BUSULFAN

Search structure
Trade Names:
Synonyms:
Status: Approved (1954)
Entry Type: Small molecule
Molecule Category: Parent
ATC: L01AB01
UNII: G1LN9045DK

Structure
InChI Key COVZYZSDYWQREU-UHFFFAOYSA-N
Smile CS(=O)(=O)OCCCCOS(C)(=O)=O
InChI
InChI=1S/C6H14O6S2/c1-13(7,8)11-5-3-4-6-12-14(2,9)10/h3-6H2,1-2H3

Physicochemical Descriptors

Property Name Value
Molecular Formula C6H14O6S2
Molecular Weight 246.31
AlogP -0.28
Hydrogen Bond Acceptor 6.0
Hydrogen Bond Donor 0.0
Number of Rotational Bond 7.0
Polar Surface Area 86.74
Molecular species None
Aromatic Rings 0.0
Heavy Atoms 14.0

Experimental and Estimated Properties

Property Name Value Unit Method
log P (octanol-water) -0.52 - EXP
Henry's Law Constant 5.16E-10 atm-m3/mole EST
Atmospheric OH Rate Constant 4.71E-12 cm3/molecule-sec EST
Melting Point 287 dec deg C EXP
Water Solubility 6.90E+04 mg/L EST
Vapor Pressure 6.65E-06 mm Hg EST

Pharmacology

Action Mechanism of Action Reference
INHIBITOR DNA inhibitor DailyMed
Targets EC50(nM) IC50(nM) Kd(nM) Ki(nM) Inhibition(%)
Transporter Electrochemical transporter SLC superfamily of solute carriers SLC21/SLCO family of organic anion transporting polypeptides
- - - - 114

Metabolites

visNetwork

Indications

Mesh Heading Maximum Phase Mesh ID Reference
Neoplasms 4 D009369 ClinicalTrials
Leukemia 4 D007938 ClinicalTrials
Neoplasms 4 D009369 ClinicalTrials
Myelodysplastic Syndromes 3 D009190 ClinicalTrials
Anemia, Refractory 3 D000753 ClinicalTrials
Leukemia, Erythroblastic, Acute 3 D004915 ClinicalTrials
Leukemia, Monocytic, Acute 3 D007948 ClinicalTrials
Leukemia, Myelomonocytic, Acute 3 D015479 ClinicalTrials
Breast Neoplasms 3 D001943 ClinicalTrials
Leukemia, Myeloid, Acute 3 D015470 ClinicalTrials
Graft vs Host Disease 3 D006086 ClinicalTrials
Multiple Myeloma 3 D009101 ClinicalTrials
Leukemia, Myelomonocytic, Chronic 3 D015477 ClinicalTrials
Breast Neoplasms 3 D001943 ClinicalTrials
Lymphoma 3 D008223 ClinicalTrials
Neuroblastoma 3 D009447 ClinicalTrials
Sarcoma 3 D012509 ClinicalTrials
Sarcoma, Ewing 3 D012512 ClinicalTrials
Anemia, Refractory, with Excess of Blasts 3 D000754 ClinicalTrials
Leukemia, Megakaryoblastic, Acute 3 D007947 ClinicalTrials
Leukemia, Myeloid, Acute 3 D015470 ClinicalTrials
Leukemia, Basophilic, Acute 3 D015471 ClinicalTrials
Granulomatous Disease, Chronic 2 D006105 ClinicalTrials
Myelodysplastic-Myeloproliferative Diseases 2 D054437 ClinicalTrials
Precursor Cell Lymphoblastic Leukemia-Lymphoma 2 D054198 ClinicalTrials
Immune System Diseases 2 D007154 ClinicalTrials
Leukemia, Lymphocytic, Chronic, B-Cell 2 D015451 ClinicalTrials
Hodgkin Disease 2 D006689 ClinicalTrials
Glioma 2 D005910 ClinicalTrials
Lymphoma, Large B-Cell, Diffuse 2 D016403 ClinicalTrials
Hematologic Neoplasms 2 D019337 ClinicalTrials
Primary Myelofibrosis 2 D055728 ClinicalTrials
Signs and Symptoms 2 D012816 ClinicalTrials
Myeloproliferative Disorders 2 D009196 ClinicalTrials
Hematologic Diseases 2 D006402 ClinicalTrials
Lymphoma, Non-Hodgkin 2 D008228 ClinicalTrials
Leukemia, Plasma Cell 2 D007952 ClinicalTrials
Breast Neoplasms, Male 2 D018567 ClinicalTrials
Leukemia, Myelomonocytic, Juvenile 2 D054429 ClinicalTrials
Inflammatory Breast Neoplasms 2 D058922 ClinicalTrials
Lymphoma, AIDS-Related 2 D016483 ClinicalTrials
Lymphoma, Mantle-Cell 2 D020522 ClinicalTrials
Thalassemia 2 D013789 ClinicalTrials
Severe Combined Immunodeficiency 2 D016511 ClinicalTrials
Anemia, Sickle Cell 2 D000755 ClinicalTrials
Osteopetrosis 2 D010022 ClinicalTrials
Central Nervous System Neoplasms 2 D016543 ClinicalTrials
Niemann-Pick Diseases 2 D009542 ClinicalTrials
Kidney Neoplasms 2 D007680 ClinicalTrials
Lymphoma, T-Cell 2 D016399 ClinicalTrials
Lymphoma, Follicular 2 D008224 ClinicalTrials
Hematologic Neoplasms 2 D019337 ClinicalTrials
Primary Myelofibrosis 2 D055728 ClinicalTrials
Fucosidosis 2 D005645 ClinicalTrials
Gangliosidosis, GM1 2 D016537 ClinicalTrials
Gaucher Disease 2 D005776 ClinicalTrials
Leukodystrophy, Globoid Cell 2 D007965 ClinicalTrials
Leukodystrophy, Metachromatic 2 D007966 ClinicalTrials
Hemoglobinopathies 2 D006453 ClinicalTrials
Wolman Disease 2 D015223 ClinicalTrials
Neuronal Ceroid-Lipofuscinoses 2 D009472 ClinicalTrials
Sandhoff Disease 2 D012497 ClinicalTrials
Tay-Sachs Disease 2 D013661 ClinicalTrials
Fanconi Anemia 2 D005199 ClinicalTrials
beta-Thalassemia 2 D017086 ClinicalTrials
Lymphoma, Follicular 2 D008224 ClinicalTrials
Plasmacytoma 2 D010954 ClinicalTrials
Histiocytosis, Langerhans-Cell 2 D006646 ClinicalTrials
Epidermolysis Bullosa 2 D004820 ClinicalTrials
Myeloproliferative Disorders 2 D009196 ClinicalTrials
Osteogenesis Imperfecta 1 D010013 ClinicalTrials
Melanoma 1 D008545 ClinicalTrials
Immunologic Deficiency Syndromes 1 D007153 ClinicalTrials
Wiskott-Aldrich Syndrome 1 D014923 ClinicalTrials
Brain Neoplasms 1 D001932 ClinicalTrials
Acquired Immunodeficiency Syndrome 1 D000163 ClinicalTrials
Liver Neoplasms 1 D008113 ClinicalTrials
Neoplasms, Germ Cell and Embryonal 1 D009373 ClinicalTrials
Genetic Diseases, Inborn 1 D030342 ClinicalTrials
X-Linked Combined Immunodeficiency Diseases 1 D053632 ClinicalTrials
Chordoma 1 D002817 ClinicalTrials
Retinoblastoma 1 D012175 ClinicalTrials
X-Linked Combined Immunodeficiency Diseases 1 D053632 ClinicalTrials
Ovarian Neoplasms 1 D010051 ClinicalTrials
Anemia 1 D000740 ClinicalTrials
HIV Infections 1 D015658 ClinicalTrials
Blast Crisis 1 D001752 ClinicalTrials

Side Effects from Label

Side effects Relative Frequency (%) Labels
Gastrointestinal disorders Nausea 98.0
General disorders and administration site conditions Mucosal inflammation 97.0
Gastrointestinal disorders Stomatitis 97.0
Gastrointestinal disorders Vomiting 95.0
General disorders and administration site conditions Decreased appetite 85.0
Gastrointestinal disorders Stomatitis 85.0
Gastrointestinal disorders Diarrhoea 84.0
Nervous system disorders Insomnia 84.0
Investigations Body temperature increased 83.0
Investigations Body temperature increased 80.0
Nervous system disorders Insomnia 80.0
General disorders and administration site conditions Oedema 79.0
Metabolism and nutrition disorders Hypomagnesaemia 77.0
Psychiatric disorders Anxiety 75.0
Gastrointestinal disorders Abdominal pain 72.0
Psychiatric disorders Anxiety 72.0
Gastrointestinal disorders Gastrointestinal pain 72.0
Gastrointestinal disorders Vomiting 72.0
Nervous system disorders Headache 69.0
Skin and subcutaneous tissue disorders Dermatitis 67.0
Skin and subcutaneous tissue disorders Rash 67.0
Endocrine disorders Hyperglycaemia 66.0
Psychiatric disorders Anxiety 65.0
Metabolism and nutrition disorders Hypokalaemia 64.0
Gastrointestinal disorders Diarrhoea 58.0
Skin and subcutaneous tissue disorders Dermatitis 57.0
Skin and subcutaneous tissue disorders Rash 57.0
General disorders and administration site conditions Asthenia 51.0
Skin and subcutaneous tissue disorders Dermatitis 50.0
Skin and subcutaneous tissue disorders Rash 50.0
Blood and lymphatic system disorders Hyperbilirubinaemia 49.0
Metabolism and nutrition disorders Hypocalcaemia 49.0
General disorders and administration site conditions Chills 46.0
Gastrointestinal disorders Dyspepsia 44.0
General disorders and administration site conditions Pain 44.0
Infections and infestations Rhinitis 44.0
Cardiac disorders Tachycardia 44.0
Gastrointestinal disorders Constipation 38.0
Vascular disorders Hypertension 36.0
General disorders and administration site conditions Oedema 36.0
Investigations Breath sounds abnormal 34.0
Respiratory, thoracic and mediastinal disorders Lung disorder 34.0
Vascular disorders Thrombosis 33.0
Infections and infestations Infection 31.0
Cardiac disorders Dizziness 30.0
Skin and subcutaneous tissue disorders Pruritus 29.0
Respiratory, thoracic and mediastinal disorders Cough 28.0
General disorders and administration site conditions Oedema 28.0
Skin and subcutaneous tissue disorders Pruritus 28.0
Gastrointestinal disorders Pharyngitis 27.0
Vascular disorders Thrombosis 27.0
Cardiac disorders Chest pain 26.0
Cardiac disorders Dizziness 26.0
Gastrointestinal disorders Dry mouth 26.0
Immune system disorders Hypersensitivity 26.0
Gastrointestinal disorders Anorectal disorder 25.0
Cardiac disorders Dyspnoea 25.0
Respiratory, thoracic and mediastinal disorders Epistaxis 25.0
General disorders and administration site conditions Inflammation 25.0
General disorders and administration site conditions Injection site inflammation 25.0
Surgical and medical procedures Vasodilation procedure 25.0
Gastrointestinal disorders Abdominal distension 23.0
Musculoskeletal and connective tissue disorders Back pain 23.0
Psychiatric disorders Depression 23.0
Investigations Blood creatinine increased 21.0
Gastrointestinal disorders Hiccups 18.0
Gastrointestinal disorders Pharyngitis 18.0
Gastrointestinal disorders Hiccups 17.0
Immune system disorders Asthma 8.0
Investigations Weight increased 8.0
Immune system disorders Asthma 7.0
Cardiac disorders Arrhythmia 5.0
Cardiac disorders Cardiomegaly 5.0
Cardiac disorders Arrhythmia 3.0
Respiratory, thoracic and mediastinal disorders Atelectasis 3.0
Cardiac disorders Haemoptysis 3.0
Respiratory, thoracic and mediastinal disorders Pleural effusion 3.0
Respiratory, thoracic and mediastinal disorders Pneumothorax 3.0
Infections and infestations Sinusitis 3.0
Nervous system disorders Agitation 2.0
Respiratory, thoracic and mediastinal disorders Atelectasis 2.0
Cardiac disorders Atrial fibrillation 2.0
Cardiac disorders Atrioventricular block complete 2.0
Cardiac disorders Cardiac tamponade 2.0
Nervous system disorders Confusional state 2.0
Psychiatric disorders Delirium 2.0
Nervous system disorders Encephalopathy 2.0
General disorders and administration site conditions Feeling abnormal 2.0
Cardiac disorders Pericardial effusion 2.0
Respiratory, thoracic and mediastinal disorders Pneumothorax 2.0
Cardiac disorders Ventricular extrasystoles 2.0
Nervous system disorders Agitation 1.0
Cardiac disorders Bradycardia 1.0
Psychiatric disorders Delirium 1.0
Nervous system disorders Encephalopathy 1.0
Psychiatric disorders Hallucination 1.0
Psychiatric disorders Nervousness 1.0
Psychiatric disorders Tension 1.0
Cardiac disorders Ventricular extrasystoles 1.0

Adverse Reactions

SOC By Demographic Distribution
System Organ Classification (SOC)
Relative Frequency (%)
Injury, poisoning and procedural complications
14.36
Infections and infestations
12.97
General disorders and administration site conditions
8.07
Respiratory, thoracic and mediastinal disorders
7.98
Vascular disorders
7.5
Blood and lymphatic system disorders
6.17
Gastrointestinal disorders
5.62
Immune system disorders
5.44
Nervous system disorders
4.77
Hepatobiliary disorders
4.73
Investigations
3.79
Cardiac disorders
2.95
Neoplasms benign, malignant and unspecified (incl cysts and polyps)
2.95
Renal and urinary disorders
2.79
Skin and subcutaneous tissue disorders
2.46
Metabolism and nutrition disorders
2.12

Cross References

Resources Reference
CAS NUMBER 55-98-1
ChEBI 28901
ChEMBL CHEMBL820
DrugBank DB01008
DrugCentral 438
EPA CompTox DTXSID3020910
FDA SRS G1LN9045DK
Human Metabolome Database HMDB0015143
Guide to Pharmacology 7136
KEGG C06862
PharmGKB PA448691
PubChem 2478
SureChEMBL SCHEMBL4373
ZINC ZINC000001530572
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