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Merck

C7495

Sigma-Aldrich

Clofarabine

≥98% (HPLC)

Synonym(e):

(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

Empirische Formel (Hill-System):
C10H11ClFN5O3
CAS-Nummer:
Molekulargewicht:
303.68
MDL-Nummer:
UNSPSC-Code:
12352200
PubChem Substanz-ID:
NACRES:
NA.77

Qualitätsniveau

Assay

≥98% (HPLC)

Form

powder

Farbe

white

Löslichkeit

DMSO: >10 mg/mL

Ersteller

Sanofi Aventis

Lagertemp.

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

InChIKey

WDDPHFBMKLOVOX-AYQXTPAHSA-N

Anwendung

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. Wirkung

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.

Leistungsmerkmale und Vorteile

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.

Piktogramme

Health hazardExclamation mark

Signalwort

Warning

Gefahreneinstufungen

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

Zielorgane

Respiratory system

Lagerklassenschlüssel

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

WGK

WGK 2

Persönliche Schutzausrüstung

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


Analysenzertifikate (COA)

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Die Dokumentenbibliothek aufrufen

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
Nobuko Hijiya et al.
Pediatric blood & cancer, 59(3), 417-422 (2012-02-23)
Clofarabine is a second-generation purine nucleoside analog and has significant anti-leukemic activity as a single agent. It is approved by the United States Food and Drug Administration (FDA) for the treatment of relapsed or refractory acute lymphoblastic leukemia (ALL) in
Results of a phase 1-2 study of clofarabine in combination with cytarabine (ara-C) in relapsed and refractory acute leukemias
Faderl S, et al.
Blood, 105(3), 940-947 (2005)
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)

Artikel

Cell cycle phases (G1, S, G2, M) regulate cell growth, DNA replication, and division in proliferating cells.

Apoptosis regulation involves multiple pathways and molecules for cellular homeostasis.

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