Cladribine

Names

[ Name ]:
Cladribine

[Synonym ]:
Litak
CDA
2-Chloro-2'-deoxyadenosine
2-Chloro-9-(2-deoxy-β-D-arabinofuranosyl)adenine
2-Chloro-2'-deoxy-adenosine
CldAdo
EINECS 224-427-9
MFCD00153939
(2R,3S,5R)-5-(6-amino-2-chloro-9H-purin-9-yl)-2-(hydroxyméthyl)tétrahydrofuran-3-ol
2-chloro-6-amino-9-(2-deoxy-β-D-erythro-pentofuranosyl)purine
Cladrivine
2CDA
2-Chloro-6-amino-9-(2-deoxy-b-D-erythro-pentofuranosyl)purine
Cladaribine
(2R,3S,5R)-5-(6-amino-2-chloro-9H-purin-9-yl)-2-(hydroxymethyl)tetrahydrofuran-3-ol
2-Chlorodeoxyadenosine
leustatin
(2R,3S,5R)-5-(6-Amino-2-chlor-9H-purin-9-yl)-2-(hydroxymethyl)tetrahydrofuran-3-ol
2-Chloro-2'-deoxy-b-adenosine
2-Chloro-2'-deoxy-β-adenosine
2-CL-DADO
Cladribine
Movectro
Leustati
adenosine, 2-chloro-2'-deoxy-

Biological Activity

[Description]:

Cladribine is an adenosine deaminase inhibitor used to treat hairy cell leukemia and multiple sclerosis. Target: Adenosine DeaminaseCladribine possesses concentration-dependent apoptosis-inducing potential in the HSB2 cells. Cladribine inhibits growth of primary mast cell (MC) and the MC line HMC-1 in a dose-dependent manner, with lower IC50 values recorded in HMC-1.2 cells harboring KIT D816V compared to HMC-1.1 cells lacking KIT D816V. Cladribine (0.7-3.5 mM) and/or diltiazem (2.4 mM), is injected intraperitoneally into adult zebrafish and red blood cell (RBC) lysates are assayed by HPLC for levels of purine nucleotides (e.g. ATP), potential biomarkers of cardiovascular health. Diltiazem increased RBC ATP concentrations, which are inhibited by co-injection of cladribine.

[Related Catalog]:

Signaling Pathways >> Metabolic Enzyme/Protease >> Adenosine Deaminase

Research Areas >> Cardiovascular Disease

[References]

[1]. Guchelaar, H.J., et al., Apoptosis- and necrosis-inducing potential of cladribine, cytarabine, cisplatin, and 5-fluorouracil in vitro: a quantitative pharmacodynamic model. Cancer Chemother Pharmacol, 1998. 42(1): p. 77-83.

[2]. Bohm, A., et al., In vitro and in vivo growth-inhibitory effects of cladribine on neoplastic mast cells exhibiting the imatinib-resistant KIT mutation D816V. Exp Hematol, 2010. 38(9): p. 744-55.

[3]. Klein, L.C., P.K. Yeung, and J.N. Berman, Cladribine inhibits a diltiazem-induced increase in red blood cell purine nucleotide concentrations in a zebrafish model. Biomarkers, 2009. 14(8): p. 554-9.

[Related Small Molecules]

PENTOSTATIN | AMPD2 inhibitor 1

Chemical & Physical Properties

[ Density]:
2.0±0.1 g/cm3

[ Boiling Point ]:
547.6±60.0 °C at 760 mmHg

[ Melting Point ]:
181-185 °C(lit.)

[ Molecular Formula ]:
C₁₀H₁₂ClN₅O₃

[ Molecular Weight ]:
285.687

[ Flash Point ]:
285.0±32.9 °C

[ Exact Mass ]:
285.062866

[ PSA ]:
119.31000

[ LogP ]:
0.02

[ Vapour Pressure ]:
0.0±1.5 mmHg at 25°C

[ Index of Refraction ]:
1.871

[ Storage condition ]:
2-8°C

[ Stability ]:
Store in Freezer

MSDS

Click to get detail MSDS

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: AU7357560

CHEMICAL NAME :: Adenosine, 2-chloro-2'-deoxy-

CAS REGISTRY NUMBER :: 4291-63-8

LAST UPDATED :: 199807

DATA ITEMS CITED :: 5

MOLECULAR FORMULA :: C10-H12-Cl-N5-O3

MOLECULAR WEIGHT :: 285.72

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Human - man

DOSE/DURATION :: 700 ug/kg/7D-C

TOXIC EFFECTS :: Skin and Appendages - dermatitis, other (after systemic exposure)

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 150 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 100 mg/kg/5D-I

TOXIC EFFECTS :: Related to Chronic Data - death

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Primate - monkey

DOSE/DURATION :: 7 mg/kg/7D-C

TOXIC EFFECTS :: Gastrointestinal - hypermotility, diarrhea Blood - granulocytopenia

MUTATION DATA

TYPE OF TEST :: DNA inhibition

TEST SYSTEM :: Human Lymphocyte

DOSE/DURATION :: 16 nmol/L

REFERENCE :: CNREA8 Cancer Research. (Public Ledger Building, Suit 816, 6th & Chestnut Sts., Philadelphia, PA 19106) V.1- 1941- Volume(issue)/page/year: 46,2362,1986

Safety Information

[ Symbol ]:

GHS06

[ Signal Word ]:
Danger

[ Hazard Statements ]:
H301 + H311 + H331-H315-H319-H335

[ Precautionary Statements ]:
Missing Phrase - N15.00950417-P261-P280-P302 + P352 + P312-P304 + P340 + P312-P403 + P233

[ Personal Protective Equipment ]:
Eyeshields;Faceshields;Gloves;type P2 (EN 143) respirator cartridges

[ Hazard Codes ]:
T:Toxic

[ Risk Phrases ]:
R23/24/25;R36/37/38

[ Safety Phrases ]:
S26-S37/39-S45-S36-S22

[ RIDADR ]:
NONH for all modes of transport

[ WGK Germany ]:
3

[ RTECS ]:
AU7357560

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

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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...

Cladribine in the treatment of acute myeloid leukemia.

Leuk. Res. 38(4) , 425-7, (2014)