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Showing metabocard for Busulfan (HMDB0015143)

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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:51 UTC
Update Date2022-03-07 02:51:52 UTC
HMDB IDHMDB0015143
Secondary Accession Numbers
  • HMDB15143
Metabolite Identification
Common NameBusulfan
DescriptionBusulfan, 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
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MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0015143 (Busulfan)

1008
  Mrv1652305271900042D          

 14 13  0  0  0  0            999 V2000
    7.3659    0.2063    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -0.2063    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    6.6515   -0.2063    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791    0.2063    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.7784   -0.5082    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.9534    0.9207    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9520    0.5082    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7770   -0.9207    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2224   -0.2063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080    0.2063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9370    0.2063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935   -0.2063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0804    0.6188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500   -0.6188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  3  1  0  0  0  0
  1  5  2  0  0  0  0
  1  6  2  0  0  0  0
  1 13  1  0  0  0  0
  2  4  1  0  0  0  0
  2  7  2  0  0  0  0
  2  8  2  0  0  0  0
  2 14  1  0  0  0  0
  3 11  1  0  0  0  0
  4 12  1  0  0  0  0
  9 10  1  0  0  0  0
  9 11  1  0  0  0  0
 10 12  1  0  0  0  0
M  END
Download

3D MOL for HMDB0015143 (Busulfan)

HMDB0015143
     RDKit          3D
Busulfan
 28 27  0  0  0  0  0  0  0  0999 V2000
    5.2171    1.1017    0.0087 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9420    0.0787    0.6855 S   0  0  0  0  0  6  0  0  0  0  0  0
    4.0721   -0.0064    2.1825 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0355   -1.3313    0.1697 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4229    0.7510    0.3724 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6120   -0.3016   -0.0095 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1449    0.0176    0.0016 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5795   -1.2525    0.3847 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0696   -1.0835    0.4483 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4558   -0.1870    1.4290 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5236    0.9717    0.8743 S   0  0  0  0  0  6  0  0  0  0  0  0
   -4.8636    0.2759   -0.0495 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0879    1.6800    2.0713 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8275    1.9558   -0.0404 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1501    1.0432   -1.0938 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0419    2.1378    0.3650 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1997    0.7919    0.3889 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9610   -0.6084   -1.0285 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8112   -1.1308    0.7157 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0303    0.8295    0.7261 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1237    0.3113   -1.0452 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3454   -2.0341   -0.3533 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2089   -1.5812    1.3630 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4901   -2.0861    0.7083 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5041   -0.8007   -0.5202 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5958    1.0943   -0.2270 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5401   -0.0808   -1.0546 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3645   -0.5560    0.4757 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  2  0
  2  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 11 13  2  0
 11 14  2  0
  1 15  1  0
  1 16  1  0
  1 17  1  0
  6 18  1  0
  6 19  1  0
  7 20  1  0
  7 21  1  0
  8 22  1  0
  8 23  1  0
  9 24  1  0
  9 25  1  0
 12 26  1  0
 12 27  1  0
 12 28  1  0
M  END
Download

3D SDF for HMDB0015143 (Busulfan)

1008
  Mrv1652305271900042D          

 14 13  0  0  0  0            999 V2000
    7.3659    0.2063    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -0.2063    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    6.6515   -0.2063    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791    0.2063    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.7784   -0.5082    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.9534    0.9207    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9520    0.5082    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7770   -0.9207    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2224   -0.2063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080    0.2063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9370    0.2063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935   -0.2063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0804    0.6188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500   -0.6188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  3  1  0  0  0  0
  1  5  2  0  0  0  0
  1  6  2  0  0  0  0
  1 13  1  0  0  0  0
  2  4  1  0  0  0  0
  2  7  2  0  0  0  0
  2  8  2  0  0  0  0
  2 14  1  0  0  0  0
  3 11  1  0  0  0  0
  4 12  1  0  0  0  0
  9 10  1  0  0  0  0
  9 11  1  0  0  0  0
 10 12  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0015143

> <DATABASE_NAME>
hmdb

> <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

> <FORMULA>
C6H14O6S2

> <MOLECULAR_WEIGHT>
246.302

> <EXACT_MASS>
246.02317956

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
28

> <JCHEM_AVERAGE_POLARIZABILITY>
23.637829810018637

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
4-(methanesulfonyloxy)butyl methanesulfonate

> <ALOGPS_LOGP>
-0.90

> <JCHEM_LOGP>
-0.7590282259999991

> <ALOGPS_LOGS>
-1.68

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_POLAR_SURFACE_AREA>
86.74000000000001

> <JCHEM_REFRACTIVITY>
49.5686

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.16e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
busulfan

> <JCHEM_VEBER_RULE>
0

$$$$
Download

3D-SDF for HMDB0015143 (Busulfan)

HMDB0015143
     RDKit          3D
Busulfan
 28 27  0  0  0  0  0  0  0  0999 V2000
    5.2171    1.1017    0.0087 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9420    0.0787    0.6855 S   0  0  0  0  0  6  0  0  0  0  0  0
    4.0721   -0.0064    2.1825 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0355   -1.3313    0.1697 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4229    0.7510    0.3724 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6120   -0.3016   -0.0095 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1449    0.0176    0.0016 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5795   -1.2525    0.3847 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0696   -1.0835    0.4483 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4558   -0.1870    1.4290 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5236    0.9717    0.8743 S   0  0  0  0  0  6  0  0  0  0  0  0
   -4.8636    0.2759   -0.0495 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0879    1.6800    2.0713 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8275    1.9558   -0.0404 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1501    1.0432   -1.0938 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0419    2.1378    0.3650 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1997    0.7919    0.3889 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9610   -0.6084   -1.0285 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8112   -1.1308    0.7157 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0303    0.8295    0.7261 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1237    0.3113   -1.0452 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3454   -2.0341   -0.3533 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2089   -1.5812    1.3630 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4901   -2.0861    0.7083 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5041   -0.8007   -0.5202 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5958    1.0943   -0.2270 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5401   -0.0808   -1.0546 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3645   -0.5560    0.4757 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  2  0
  2  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 11 13  2  0
 11 14  2  0
  1 15  1  0
  1 16  1  0
  1 17  1  0
  6 18  1  0
  6 19  1  0
  7 20  1  0
  7 21  1  0
  8 22  1  0
  8 23  1  0
  9 24  1  0
  9 25  1  0
 12 26  1  0
 12 27  1  0
 12 28  1  0
M  END
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PDB for HMDB0015143 (Busulfan)

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
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3D PDB for HMDB0015143 (Busulfan)

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
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SMILES for HMDB0015143 (Busulfan)

CS(=O)(=O)OCCCCOS(C)(=O)=O
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INCHI for HMDB0015143 (Busulfan)

InChI=1S/C6H14O6S2/c1-13(7,8)11-5-3-4-6-12-14(2,9)10/h3-6H2,1-2H3
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View in JSmolView NMR AssignmentsView Stereo Labels
Synonyms
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
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).
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassOrganic sulfonic acids and derivatives
Sub ClassOrganosulfonic 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
Physiological effectNot Available
Disposition
Biological locationSource
ProcessNot Available
RoleNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point287 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility5.16 g/LNot Available
LogP-0.3Not Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
Predicted Chromatographic Properties
Spectra
Biological Properties
Cellular Locations
  • Cytoplasm
  • Membrane
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB01008 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB01008 details
Abnormal Concentrations
Not Available
Predicted Concentrations
BiospecimenValueOriginal ageOriginal sexOriginal conditionComments
Blood0.000 uMAdult (>18 years old)BothNormalPredicted based on drug qualities
Blood0.000 umol/mmol creatinineAdult (>18 years old)BothNormalPredicted based on drug qualities
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB01008
Phenol Explorer Compound IDNot Available
FooDB 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
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
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

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
  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 ]
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
  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 ]
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
  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 ]