NELARABINE

Search structure
Trade Names:
Synonyms:
MAY
Status: Approved (2005)
Entry Type: Small molecule
Molecule Category: UNKNOWN Prodrug
ATC: L01BB07
UNII: 60158CV180

Structure
InChI Key IXOXBSCIXZEQEQ-UHTZMRCNSA-N
Smile COc1nc(N)nc2c1ncn2[C@@H]1O[C@H](CO)[C@@H](O)[C@@H]1O
InChI
InChI=1S/C11H15N5O5/c1-20-9-5-8(14-11(12)15-9)16(3-13-5)10-7(19)6(18)4(2-17)21-10/h3-4,6-7,10,17-19H,2H2,1H3,(H2,12,14,15)/t4-,6-,7+,10-/m1/s1

Physicochemical Descriptors

Property Name Value
Molecular Formula C11H15N5O5
Molecular Weight 297.27
AlogP -1.97
Hydrogen Bond Acceptor 10.0
Hydrogen Bond Donor 4.0
Number of Rotational Bond 3.0
Polar Surface Area 148.77
Molecular species NEUTRAL
Aromatic Rings 2.0
Heavy Atoms 21.0

Pharmacology

Action Mechanism of Action Reference
INHIBITOR DNA inhibitor DailyMed

Indications

Mesh Heading Maximum Phase Mesh ID Reference
Precursor Cell Lymphoblastic Leukemia-Lymphoma 3 D054198 ClinicalTrials
Precursor T-Cell Lymphoblastic Leukemia-Lymphoma 3 D054218 ClinicalTrials
Precursor Cell Lymphoblastic Leukemia-Lymphoma 3 D054198 ClinicalTrials
Mycosis Fungoides 2 D009182 ClinicalTrials
Leukemia, Biphenotypic, Acute 2 D015456 ClinicalTrials
Lymphoma 2 D008223 ClinicalTrials
Sezary Syndrome 2 D012751 ClinicalTrials
Leukemia 2 D007938 ClinicalTrials
Myeloproliferative Disorders 1 D009196 ClinicalTrials
Myelodysplastic Syndromes 1 D009190 ClinicalTrials
Leukemia, Lymphoid 1 D007945 ClinicalTrials
Multiple Myeloma 1 D009101 ClinicalTrials

Related Entries

Scaffolds

Side Effects from Label

Side effects Relative Frequency (%) Labels
Blood and lymphatic system disorders Anaemia 99.0
Blood and lymphatic system disorders Anaemia 95.0
Blood and lymphatic system disorders Neutropenia 94.0
Blood and lymphatic system disorders Thrombocytopenia 88.0
Blood and lymphatic system disorders Thrombocytopenia 86.0
Blood and lymphatic system disorders Neutropenia 81.0
Blood and lymphatic system disorders Neutropenia 62.0
General disorders and administration site conditions Asthenia 50.0
General disorders and administration site conditions Fatigue 50.0
Blood and lymphatic system disorders Neutropenia 49.0
Blood and lymphatic system disorders Anaemia 45.0
Gastrointestinal disorders Nausea 41.0
Blood and lymphatic system disorders Leukopenia 38.0
Blood and lymphatic system disorders Thrombocytopenia 37.0
Blood and lymphatic system disorders Thrombocytopenia 32.0
Blood and lymphatic system disorders Thrombocytopenia 27.0
Respiratory, thoracic and mediastinal disorders Cough 25.0
Investigations Body temperature increased 23.0
Nervous system disorders Somnolence 23.0
Gastrointestinal disorders Diarrhoea 22.0
Blood and lymphatic system disorders Thrombocytopenia 22.0
Gastrointestinal disorders Vomiting 22.0
Gastrointestinal disorders Constipation 21.0
Cardiac disorders Dizziness 21.0
Nervous system disorders Nervous system disorder 21.0
Blood and lymphatic system disorders Anaemia 20.0
Cardiac disorders Dyspnoea 20.0
Nervous system disorders Somnolence 20.0
General disorders and administration site conditions Asthenia 17.0
Nervous system disorders Headache 17.0
Nervous system disorders Hypoaesthesia 17.0
Blood and lymphatic system disorders Neutropenia 17.0
Nervous system disorders Headache 15.0
General disorders and administration site conditions Oedema 15.0
Nervous system disorders Paraesthesia 15.0
Blood and lymphatic system disorders Anaemia 14.0
Cardiac disorders Dizziness 14.0
Blood and lymphatic system disorders Leukopenia 14.0
Blood and lymphatic system disorders Neutropenia 14.0
Musculoskeletal and connective tissue disorders Musculoskeletal discomfort 13.0
Musculoskeletal and connective tissue disorders Myalgia 13.0
Nervous system disorders Peripheral sensory neuropathy 13.0
Blood and lymphatic system disorders Febrile neutropenia 12.0
Nervous system disorders Nervous system disorder 12.0
Vascular disorders Petechiae 12.0
Investigations Transaminases increased 12.0
Investigations Blood potassium decreased 11.0
Nervous system disorders Headache 11.0
General disorders and administration site conditions Oedema 11.0
General disorders and administration site conditions Pain 11.0
Nervous system disorders Paraesthesia 11.0
Blood and lymphatic system disorders Anaemia 10.0
General disorders and administration site conditions Asthenia 10.0
Investigations Blood albumin decreased 10.0
Investigations Blood bilirubin increased 10.0
General disorders and administration site conditions Fatigue 10.0
Nervous system disorders Hypoaesthesia 10.0
Respiratory, thoracic and mediastinal disorders Pleural effusion 10.0
Gastrointestinal disorders Vomiting 10.0
Gastrointestinal disorders Abdominal pain 9.0
Musculoskeletal and connective tissue disorders Arthralgia 9.0
Nervous system disorders Ataxia 9.0
General disorders and administration site conditions Decreased appetite 9.0
Blood and lymphatic system disorders Febrile neutropenia 9.0
Gastrointestinal disorders Gastrointestinal pain 9.0
Infections and infestations Infection 9.0
Musculoskeletal and connective tissue disorders Musculoskeletal discomfort 9.0
Musculoskeletal and connective tissue disorders Back pain 8.0
Investigations Blood calcium decreased 8.0
General disorders and administration site conditions Chills 8.0
Nervous system disorders Confusional state 8.0
Cardiac disorders Dizziness 8.0
Respiratory, thoracic and mediastinal disorders Epistaxis 8.0
General disorders and administration site conditions Feeling abnormal 8.0
Nervous system disorders Headache 8.0
Vascular disorders Hypotension 8.0
Nervous system disorders Muscular weakness 8.0
Nervous system disorders Nervous system disorder 8.0
Infections and infestations Pneumonia 8.0
Cardiac disorders Sinus tachycardia 8.0
Gastrointestinal disorders Stomatitis 8.0
Investigations Blood bilirubin increased 7.0
Metabolism and nutrition disorders Dehydration 7.0
Cardiac disorders Dyspnoea 7.0
Nervous system disorders Insomnia 7.0
Blood and lymphatic system disorders Leukopenia 7.0
Nervous system disorders Nervous system disorder 7.0
Nervous system disorders Neuritis 7.0
Musculoskeletal and connective tissue disorders Pain in extremity 7.0
Nervous system disorders Peripheral motor neuropathy 7.0
Nervous system disorders Peripheral sensory neuropathy 7.0
Infections and infestations Sinusitis 7.0
Nervous system disorders Somnolence 7.0
Gastrointestinal disorders Abdominal distension 6.0
Nervous system disorders Altered state of consciousness 6.0
Investigations Aspartate aminotransferase increased 6.0
General disorders and administration site conditions Asthenia 6.0
Nervous system disorders Ataxia 6.0
Investigations Blood creatinine increased 6.0
Investigations Blood glucose decreased 6.0
Investigations Blood magnesium decreased 6.0
Convulsion 6.0
Nervous system disorders Depressed level of consciousness 6.0
Psychiatric disorders Depression 6.0
Endocrine disorders Hyperglycaemia 6.0
Nervous system disorders Hypoaesthesia 6.0
Nervous system disorders Neuropathy peripheral 6.0
Nervous system disorders Peripheral sensory neuropathy 6.0
Investigations Blood albumin decreased 5.0
Investigations Body temperature increased 5.0
Cardiac disorders Chest pain 5.0
Nervous system disorders Hypoaesthesia 5.0
Infections and infestations Infection 5.0
Nervous system disorders Muscular weakness 5.0
Nervous system disorders Neuropathy peripheral 5.0
General disorders and administration site conditions Non-cardiac chest pain 5.0
Respiratory, thoracic and mediastinal disorders Pleural effusion 5.0
Nervous system disorders Tremor 5.0
Respiratory, thoracic and mediastinal disorders Wheezing 5.0
Nervous system disorders Altered state of consciousness 4.0
Investigations Blood glucose decreased 4.0
Investigations Blood potassium decreased 4.0
Convulsion 4.0
Nervous system disorders Depressed level of consciousness 4.0
Cardiac disorders Dyspnoea 4.0
Nervous system disorders Headache 4.0
Nervous system disorders Hypoaesthesia 4.0
Musculoskeletal and connective tissue disorders Motor dysfunction 4.0
Nervous system disorders Nervous system disorder 4.0
Nervous system disorders Neuritis 4.0
Nervous system disorders Neuropathy peripheral 4.0
Nervous system disorders Paraesthesia 4.0
Nervous system disorders Peripheral motor neuropathy 4.0
Infections and infestations Pneumonia 4.0
Nervous system disorders Somnolence 4.0
Investigations Transaminases increased 4.0
Nervous system disorders Tremor 4.0
Nervous system disorders Amnesia 3.0
Convulsion 3.0
Metabolism and nutrition disorders Dehydration 3.0
Gastrointestinal disorders Dysgeusia 3.0
Nervous system disorders Headache 3.0
Nervous system disorders Neuritis 3.0
General disorders and administration site conditions Pain 3.0
Nervous system disorders Peripheral motor neuropathy 3.0
Nervous system disorders Somnolence 3.0
Nervous system disorders Tremor 3.0
Nervous system disorders Amnesia 2.0
General disorders and administration site conditions Asthenia 2.0
Nervous system disorders Ataxia 2.0
General disorders and administration site conditions Balance disorder 2.0
Investigations Blood bilirubin increased 2.0
Investigations Blood magnesium decreased 2.0
Investigations Blood potassium decreased 2.0
Nervous system disorders Confusional state 2.0
Gastrointestinal disorders Dysgeusia 2.0
Cardiac disorders Dyspnoea 2.0
General disorders and administration site conditions Fatigue 2.0
General disorders and administration site conditions Feeling abnormal 2.0
Nervous system disorders Headache 2.0
Nervous system disorders Hypoaesthesia 2.0
Infections and infestations Infection 2.0
Nervous system disorders Nervous system disorder 2.0
Nervous system disorders Neuritis 2.0
Nervous system disorders Neuropathy peripheral 2.0
Nervous system disorders Paraesthesia 2.0
Nervous system disorders Peripheral motor neuropathy 2.0
Vascular disorders Petechiae 2.0
Nervous system disorders Sensory loss 2.0
Nervous system disorders Tremor 2.0
Gastrointestinal disorders Abdominal pain 1.0
Nervous system disorders Altered state of consciousness 1.0
Nervous system disorders Amnesia 1.0
Musculoskeletal and connective tissue disorders Arthralgia 1.0
Investigations Aspartate aminotransferase increased 1.0
General disorders and administration site conditions Asthenia 1.0
Nervous system disorders Ataxia 1.0
General disorders and administration site conditions Balance disorder 1.0
Investigations Blood albumin decreased 1.0
Investigations Blood calcium decreased 1.0
Gastrointestinal disorders Constipation 1.0
Metabolism and nutrition disorders Dehydration 1.0
Nervous system disorders Depressed level of consciousness 1.0
Psychiatric disorders Depression 1.0
Gastrointestinal disorders Diarrhoea 1.0
Gastrointestinal disorders Dysgeusia 1.0
Blood and lymphatic system disorders Febrile neutropenia 1.0
Gastrointestinal disorders Gastrointestinal pain 1.0
Grand mal convulsion 1.0
Nervous system disorders Headache 1.0
Endocrine disorders Hyperglycaemia 1.0
Nervous system disorders Hypoaesthesia 1.0
Vascular disorders Hypotension 1.0
Infections and infestations Infection 1.0
Musculoskeletal and connective tissue disorders Motor dysfunction 1.0
Musculoskeletal and connective tissue disorders Musculoskeletal discomfort 1.0
Musculoskeletal and connective tissue disorders Myalgia 1.0
Nervous system disorders Nervous system disorder 1.0
Nervous system disorders Neuritis 1.0
Nervous system disorders Neuropathy peripheral 1.0
General disorders and administration site conditions Non-cardiac chest pain 1.0
Musculoskeletal and connective tissue disorders Pain in extremity 1.0
Nervous system disorders Paraesthesia 1.0
Nervous system disorders Peripheral motor neuropathy 1.0
Respiratory, thoracic and mediastinal disorders Pleural effusion 1.0
Infections and infestations Pneumonia 1.0
Infections and infestations Sinusitis 1.0
Cardiac disorders Sinus tachycardia 1.0
Nervous system disorders Somnolence 1.0
Nervous system disorders Status epilepticus 1.0
Gastrointestinal disorders Stomatitis 1.0
Nervous system disorders Tremor 1.0
Gastrointestinal disorders Vomiting 1.0

Adverse Reactions

SOC By Demographic Distribution
System Organ Classification (SOC)
Relative Frequency (%)
Nervous system disorders
25.26
Investigations
9.9
Blood and lymphatic system disorders
7.32
General disorders and administration site conditions
7.15
Infections and infestations
6.3
Musculoskeletal and connective tissue disorders
5.77
Skin and subcutaneous tissue disorders
5.73
Gastrointestinal disorders
5.52
Psychiatric disorders
4.0
Respiratory, thoracic and mediastinal disorders
3.4
Injury, poisoning and procedural complications
3.04
Metabolism and nutrition disorders
2.48
Neoplasms benign, malignant and unspecified (incl cysts and polyps)
2.48
Hepatobiliary disorders
2.33
Renal and urinary disorders
2.33
Vascular disorders
2.3

Cross References

Resources Reference
CAS NUMBER 121032-29-9
ChEBI 63612
ChEMBL CHEMBL1201112
DrugBank DB01280
DrugCentral 1892
EPA CompTox DTXSID6046842
FDA SRS 60158CV180
Human Metabolome Database HMDB0015401
Guide to Pharmacology 7090
PharmGKB PA164752425
PubChem 3011155
SureChEMBL SCHEMBL18820
ZINC ZINC000003823492
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