CAS 123318-82-1|Clofarabine

Introduction：Basic information about CAS 123318-82-1|Clofarabine, including its chemical name, molecular formula, synonyms, physicochemical properties, and safety information, etc.

Table of Contents

1. Names
2. Clofarabine BiologicalActivity
3. Chemical & Physical Properties
4. Toxicological Information
CHEMICAL IDENTIFICATION
HEALTH HAZARD DATA
ACUTE TOXICITY DATA
MUTATION DATA
5. Safety Information
6. Articles40
7. Synonyms

Common Name	Clofarabine
CAS Number	123318-82-1	Molecular Weight	303.677
Density	2.1±0.1 g/cm3	Boiling Point	599.5±60.0 °C at 760 mmHg
Molecular Formula	C₁₀H₁₁ClFN₅O₃	Melting Point	228-231 °C
MSDS	ChineseUSA	Flash Point	316.4±32.9 °C
Symbol	GHS06	Signal Word	Danger

Names

Name	clofarabine
Synonym	More Synonyms

Clofarabine BiologicalActivity

Description	Clofarabine(Clolar; Clofarex) inhibits the enzymatic activities of ribonucleotide reductase (IC50 = 65 nM) and DNA polymerase.IC50 Value: 65 nMTarget: in vitro: Clofarabine is a second generation purine nucleoside analog with antineoplastic activity. It is phosphorylated intracellularly, which inhibits the enzymatic activities of ribonucleotide reductase (IC50 = 65 nM) and DNA polymerase, resulting in inhibition of DNA repair and synthesis of DNA and RNA. This nucleoside analog also disrupts mitochondrial function and membrane integrity, resulting in the release of pre-apoptotic factors, including cytochrome C and apoptotic-inducing factor, which activate apoptosis.in vivo: Clofarabine is used for treating relapsed or refractory acute lymphoblastic leukaemia (ALL) in children, after at least two other types of treatment have failed.
Related Catalog	Signaling Pathways >>Autophagy >>AutophagySignaling Pathways >>Cell Cycle/DNA Damage >>Nucleoside Antimetabolite/AnalogResearch Areas >>CancerResearch Areas >>Metabolic Disease
References	[1]. Bonate et al Discovery and development of clofarabine: a nucleoside analogue for treating cancer. Nat.Rev.Drug Discov. (2006)5 855. [2]. Ghanem H, Kantarjian H, Ohanian M, Jabbour E.The Role of Clofarabine in Acute Myeloid Leukemia.Leuk Lymphoma. 2012 Sep 7. [3]. Abd Elmoneim A, Gore L, Ricklis RM, Boklan J, Cooper T, Narendran A, Rolla K, Scott T, Arceci RJ.Phase I dose-escalation trial of clofarabine followed by escalating doses of fractionated cyclophosphamide in children with relapsed or refractory acute leukemias.Pediatr Blood Cancer. 2012 Aug 8. doi: 10.1002/pbc.24264. [4]. Thudium KE, Ghoshal S, Fetterly GJ, Haese JP, Karpf AR, Wetzler M.Synergism between clofarabine and decitabine through p53R2: A pharmacodynamic drug-drug interaction modeling.Leuk Res. 2012 Aug 9. [5]. Aye Y, Brignole EJ, Long MJ, Chittuluru J, Drennan CL, Asturias FJ, Stubbe J.Clofarabine Targets the Large Subunit (α) of Human Ribonucleotide Reductase in Live Cells by Assembly into Persistent Hexamers.Chem Biol. 2012 Jul 27;19(7):799-805.

Description

Clofarabine(Clolar; Clofarex) inhibits the enzymatic activities of ribonucleotide reductase (IC50 = 65 nM) and DNA polymerase.IC50 Value: 65 nMTarget: in vitro: Clofarabine is a second generation purine nucleoside analog with antineoplastic activity. It is phosphorylated intracellularly, which inhibits the enzymatic activities of ribonucleotide reductase (IC50 = 65 nM) and DNA polymerase, resulting in inhibition of DNA repair and synthesis of DNA and RNA. This nucleoside analog also disrupts mitochondrial function and membrane integrity, resulting in the release of pre-apoptotic factors, including cytochrome C and apoptotic-inducing factor, which activate apoptosis.in vivo: Clofarabine is used for treating relapsed or refractory acute lymphoblastic leukaemia (ALL) in children, after at least two other types of treatment have failed.

Related Catalog

Signaling Pathways >>Autophagy >>AutophagySignaling Pathways >>Cell Cycle/DNA Damage >>Nucleoside Antimetabolite/AnalogResearch Areas >>CancerResearch Areas >>Metabolic Disease

References

[1]. Bonate et al Discovery and development of clofarabine: a nucleoside analogue for treating cancer. Nat.Rev.Drug Discov. (2006)5 855.

[2]. Ghanem H, Kantarjian H, Ohanian M, Jabbour E.The Role of Clofarabine in Acute Myeloid Leukemia.Leuk Lymphoma. 2012 Sep 7.

[3]. Abd Elmoneim A, Gore L, Ricklis RM, Boklan J, Cooper T, Narendran A, Rolla K, Scott T, Arceci RJ.Phase I dose-escalation trial of clofarabine followed by escalating doses of fractionated cyclophosphamide in children with relapsed or refractory acute leukemias.Pediatr Blood Cancer. 2012 Aug 8. doi: 10.1002/pbc.24264.

[4]. Thudium KE, Ghoshal S, Fetterly GJ, Haese JP, Karpf AR, Wetzler M.Synergism between clofarabine and decitabine through p53R2: A pharmacodynamic drug-drug interaction modeling.Leuk Res. 2012 Aug 9.

[5]. Aye Y, Brignole EJ, Long MJ, Chittuluru J, Drennan CL, Asturias FJ, Stubbe J.Clofarabine Targets the Large Subunit (α) of Human Ribonucleotide Reductase in Live Cells by Assembly into Persistent Hexamers.Chem Biol. 2012 Jul 27;19(7):799-805.

Chemical & Physical Properties

Density	2.1±0.1 g/cm3
Boiling Point	599.5±60.0 °C at 760 mmHg
Melting Point	228-231 °C
Molecular Formula	C₁₀H₁₁ClFN₅O₃
Molecular Weight	303.677
Flash Point	316.4±32.9 °C
Exact Mass	303.053436
PSA	119.31000
LogP	0.24
Vapour Pressure	0.0±1.8 mmHg at 25°C
Index of Refraction	1.844
InChIKey	WDDPHFBMKLOVOX-AYQXTPAHSA-N
SMILES	Nc1nc(Cl)nc2c1ncn2C1OC(CO)C(O)C1F

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: UD7473000

CHEMICAL NAME :: 9H-Purin-6-amine, 2-chloro-9-(2-deoxy-2-fluoro-beta-D-arabinofuranosyl) -

CAS REGISTRY NUMBER :: 123318-82-1

LAST UPDATED :: 199706

DATA ITEMS CITED :: 1

MOLECULAR FORMULA :: C10-H11-Cl-F-N5-O3

MOLECULAR WEIGHT :: 303.71

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

MUTATION DATA

TYPE OF TEST :: DNA inhibition

TEST SYSTEM :: Human Leukocyte

DOSE/DURATION :: 50 nmol/L

REFERENCE :: CNREA8 Cancer Research. (Public Ledger Building, Suit 816, 6th & Chestnut Sts., Philadelphia, PA 19106) V.1- 1941- Volume(issue)/page/year: 51,2386,1991

Safety Information

Symbol	GHS06
Signal Word	Danger
Hazard Statements	H300
Precautionary Statements	P264-P301 + P310
Personal Protective Equipment	Eyeshields;Faceshields;Gloves;type P2 (EN 143) respirator cartridges
Hazard Codes	Xi,C
Risk Phrases	R36/37/38:Irritating to eyes, respiratory system and skin . R20/21/22:Harmful by inhalation, in contact with skin and if swallowed .
Safety Phrases	S26-S36-S45-S36/37/39
RIDADR	UN 2735 8/PG 3
WGK Germany	3
RTECS	DP5550000
Packaging Group	III
Hazard Class	8

Articles40

The potential of clofarabine in MLL-rearranged infant acute lymphoblastic leukaemia.

Eur. J. Cancer 51 , 2008-21, (2015)

MLL-rearranged acute lymphoblastic leukaemia (ALL) in infants is the most difficult-to-treat type of childhood ALL, displaying a chemotherapy-resistant phenotype, and unique histone modifications, gen...

Preclinical examination of clofarabine in pediatric ependymoma: intratumoral concentrations insufficient to warrant further study.

Cancer Chemother. Pharmacol. 75 , 897-906, (2015)

Clofarabine, a deoxyadenosine analog, was an active anticancer drug in our in vitro high-throughput screening against mouse ependymoma neurospheres. To characterize the clofarabine disposition in mice...

Knockdown of Bcl-xL enhances growth-inhibiting and apoptosis-inducing effects of resveratrol and clofarabine in malignant mesothelioma H-2452 cells.

J. Korean Med. Sci. 29(11) , 1464-72, (2014)

Mcl-1 and Bcl-xL, key anti-apoptotic proteins of the Bcl-2 family, have attracted attention as important molecules in the cell survival and drug resistance. In this study, we investigated whether inhi...

Synonyms

Clofarex

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

(2R,3R,4S,5R)-5-(6-amino-2-chloro-9H-purin-9-yl)-4-fluoro-2-(hydroxyméthyl)tétrahydrofuran-3-ol

9H-Purin-6-amine, 2-chloro-9-(2-deoxy-2-fluoro-β-D-arabinofuranosyl)-

2-Chloro-9-(2-deoxy-2-fluoro-β-D-arabinofuranosyl)adenine

(2R,3R,4S,5R)-5-(6-Amino-2-chlor-9H-purin-9-yl)-4-fluor-2-(hydroxymethyl)tetrahydrofuran-3-ol

(2R,3R,4S,5R)-5-(6-amino-2-chloro-9H-purin-9-yl)-4-fluoro-2-(hydroxymethyl)tetrahydrofuran-3-ol

2-chloro-2'-arabino-fluoro-2'-deoxyadenosine

Cl-F-Ara-A

Clofarabine

Clofarabine [USAN]

Clolar

2-Chloro-9-(2-deoxy-2-fluoro-β-D-arabinofuranosyl)-9H-purin-6-amine

MFCD00871077

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