CLOFARABINE

Search structure
Trade Names:
Synonyms:
Status: Approved (2004)
Entry Type: Small molecule
Molecule Category: UNKNOWN Prodrug
ATC: L01BB06
UNII: 762RDY0Y2H

Structure
InChI Key WDDPHFBMKLOVOX-AYQXTPAHSA-N
Smile Nc1nc(Cl)nc2c1ncn2[C@@H]1O[C@H](CO)[C@@H](O)[C@@H]1F
InChI
InChI=1S/C10H11ClFN5O3/c11-10-15-7(13)5-8(16-10)17(2-14-5)9-4(12)6(19)3(1-18)20-9/h2-4,6,9,18-19H,1H2,(H2,13,15,16)/t3-,4+,6-,9-/m1/s1

Physicochemical Descriptors

Property Name Value
Molecular Formula C10H11ClFN5O3
Molecular Weight 303.68
AlogP -0.35
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 20.0

Pharmacology

Action Mechanism of Action Reference
INHIBITOR DNA inhibitor DailyMed
Primary Target
ribonucleotide reductase regulatory subunit M2
Targets EC50(nM) IC50(nM) Kd(nM) Ki(nM) Inhibition(%)
Enzyme Phosphodiesterase Phosphodiesterase 2 Phosphodiesterase 2A
- 3120 - - 32

Indications

Mesh Heading Maximum Phase Mesh ID Reference
Precursor Cell Lymphoblastic Leukemia-Lymphoma 4 D054198 ClinicalTrials
Neoplasms 4 D009369 ClinicalTrials
Precursor Cell Lymphoblastic Leukemia-Lymphoma 4 D054198 ClinicalTrials
Neoplasms 4 D009369 ClinicalTrials
Leukemia, Myeloid, Acute 3 D015470 ClinicalTrials
Leukemia 3 D007938 ClinicalTrials
Hodgkin Disease 2 D006689 ClinicalTrials
Myelodysplastic Syndromes 2 D009190 ClinicalTrials
Multiple Myeloma 2 D009101 ClinicalTrials
Leukemia, Lymphocytic, Chronic, B-Cell 2 D015451 ClinicalTrials
Lymphoma, Non-Hodgkin 2 D008228 ClinicalTrials
Leukemia, Myelomonocytic, Chronic 2 D015477 ClinicalTrials
Osteopetrosis 2 D010022 ClinicalTrials
Hematologic Diseases 2 D006402 ClinicalTrials
Graft vs Host Disease 2 D006086 ClinicalTrials
Leukemia, Myelogenous, Chronic, BCR-ABL Positive 2 D015464 ClinicalTrials
Lymphoma 2 D008223 ClinicalTrials
Histiocytosis, Langerhans-Cell 2 D006646 ClinicalTrials
Leukemia, Promyelocytic, Acute 1 D015473 ClinicalTrials
Lymphoma, T-Cell 1 D016399 ClinicalTrials
Lymphoma, Follicular 1 D008224 ClinicalTrials

Related Entries

MCS

Scaffolds

Side Effects from Label

Side effects Relative Frequency (%) Labels
Blood and lymphatic system disorders Leukopenia 87.7
Blood and lymphatic system disorders Anaemia 83.3
Blood and lymphatic system disorders Lymphopenia 82.3
Blood and lymphatic system disorders Thrombocytopenia 80.7
Investigations Alanine aminotransferase increased 80.5
Blood and lymphatic system disorders Thrombocytopenia 79.8
Blood and lymphatic system disorders Anaemia 75.4
Investigations Aspartate aminotransferase increased 74.0
Blood and lymphatic system disorders Neutropenia 63.7
Gastrointestinal disorders Vomiting 59.0
Investigations Blood creatinine increased 49.5
Investigations Blood bilirubin increased 44.7
Investigations Alanine aminotransferase increased 43.4
Investigations Aspartate aminotransferase increased 36.0
Cardiac disorders Tachycardia 35.0
Nervous system disorders Headache 24.0
Skin and subcutaneous tissue disorders Dermatitis 21.0
Skin and subcutaneous tissue disorders Rash 21.0
Gastrointestinal disorders Diarrhoea 20.0
Skin and subcutaneous tissue disorders Pruritus 20.0
Investigations Body temperature increased 19.0
General disorders and administration site conditions Asthenia 14.0
General disorders and administration site conditions Fatigue 14.0
Investigations Blood bilirubin increased 13.2
Psychiatric disorders Anxiety 12.0
General disorders and administration site conditions Flushing 11.0
General disorders and administration site conditions Mucosal inflammation 11.0
Investigations Blood creatinine increased 7.8

Adverse Reactions

SOC By Demographic Distribution
System Organ Classification (SOC)
Relative Frequency (%)
General disorders and administration site conditions
10.92
Infections and infestations
10.71
Blood and lymphatic system disorders
10.46
Investigations
9.58
Respiratory, thoracic and mediastinal disorders
7.67
Gastrointestinal disorders
6.14
Vascular disorders
6.08
Injury, poisoning and procedural complications
5.52
Metabolism and nutrition disorders
5.4
Nervous system disorders
4.41
Cardiac disorders
4.18
Renal and urinary disorders
3.68
Hepatobiliary disorders
3.66
Skin and subcutaneous tissue disorders
3.66
Immune system disorders
2.2

Cross References

Resources Reference
CAS NUMBER 123318-82-1
ChEBI 681569
ChEMBL CHEMBL1750
DrugBank DB00631
DrugCentral 691
EPA CompTox DTXSID5046437
FDA SRS 762RDY0Y2H
Human Metabolome Database HMDB0014769
Guide to Pharmacology 6802
PDB CFB
PharmGKB PA164754863
PubChem 119182
SureChEMBL SCHEMBL9040
ZINC ZINC000003798247
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