Cositecan†
* Belotecan
* Gimatecan
* Exatecan
* Irinotecan#
* Lurtotecan‡
* Silatecan§
* Topotecan
* Rubitecan‡)

|

II|

* Podophyllum (Etoposide#
* Teniposide)

II+Intercalation|

* Anthracyclines (Aclarubicin
* Daunorubicin#
* Doxorubicin#
* Epirubicin
* Idarubicin
* Amrubicin†
* Pirarubicin
* Valrubicin
* Zorubicin)
* Anthracenediones (Mitoxantrone
* Pixantrone)

Crosslinking of DNA
(CCNS)|

| Alkylating|

* Nitrogen mustards: Chlormethine
* Cyclophosphamide# (Ifosfamide#
* Trofosfamide)
* Chlorambucil# (Melphalan
* Prednimustine)
* Bendamustine#
* Uramustine

* Nitrosoureas: Carmustine
* Lomustine (Semustine)
* Fotemustine
* Nimustine
* Ranimustine
* Streptozocin

* Alkyl sulfonates: Busulfan (Mannosulfan
* Treosulfan)

* Aziridines: Carboquone
* Thiotepa
* Triaziquone
* Triethylenemelamine

|

Platinum-based|

* Carboplatin#
* Cisplatin#
* Dicycloplatin
* Nedaplatin
* Oxaliplatin#
* Satraplatin

Nonclassical|

* Hydrazines (Procarbazine#)
* Triazenes (Dacarbazine#
* Temozolomide)
* Altretamine
* Mitobronitol
* Pipobroman

Intercalation|

* Streptomyces (Actinomycin#
* Bleomycin#
* Mitomycins
* Plicamycin)

Photosensitizers/PDT|

* Aminolevulinic acid / Methyl aminolevulinate
* Efaproxiral
* Porphyrin derivatives (Porfimer sodium
* Talaporfin
* Temoporfin
* Verteporfin)

Other|

| Enzyme inhibitors|

* FI (Tipifarnib§)
* CDK inhibitors (Abemaciclib
* Alvocidib†
* Palbociclib
* Ribociclib
* Seliciclib†)
* PrI
* Bortezomib
* Carfilzomib
* Ixazomib
* PhI (Anagrelide)
* IMPDI (Tiazofurin§)
* LI (Masoprocol)
* PARP inhibitor (Niraparib
* Olaparib
* Rucaparib)
* HDAC (Belinostat
* Panobinostat
* Romidepsin
* Vorinostat)
* PIKI (Idelalisib)

|

Receptor antagonists|

* ERA (Atrasentan)
* Retinoid X receptor (Bexarotene)
* Sex steroid (Testolactone)

Other/ungrouped|

* Amsacrine
* Trabectedin
* Retinoids (Alitretinoin
* Tretinoin#)
* Arsenic trioxide
* Asparagine depleters (Asparaginase#/Pegaspargase)
* Celecoxib
* Demecolcine
* Elesclomol§
* Elsamitrucin
* Estramustine phosphate
* Etoglucid
* Lonidamine
* Lucanthone
* Mitoguazone
* Mitotane
* Oblimersen†
* Omacetaxine mepesuccinate
* Eribulin

* #WHO-EM
* ‡Withdrawn from market
* Clinical trials:
* †Phase III
* §Never to phase III

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