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C7495

Sigma-Aldrich

Clofarabine

≥98% (HPLC)

Synonyme(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

Formule empirique (notation de Hill):
C10H11ClFN5O3
Numéro CAS:
123318-82-1
Poids moléculaire :
303.68
Numéro MDL:
MFCD00871077
Code UNSPSC :
12352200
ID de substance PubChem :
329775078
Nomenclature NACRES :
NA.77

Pureté

≥98% (HPLC)

Forme

powder

Couleur

white

Solubilité

DMSO: >10 mg/mL

Auteur

Sanofi Aventis

Température de stockage

2-8°C

Chaîne SMILES 

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

Clé InChI

WDDPHFBMKLOVOX-AYQXTPAHSA-N

Informations sur le gène

human ... POLA1(5422) , POLA2(23649) , POLD1(5424) , POLD2(5425) , POLD3(10714) , POLD4(57804) , POLE(5426) , POLE2(5427) , POLE3(54107) , PRIM1(5557) , PRIM2(5558) , RRM1(6240) , RRM2(6241) , RRM2B(50484)

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.

Actions biochimiques/physiologiques

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.

Caractéristiques et avantages

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.

Pictogrammes

Health hazardExclamation mark
GHS08,GHS07

Mention d'avertissement

Warning

Classification des risques

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

Organes cibles

Respiratory system

Code de la classe de stockage

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

Classe de danger pour l'eau (WGK)

WGK 2

Équipement de protection individuelle

Eyeshields, Faceshields, Gloves, type P2 (EN 143) respirator cartridges

Certificats d'analyse (COA)

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Consulter la Bibliothèque de documents

Interaction of anticancer drug clofarabine with human serum albumin and human alpha-1 acid glycoprotein. Spectroscopic and molecular docking approach
Ajmal MR, et al.
Journal of Pharmaceutical and Biomedical Analysis, 135(2), 106-115 (2017)
Anna Zhenchuk et al.
Biochemical pharmacology, 78(11), 1351-1359 (2009-07-07)
Clofarabine, a next-generation deoxyadenosine analogue, was developed on the basis of experience with cladribine and fludarabine in order to achieve higher efficacy and avoid extramedullary toxicity. During the past decade this is the only drug granted approval for treatment of
Hady Ghanem et al.
Leukemia & lymphoma, 54(4), 688-698 (2012-09-11)
Clofarabine is a second-generation purine nucleoside analog that has been synthesized to overcome the limitations and incorporate the best qualities of fludarabine and cladribine. Clofarabine acts by inhibiting ribonucleotide reductase and DNA polymerase, thereby depleting the amount of intracellular deoxynucleoside
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
Andrea Ghelli Luserna Di Rorà et al.
Cancers, 11(11) (2019-11-14)
Screening for synthetic lethality markers has demonstrated that the inhibition of the cell cycle checkpoint kinases WEE1 together with CHK1 drastically affects stability of the cell cycle and induces cell death in rapidly proliferating cells. Exploiting this finding for a
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