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cladribine   Click here for help

GtoPdb Ligand ID: 4799

Synonyms: Leustatin® | Litak® | Mavenclad®
Approved drug PDB Ligand
cladribine is an approved drug (FDA (1993), EMA (2004))
Compound class: Synthetic organic
Comment: Cladribine is a purine (adenosine) analogue and an antineoplastic and immunosuppressant agent

cladribine is commercially available from our sponsors

2D Structure
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2D Structure

An image of the ligand's 2D structure. For small molecules with SMILES these are drawn using the NCI/CADD Chemical Identifier Resolver. Click on the image to access the chemical structure search tool with the ligand pre-loaded in the structure editor. For other types of ligands, e.g. longer nucleotides and peptides, a manually drawn representation of the molecule may be provided.

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Physico-chemical Properties
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Physico-chemical Properties

Calculated molecular properties are available for small molecules and natural products (not peptides). Properties were generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/). All properties were selected to enable the prediction of the Lipinski Rule-of-Five profile or ‘druglikeness’ for each ligand. For more info on each category see the help pages.

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Hydrogen bond acceptors 7
Hydrogen bond donors 3
Rotatable bonds 2
Topological polar surface area 119.31
Molecular weight 285.06
XLogP -0.1
No. Lipinski's rules broken 0

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
SMILES / InChI / InChIKey
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SMILES / InChI / InChIKey

SMILES (Simplified Molecular Input Line Entry Specification) A specification for unambiguously describing the structure of chemical molecules using short ASCII strings. Canonical SMILES specify a unique representation of the 2D structure without chiral or isotopic specifications. Isomeric SMILES include chiral specification and isotopes.

Standard InChI (IUPAC International Chemical Identifier) and InChIKey InChI is a non-proprietary, standard, textual identifier for chemical substances designed to facilitate linking of information and database searching. An InChIKey is a simplified version of a full InChI, designed for easier web searching.

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)

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Canonical SMILES OCC1OC(CC1O)n1cnc2c1nc(Cl)nc2N
Isomeric SMILES OC[C@H]1O[C@H](C[C@@H]1O)n1cnc2c1nc(Cl)nc2N
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
InChI Key PTOAARAWEBMLNO-KVQBGUIXSA-N

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
Classification Click here for help
Compound class Synthetic organic
Approved drug? Yes. US FDA (1993)  |  EU EMA (2004)
WHO Essential Medicine WHO Essential Medicines List (EML) (23rd List, 2023). Access PDF version.
Click to view more information about the WHO Model Lists of Essential Medicines.
IUPAC Name Click here for help
(2R,3S,5R)-5-(6-amino-2-chloro-9H-purin-9-yl)-2-(hydroxymethyl)oxolan-3-ol
International Nonproprietary Names Click here for help
INN number INN
6997 cladribine
Synonyms Click here for help
Leustatin® | Litak® | Mavenclad®
Database Links Click here for help
CAS Registry No. 4291-63-8
ChEMBL Ligand CHEMBL1619
DrugBank Ligand DB00242
DrugCentral Ligand 667
GtoPdb PubChem SID 178101501
PubChem CID 20279
RCSB PDB Ligand CL9
Search Google for chemical match using the InChIKey PTOAARAWEBMLNO-KVQBGUIXSA-N
Search Google for chemicals with the same backbone PTOAARAWEBMLNO
Search PubMed clinical trials cladribine
Search PubMed titles cladribine
Search PubMed titles/abstracts cladribine
UniChem Compound Search for chemical match using the InChIKey PTOAARAWEBMLNO-KVQBGUIXSA-N
UniChem Connectivity Search for chemical match using the InChIKey PTOAARAWEBMLNO-KVQBGUIXSA-N
Wikipedia Cladribine

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MedChemExpress
Cladribine (links to external site)
Cat. No. HY-13599