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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (3) Show 3 proteins XML

enzymes (3) Show 3 proteins

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-06 15:16:51 UTC

Update Date

2022-03-07 02:51:52 UTC

HMDB ID

HMDB0015143

Secondary Accession Numbers

HMDB15143

Metabolite Identification

Common Name

Busulfan

Description

Busulfan, also known as busulphano or myleran, belongs to the class of organic compounds known as organosulfonic acid esters. These are esters of sulfonic acid, which have the general structure RS(=O)2OR' (R,R' = organyl, not H). Busulfan is a drug which is used for use in combination with cyclophosphamide as a conditioning regimen prior to allogeneic hematopoietic progenitor cell transplantation for chronic myelogenous (myeloid, myelocytic, granulocytic) leukemia (fda has designated busulfan as an orphan drug for this use). it is also used as a component of pretransplant conditioning regimens in patients undergoing bone marrow transplantation for acute myeloid leukemia and nonmalignant diseases. It is also used as an insect sterilant. Busulfan is possibly neutral. Busulfan is formally rated as a carcinogen (by IARC 1) and is also a potentially toxic compound. A methanesulfonate ester that is butane-1,4-diol in which the hydrogens of the hydroxy groups are replaced by methanesulfonyl groups. An alkylating antineoplastic agent, it is used for the treatment of chronic myeloid leukemia (although it has been largely replaced by newer drugs).

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

HEADER    PROTEIN                                 27-MAY-19   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 1008                                              
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-MAY-19         0                                  
HETATM    1  S   UNK     0      13.750   0.385   0.000  0.00  0.00           S+0
HETATM    2  S   UNK     0       4.414  -0.385   0.000  0.00  0.00           S+0
HETATM    3  O   UNK     0      12.416  -0.385   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0       5.748   0.385   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0      14.520  -0.949   0.000  0.00  0.00           O+0
HETATM    6  O   UNK     0      12.980   1.719   0.000  0.00  0.00           O+0
HETATM    7  O   UNK     0       3.644   0.949   0.000  0.00  0.00           O+0
HETATM    8  O   UNK     0       5.184  -1.719   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       9.748  -0.385   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       8.415   0.385   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      11.082   0.385   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       7.081  -0.385   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      15.083   1.155   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       3.080  -1.155   0.000  0.00  0.00           C+0
CONECT    1    3    5    6   13                                             
CONECT    2    4    7    8   14                                             
CONECT    3    1   11                                                       
CONECT    4    2   12                                                       
CONECT    5    1                                                            
CONECT    6    1                                                            
CONECT    7    2                                                            
CONECT    8    2                                                            
CONECT    9   10   11                                                       
CONECT   10    9   12                                                       
CONECT   11    3    9                                                       
CONECT   12    4   10                                                       
CONECT   13    1                                                            
CONECT   14    2                                                            
MASTER        0    0    0    0    0    0    0    0   14    0   26    0
END

COMPND    HMDB0015143
HETATM    1  C1  UNL     1       5.217   1.102   0.009  1.00  0.00           C  
HETATM    2  S1  UNL     1       3.942   0.079   0.686  1.00  0.00           S  
HETATM    3  O1  UNL     1       4.072  -0.006   2.183  1.00  0.00           O  
HETATM    4  O2  UNL     1       4.035  -1.331   0.170  1.00  0.00           O  
HETATM    5  O3  UNL     1       2.423   0.751   0.372  1.00  0.00           O  
HETATM    6  C2  UNL     1       1.612  -0.302  -0.010  1.00  0.00           C  
HETATM    7  C3  UNL     1       0.145   0.018   0.002  1.00  0.00           C  
HETATM    8  C4  UNL     1      -0.580  -1.252   0.385  1.00  0.00           C  
HETATM    9  C5  UNL     1      -2.070  -1.084   0.448  1.00  0.00           C  
HETATM   10  O4  UNL     1      -2.456  -0.187   1.429  1.00  0.00           O  
HETATM   11  S2  UNL     1      -3.524   0.972   0.874  1.00  0.00           S  
HETATM   12  C6  UNL     1      -4.864   0.276  -0.049  1.00  0.00           C  
HETATM   13  O5  UNL     1      -4.088   1.680   2.071  1.00  0.00           O  
HETATM   14  O6  UNL     1      -2.828   1.956  -0.040  1.00  0.00           O  
HETATM   15  H1  UNL     1       5.150   1.043  -1.094  1.00  0.00           H  
HETATM   16  H2  UNL     1       5.042   2.138   0.365  1.00  0.00           H  
HETATM   17  H3  UNL     1       6.200   0.792   0.389  1.00  0.00           H  
HETATM   18  H4  UNL     1       1.961  -0.608  -1.029  1.00  0.00           H  
HETATM   19  H5  UNL     1       1.811  -1.131   0.716  1.00  0.00           H  
HETATM   20  H6  UNL     1      -0.030   0.830   0.726  1.00  0.00           H  
HETATM   21  H7  UNL     1      -0.124   0.311  -1.045  1.00  0.00           H  
HETATM   22  H8  UNL     1      -0.345  -2.034  -0.353  1.00  0.00           H  
HETATM   23  H9  UNL     1      -0.209  -1.581   1.363  1.00  0.00           H  
HETATM   24  H10 UNL     1      -2.490  -2.086   0.708  1.00  0.00           H  
HETATM   25  H11 UNL     1      -2.504  -0.801  -0.520  1.00  0.00           H  
HETATM   26  H12 UNL     1      -5.596   1.094  -0.227  1.00  0.00           H  
HETATM   27  H13 UNL     1      -4.540  -0.081  -1.055  1.00  0.00           H  
HETATM   28  H14 UNL     1      -5.364  -0.556   0.476  1.00  0.00           H  
CONECT    1    2   15   16   17
CONECT    2    3    3    4    4
CONECT    2    5
CONECT    5    6
CONECT    6    7   18   19
CONECT    7    8   20   21
CONECT    8    9   22   23
CONECT    9   10   24   25
CONECT   10   11
CONECT   11   12   13   13   14
CONECT   11   14
CONECT   12   26   27   28
END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
1,4-Bis(methanesulfonoxy)butane	ChEBI
1,4-Butanediol dimethanesulfonate	ChEBI
1,4-Dimesyloxybutane	ChEBI
1,4-Dimethanesulfonoxybutane	ChEBI
Bisulfex	ChEBI
Busulfano	ChEBI
Busulfanum	ChEBI
Leucosulfan	ChEBI
Mablin	ChEBI
Mielucin	ChEBI
Misulban	ChEBI
Mitostan	ChEBI
Myeloleukon	ChEBI
Myleran	ChEBI
Tetramethylene bis(methanesulfonate)	ChEBI
1,4-Bis(methanesulphonoxy)butane	Generator
1,4-Butanediol dimethanesulfonic acid	Generator
1,4-Butanediol dimethanesulphonate	Generator
1,4-Butanediol dimethanesulphonic acid	Generator
1,4-Dimethanesulphonoxybutane	Generator
Bisulphex	Generator
Busulphano	Generator
Busulphanum	Generator
Leucosulphan	Generator
Tetramethylene bis(methanesulfonic acid)	Generator
Tetramethylene bis(methanesulphonate)	Generator
Tetramethylene bis(methanesulphonic acid)	Generator
Busulphan	Generator
Busulphane	HMDB
Butanedioldimethanesulfonate	HMDB
Buzulfan	HMDB
Sulfabutin	HMDB
Sulphabutin	HMDB
Tetramethylene dimethane sulfonate	HMDB
Tetramethylenester kyseliny methansulfonove	HMDB
Busulfan wellcome brand	HMDB
Busulfex	HMDB
Orphan brand OF busulfan	HMDB
Busulfan glaxosmithkline brand	HMDB
Busulfan orphan brand	HMDB
Busulfan wellcome	HMDB
Myelosan	HMDB
Mylecytan	HMDB
Wellcome, busulfan	HMDB
Glaxo wellcome brand OF busulfan	HMDB
Glyzophrol	HMDB
Myléran	HMDB
Wellcome brand OF busulfan	HMDB
GlaxoSmithKline brand OF busulfan	HMDB
N-Butane-1,3-di(methylsulfonate)	HMDB

Chemical Formula

C₆H₁₄O₆S₂

Average Molecular Weight

246.302

Monoisotopic Molecular Weight

246.02317956

IUPAC Name

4-(methanesulfonyloxy)butyl methanesulfonate

Traditional Name

busulfan

CAS Registry Number

55-98-1

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 Key

COVZYZSDYWQREU-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as organosulfonic acid esters. These are esters of sulfonic acid, which have the general structure RS(=O)2OR' (R,R' = organyl, not H).

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Organic sulfonic acids and derivatives

Sub Class

Organosulfonic acids and derivatives

Direct Parent

Organosulfonic 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 Framework

Aliphatic acyclic compounds

External Descriptors

methanesulfonate ester (CHEBI:28901 )

Ontology

Not Available

Urine (PMID: 21059682)

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 21059682)

Cellular substructure

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	287 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	5.16 g/L	Not Available
LogP	-0.3	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	5.16 g/L	ALOGPS
logP	-0.9	ALOGPS
logP	-0.76	ChemAxon
logS	-1.7	ALOGPS
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	86.74 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	49.57 m³·mol⁻¹	ChemAxon
Polarizability	23.64 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	156.082	31661259
DarkChem	[M-H]-	149.833	31661259
DeepCCS	[M+H]+	151.329	30932474
DeepCCS	[M-H]-	147.501	30932474
DeepCCS	[M-2H]-	185.027	30932474
DeepCCS	[M+Na]+	160.564	30932474
AllCCS	[M+H]+	153.6	32859911
AllCCS	[M+H-H2O]+	150.3	32859911
AllCCS	[M+NH4]+	156.7	32859911
AllCCS	[M+Na]+	157.6	32859911
AllCCS	[M-H]-	148.4	32859911
AllCCS	[M+Na-2H]-	149.8	32859911
AllCCS	[M+HCOO]-	151.3	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Busulfan	CS(=O)(=O)OCCCCOS(C)(=O)=O	3921.1	Standard polar	33892256
Busulfan	CS(=O)(=O)OCCCCOS(C)(=O)=O	1673.5	Standard non polar	33892256
Busulfan	CS(=O)(=O)OCCCCOS(C)(=O)=O	1866.7	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Busulfan GC-MS (Non-derivatized) - 70eV, Positive	splash10-0a6r-4910000000-e9ddf91161b812713ab4	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Busulfan GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental LC-MS/MS	LC-MS/MS Spectrum - Busulfan LC-ESI-qTof , Positive-QTOF	splash10-014i-1490000000-7895468c598e6a0480c8	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Busulfan LC-ESI-qTof , Positive-QTOF	splash10-014i-0390000000-19a6e15d2bf397b244b1	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Busulfan , positive-QTOF	splash10-014i-0390000000-19a6e15d2bf397b244b1	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Busulfan , positive-QTOF	splash10-014i-1490000000-7895468c598e6a0480c8	2017-09-14	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Busulfan 10V, Positive-QTOF	splash10-0002-0290000000-d4b566ed54a53c849786	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Busulfan 20V, Positive-QTOF	splash10-0udi-3910000000-3801100c88a8c43def33	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Busulfan 40V, Positive-QTOF	splash10-004r-9500000000-3dec1d870a9203efd37f	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Busulfan 10V, Negative-QTOF	splash10-0002-3090000000-aa607731139624cbe5bc	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Busulfan 20V, Negative-QTOF	splash10-004i-9110000000-7405cd0ebfa01ce907a0	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Busulfan 40V, Negative-QTOF	splash10-004i-9000000000-4e28fa66f6cebb7272cc	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Busulfan 10V, Positive-QTOF	splash10-0uka-9530000000-c112640ccc30da208327	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Busulfan 20V, Positive-QTOF	splash10-0a4j-9000000000-ed8101663b60977229ec	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Busulfan 40V, Positive-QTOF	splash10-0a4i-9000000000-4f0ac4d1c58f92828a43	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Busulfan 10V, Negative-QTOF	splash10-0002-0090000000-1d2d39d4577a3e5e71ad	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Busulfan 20V, Negative-QTOF	splash10-000j-2960000000-3752c572e539716a5e2e	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Busulfan 40V, Negative-QTOF	splash10-002f-9100000000-644c96579ffd326045dc	2021-10-11	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Membrane

Biospecimen Locations

Blood
Urine

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB01008	21059682	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB01008	21059682	details

Abnormal Concentrations

Not Available

Predicted Concentrations

Biospecimen	Value	Original age	Original sex	Original condition	Comments
Blood	0.000 uM	Adult (>18 years old)	Both	Normal	Predicted based on drug qualities
Blood	0.000 umol/mmol creatinine	Adult (>18 years old)	Both	Normal	Predicted based on drug qualities

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB01008

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

2384

KEGG Compound ID

C06862

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Busulfan

METLIN ID

Not Available

PubChem Compound

2478

PDB ID

Not Available

ChEBI ID

28901

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

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 ]
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 ]
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 ]
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 ]
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 ]
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 ]
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 ]
(). FDA label . .

Enzymes

Enzyme Details

1. Glutathione S-transferase A1

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

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 ]
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 ]
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 ]

Enzyme Details

2. Glutathione S-transferase A2

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

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 ]

Enzyme Details

3. Cytochrome P450 3A4

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

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 ]

Showing metabocard for Busulfan (HMDB0015143)

MOL for HMDB0015143 (Busulfan)

3D MOL for HMDB0015143 (Busulfan)

3D SDF for HMDB0015143 (Busulfan)

3D-SDF for HMDB0015143 (Busulfan)

PDB for HMDB0015143 (Busulfan)

3D PDB for HMDB0015143 (Busulfan)

SMILES for HMDB0015143 (Busulfan)

INCHI for HMDB0015143 (Busulfan)

Structure for HMDB0015143 (Busulfan)

3D Structure for HMDB0015143 (Busulfan)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

Enzymes

References

References

References