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Cladribine
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Name

Cladribine

 EINECS 224-427-9
CAS No. 4291-63-8 Density 1.402 g/cm3
PSA 119.31000 LogP 0.28380
Solubility N/A Melting Point 181-185 °C(lit.)
Formula C10H12ClN5O3 Boiling Point 387.1 °C at 760 mmHg
Molecular Weight 285.69 Flash Point 187.9 °C
Transport Information N/A Appearance White Crystalline Solid
Safety 26-45-36-22 Risk Codes 36/37/38-23/24/25
Molecular Structure Molecular Structure of 4291-63-8 (Cladribine) Hazard Symbols ToxicT
Synonyms

2-Chloro-2-deoxy-beta-adenosine;2-Chloro-6-amino-9-(2-deoxy-beta-D-erythropentofuranosyl)purine;Chlorodeoxyadenosine;RWJ 26251;Adenosine,2-chloro-2'-deoxy-;Leustatin;24757-90-2;2-CdA;2-Chlorodeoxyadenosine;Adenosine, 2-chloro-2-deoxy;Cladribine(Base);Cadribine;Leustatin (TN);Cladribine [USAN:BAN:INN];2-Chloro-2-deoxyadenosine;

Article Data 38

Cladribine Synthetic route

3-benzyl-1-{2-chloro-9-[2-deoxy-3,5-di-O-(p-toluoyl)-β-D-erythro-pentofuranosyl]-purin-6-yl}-2-propylimidazolium iodide

4291-63-8

2-chloro-2'-deoxyadenosine

Conditions
ConditionsYield
With ammonia In methanol at 60℃; for 11h;100%
With ammonia In methanol at 60℃;59%
1448245-68-8

2-chloro-N6,N6-dibenzoyl-3′,5′-O-dibenzoyl-2′-deoxyadenosine

4291-63-8

2-chloro-2'-deoxyadenosine

Conditions
ConditionsYield
With ammonia In methanol at 0 - 20℃; for 12h;95%
500225-62-7

9-(3,5-di-O-benzoyl-2-deoxy-β-D-erythro-pentofuranosyl)-2,6-dichloropurine

4291-63-8

2-chloro-2'-deoxyadenosine

Conditions
ConditionsYield
With ammonia In methanol; dichloromethane at 80℃; for 7h;94%
146196-13-6

6-amino-2-chloro-9-(2'deoxy-3',5'-di-O-acetyl-β-D-erythro-pentofuranosyl)-9H-purine

4291-63-8

2-chloro-2'-deoxyadenosine

Conditions
ConditionsYield
With sodium carbonate In methanol at 20℃; for 2h; pH=8 - 9;93%
With ammonia In methanol at 0 - 20℃;0.62 g
908006-51-9

2-chloro-6-amino-9-[3,5-di-O-(4-chlorobenzoyl)-2-deoxy-β-D-ribofuranosyl]-purine

1266098-30-9

2-chloro-6-trimethylsilylamino-9-[3,5-di-O-(4-chlorobenzoyl)-2-deoxy-β-D-ribofuranosyl]-purine

4291-63-8

2-chloro-2'-deoxyadenosine

Conditions
ConditionsYield
With sodium methylate In methanol at 20 - 30℃; for 6h;90%

2'-deoxyribose 1-phosphate diammonium salt

1839-18-5

2-chloroadenine

4291-63-8

2-chloro-2'-deoxyadenosine

Conditions
ConditionsYield
With magnesium hydroxide; purine nucleoside phosphorylase In water at 45℃;88%
24638-92-4

9-(3,5-di-O-acetyl-2-deoxy-β-D-erythro-pentofuranosyl)-2,6-dichloropurine

4291-63-8

2-chloro-2'-deoxyadenosine

Conditions
ConditionsYield
With ammonia In methanol; dichloromethane at 80℃; for 7h;87%
38925-80-3

2,6-Dichloro-9-(2-deoxy-3,5-di-O-p-toluoyl-β-D-erythro-pentofuranosyl)-purine

4291-63-8

2-chloro-2'-deoxyadenosine

Conditions
ConditionsYield
With ammonia In methanol at 110℃; for 5h; Sealed tube;86%
With ammonia In methanol at 100℃; for 5h;71%
914084-44-9

2-chloro-9-[2-deoxy-3,5-di-O-(p-toluoyl)-β-D-erythro-pentofuranosyl]-6-(2-pentylimidazol-1-yl)purine

4291-63-8

2-chloro-2'-deoxyadenosine

Conditions
ConditionsYield
With ammonia In methanol at 60℃; for 13h;85%
914084-41-6

2-chloro-9-[2-deoxy-3,5-di-O-(p-toluoyl)-β-D-erythro-pentofuranosyl]-6-(2-propylimidazol-1-yl)purine

67-56-1

methanol

A

146196-07-8

2-chloro-9-(2'deoxy-β-D-erythro-pentofuranosyl)-6-methoxy-9H-purine

B

4291-63-8

2-chloro-2'-deoxyadenosine

Conditions
ConditionsYield
With ammonia at 40℃; for 15h;A 85%
B n/a

Cladribine Specification

1. Introduction of Cladribine
Cladribine (CAS NO.4291-63-8) is a white crystalline solid. Its IUPAC Name is (2R,3S,5R)-5-(6-amino-2-chloropurin-9-yl)-2-(hydroxymethyl)oxolan-3-ol. Its water solubility is 6.35e+00 g/l. The Classification Code is Antineoplastic; Antineoplastic agents; Drug / Therapeutic Agent; Human Data; Immunologic Factors; Immunosuppressive agents; Mutation data; Reproductive Effect. Cladribine belongs to Bases & Related Reagents;Nucleotides;Pharmaceuticals;API. Besides, it should be stored in Freezer.

2. Properties of Cladribine
Physical properties about Cladribine are:
(1)Index of Refraction: 1.87; (2)Molar Refractivity: 63.7 cm3; (3)Molar Volume: 140.1 cm3; (4)Polarizability: 25.25×10-24cm3; (5)Surface Tension: 93.5 dyne/cm; (6)Density: 2.03 g/cm3; (7)Flash Point: 285 °C; (8)Enthalpy of Vaporization: 87.03 kJ/mol; (9)Melting Point: 181-185 °C(lit.); (10)Boiling Point: 547.6 °C at 760 mmHg; (11)Vapour Pressure: 7.95E-13 mmHg at 25°C.

3. Structure Descriptors of Cladribine
(1)Canonical SMILES: C1C(C(OC1N2C=NC3=C2N=C(N=C3N)Cl)CO)O
(2)Isomeric SMILES: C1[C@@H]([C@H](O[C@H]1N2C=NC3=C2N=C(N=C3N)Cl)CO)O
(3)InChI: InChI=1S/C10H12ClN5O3/c11-10-14-8(12)7-9(15-10)16(3-13-7)6-1-4(18)5(2-17)19-6/h3-6,17-18H,1-2H2,(H2,12,14,15)/t4-,5+,6+/m0/s1
(4)InChIKey: PTOAARAWEBMLNO-KVQBGUIXSA-N

4. Toxicity of Cladribine

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
man TDLo intravenous 700ug/kg/7D-C (0.7mg/kg) SKIN AND APPENDAGES (SKIN): "DERMATITIS, OTHER: AFTER SYSTEMIC EXPOSURE" American Journal of Hematology. Vol. 53, Pg. 209, 1996.
mouse LD50 intraperitoneal 150mg/kg (150mg/kg)   Leukemia and Lymphoma. Vol. 5, Pg. 1, 1991.

5. Safety information of Cladribine
Hazard Codes: ToxicT
Risk Statements: 36/37/38-23/24/25
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: 26-37/39-45-36-22 
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 the label whenever possible.) 
S36:Wear suitable protective clothing. 
S22:Do not breathe dust.
WGK Germany: 3
RTECS: AU7357560

6. Uses of Cladribine
Cladribine is a substituted purine nucleoside with antileukemic activity. Cladribine is a drug used to treat hairy cell leukemia. As a purine analog, it is a synthetic anti-cancer agent that also suppresses the immune system. Chemically, it mimics the nucleoside adenosine and thus inhibits the enzyme adenosine deaminase, which interferes with the cell's ability to process DNA.

7. Production of Cladribine
Cladribine can be got from 2-Deoxy-D-ribose. The detail is as follows:

Production of Cladribine

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