CLADRIBINE

Search structure
Trade Names:
Synonyms:
Status: Approved (1993)
Entry Type: Small molecule
Molecule Category: UNKNOWN
ATC: L01BB04
UNII: 47M74X9YT5

Structure
InChI Key PTOAARAWEBMLNO-KVQBGUIXSA-N
Smile 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

Physicochemical Descriptors

Property Name Value
Molecular Formula C10H12ClN5O3
Molecular Weight 285.69
AlogP -0.3
Hydrogen Bond Acceptor 8.0
Hydrogen Bond Donor 3.0
Number of Rotational Bond 2.0
Polar Surface Area 119.31
Molecular species NEUTRAL
Aromatic Rings 2.0
Heavy Atoms 19.0

Pharmacology

Action Mechanism of Action Reference
INHIBITOR DNA inhibitor DailyMed
Targets EC50(nM) IC50(nM) Kd(nM) Ki(nM) Inhibition(%)
Enzyme Phosphodiesterase Phosphodiesterase 2 Phosphodiesterase 2A
- - - - 8
Membrane receptor Family A G protein-coupled receptor Small molecule receptor (family A GPCR) Nucleotide-like receptor (family A GPCR) Adenosine receptor
- - - 20400 -

Indications

Mesh Heading Maximum Phase Mesh ID Reference
Lymphoma 3 D008223 ClinicalTrials
Leukemia, Myeloid, Acute 3 D015470 ClinicalTrials
Lymphoma, T-Cell, Peripheral 3 D016411 ClinicalTrials
Multiple Sclerosis, Relapsing-Remitting 3 D020529 ClinicalTrials
Leukemia 3 D007938 ClinicalTrials
Leukemia, Lymphocytic, Chronic, B-Cell 3 D015451 ClinicalTrials
Cholangitis, Sclerosing 2 D015209 ClinicalTrials
Leukemia, Biphenotypic, Acute 2 D015456 ClinicalTrials
Lymphoma, Mantle-Cell 2 D020522 ClinicalTrials
Lymphoma, B-Cell, Marginal Zone 2 D018442 ClinicalTrials
Histiocytosis 2 D015614 ClinicalTrials
Myelodysplastic Syndromes 2 D009190 ClinicalTrials
Precursor Cell Lymphoblastic Leukemia-Lymphoma 2 D054198 ClinicalTrials
Mastocytosis, Systemic 2 D034721 ClinicalTrials
Histiocytosis, Langerhans-Cell 2 D006646 ClinicalTrials
Blast Crisis 2 D001752 ClinicalTrials
Leukemia, Myeloid 2 D007951 ClinicalTrials
Multiple Myeloma 1 D009101 ClinicalTrials
Myeloproliferative Disorders 1 D009196 ClinicalTrials
Graft vs Host Disease 1 D006086 ClinicalTrials
Central Nervous System Neoplasms 1 D016543 ClinicalTrials

Related Entries

Scaffolds

Side Effects from Label

Side effects Relative Frequency (%) Labels
Investigations Body temperature increased 69.0
Blood and lymphatic system disorders Febrile neutropenia 47.0
General disorders and administration site conditions Asthenia 45.0
General disorders and administration site conditions Fatigue 45.0
Investigations Body temperature increased 33.0
General disorders and administration site conditions Asthenia 31.0
General disorders and administration site conditions Fatigue 31.0
Infections and infestations Pneumonia 28.7
Infections and infestations Infection 28.0
Gastrointestinal disorders Nausea 28.0
Skin and subcutaneous tissue disorders Dermatitis 27.0
Skin and subcutaneous tissue disorders Rash 27.0
Nervous system disorders Headache 22.0
Gastrointestinal disorders Nausea 22.0
Infections and infestations Bacterial infection 21.8
Infections and infestations Viral skin infection 20.8
General disorders and administration site conditions Injection site reaction 19.0
General disorders and administration site conditions Decreased appetite 17.0
Skin and subcutaneous tissue disorders Dermatitis 16.0
Skin and subcutaneous tissue disorders Rash 16.0
Nervous system disorders Headache 14.0
Gastrointestinal disorders Vomiting 13.0
General disorders and administration site conditions Inflammation 12.9
Infections and infestations Upper respiratory tract infection 12.9
Blood and lymphatic system disorders Thrombocytopenia 12.0
Infections and infestations Candida infection 11.9
Gastrointestinal disorders Oral candidiasis 11.9
Infections and infestations Skin infection 11.9
Infections and infestations Urinary tract infection 11.9
General disorders and administration site conditions Administration site reaction 11.0
General disorders and administration site conditions Asthenia 11.0
Investigations Breath sounds abnormal 11.0
General disorders and administration site conditions Fatigue 11.0
Nervous system disorders Headache 11.0
Respiratory, thoracic and mediastinal disorders Cough 10.0
Skin and subcutaneous tissue disorders Dermatitis 10.0
Blood and lymphatic system disorders Purpura 10.0
Skin and subcutaneous tissue disorders Rash 10.0
Blood and lymphatic system disorders Vascular purpura 10.0
General disorders and administration site conditions Asthenia 9.0
Investigations Breath sounds abnormal 9.0
General disorders and administration site conditions Chills 9.0
Gastrointestinal disorders Constipation 9.0
Cardiac disorders Dizziness 9.0
General disorders and administration site conditions Injection site reaction 9.0
Gastrointestinal disorders Vomiting 9.0
General disorders and administration site conditions Inflammation 8.9
General disorders and administration site conditions Decreased appetite 8.0
Blood and lymphatic system disorders Febrile neutropenia 8.0
Vascular disorders Petechiae 8.0
Infections and infestations Pneumonia 7.3
Respiratory, thoracic and mediastinal disorders Cough 7.0
Gastrointestinal disorders Diarrhoea 7.0
General disorders and administration site conditions Discomfort 7.0
Cardiac disorders Dyspnoea 7.0
General disorders and administration site conditions Feeling abnormal 7.0
Nervous system disorders Headache 7.0
General disorders and administration site conditions Ill-defined disorder 7.0
Nervous system disorders Insomnia 7.0
General disorders and administration site conditions Malaise 7.0
Musculoskeletal and connective tissue disorders Musculoskeletal discomfort 7.0
Musculoskeletal and connective tissue disorders Myalgia 7.0
Infections and infestations Pneumonia 7.0
Gastrointestinal disorders Abdominal pain 6.0
General disorders and administration site conditions Asthenia 6.0
Cardiac disorders Dizziness 6.0
Skin and subcutaneous tissue disorders Erythema 6.0
Gastrointestinal disorders Gastrointestinal pain 6.0
Investigations Haemoglobin 6.0
Vascular disorders Haemorrhage 6.0
Musculoskeletal and connective tissue disorders Musculoskeletal discomfort 6.0
Musculoskeletal and connective tissue disorders Myalgia 6.0
General disorders and administration site conditions Oedema 6.0
General disorders and administration site conditions Pain 6.0
Vascular disorders Petechiae 6.0
Infections and infestations Pneumonia 6.0
Skin and subcutaneous tissue disorders Pruritus 6.0
Cardiac disorders Tachycardia 6.0
Blood and lymphatic system disorders Thrombocytopenia 6.0
Infections and infestations Skin infection 5.7
Musculoskeletal and connective tissue disorders Arthralgia 5.0
General disorders and administration site conditions Discomfort 5.0
Cardiac disorders Dyspnoea 5.0
Respiratory, thoracic and mediastinal disorders Epistaxis 5.0
General disorders and administration site conditions Feeling abnormal 5.0
General disorders and administration site conditions Ill-defined disorder 5.0
General disorders and administration site conditions Malaise 5.0
Musculoskeletal and connective tissue disorders Musculoskeletal discomfort 5.0
Vascular disorders Phlebitis 5.0
Gastrointestinal disorders Abdominal pain 4.0
Investigations Breath sounds abnormal 4.0
Gastrointestinal disorders Constipation 4.0
Gastrointestinal disorders Gastrointestinal pain 4.0
Musculoskeletal and connective tissue disorders Arthralgia 3.0
General disorders and administration site conditions Hyperhidrosis 3.0
Nervous system disorders Insomnia 3.0
Musculoskeletal and connective tissue disorders Musculoskeletal discomfort 3.0
Infections and infestations Bacteraemia 2.0
Infections and infestations Cellulitis 2.0
General disorders and administration site conditions Chills 2.0
Blood and lymphatic system disorders Ecchymosis 2.0
Cardiac disorders Oedema peripheral 2.0
Vascular disorders Petechiae 2.0
Vascular disorders Phlebitis 2.0
Skin and subcutaneous tissue disorders Pruritus 2.0
Cardiac disorders Tachycardia 2.0
Vascular disorders Thrombosis 2.0
Blood and lymphatic system disorders Anaemia 1.0
Psychiatric disorders Anxiety 1.0
Injury, poisoning and procedural complications Contusion 1.0
Gastrointestinal disorders Flatulence 1.0
Infections and infestations Localised infection 1.0
Nervous system disorders Muscular weakness 1.0
Respiratory, thoracic and mediastinal disorders Rales 1.0
Immune system disorders Toxic epidermal necrolysis 1.0
Metabolism and nutrition disorders Tumour lysis syndrome 1.0
Blood and lymphatic system disorders Myelodysplastic syndrome 0.03

Adverse Reactions

SOC By Demographic Distribution
System Organ Classification (SOC)
Relative Frequency (%)
Blood and lymphatic system disorders
13.59
General disorders and administration site conditions
10.05
Infections and infestations
9.52
Nervous system disorders
8.8
Injury, poisoning and procedural complications
6.96
Respiratory, thoracic and mediastinal disorders
6.76
Investigations
6.5
Gastrointestinal disorders
6.11
Neoplasms benign, malignant and unspecified (incl cysts and polyps)
5.78
Skin and subcutaneous tissue disorders
4.6
Vascular disorders
3.87
Musculoskeletal and connective tissue disorders
3.28
Cardiac disorders
2.56
Hepatobiliary disorders
2.1
Metabolism and nutrition disorders
2.04

Cross References

Resources Reference
CAS NUMBER 4291-63-8
ChEBI 567361
ChEMBL CHEMBL1619
DrugBank DB00242
DrugCentral 667
EPA CompTox DTXSID8022828
FDA SRS 47M74X9YT5
Human Metabolome Database HMDB0014387
Guide to Pharmacology 4799
PDB CL9
PharmGKB PA449027
PubChem 20279
SureChEMBL SCHEMBL3775
ZINC ZINC000003798064
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