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Key Documents

C7495

Sigma-Aldrich

Clofarabine

≥98% (HPLC)

Synonym(s):

(2R,3R,4S,5R)-5-(6-amino-2-chloropurin-9-yl)-4-fluoro-2-(hydroxymethyl)oxolan-3-ol, 2-chloro-2′-arabino-fluoro-2′-deoxyadenosine

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About This Item

Empirical Formula (Hill Notation):
C10H11ClFN5O3
CAS Number:
Molecular Weight:
303.68
MDL number:
UNSPSC Code:
12352200
PubChem Substance ID:
NACRES:
NA.77

Assay

≥98% (HPLC)

form

powder

color

white

solubility

DMSO: >10 mg/mL

originator

Sanofi Aventis

storage temp.

2-8°C

SMILES string

Nc1nc(Cl)nc2n(cnc12)[C@@H]3O[C@H](CO)[C@@H](O)[C@@H]3F

InChI

1S/C10H11ClFN5O3/c11-10-15-7(13)5-8(16-10)17(2-14-5)9-4(12)6(19)3(1-18)20-9/h2-4,6,9,18-19H,1H2,(H2,13,15,16)/t3-,4+,6-,9-/m1/s1

InChI key

WDDPHFBMKLOVOX-AYQXTPAHSA-N

Application

Clofarabine has been used in a cell viability assay to analyze the sensitivity of the isogenic cell lines towards clofarabine. It is also used to study the interaction of anticancer drug clofarabine with human serum albumin and human α-1 acid glycoprotein.

Biochem/physiol Actions

Clofarabine is a purine nucleoside antimetabolite. Clofarabine is toxic to nondividing lymphocytes and monocytes.
Clofarabine is a second-generation nucleoside analog, used in cancer treatments. Clofarabine is metabolized to 5′-triphosphate and is known to block DNA synthesis. The human equilibrative nucleoside transporters (hENT1 and hENT2) and human concentrative nucleoside transporter (hCNT2 and hCNT3) mediates clofarabine transport into the cell. It also serves as a substrate for mitochondrial deoxyguanosine kinase. Clofarabine is an inhibitor of ribonucleotide reductase. It resists the phosphorolytic cleavage catalyzed by purine nucleoside phosphorylase of bacterias. Clofarabine also withstands deamination by adenosine deaminase.

Features and Benefits

This compound is a featured product for Apoptosis research. Click here to discover more featured Apoptosis products. Learn more about bioactive small molecules for other areas of research at sigma.com/discover-bsm.
This compound was developed by Sanofi Aventis. To browse the list of other pharma-developed compounds and Approved Drugs/Drug Candidates, click here.

Pictograms

Health hazardExclamation mark

Signal Word

Warning

Hazard Classifications

Acute Tox. 4 Dermal - Acute Tox. 4 Inhalation - Acute Tox. 4 Oral - Carc. 2 - Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

Storage Class Code

6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

WGK

WGK 2

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Stratification of nucleoside analog chemotherapy using 1-(2?-deoxy-2?-18F-fluoro-beta-D-arabinofuranosyl) cytosine and 1-(2?-deoxy-2?-18F-fluoro-beta-L-arabinofuranosyl)-5-methylcytosine PET
Lee JT, et al.
Journal of Nuclear Medicine, 53(2), 275-275 (2012)
Modified Nucleosides: in Biochemistry, Biotechnology and Medicine, 639-639 (2008)
Stephen J Simko et al.
Pediatric blood & cancer, 61(3), 479-487 (2013-10-10)
Existing therapies for recurrent or refractory histiocytoses, including Langerhans cell histiocytosis (LCH), juvenile xanthogranuloma (JXG), and Rosai-Dorfman disease (RDD), have limited effectiveness. We report our experience with using clofarabine as therapy in children with recurrent or refractory histiocytic disorders, including
Peter L Bonate et al.
Nature reviews. Drug discovery, 5(10), 855-863 (2006-10-04)
The treatment of acute leukaemias, which are the most common paediatric cancers, has improved considerably in recent decades, with complete response rates approaching approximately 90% in some cases. However, there remains a major need for treatments for patients who do
Michał Gorzkiewicz et al.
Macromolecular rapid communications, 40(15), e1900181-e1900181 (2019-05-29)
Poly(propyleneimine) glycodendrimers are proposed as nanocarriers for triphosphate forms of anticancer adenosine analogues to improve the efficiency of chemotherapy and to overcome drug resistance mechanisms. This approach has proven successful for fludarabine administration-an autonomous way of cellular entry of a

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