ChemicalBook--->CAS DataBase List--->4291-63-8

4291-63-8

4291-63-8 Structure

4291-63-8 Structure
IdentificationMore
[Name]

Cladribine
[CAS]

4291-63-8
[Synonyms]

1,1-CYCLOHEXANEDIACETIC ACID
2CDA
2-CHLORO-2'-DEOXYADENOSINE
2-CL-DADO
CDA
CLADRIBINE
CLADRIBINE CDA
Cyclohexanediacetic acid
LABOTEST-BB LT01147851
2-chloro-2’-deoxy-adenosin
2-chlorodeoxyadenosine
leustatin
nsc105014-f
rwj26251
2'-Deoxy-2-chloroadenosine
2-CHLORO-2'-DEOXY-D-ADENOSINE
Leustati
Adenosine, 2-chloro-2'-deoxy-
CLADRIBINE [2-CHLORO-2''-DEOXYADENOSINE]
2-CHLORO-2''-DEOXYADENOSINE (CDA: CLADRIBINE)
[EINECS(EC#)]

224-427-9
[Molecular Formula]

C10H12ClN5O3
[MDL Number]

MFCD00153939
[Molecular Weight]

285.69
[MOL File]

4291-63-8.mol
Chemical PropertiesBack Directory
[Appearance]

White Crystalline Solid
[Melting point ]

181-185 °C(lit.)
[alpha ]

D25 -18.8° (c = 1 in DMF)
[Boiling point ]

547.6±60.0 °C(Predicted)
[density ]

2.03±0.1 g/cm3(Predicted)
[storage temp. ]

2-8°C
[solubility ]

Slightly soluble in water, soluble in dimethyl sulfoxide, slightly soluble in methanol, practically insoluble in acetonitrile. It shows polymorphism (5.9).
[form ]

White solid
[pka]

13.75±0.60(Predicted)
[color ]

White to Pale Yellow
[Usage]

It is a substituted purine nucleoside with antileukemic activity
[λmax]

265nm(EtOH aq.)(lit.)
[Merck ]

14,2337
[Stability:]

Store in Freezer
[InChIKey]

PTOAARAWEBMLNO-HSUXUTPPSA-N
[CAS DataBase Reference]

4291-63-8(CAS DataBase Reference)
Safety DataBack Directory
[Hazard Codes ]

T
[Risk Statements ]

R36/37/38:Irritating to eyes, respiratory system and skin .
R23/24/25:Toxic by inhalation, in contact with skin and if swallowed .
[Safety Statements ]

S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S37/39:Wear suitable gloves and eye/face protection .
S45:In case of accident or if you feel unwell, seek medical advice immediately (show label where possible) .
S36:Wear suitable protective clothing .
S22:Do not breathe dust .
[RIDADR ]

UN 2811 6.1 / PGIII
[WGK Germany ]

3
[RTECS ]

AU7357560
[HS Code ]

29349900
[Hazardous Substances Data]

4291-63-8(Hazardous Substances Data)
[Toxicity]

LD50 intraperitoneal in mouse: 150mg/kg
Raw materials And Preparation ProductsBack Directory
[Raw materials]

Chloroform-->Silica gel-->Furan-->2,6-Dichloropurine-->4-Dimethylaminopyridine-->Tributyltin Hydride-->[1,2-Bis(diphenylphosphino)ethane]dichloropalladium(II)-->Sodium chloride-->2,2'-Azobis(2-methylpropionitrile)-->1,1,3,3-TETRAISOPROPYLDISILOXANE
Material Safety Data Sheet(MSDS)Back Directory
[msds information]

2-Chloro-2'-deoxyadenosine(4291-63-8).msds
Questions And AnswerBack Directory
[Description]

Cladribine (2-chloro-2′-deoxyadenosine) is an adenosine deaminase-resistant analogue of deoxyadenosine. The drug has a broad range of in vitro activity against both lymphoid and myeloid neoplasms [mean IC50values (drug concentration required to inhibit cell growth by 50% of control): 20 to 87 nmol/L]. But it possesses little activity against multiple myeloma specimens and many solid tumor cell lines. Monocytes are highly sensitive to cladribine in vitro. Cladribine demonstrates activity against both dividing and nondividing cells and this activity distinguishes it from many other agents. It has activity in murine models of leukaemia. Cladribine is used to treat chronic progressive multiple sclerosis, hairy cell leukemia, systemic mastocytosis, and histiocytosis (including Erdheim–Chester disease and Langerhans cell histiocytosis).
After a 2-hour intravenous infusion of cladribine 0.14 mg/kg/day, the mean maximum plasma drug concentration was 198 nmol/L. Intracellular concentrations of phosphorylated cladribine derivatives exceed plasma concentrations 128- to 375-fold. Cladribine penetrates into the CSF. The terminal elimination half-life (6.7 hours) is long, which suggests that the drug may be administered intermittently without loss of efficacy. The volume of distribution of cladribine is 9.2 L/kg.
[References]

[1] J.C Sipe,  J. S Romine, R. McMillan, E. Beutler, J. C. Sipe, J. S. Romine, J. Zyroff (1994) Cladribine in treatment of chronic progressive multiple sclerosis, 344, 9-13
[2] Alan Saven, Carol Burian (1999) Cladribine Activity in Adult Langerhans-Cell Histiocytosis, 93, 4125-4130
[3] https://en.wikipedia.org/wiki/Cladribine
[4] Harriet M. Bryson, Eugene M. Sorkin (1993) Cladribine: A Review of its pharmacodynamic and pharmacokinetic properties and therapeutic potential in haematological malignancies, 46, 872-894
Hazard InformationBack Directory
[Chemical Properties]

White Crystalline Solid
[Originator]

Johnson & Johnson (U.S.A.)
[Uses]

It is a substituted purine nucleoside with antileukemic activity
[Definition]

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.
[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.
[Manufacturing Process]

Manufacturing process for Cladribine includes these steps as follows: Preparation of 2',3',5'-O-triacetyl guanosine;Preparation of 9-(2',3',5'-O-triacetyl-β-D-ribofuranosyl)-2-amino-6- chloropurine;Preparation of 9-(2',3',5'-O-triacetyl-β-D-ribofuranosyl)-2,6-dichloropurine;Preparation of 2-chloroadenosine;Preparation of 2-chloro-(3',5'-O-tetraisopropyldisiloxyl)adenosine; Preparation of 2-chloro-2'-O-phenoxythiocarbonyl-(3',5'-O-tetraisopropyldisiloxyl)adenosine; Preparation of 2-chloro-2'-deoxy-(3',5'-O-tetraisopropyldisiloxyl)adenosine; Preparation of 2-chloro-2'-deoxy-adenosine.
[Brand name]

Leustatin (Ortho Biotech).
[Therapeutic Function]

Cytostatic
[General Description]

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.
[Biochem/physiol Actions]

Deoxyadenosine analog resistant to adenosine deaminase; antileukemic with immunosuppressive activity
[Clinical Use]

Antineoplastic agent:
Hairy cell leukaemia (HCL)

Chronic lymphocytic leukaemia (CLL) in patients who have failed to respond to standard regimens.
[Drug interactions]

Potentially hazardous interactions with other drugs
Antipsychotics: avoid with clozapine - increased risk of agranulocytosis.
Antivirals: avoid with lamivudine.
Caution when administering with any other immunosuppressive or myelosuppressive therapy
[Metabolism]

Cladribine is extensively distributed and penetrates into the CNS. Cladribine is phosphorylated within cells by deoxycytidine kinase to form 2-chlorodeoxyadenosine- 5′-monophosphate which is further phosphorylated to the diphosphate by nucleoside monophosphate kinase and to the active metabolite 2-chlorodeoxyadenosine-5′- triphosphate (CdATP) by nucleoside diphosphate kinase. CdATP inhibits DNA synthesis and repair, particularly in lymphocytes and monocytes
There is little information available on the route of excretion of cladribine in man. An average of 18% of the administered dose has been reported to be excreted in urine of patients with solid tumours during a 5-day continuous intravenous infusion.
[storage]

Store at +4°C
Spectrum DetailBack Directory
[Spectrum Detail]

Cladribine(4291-63-8)1HNMR
Well-known Reagent Company Product InformationBack Directory
[Sigma Aldrich]

4291-63-8(sigmaaldrich)
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