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????? ??? ???
?? ??:
4291-63-8
???:
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???(??):
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Cladribine
???(??):
CDA;Leustat;(2R,3S,5R)-5-(6-aMino-2-chloro-9H-purin-9-yl)-2-(hydroxyMethyl)tetrahydrofuran-3-ol;2CDA;CldAdo;2-Cl-dA;Jk 6251;CS-1392;rwj26251;Leustati
CBNumber:
CB4222723
???:
C10H12ClN5O3
??? ??:
285.69
MOL ??:
4291-63-8.mol
MSDS ??:
SDS

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???
181-185 °C(lit.)
??
D25 -18.8° (c = 1 in DMF)
?? ?
547.6±60.0 °C(Predicted)
??
2.03±0.1 g/cm3(Predicted)
?? ??
-20°C
???
?? ?? ????, ??? ?????? ????, ???? ?? ????, ???????? ?? ???? ????. ???(5.9)? ?????.
?? ?? (pKa)
13.75±0.60(Predicted)
??? ??
?? ??
??
???? ?? ???
?? ??(λmax)
265nm(EtOH aq.)(lit.)
Merck
14,2337
???
???? ??
InChIKey
PTOAARAWEBMLNO-HSUXUTPPSA-N
CAS ??????
4291-63-8(CAS DataBase Reference)
??
  • ?? ? ?? ??
  • ?? ? ???? ?? (GHS)
??? ?? T
?? ???? ?? 36/37/38-23/24/25
????? 26-37/39-45-36-22
????(UN No.) UN 2811 6.1 / PGIII
WGK ?? 3
RTECS ?? AU7357560
HS ?? 29349990
?? ?? ??? 4291-63-8(Hazardous Substances Data)
?? LD50 intraperitoneal in mouse: 150mg/kg
????(GHS): GHS hazard pictogramsGHS hazard pictograms
?? ?: Danger
??·?? ??:
?? ??·?? ?? ?? ?? ?? ?? ? ?? ?? P- ??
H301 ??? ??? ?? ?? ?? - ?? ?? 3 ?? GHS hazard pictograms P264, P270, P301+P310, P321, P330,P405, P501
H341 ???? ??? ??? ??? ??? (????? ???? ????? ???? ???? ???? ??? ?? ????? ??? ???? ??) ???? ???? ?? ?? 2 ?? P201,P202, P281, P308+P313, P405,P501
H372 ??? ?? ?? ???? ??(??, ??? ?? ??? ?? ??? ??)? ??? ??? ?? ???? ?? - ?? ?? ?? 1 ?? GHS hazard pictograms P260, P264, P270, P314, P501
??????:
P201 ?? ? ?? ???? ?????.
P202 ?? ?? ?? ??? ?? ???? ??? ???? ???.
P260 ??·?·??·???·??·...·????? ???? ???.
P264 ?? ??? ?? ??? ????.
P264 ?? ??? ?? ??? ????.
P270 ? ??? ??? ??? ???, ???? ???? ???.
P301+P310 ???? ?? ????(??)? ??? ????.
NFPA 704
0
4 0

????? MSDS


2-Chloro-2'-deoxyadenosine

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Cladribine, an adenosine deaminase inhibitor, was introduced in the United States as a single intravenous treatment for hairy cell leukemia. The incorporation of a chlorine atom at the 2-position of deoxyadenosine renders cladribine more resistant to enzymatic attack by adenosine deaminase, resulting in a more prolonged cytotoxic effect. Cladribine efficiently crosses lymphocyte and monocyte cell membranes and is metabolized in cells to the biologically active triphosphate, which inhibits DNA synthesis. While most antineoplastic drugs are active primarily against dividing cells, cladribine destroys both resting and proliferating cells. Its potential uses in the treatment of autoimmune hemolytic anemia, multiple sclerosis, chronic lymphocytic leukemia and various lymphomas have also been evaluated.

??? ??

White Crystalline Solid

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It is a substituted purine nucleoside with antileukemic activity

Indications

Cladribine (Leustatin) is a synthetic purine nucleoside that is converted to an active cytotoxic metabolite by the enzyme deoxycytidine kinase. Like the other purine antimetabolites, it is relatively selective for both normal and malignant lymphoid cells and kills resting as well as dividing cells by mechanisms that are not completely understood.
The drug is highly active against hairy cell leukemia, producing complete remissions in more than 60% of patients treated with a single 7-day course. Activity has also been noted in other low-grade lymphoid malignancies. The major side effect is myelosuppression.

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ChEBI: 2'-Deoxyadenosine in which the hydrogen at position 2 on the purine ring has been substituted by chlorine. It inhibits the synthesis and repair of DNA, particularly in lymphocytes and monocytes, and is used as an antimetabolite antineoplastic drug for the treatment of lymphoid malignancies including hairy-cell leukaemia and chronic lymphocytic leukaemia.

?? ??

The drug is available in a 10-mg or 10-mL single-use vialfor IV use. Cladribine is used for chronic lymphocyticleukemia, hairy cell leukemia, and non-Hodgkin’s lymphoma.The mechanism of action of this purine deoxyadenosineanalog involves incorporation into DNA resultingin inhibition of DNA chain extension and inhibitionof DNA synthesis and function. This incorporation intoDNA occurs via the triphosphate metabolite active species.The 2-chloro group on the adenine ring produces resistanceto breakdown by adenosine deaminase. Resistance to the anticancereffects can occur because of decreased expressionof the activating enzyme or overexpression of the catabolicenzymes. Oral bioavailability is variable and averages about50%. The drug crosses the blood-brain barrier; however,CSF concentrations reach only 25% of those in plasma. Thedrug is selectively activated inside the cell, and intracellularconcentrations of phosphorylated metabolites exceed thosein plasma. Toxicities include myelosuppression, neutropenia,immunosuppression, fever, nausea, and vomiting.

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