Cladribine

Modify Date: 2024-01-02 15:59:16

Cladribine Structure
Cladribine structure
 Common Name Cladribine
CAS Number 4291-63-8 Molecular Weight 285.687
Density 2.0±0.1 g/cm3 Boiling Point 547.6±60.0 °C at 760 mmHg
Molecular Formula C10H12ClN5O3 Melting Point 181-185 °C(lit.)
MSDS Chinese USA Flash Point 285.0±32.9 °C
Symbol GHS06
GHS06		 Signal Word Danger

 Use of Cladribine


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.

 Names

Name cladribine
Synonym More Synonyms

 Cladribine 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
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.

 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

 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
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

 Articles78

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Cladribine in the treatment of acute myeloid leukemia.

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

 Synonyms

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-
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cladribine
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