clofarabine

Also known as CAFdA, Cl-F-araA, Clolar®, Evoltra®, Cl-F-Ara-A, (2R,3R,4S,5R)-5-(6-amino-2-chloropurin-9-yl)-4-fluoro-2-(hydroxymethyl)oxolan-3-ol, 2-chloro-9-(2'-deoxy-2'-fluoro-beta-D-arabinofuranosyl)adenine, 2-chloro-9-(2-deoxy-2-fluoro-beta-D-arabinofuranosyl)adenine

Clofarabine is a purine nucleoside antimetabolite marketed in the United States and Canada as Clolar. In Europe and Australia/New Zealand the product is marketed under the name Evoltra. It is FDA-approved for treating relapsed or refractory acute lymphoblastic leukaemia (ALL) in children after at least two other types of treatment have failed. Some investigations of effectiveness in cases of acute myeloid leukaemia (AML) and juvenile myelomonocytic leukaemia (JMML) have been carried out. Ongoing trials are assessing its efficacy for managing other cancers.

In the Vinony graph

Vinony's link graph records 285 inbound references to clofarabine, and connects out to tiazofurin, liver and human pregnancy.

It is catalogued under topics including Arabinosides, Drug has EMA link and Drugs with non-standard legal status.

Vinony links it to 10 Wikipedia language editions.

Key facts

Drug.verifiedrevid: 460042726
Drug.image: Clofarabine.svg
Drug.image_class: skin-invert-image
Drug.tradename: Clolar, Evoltra
Drug.MedlinePlus: a607012
Drug.DailyMedID: Clofarabine
Drug.licence_EU: yes
Drug.routes_of_administration: Intravenous
Drug.ATC_prefix: L01
Drug.ATC_suffix: BB06
Drug.legal_AU: S4
Drug.legal_US: Rx-only
Drug.legal_EU: Rx-only
Drug.legal_status: Rx-only
Drug.CAS_number: 123318-82-1
Drug.PubChem: 119182
Drug.IUPHAR_ligand: 6802
Drug.DrugBank: DB00631

via Wikipedia infobox

Chemical data

Formula: C10H11ClFN5O3
Molecular weight: 303.68 g/mol
IUPAC name: (2R,3R,4S,5R)-5-(6-amino-2-chloropurin-9-yl)-4-fluoro-2-(hydroxymethyl)oxolan-3-ol
SMILES: C1=NC2=C(N=C(N=C2N1[C@H]3[C@H]([C@@H]([C@H](O3)CO)O)F)Cl)N
InChIKey: WDDPHFBMKLOVOX-AYQXTPAHSA-N
XLogP: 0.9
Polar surface area: 119 Å²
H-bond donors: 3
H-bond acceptors: 8
Formal charge: 0

via PubChem

Drug data · ChEMBL

Max clinical phase: Approved
Molecule type: Small molecule
First approval: 2004
Admin. routes: parenteral
Indications: leukemia, myelodysplastic syndrome, acute myeloid leukemia, acute lymphoblastic leukemia

via ChEMBL · EBI

Research

688 papers

Clofarabine.2012
Clofarabine.Nature reviews. Drug discovery · 2005
Clofarabine monotherapy in aggressive, relapsed and refractory Langerhans cell histiocytosis.British journal of haematology · 2024
Clofarabine.Drugs in R&D · 2004
Clofarabine in leukemia.Expert review of hematology · 2010

via PubMed

Wikidata facts

Mass: 303.053
Has use: medication

Show 6 more facts

chemical formula: C₁₀H₁₁ClFN₅O₃
canonical SMILES: C1=NC2=C(N1C3C(C(C(O3)CO)O)F)N=C(N=C2N)Cl
isomeric SMILES: C1=NC2=C(N1[C@H]3[C@H]([C@@H]([C@H](O3)CO)O)F)N=C(N=C2N)Cl
World Health Organisation international non-proprietary name: clofarabine
medical condition treated: acute myeloid leukemia
Commons category: Clofarabine

Sources (4)

via Wikidata · CC0

~5 min read

Encyclopedic overview

8 sections

Contents

Approval
Side effects
Contraindications
Drug interactions
Delivery
Biology
References
External links

==Approval== Clolar was Food and Drug Administration (FDA) approved 28 December 2004. (Under accelerated approval regulations requiring further clinical studies.)

Excerpted from Wikipedia’s “clofarabine” article, available under the CC BY-SA 4.0 licence.