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Basic Information

Molecular Structure:
CAS No.:	4291-63-8
Name:	Cladribine
Article Data:	38

Formula:	C₁₀H₁₂ClN₅O₃
Molecular Weight:	285.69
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;
EINECS:	224-427-9
Density:	1.402 g/cm³
Melting Point:	181-185 °C(lit.)
Boiling Point:	387.1 °C at 760 mmHg
Flash Point:	187.9 °C
Appearance:	White Crystalline Solid
Hazard Symbols:	T
Risk Codes:	36/37/38-23/24/25
Safety:	26-45-36-22
PSA:	119.31000
LogP:	0.28380

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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

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

...Expand

Raw Materials

50-89-5

67-56-1

79999-39-6

Downstream Products

106449-56-3

961-07-9

1839-18-5

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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: Toxic

T
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: