Cladribine (CED0003618)

Record Information

Version

1.0

Creation Date

2014-09-11 05:16:01 UTC

Update Date

2026-08-17 23:12:04 UTC

SynCED ID

CED0003618

Secondary Accession Numbers

CHEM003731
T3D4774

Identification

Common Name

Cladribine

Class

Small Molecule

Description

Cladribine is an exogenous solid with the chemical formula C10H12ClN5O3 and an average molecular weight of 285.69 g/mol. Cladribine belongs to the purine 2'-deoxyribonucleosides, a subclass of purine nucleosides within the organic compounds. It is an antineoplastic agent used in the treatment of lymphoproliferative diseases, including hairy-cell leukemia. The compound is found in or released from nine recorded sources. These include healthcare, pharmaceuticals, and veterinary products, specifically immunosuppressants and antineoplastic agents; household cleaning and consumer products, including tobacco smoke filters and non electric simulated smoking devices; and electrical and electronic equipment, such as magnets, television systems, radio transmission systems, line transmission systems, and electrically stimulated smoking devices. Recorded exposure routes for this substance include subcutaneous, oral, and intravenous administration. Cladribine interacts with 15 recorded protein targets. These targets include the androgen receptor (AR), the estrogen receptor (ESR1), 3',5'-cyclic-AMP phosphodiesterase 4A (PDE4A), and it acts as an inducer or inhibitor of cellular tumor antigen p53 (TP53), along with 11 other proteins.

Contaminant Type

Amine
Antineoplastic Agent
Drug
Ether
Human Neurotoxin
Immunosuppressive Agent
Metabolite
Organic Compound
Organochloride
Synthetic Compound

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
(2R,3S,5R)-5-(6-Amino-2-chloropurin-9-yl)-2-(hydroxymethyl)oxolan-3-ol	ChEBI
2-CdA	ChEBI
2-Chloro-2'-deoxy-beta-adenosine	ChEBI
2-Chloro-6-amino-9-(2-deoxy-beta-D-erythro-pentofuranosyl)purine	ChEBI
2-Chloro-deoxyadenosine	ChEBI
2-Chlorodeoxyadenosine	ChEBI
2ClAdo	ChEBI
Cladribina	ChEBI
Cladribinum	ChEBI
CldAdo	ChEBI
Leustatin	Kegg
Mavenclad	Kegg
2-Chloro-2'-deoxy-b-adenosine	Generator
2-Chloro-2'-deoxy-β-adenosine	Generator
2-Chloro-6-amino-9-(2-deoxy-b-D-erythro-pentofuranosyl)purine	Generator
2-Chloro-6-amino-9-(2-deoxy-β-D-erythro-pentofuranosyl)purine	Generator
2-Chloro-2'-deoxyadenosine	HMDB
Chlorodeoxyadenosine	HMDB
2'-Deoxy-2-chloroadenosine	HMDB

Chemical Formula

C₁₀H₁₂ClN₅O₃

Average Molecular Mass

285.687 g/mol

Monoisotopic Mass

285.063 g/mol

CAS Registry Number

4291-63-8

IUPAC Name

(2R,3S,5R)-5-(6-amino-2-chloro-9H-purin-9-yl)-2-(hydroxymethyl)oxolan-3-ol

Traditional Name

cladribine

SMILES

NC1=C2N=CN([C@H]3C[C@H](O)[C@@H](CO)O3)C2=NC(Cl)=N1

InChI Identifier

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

InChI Key

PTOAARAWEBMLNO-KVQBGUIXSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as purine 2'-deoxyribonucleosides. Purine 2'-deoxyribonucleosides are compounds consisting of a purine linked to a ribose which lacks a hydroxyl group at position 2.

Kingdom

Organic compounds

Super Class

Nucleosides, nucleotides, and analogues

Class

Purine nucleosides

Sub Class

Purine 2'-deoxyribonucleosides

Direct Parent

Purine 2'-deoxyribonucleosides

Alternative Parents

Substituents

Purine 2'-deoxyribonucleoside
6-aminopurine
Imidazopyrimidine
Purine
Aminopyrimidine
2-halopyrimidine
Halopyrimidine
N-substituted imidazole
Aryl chloride
Aryl halide
Pyrimidine
Imidolactam
Tetrahydrofuran
Heteroaromatic compound
Imidazole
Azole
Secondary alcohol
Oxacycle
Azacycle
Organoheterocyclic compound
Organohalogen compound
Primary alcohol
Primary amine
Amine
Alcohol
Organic nitrogen compound
Hydrocarbon derivative
Organopnictogen compound
Organic oxygen compound
Organochloride
Organonitrogen compound
Organooxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

organochlorine compound (CHEBI:567361 )
purine 2'-deoxyribonucleoside (CHEBI:567361 )

Biological Properties

Status

Detected and Not Quantified

Origin

Exogenous

Cellular Locations

Cytoplasm
Extracellular
Membrane

Biofluid Locations

Not Available

Tissue Locations

Not Available

Applications

Not Available

Biological Roles

antimetabolite (PMC7504730 )?A chemical that inhibits the use of a metabolite, which is another chemical that is part of normal metabolism
antiviral agent (PMC11188666 )?
drug (PMC8613159 )?
inhibitor (PMC8613159 )?
prodrug (PMC8613159 , PMC8613159 )?

Chemical Roles

Not Available

Organoleptic Effects

Not Available

Physical Properties

State

Solid

Appearance

White powder.

Experimental Properties

Property	Value
Melting Point	215°C
Boiling Point	Not Available
Solubility	6.35e+00 g/L

Predicted Properties

Property	Value	Source
Water Solubility	6.35 g/L	ALOGPS
logP	-0.12	ALOGPS
logP	-0.28	ChemAxon
logS	-1.6	ALOGPS
pKa (Strongest Acidic)	13.89	ChemAxon
pKa (Strongest Basic)	1.33	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	119.31 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	67.18 m³·mol⁻¹	ChemAxon
Polarizability	25.93 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
Predicted GC-MS	Predicted GC-MS Spectrum	splash10-0006-9140000000-2241274903b14d6388f8	Not Available	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum	splash10-006x-9003100000-a89891be7a06bbd5506c	Not Available	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum	Not Available	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-00di-1910000000-ab013e8ee7a199f7832a	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-00e9-2900000000-e03a0a91db8b01dbf975	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-00di-1910000000-ab013e8ee7a199f7832a	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-00e9-2900000000-e03a0a91db8b01dbf975	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-001i-0190000000-05b17eee8a4c08986cb6	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-001j-0960000000-0d9006c856af92145663	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-0159-9800000000-8fab0ce14314864acddb	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-001i-3900000000-1e50884799359687c7e6	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-001i-0900000000-212e968f1960bfdb6eb9	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-001i-1900000000-02d458221e661841d56f	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-001i-0790000000-67b2d564dceedaaa13f9	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-001i-1900000000-a7de88853c9f6d670469	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-00di-2900000000-cdfa1c97765dc0e2b44d	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-0089-1900000000-e6ecaf5468250a1f5477	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-00di-0930000000-7147248d1818af3d9fe1	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-00di-0900000000-6e9123e18d8f115cbf6f	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-00di-0900000000-27a9b8fbe0ffb19d00b6	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-00di-2900000000-ab1e61284e7768836426	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-00di-0920000000-8e9ebddc65823aa84924	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-00di-0900000000-0b29ceb8b9b509f8d741	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-00di-0900000000-f0f21af02a8d1d299e4a	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-00e9-0290000000-7a1cc2a1753c44b0a43d	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-014i-0910000000-7d61665b0d4c6756760f	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-00lr-1900000000-345fc7c0125888e844c5	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-00di-0900000000-fa3ec9f7b8f59958cd43	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-00di-0900000000-fa3ec9f7b8f59958cd43	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0089-0900000000-e6f91c18410006206b44	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-001i-0190000000-780fad8d708109329d78	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0159-0910000000-a43fb0986a12415c3b0c	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-001i-2900000000-b746c8d1c6ced4365729	Not Available	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, D₂O, predicted)	Not Available	Not Available	View Spectrum
1D NMR	¹H NMR Spectrum (1D, D₂O, predicted)	Not Available	Not Available	View Spectrum

Toxicity Profile

Toxicity Values

Toxicity Value	Organism	Dose Descriptor	Route of Exposure	Predicted or Experimental	Toxicity Rating	Reference
746.0 Log mg/kg [420:1300]	Rat	LD50	oral	predicted	Not Available	Not Available

Toxicity / Toxin Class

Not Available

Mechanism of Toxicity

Cladribine is structurally related to fludarabine and pentostatin but has a different mechanism of action. Although the exact mechanism of action has not been fully determined, evidence shows that cladribine is phosphorylated by deoxycytidine kinase to the nucleotidecladribine triphosphate (CdATP; 2-chloro-2ду_-deoxyadenosine 5ду_-triphosphate), which accumulates and is incorporated into DNA in cells such as lymphocytes that contain high levels of deoxycytidine kinase and low levels of deoxynucleotidase, resulting in DNA strand breakage and inhibition of DNA synthesis and repair. High levels of CdATP also appear to inhibit ribonucleotide reductase, which leads to an imbalance in triphosphorylated deoxynucleotide (dNTP) pools and subsequent DNA strand breaks, inhibition of DNA synthesis and repair, nicotinamide adenine dinucleotide (NAD) and ATP depletion, and cell death. Unlike other antimetabolite drugs, cladribine has cytotoxic effects on resting as well as proliferating lymphocytes. However, it does cause cells to accumulate at the G1/S phase junction, suggesting that cytotoxicity is associated with events critical to cell entry into S phase. It also binds purine nucleoside phosphorylase (PNP), however no relationship between this binding and a mechanism of action has been established.

Carcinogenicity (IARC Classification)

No indication of carcinogenicity to humans (not listed by IARC).

Minimum Risk Level

Not Available

Symptoms

Symptoms of overdose include irreversible neurologic toxicity (paraparesis/quadriparesis), acute nephrotoxicity, and severe bone marrow suppression resulting in neutropenia, anemia and thrombocytopenia.

Treatment

Not Available

Health Effects

Health Effect	Relationship	Direction	Description	Reference
cancer	Not Available	Not Available	Cancer is a group of diseases involving abnormal cell growth with the potential to invade or spread to other parts of the body. Possible signs and symptoms include a lump, abnormal bleeding, prolonged cough, unexplained weight loss, and a change in bowel movements. There are over 100 types of cancers affect humans. The risk of developing certain cancers can be reduced by not smoking, maintaining a healthy weight, not drinking too much alcohol, eating plenty of vegetables, fruits and whole grains, vaccination against certain infectious diseases, not eating too much processed and red meat and avoiding too much sunlight exposure. Cancer is often treated with some combination of radiation therapy, surgery, chemotherapy and targeted therapy. The majority of cancers, some 90–95% of cases, are due to genetic mutations from environmental and lifestyle factors. The remaining 5–10% are due to inherited genetics.	PMC7504730
hemolysis	Associated With?	Not Available	Not Available	PMC7152208
hairy cell leukemia	Not Available	Not Available	Not Available	PMC7123643

Exposure Sources

Source ID	Source	Sector	Reference
CEDs000233	Brushes?Brushes used in personal care and cosmetics can be a source of synthetic chemical contamination due to the materials and coatings used in their manufacturing.	Personal care & cosmetics	PubChem
CEDs000358	Antineoplastic agents?Antineoplastic agents are a class of synthetic chemicals used primarily in the treatment of cancer.	Healthcare, pharmaceuticals & veterinary products	Not Available
CEDs000362	Immunosuppressants?Immunosuppressants are synthetic chemicals used to inhibit the immune response, primarily in patients undergoing organ transplants or those with autoimmune disorders.	Healthcare, pharmaceuticals & veterinary products	Not Available
CEDs000511	Conductors Or Conductive Bodies Characterised By The Conductive Materials?Conductors, or conductive bodies, are materials that allow the flow of electrical current, typically made from metals such as copper, aluminum, or silver.	Electrical & Electronic Equipment	PubChem
CEDs000518	Electrically Stimulated Smoking Devices?Electrically stimulated smoking devices, commonly known as e-cigarettes or vape pens, utilize electrical components to heat a liquid solution, often containing nicotine, flavorings, and other additives, to produce an aerosol for inhalation.	Electrical & Electronic Equipment	PubChem
CEDs000519	Electrodes?Electrodes, used in various electrical and electronic applications, can be a source of synthetic chemical contamination due to the materials from which they are constructed and the processes involved in their manufacturing.	Electrical & Electronic Equipment	PubChem
CEDs000525	Line Transmission Systems?Line Transmission Systems, commonly used for the distribution of electrical energy, can be a source of synthetic chemical contamination through the insulation materials and coatings utilized in their construction.	Electrical & Electronic Equipment	PubChem
CEDs000527	Magnets?Magnets, commonly used in various electrical and electronic applications, can be a source of synthetic chemical contamination due to the materials used in their production.	Electrical & Electronic Equipment	PubChem
CEDs000530	Radio Transmission Systems?Radio transmission systems utilize a variety of synthetic chemicals in their manufacturing and maintenance processes.	Electrical & Electronic Equipment	PubChem
CEDs000537	Television Systems?Television systems can be a source of synthetic chemical contamination due to the various materials and components used in their manufacture and operation.	Electrical & Electronic Equipment	PubChem
CEDs000559	Non Electric Simulated Smoking Devices?Non-electric simulated smoking devices, often designed to mimic the experience of smoking without combustion, can be sources of synthetic chemical contamination due to the materials and chemicals used in their construction and operation.	Household cleaning & consumer products	PubChem
CEDs000569	Tobacco Smoke Filters?Tobacco smoke filters are designed to reduce the inhalation of harmful substances in cigarette smoke, including tar and other particulate matter.	Household cleaning & consumer products	PubChem
CEDs000580	Manufacture Preparation Of Tobacco Products?The manufacture and preparation of tobacco products involve various processes that can result in the introduction of synthetic chemicals into the environment.	Industrial manufacturing & chemical processing	PubChem
CEDs000610	Aftersun Products?Aftersun products are designed to soothe and hydrate the skin after sun exposure, often containing various synthetic chemicals such as emollients, preservatives, and fragrances.	Personal care & cosmetics	PubChem
CEDs000611	Anti Perspirants Or Body Deoderants?Antiperspirants and body deodorants commonly contain synthetic chemicals such as aluminum compounds, parabens, and synthetic fragrances.	Personal care & cosmetics	PubChem
CEDs000615	Eye Makeup Products?Eye makeup products, including mascaras, eyeliners, and eyeshadows, often contain a variety of synthetic chemicals such as pigments, preservatives, and film-forming agents.	Personal care & cosmetics	PubChem
CEDs000632	Apparel?Apparel production often involves the use of various synthetic chemicals, including dyes, finishing agents, and preservatives.	Textiles, leather & furnishings	PubChem
CEDs000642	Footwear?Footwear production often involves the use of various synthetic chemicals, such as adhesives, dyes, and treatments, which can contribute to environmental contamination.	Textiles, leather & furnishings	PubChem
CEDs000650	Purses Luggage Hand Bags?Purses, luggage, and handbags are often manufactured using synthetic materials such as polyvinyl chloride (PVC), polyurethane, and various types of nylon.	Textiles, leather & furnishings	PubChem
CEDs000662	Yarns Or Threads?Yarns or threads used in textiles can be a source of synthetic chemical contamination due to the production processes and treatments they undergo.	Textiles, leather & furnishings	PubChem
CEDs000684	Cements?Cements are a composite material primarily used as a binding agent in construction applications, formed by the calcination of limestone and clay minerals at high temperatures.	Building & Construction	PubChem
CEDs000685	Ceramics?Ceramics can be a source of synthetic chemical contamination through various additives and processing agents used in their production.	Building & Construction	PubChem
CEDs000686	Clay Wares?Clay wares are ceramic products made from natural clay, often utilized in various construction applications such as tiles, bricks, and sanitary ware.	Building & Construction	PubChem
CEDs000692	Silica Free Oxide Glass?Silica Free Oxide Glass is a type of glass that is produced using alternative materials to traditional silica-based formulations.	Building & Construction	PubChem
CEDs000696	Nanotechnology?Nanotechnology involves the manipulation of materials at the molecular or atomic level, typically within the range of 1 to 100 nanometers.	Industrial manufacturing & chemical processing	PubChem
CEDs000698	Jewellery?Jewellery production often involves the use of various synthetic chemicals during the extraction and processing of metals.	Mining & metal processing	PubChem
CEDs000732	Spectacle Cases?Spectacle cases can serve as a source of synthetic chemical contamination due to the materials used in their production, such as polycarbonate, PVC, and various plastics, which may leach harmful substances over time.	Healthcare, pharmaceuticals & veterinary products	PubChem
CEDs000740	Paper?Paper production involves the processing of wood fibers and the use of various chemicals, which can lead to synthetic chemical contamination.	Paper, pulp & fiber products	PubChem
CEDs000741	Pigment Pastes?Pigment pastes are concentrated dispersions of pigments used to impart color and properties to materials.	Paper, pulp & fiber products	PubChem
CEDs000744	Water, Wastewater, & Sewage Treatment?Water, wastewater, and sewage treatment processes are critical for managing and mitigating pollutants in water systems.	Wastewater, sanitation & biosolids	PubChem

Pathways

3 pathwaysPathway Source: PathBank

Cladribine Action Pathway

Cladribine Drug Metabolism Action Pathway

Cladribine Predicted Metabolism Pathway

Targets

Structure	Protein	UniProt ID	Organism	Relationship	Details
Click to view 3D structure	Adenosine receptor A1	P25099	Rattus norvegicus	Predicted (SEA)	Prediction Confidence Score 0.608 Applicability Domain 1.0 Statistical Significance 9.50e-04 Supporting Reference Compounds 221 E-value 7.39568
Click to view 3D structure	cGMP-dependent 3',5'-cyclic phosphodiesterase	O00408	Humans	Predicted (SEA)	Prediction Confidence Score 0.544 Applicability Domain 1.0 Statistical Significance 1.20e-04 Supporting Reference Compounds 119 E-value 0.934191
Click to view 3D structure	Adenosine receptor A3	P0DMS8	Humans	Predicted (SEA)	Prediction Confidence Score 0.531 Applicability Domain 0.654 Statistical Significance 0.0028 Supporting Reference Compounds 391 E-value 22.1092
Click to view 3D structure	Adenosine receptor A2a	P30543	Rattus norvegicus	Predicted (SEA)	Prediction Confidence Score 0.497 Applicability Domain 0.654 Statistical Significance 0.003 Supporting Reference Compounds 174 E-value 23.0434
Click to view 3D structure	Adenosine receptor A1	P30542	Humans	Predicted (SEA)	Prediction Confidence Score 0.488 Applicability Domain 0.654 Statistical Significance 0.0037 Supporting Reference Compounds 302 E-value 28.7264
Click to view 3D structure	Adenosine receptor A2a	P29274	Humans	Predicted (SEA)	Prediction Confidence Score 0.488 Applicability Domain 0.654 Statistical Significance 0.0039 Supporting Reference Compounds 303 E-value 30.0498
Click to view 3D structure	Adenosine receptor A3	P28647	Rattus norvegicus	Predicted (SEA)	Prediction Confidence Score 0.474 Applicability Domain 0.654 Statistical Significance 0.0024 Supporting Reference Compounds 71 E-value 18.4503
Click to view 3D structure	Adenosine receptor A1	P28190	Bos taurus	Predicted (SEA)	Prediction Confidence Score 0.464 Applicability Domain 0.654 Statistical Significance 0.0017 Supporting Reference Compounds 72 E-value 13.0008
Click to view 3D structure	Heat shock protein HSP 90-alpha	P07900	Humans	Predicted (SEA)	Prediction Confidence Score 0.464 Applicability Domain 0.654 Statistical Significance 0.0017 Supporting Reference Compounds 109 E-value 13.5458
Click to view 3D structure	Endoplasmin	P14625	Humans	Predicted (SEA)	Prediction Confidence Score 0.464 Applicability Domain 0.654 Statistical Significance 0.0014 Supporting Reference Compounds 31 E-value 10.9767
Click to view 3D structure	Adenosine receptor A1	P47745	Cavia porcellus	Predicted (SEA)	Prediction Confidence Score 0.451 Applicability Domain 0.654 Statistical Significance 0.0013 Supporting Reference Compounds 38 E-value 9.88685
Click to view 3D structure	5-hydroxytryptamine receptor 2A	P28223	Humans	Predicted (SEA)	Prediction Confidence Score 0.436 Applicability Domain 0.654 Statistical Significance 0.0116 Supporting Reference Compounds 955 E-value 90.3051
Click to view 3D structure	Adenosine receptor A2b	P29275	Humans	Predicted (SEA)	Prediction Confidence Score 0.42 Applicability Domain 0.446 Statistical Significance 0.0054 Supporting Reference Compounds 187 E-value 41.8829
Click to view 3D structure	CD99 antigen	P14209	Humans	Predicted (SEA)	Prediction Confidence Score 0.394 Applicability Domain 0.394 Statistical Significance 3.90e-04 Supporting Reference Compounds 1 E-value 3.03612
Click to view 3D structure	P2Y purinoceptor 1	P47900	Humans	Predicted (SEA)	Prediction Confidence Score 0.391 Applicability Domain 0.471 Statistical Significance 0.0027 Supporting Reference Compounds 42 E-value 21.3307
Click to view 3D structure	A1 adenosine receptor	Q4VQ11	Sus scrofa	Predicted (SEA)	Prediction Confidence Score 0.381 Applicability Domain 0.446 Statistical Significance 7.60e-04 Supporting Reference Compounds 9 E-value 5.91654
Click to view 3D structure	Serine--tRNA ligase	P95689	Staphylococcus aureus (strain NCTC 8325 / PS 47)	Predicted (SEA)	Prediction Confidence Score 0.378 Applicability Domain 0.452 Statistical Significance 0.0013 Supporting Reference Compounds 2 E-value 9.809
Click to view 3D structure	P2Y purinoceptor 11	Q96G91	Humans	Predicted (SEA)	Prediction Confidence Score 0.375 Applicability Domain 0.471 Statistical Significance 0.0018 Supporting Reference Compounds 13 E-value 14.0129
Click to view 3D structure	Ribonuclease pancreatic	P07998	Humans	Predicted (SEA)	Prediction Confidence Score 0.375 Applicability Domain 0.375 Statistical Significance 5.40e-04 Supporting Reference Compounds 1 E-value 4.20386
Click to view 3D structure	Non-secretory ribonuclease	P10153	Humans	Predicted (SEA)	Prediction Confidence Score 0.375 Applicability Domain 0.375 Statistical Significance 5.40e-04 Supporting Reference Compounds 1 E-value 4.20386
Click to view 3D structure	Adenosylhomocysteinase	P50250	Plasmodium falciparum (isolate 3D7)	Predicted (SEA)	Prediction Confidence Score 0.373 Applicability Domain 0.448 Statistical Significance 1.10e-04 Supporting Reference Compounds 4 E-value 0.856341
Click to view 3D structure	Adenosine receptor A3	Q61618	Mus musculus	Predicted (SEA)	Prediction Confidence Score 0.373 Applicability Domain 0.446 Statistical Significance 0.003 Supporting Reference Compounds 72 E-value 23.0434
Click to view 3D structure	5-hydroxytryptamine receptor 2B	P41595	Humans	Predicted (SEA)	Prediction Confidence Score 0.371 Applicability Domain 0.508 Statistical Significance 0.013 Supporting Reference Compounds 686 E-value 101.593
Click to view 3D structure	Adenosine receptor A1	Q60612	Mus musculus	Predicted (SEA)	Prediction Confidence Score 0.371 Applicability Domain 0.446 Statistical Significance 0.0031 Supporting Reference Compounds 51 E-value 23.8219
Click to view 3D structure	High affinity choline transporter 1	Q9GZV3	Humans	Predicted (SEA)	Prediction Confidence Score 0.371 Applicability Domain 0.654 Statistical Significance 0.002 Supporting Reference Compounds 75 E-value 15.4141
Click to view 3D structure	Vascular endothelial growth factor receptor 2	P35918	Mouse	Known	Not Available
Click to view 3D structure	Broad substrate specificity ATP-binding cassette transporter ABCG2	Q9UNQ0	Humans	Known	Not Available
Click to view 3D structure	Purine nucleoside phosphorylase	P00491	Humans	Known	Not Available
Click to view 3D structure	Ribonucleoside-diphosphate reductase large subunit	P23921	Humans	Known	Not Available
Click to view 3D structure	Ribonucleoside-diphosphate reductase subunit M2	P31350	Humans	Known	Not Available
Click to view 3D structure	Ribonucleoside-diphosphate reductase subunit M2 B	Q7LG56	Humans	Known	Not Available
Click to view 3D structure	DNA polymerase alpha catalytic subunit	P09884	Humans	Known	Not Available
Click to view 3D structure	DNA polymerase epsilon catalytic subunit A	Q07864	Humans	Known	Not Available
Click to view 3D structure	DNA polymerase epsilon subunit 2	P56282	Humans	Known	Not Available
Click to view 3D structure	DNA polymerase epsilon subunit 3	Q9NRF9	Humans	Known	Not Available
Click to view 3D structure	DNA polymerase epsilon subunit 4	Q9NR33	Humans	Known	Not Available
Click to view 3D structure	Androgen receptor	P10275	Humans	Known	Not Available
Click to view 3D structure	Cellular tumor antigen p53	P04637	Humans	Known	Not Available
Click to view 3D structure	Estrogen receptor	P03372	Humans	Known	Not Available
Click to view 3D structure	3',5'-cyclic-AMP phosphodiesterase 4A	P27815	Humans	Known	Not Available

Concentrations

Not Available

External Links

DrugBank ID

DB00242

HMDB ID

HMDB0014387

FooDB ID

Not Available

Phenol Explorer ID

Not Available

KNApSAcK ID

Not Available

BiGG ID

Not Available

BioCyc ID

Not Available

METLIN ID

Not Available

PDB ID

Wikipedia Link

Chemspider ID

ChEBI ID

PubChem Compound ID

Kegg Compound ID

Not Available

YMDB ID

Not Available

ECMDB ID

Not Available

References

Synthesis Reference

Szepsel Gerszberg, “Method for the production of 2-chloro-2' -deoxyadenosine (cladribine) and its 3,5-di-O-p-toluoyl derivative.” U.S. Patent US20020052491, issued May 02, 2002.

MSDS

Link

General References

Sampat K, Kantarjian H, Borthakur G: Clofarabine: emerging role in leukemias. Expert Opin Investig Drugs. 2009 Oct;18(10):1559-64. doi: 10.1517/13543780903173222. [PubMed: 19715446]
Kantarjian HM, Jeha S, Gandhi V, Wess M, Faderl S: Clofarabine: past, present, and future. Leuk Lymphoma. 2007 Oct;48(10):1922-30. [PubMed: 17852710]
Zhenchuk A, Lotfi K, Juliusson G, Albertioni F: Mechanisms of anti-cancer action and pharmacology of clofarabine. Biochem Pharmacol. 2009 Dec 1;78(11):1351-9. doi: 10.1016/j.bcp.2009.06.094. Epub 2009 Jul 1. [PubMed: 19576186]
Warnke C, Wiendl H, Hartung HP, Stuve O, Kieseier BC: Identification of targets and new developments in the treatment of multiple sclerosis--focus on cladribine. Drug Des Devel Ther. 2010 Jul 21;4:117-26. [PubMed: 20689698]
Sigal DS, Miller HJ, Schram ED, Saven A: Beyond hairy cell: the activity of cladribine in other hematologic malignancies. Blood. 2010 Oct 21;116(16):2884-96. doi: 10.1182/blood-2010-02-246140. Epub 2010 Jul 15. [PubMed: 20634380]
Khalid BA, Hamilton NT, Cauchi MN: Binding of thyroid microsomes by lymphocytes from patients with thyroid disease and normal subjects. Clin Exp Immunol. 1976 Jan;23(1):28-32. [PubMed: 1261088]
Larson ML, Venugopal P: Clofarabine: a new treatment option for patients with acute myeloid leukemia. Expert Opin Pharmacother. 2009 Jun;10(8):1353-7. doi: 10.1517/14656560902997990. [PubMed: 19463072]
Dimopoulos MA, Weber DM, Kantarjian H, Keating M, Alexanian R: 2Chlorodeoxyadenosine therapy of patients with Waldenstrom macroglobulinemia previously treated with fludarabine. Ann Oncol. 1994 Mar;5(3):288-9. [PubMed: 7514439]

Cladribine (CED0003618)

Structure for CHEM003731: Cladribine

Structure