Chemical substance record

Cladribine

4291-63-8C₁₀H₁₂ClN₅O₃285.691 g/mol

Organic/Inorganic Small MoleculeChEBI source record

2'-Deoxyadenosine in which the hydrogen at position 2 on the purine ring has been substituted by chlorine. It inhibits the synthesis and repair of DNA, particularly in lymphocytes and monocytes, and is used as an antimetabolite antineoplastic drug for the treatment of lymphoid malignancies including hairy-cell leukaemia and chronic lymphocytic leukaemia. — ChEBI

Safety references

Safety documents & references

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Identity & molecular properties

Source-linked values

CAS number	4291-63-8	ChEBI ↗
Molecular formula	C₁₀H₁₂ClN₅O₃	ChEBI ↗
Molar mass	285.691 g/mol	ChEBI ↗
Monoisotopic mass	285.06287 Da	ChEBI ↗
Formal charge	0	ChEBI ↗
ChEBI identifier	CHEBI:567361	ChEBI ↗

Cross-source molecular data

PubChem

Molar mass	285.69 g/mol	PubChem ↗
Exact mass	285.0628670 Da	PubChem ↗
Computed XLogP	0.8	PubChem ↗
Topological polar surface area (Å²)	119	PubChem ↗
H-bond donors	3	PubChem ↗
H-bond acceptors	7	PubChem ↗
Rotatable bonds	2	PubChem ↗

PubChem computed values are shown separately from the ChEBI record. An exact InChIKey match was used to connect the records. Molecular descriptors do not describe a supplied product’s purity, particle size or performance.

Names & structural identifiers

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Source preferred name

cladribine

IUPAC name

2-chloro-2'-deoxyadenosine

InChIKey

PTOAARAWEBMLNO-KVQBGUIXSA-N

SMILES

Nc1nc(Cl)nc2c1ncn2[C@H]1C[C@H](O)[C@@H](CO)O1

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

Names & synonyms

2-chloro-2'-deoxyadenosinecladribinacladribinum

Names are supplied by ChEBI. Trade names and related synonyms may describe a broader product context.

Classification & relationships

ChEBI ontology

purine 2'-deoxyribonucleosideChEBI parent class · 19254 ↗organochlorine compoundChEBI parent class · 36683 ↗

nucleoside organochlorine compound organic heterocyclic compound organic molecular entity

Roles recorded in ChEBI

antineoplastic agentimmunosuppressive agentanti-anaemic agent

Database role annotations describe reported biological or chemical roles; they are not product approvals or recommendations for use.

Mass ↔ amount of substance

Calculated from sourced mass

Amount

Input unit

Equivalent amount

0.00350029 mol

Uses 285.691 g/mol from ChEBI. Assumes the substance described by this record; no purity or concentration correction is applied.

Elemental composition

Theoretical mass fractions

C

Carbon · 10 atoms

42.04%

N

Nitrogen · 5 atoms

24.51%

O

Oxygen · 3 atoms

16.80%

Cl

Chlorine · 1 atom

12.41%

H

Hydrogen · 12 atoms

4.23%

Calculated theoretical mass fractions from the reported formula and PubChem periodic-table atomic masses. These are not assay or purity results.

Research & patent references

Selected source associations

Deoxyribonucleoside kinases activate nucleoside antibiotics in severely pathogenic bacteria. ↗Antimicrobial agents and chemotherapy · 2007 Aug · PMID 17526755

Elucidation of different binding modes of purine nucleosides to human deoxycytidine kinase. ↗Journal of medicinal chemistry · 2008 Jul 24 · PMID 18570408

EP173059 · Patent reference ↗Patent cross-reference supplied by ChEBI. Association alone does not establish claim scope.

US4760137 · Patent reference ↗Patent cross-reference supplied by ChEBI. Association alone does not establish claim scope.

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Sources & record history

Checked 27 Sep 2026

Identity, formula, mass, synonyms & ontologyEMBL-EBI ChEBI · CHEBI:567361

Release 255, 9 September 2026. ChEBI three-star (manually annotated) source entry. View original record ↗ · CC BY 4.0

Additional molecular descriptorsNCBI PubChem · CID 20279 · retrieved 2026-09-27

PubCAS formats source data, connects references and computes explicitly labelled conversions. CAS cross-references are supplied by ChEBI; they do not constitute CAS verification or endorsement.

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