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Record Information
Version4.0
Creation Date2012-09-06 15:16:51 UTC
Update Date2017-09-27 08:27:50 UTC
HMDB IDHMDB0015143
Secondary Accession Numbers
  • HMDB15143
Metabolite Identification
Common NameBusulfan
DescriptionAn alkylating agent having a selective immunosuppressive effect on bone marrow. It has been used in the palliative treatment of chronic myeloid leukemia (myeloid leukemia, chronic), but although symptomatic relief is provided, no permanent remission is brought about. According to the Fourth Annual Report on Carcinogens (NTP 85-002, 1985), busulfan is listed as a known carcinogen. [PubChem]
Structure
Thumb
Synonyms
ValueSource
1,4-Bis(methanesulfonoxy)butaneChEBI
1,4-Butanediol dimethanesulfonateChEBI
1,4-DimesyloxybutaneChEBI
1,4-DimethanesulfonoxybutaneChEBI
BisulfexChEBI
BusulfanoChEBI
BusulfanumChEBI
LeucosulfanChEBI
MablinChEBI
MielucinChEBI
MisulbanChEBI
MitostanChEBI
MyeloleukonChEBI
MyleranChEBI
Tetramethylene bis(methanesulfonate)ChEBI
1,4-Bis(methanesulphonoxy)butaneGenerator
BusulphanGenerator
1,4-Butanediol dimethanesulfonic acidGenerator
1,4-Butanediol dimethanesulphonateGenerator
1,4-Butanediol dimethanesulphonic acidGenerator
1,4-DimethanesulphonoxybutaneGenerator
BisulphexGenerator
BusulphanoGenerator
BusulphanumGenerator
LeucosulphanGenerator
Tetramethylene bis(methanesulfonic acid)Generator
Tetramethylene bis(methanesulphonate)Generator
Tetramethylene bis(methanesulphonic acid)Generator
BusulphaneHMDB
ButanedioldimethanesulfonateHMDB
BuzulfanHMDB
SulfabutinHMDB
SulphabutinHMDB
Tetramethylene dimethane sulfonateHMDB
Tetramethylenester kyseliny methansulfonoveHMDB
Busulfan wellcome brandMeSH
BusulfexMeSH
Orphan brand OF busulfanMeSH
Busulfan glaxosmithkline brandMeSH
Busulfan orphan brandMeSH
Busulfan wellcomeMeSH
MyelosanMeSH
MylecytanMeSH
Wellcome, busulfanMeSH
glaxo Wellcome brand OF busulfanMeSH
GlyzophrolMeSH
MyléranMeSH
Wellcome brand OF busulfanMeSH
GlaxoSmithKline brand OF busulfanMeSH
N-Butane-1,3-di(methylsulfonate)MeSH
Chemical FormulaC6H14O6S2
Average Molecular Weight246.302
Monoisotopic Molecular Weight246.02317956
IUPAC Name4-(methanesulfonyloxy)butyl methanesulfonate
Traditional Namebusulfan
CAS Registry Number55-98-1
SMILES
CS(=O)(=O)OCCCCOS(C)(=O)=O
InChI Identifier
InChI=1S/C6H14O6S2/c1-13(7,8)11-5-3-4-6-12-14(2,9)10/h3-6H2,1-2H3
InChI KeyCOVZYZSDYWQREU-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of chemical entities known as organosulfonic acid esters. These are esters of sulfonic acid, which have the general structure RS(=O)2OR' (R,R' = organyl, not H).
KingdomChemical entities
Super ClassOrganic compounds
ClassOrganic acids and derivatives
Sub ClassOrganic sulfonic acids and derivatives
Direct ParentOrganosulfonic acid esters
Alternative Parents
Substituents
  • Organosulfonic acid ester
  • Sulfonic acid ester
  • Sulfonyl
  • Methanesulfonate
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organosulfur compound
  • Organooxygen compound
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Disposition

Biological Location:

  Subcellular:

  Biofluid and excreta:

Route of exposure:

  Enteral:

Role

Industrial application:

  Pharmaceutical industry:

Indirect biological role:

Physiological effect

Health effect:

  Health condition:

    Gastrointestinal disorders:

    General disorders and administration site conditions:

    Respiratory, thoracic and mediastinal disorders:

    Psychiatric disorders:

  Observation:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point287 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility5.16 g/LNot Available
LogP-0.3Not Available
Predicted Properties
PropertyValueSource
Water Solubility5.16 g/LALOGPS
logP-0.9ALOGPS
logP-0.76ChemAxon
logS-1.7ALOGPS
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area86.74 ŲChemAxon
Rotatable Bond Count7ChemAxon
Refractivity49.57 m³·mol⁻¹ChemAxon
Polarizability23.64 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a6r-4910000000-e9ddf91161b812713ab4View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-qTof , Positivesplash10-014i-1490000000-7895468c598e6a0480c8View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-qTof , Positivesplash10-014i-0390000000-19a6e15d2bf397b244b1View in MoNA
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-014i-0390000000-19a6e15d2bf397b244b1View in MoNA
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-014i-1490000000-7895468c598e6a0480c8View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0002-0290000000-d4b566ed54a53c849786View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0udi-3910000000-3801100c88a8c43def33View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-004r-9500000000-3dec1d870a9203efd37fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-3090000000-aa607731139624cbe5bcView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-9110000000-7405cd0ebfa01ce907a0View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9000000000-4e28fa66f6cebb7272ccView in MoNA
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
Biological Properties
Cellular Locations
  • Cytoplasm
  • Membrane
Biofluid Locations
  • Blood
  • Urine
Tissue LocationNot Available
PathwaysNot Available
NameSMPDB/PathwhizKEGG
No entries found
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB01008 details
UrineExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB01008 details
Abnormal Concentrations
Not Available
Predicted Concentrations
BiofluidValueOriginal ageOriginal sexOriginal conditionComments
Blood0-4 uMAdult (>18 years old)BothNormalPredicted based on drug qualities
Blood0-2 umol/mmol creatinineAdult (>18 years old)BothNormalPredicted based on drug qualities
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB01008
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID2384
KEGG Compound IDC06862
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkBusulfan
METLIN IDNot Available
PubChem Compound2478
PDB IDNot Available
ChEBI ID28901
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Hall AG, Tilby MJ: Mechanisms of action of, and modes of resistance to, alkylating agents used in the treatment of haematological malignancies. Blood Rev. 1992 Sep;6(3):163-73. [PubMed:1422285 ]
  2. Lesurtel M, Graf R, Aleil B, Walther DJ, Tian Y, Jochum W, Gachet C, Bader M, Clavien PA: Platelet-derived serotonin mediates liver regeneration. Science. 2006 Apr 7;312(5770):104-7. [PubMed:16601191 ]
  3. Nath CE, Shaw PJ: Busulphan in blood and marrow transplantation: dose, route, frequency and role of therapeutic drug monitoring. Curr Clin Pharmacol. 2007 Jan;2(1):75-91. [PubMed:18690856 ]
  4. Krivoy N, Hoffer E, Lurie Y, Bentur Y, Rowe JM: Busulfan use in hematopoietic stem cell transplantation: pharmacology, dose adjustment, safety and efficacy in adults and children. Curr Drug Saf. 2008 Jan;3(1):60-6. [PubMed:18690982 ]
  5. Ciurea SO, Andersson BS: Busulfan in hematopoietic stem cell transplantation. Biol Blood Marrow Transplant. 2009 May;15(5):523-36. doi: 10.1016/j.bbmt.2008.12.489. Epub 2009 Feb 12. [PubMed:19361744 ]
  6. McCune JS, Holmberg LA: Busulfan in hematopoietic stem cell transplant setting. Expert Opin Drug Metab Toxicol. 2009 Aug;5(8):957-69. doi: 10.1517/17425250903107764. [PubMed:19611402 ]
  7. Valdez BC, Andersson BS: Interstrand crosslink inducing agents in pretransplant conditioning therapy for hematologic malignancies. Environ Mol Mutagen. 2010 Jul;51(6):659-68. doi: 10.1002/em.20603. [PubMed:20577993 ]
  8. (). FDA label . .

Enzymes

General function:
Involved in glutathione transferase activity
Specific function:
Conjugation of reduced glutathione to a wide number of exogenous and endogenous hydrophobic electrophiles.
Gene Name:
GSTA1
Uniprot ID:
P08263
Molecular weight:
25630.785
References
  1. Kusama M, Kubota T, Matsukura Y, Matsuno K, Ogawa S, Kanda Y, Iga T: Influence of glutathione S-transferase A1 polymorphism on the pharmacokinetics of busulfan. Clin Chim Acta. 2006 Jun;368(1-2):93-8. Epub 2006 Jan 31. [PubMed:16448639 ]
  2. Elhasid R, Krivoy N, Rowe JM, Sprecher E, Adler L, Elkin H, Efrati E: Influence of glutathione S-transferase A1, P1, M1, T1 polymorphisms on oral busulfan pharmacokinetics in children with congenital hemoglobinopathies undergoing hematopoietic stem cell transplantation. Pediatr Blood Cancer. 2010 Dec 1;55(6):1172-9. doi: 10.1002/pbc.22739. [PubMed:20672371 ]
  3. Vassord C, Lapoumeroulie C, Koumaravelou K, Srivastava A, Krishnamoorthy R: Endothelial cells do not express GSTA1: potential relevance to busulfan-mediated endothelial damage during haematopoietic stem cell transplantation. Eur J Haematol. 2008 Apr;80(4):299-302. doi: 10.1111/j.1600-0609.2008.01031.x. Epub 2008 Jan 14. [PubMed:18194479 ]
General function:
Involved in glutathione transferase activity
Specific function:
Conjugation of reduced glutathione to a wide number of exogenous and endogenous hydrophobic electrophiles.
Gene Name:
GSTA2
Uniprot ID:
P09210
Molecular weight:
25663.675
References
  1. Vassord C, Lapoumeroulie C, Koumaravelou K, Srivastava A, Krishnamoorthy R: Endothelial cells do not express GSTA1: potential relevance to busulfan-mediated endothelial damage during haematopoietic stem cell transplantation. Eur J Haematol. 2008 Apr;80(4):299-302. doi: 10.1111/j.1600-0609.2008.01031.x. Epub 2008 Jan 14. [PubMed:18194479 ]
General function:
Involved in monooxygenase activity
Specific function:
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation reactions (e.g. caffeine 8-oxidation, omeprazole sulphoxidation, midazolam 1'-hydroxylation and midazolam 4-hydroxylation) of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Acts as a 1,8-cineole 2-exo-monooxygenase. The enzyme also hydroxylates etoposide.
Gene Name:
CYP3A4
Uniprot ID:
P08684
Molecular weight:
57255.585
References
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]