2-Chloro-6-amino-9-(2-deoxy-b-D-erythro-pentofuranosyl)purine
Cladribine
CAS: 4291-63-8
Molecular Formula: C10H12ClN5O3
2-Chloro-6-amino-9-(2-deoxy-b-D-erythro-pentofuranosyl)purine - Names and Identifiers
| Name | Cladribine |
| Synonyms | CDA 2CDA 2-CL-DADO CLADRIBINE Cladribine CLADRIBINE CDA LABOTEST-BB LT01147851 2-chloro-2'-deoxyadenosine 2-CHLORO-2'-DEOXYADENOSINE 2-chloro-9-(2-deoxypentofuranosyl)-9H-purin-6-amine 2-Chloro-6-amino-9-(2-deoxy-b-D-erythro-pentofuranosyl)purine 2-chloro-9-(2-deoxy-β-D-threo-pentofuranosyl)-9H-purin-6-amine |
| CAS | 4291-63-8 |
| EINECS | 636-978-6 |
| InChI | InChI=1/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-/m1/s1 |
| InChIKey | PTOAARAWEBMLNO-HSUXUTPPSA-N |
2-Chloro-6-amino-9-(2-deoxy-b-D-erythro-pentofuranosyl)purine - Physico-chemical Properties
| Molecular Formula | C10H12ClN5O3 |
| Molar Mass | 285.69 |
| Density | 2.03±0.1 g/cm3(Predicted) |
| Melting Point | 181-185°C(lit.) |
| Boling Point | 547.6±60.0 °C(Predicted) |
| Specific Rotation(α) | D25 -18.8° (c = 1 in DMF) |
| Solubility | Slightly soluble in water, soluble in dimethyl sulfoxide, slightly soluble in methanol, practically insoluble in acetonitrile. It shows polymorphism (5.9). |
| Appearance | White solid |
| Color | White to Pale Yellow |
| Maximum wavelength(λmax) | ['265nm(EtOH aq.)(lit.)'] |
| Merck | 14,2337 |
| pKa | 13.75±0.60(Predicted) |
| Storage Condition | -20°C |
| Stability | Store in Freezer |
| Sensitive | Sensitive to heat |
| Physical and Chemical Properties | Crystallized from water, softened at 210-215 °c, and turned brown after curing; Crystallized from ethanol, melting point 22023 (softening), solidified, turned brown, and no longer melted at <300 °c. [Α] D23-18.8 °(C = 1, dimethylformamide). UV maximum absorption (0.1mol/L sodium hydroxide):265nm:(0.1mol/L hydrochloric acid):265nm. |
| Use | It is a chlorinated purine nucleoside with activity against lymphoproliferative disorders, such as hairy cell leukemia (HCL) and multiple myeloma (MM). 2-CdA resists ADA degradation and is phosphorylated to CdATP in lymphocytes. CdATP incorporation I |
| In vitro study | Cladribine exerts marked activity against hairy cell leukemia (HCL), a chronic B- cell lymphoproliferative disease, prolonging complete remission. Cladribine induces the accumulation of DNA strand breaks and subsequently activates the tumor suppressor gene p53 in lymphocytes. Cladribine may regulate STAT3 activity in MM cells. Cladribine dose-dependently inhibited proliferation/survival of U266,RPMI8226 and MM1.S cells. Among them, U266 had the lowest sensitivity to cladribine and the highest sensitivity to MM1.S. Cladribine treatment gradually increased the proportion of cells in the G1 phase of the cell cycle and decreased S-phase cells. Cladribine treatment after 24 hours appears to be able to increase the proportion of G2-M phase in U266 cells. A dose-dependent increase in cladribine-induced apoptosis was observed in both RPMI8226 and MM1.S cells. 0.2 μm cladribine treatment time-dependently significantly induced caspase-3,-8, and -9 activation and PARP cleavage in MM1.S. Cladribine significantly reduced phospho-STAT3 (P-STAT3) levels in a dose-dependent manner, but did not affect total STAT3 protein levels. Cladribine has the potential to induce apoptosis in a concentration-dependent manner in HSB2 cells. Cladribine inhibited the growth of primary mast cells (MC) and MC lineage HMC-1 in a dose-dependent manner, HMC-1.2 cells containing KIT D816V compared to HMC-1.1 cells lacking KIT D816V, has a lower IC50 value. Cladribine reduced CD14 |
| In vivo study | Cladribine (0.7-3.5 mM) and/or diltiazem (2.4 mM), injected intraperitoneally into adult zebrafish, analyzed by HPLC for potential markers of cardiovascular health, red blood cells (RBC) lysate levels of purine nucleotides (e. G., ATP). Diltiazem increased RBC ATP concentrations, an effect that was inhibited by coinjection of cladribine. After administration of Ia and s.c., Cladribine plasma concentrations sharply decreased with a biphasic decline. After a single dose of Cladribine injected at 1 mg/kg ia and 2 mg/kg s.c., the AUD and t 1/2β were 0.66: 1.2 μg × h/mL and 3.5: 4.5 h, respectively. |
2-Chloro-6-amino-9-(2-deoxy-b-D-erythro-pentofuranosyl)purine - Risk and Safety
| Hazard Symbols | T - Toxic |
| Risk Codes | R36/37/38 - Irritating to eyes, respiratory system and skin. R23/24/25 - Toxic by inhalation, in contact with skin and if swallowed. |
| Safety Description | 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. |
| UN IDs | UN 2811 6.1 / PGIII |
| WGK Germany | 3 |
| RTECS | AU7357560 |
| HS Code | 29349990 |
| Toxicity | LD50 intraperitoneal in mouse: 150mg/kg |
2-Chloro-6-amino-9-(2-deoxy-b-D-erythro-pentofuranosyl)purine - Nature
Open Data Verified Data
crystallized from water, softened at 210~215 ℃, and turned brown after curing; Crystallized from ethanol, melting point 220 ℃ (softening), solidified, turned brown, no more melting at <300 °c. UV maximum absorption (0.1 mol/L sodium hydroxide):265nm} (0.1 mol/L hydrochloric acid):265nm.
Last Update：2024-01-02 23:10:35
2-Chloro-6-amino-9-(2-deoxy-b-D-erythro-pentofuranosyl)purine - Preparation Method
Open Data Verified Data
2,6-= oxypurine and sodium hydride were suspended in anhydrous acetonitrile and stirred at room temperature under nitrogen. Under stirring, 1 monochloro-2-deoxy-3, 5-=-0-p-toluoyl-a-D erythro-furanpentose was added. After completion, a small amount of insoluble matter was filtered off by filtration, and the filtrate was concentrated. The remaining oil was chromatographed on a silica gel column eluting with toluene/acetone and crystallized from ethanol. The resulting compound was dissolved in saturated ammonia in methanol and stirred. It was then evaporated to dryness and the material obtained was chromatographed on a silica gel column eluting with chloroform/methanol. Re-ethanol crystallization, I. E. Cladribine.
Last Update：2022-01-01 09:09:06
2-Chloro-6-amino-9-(2-deoxy-b-D-erythro-pentofuranosyl)purine - Introduction
Cladribine is an adenosine deaminase inhibitor that acts on U266, RPMI8226, and MM1.S cells with IC50 of about 2.43 μM, 0.75 μM, and 0.18 μM, respectively.
Last Update：2022-10-16 17:25:12
2-Chloro-6-amino-9-(2-deoxy-b-D-erythro-pentofuranosyl)purine - Use
Open Data Verified Data
developed by Ortho Biotech, Inc., USA, launched in 1993. It is a deoxyadenosine analog resistant to adenosine deaminase. For active hairy cell leukemia.
Last Update：2022-01-01 09:09:07
2-Chloro-6-amino-9-(2-deoxy-b-D-erythro-pentofuranosyl)purine - Reference Information
| functional indications | mainly has a good effect on hairy cell leukemia, and is also effective for other lymphomas and leukemias. |
| biological activity | Cladribine (Leustatin, 2-CdA, 2-lorodeoxyadenosine, 2-Chloro-2 ′-deoxyadenosine, CldAdo) is an adenosine deaminase inhibitor that acts on U266, RPMI8226, and MM1.S cells with IC50 of about 2.43 μM, 0.75 μM, and 0.18 μM, respectively. |
| Target | Value |
| Adenosine deaminase (MM1.S cells) | 0.18 μM |
| Adenosine deaminase (RPMI8226 cells) | 0.75 μM |
| Adenosine deaminase (U266 cells) | 2.43 μM |
| Use | is a deoxyadenosine analog resistant to adenosine deaminase. For active hairy cell leukemia. |
| production method | 2,6-dichloropurine (I)(0.95g,5 mmo1) and sodium hydride (50% dispersed oil, 0.25g,5.2 mmo1) are suspended in 35ml of anhydrous acetonitrile and stirred under room temperature and nitrogen protection for 30min. 1-chloro -2-deoxy -3,5-di-O-p-toluenoyl-α-D-red-furan pentose (II)(1.95g,5 mmo1) was added in batches within 20min under stirring. Add it and stir for another 15 hours. A small amount of insoluble matter is filtered out and the filtrate is concentrated. The remaining oil was chromatography with silica gel column and eluted with toluene-acetone (9:1, volume ratio). The obtained solid was crystallized with ethanol to obtain 1.60g compound (Ⅲ) with 59% yield and 159-162 ℃ melting point. Compound (III)(2.50g,4.6 mmo1) is dissolved in 60ml of saturated ammonia methanol solution (saturated at 0 ℃) and stirred at 100 ℃ for 5 hours. Evaporation to dryness, the remainder is chromatography with silica gel column and eluted with chloroform-methanol (8:2, volume ratio). Re-ethanol crystallization, 0.87g cladribine, 71% yield, melting point 220 ℃ (softening). |
| toxic substance data | information provided by: pubchem.ncbi.nlm.nih.gov (external link) |
Last Update：2024-04-09 19:05:12
Supplier List
Spot supply
Product Name: Cladribine Visit Supplier Webpage Request for quotationCAS: 4291-63-8
Tel: 18301782025
Email: 3008007409@qq.com
Mobile: 18021002903
QQ: 3008007409
Wechat: 18301782025
Multiple Specifications
Product Name: Cladribine Request for quotationCAS: 4291-63-8
Tel: +86-571-88162785
Email: Lucy@verypharm.com
Mobile: +86-13606544505
QQ: 472954302
Product List: View Catalog
Spot supply
Product Name: Cladribine Visit Supplier Webpage Request for quotationCAS: 4291-63-8
Tel: 18301782025
Email: 3008007409@qq.com
Mobile: 18021002903
QQ: 3008007409
Wechat: 18301782025
Multiple Specifications
Product Name: Cladribine Request for quotationCAS: 4291-63-8
Tel: +86-571-88162785
Email: Lucy@verypharm.com
Mobile: +86-13606544505
QQ: 472954302
Product List: View Catalog
View History