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Showing metabocard for 3-Dechloroethylifosfamide (HMDB0013858)

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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:00:14 UTC
Update Date2023-02-21 17:18:05 UTC
HMDB IDHMDB0013858
Secondary Accession Numbers
  • HMDB13858
Metabolite Identification
Common Name3-Dechloroethylifosfamide
Description3-Dechloroethylifosfamide is an inactive metabolite of the antitumour, alkylating drug Ifosfamide. It is a member of the compound class called oxazaphosphorines Oxazaphosphorines are any saturated six-membered heterocycle containing three carbon atoms and one each of oxygen, nitrogen and phosphorus, especially one in which the phosphorus atom is linked to both the nitrogen and oxygen atoms. It is formed from its side-chain oxidation leading to the liberation of chloroacetaldehyde (PMID: 9054957 ). 3-dechloroethylifosfamide can be biosynthesized from ifosfamide through the action of several CYP450 enzymes including CYP3A4, CYP3A5, and CYP2B6 (PMID: 15875221 ). The duration of ifosfamide infusion influences the amount of 3-dechloroethylifosfamide that is produced (PMID: 11408362 ). 3-dechloroethylifosfamide is only found in individuals who have consumed or received the drug Ifosfamide.
Structure
Data?1676999885
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0013858 (3-Dechloroethylifosfamide)

  Mrv0541 06191310212D          

 11 11  0  0  0  0            999 V2000
    8.7176   -6.0763    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    8.7176   -3.2185    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
    9.4319   -2.8060    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.1301   -3.9331    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.0031   -2.8060    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.3051   -3.9331    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.0031   -1.9812    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7176   -1.5687    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4319   -1.9812    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7176   -4.6475    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3051   -5.3620    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1 11  1  0  0  0  0
  2  3  1  0  0  0  0
  2  4  2  0  0  0  0
  2  5  1  0  0  0  0
  2  6  1  0  0  0  0
  3  9  1  0  0  0  0
  5  7  1  0  0  0  0
  6 10  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
 10 11  1  0  0  0  0
M  END
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3D MOL for HMDB0013858 (3-Dechloroethylifosfamide)

HMDB0060881
     RDKit          3D
Dechloroethyl cyclophosphamide
 23 23  0  0  0  0  0  0  0  0999 V2000
   -0.1042    0.2002    1.4966 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0248    0.5586    0.0191 P   0  0  0  0  0  5  0  0  0  0  0  0
    1.5554    1.0866   -0.4263 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.5572    0.8541    0.5914 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4182   -0.3474    0.2707 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0671   -1.0173    1.7949 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -0.5880   -0.7830   -0.9162 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9764   -1.0437   -0.8401 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8901    0.0368   -0.4296 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3431    1.1692    0.3538 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2085    1.7625   -0.2090 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8118    0.6640   -1.3417 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1311    0.7407    1.6058 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2400    1.7386    0.6270 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7865   -1.1227   -0.1891 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2996   -0.0699   -0.3388 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0066   -1.6034   -0.6799 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1145   -1.9747   -0.2313 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2959   -1.3622   -1.8683 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6874   -0.4261    0.2094 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4554    0.4730   -1.2931 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1145    1.9607    0.3999 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0708    0.8816    1.3950 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  2  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11  2  1  0
  3 12  1  0
  4 13  1  0
  4 14  1  0
  5 15  1  0
  5 16  1  0
  7 17  1  0
  8 18  1  0
  8 19  1  0
  9 20  1  0
  9 21  1  0
 10 22  1  0
 10 23  1  0
M  END
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3D SDF for HMDB0013858 (3-Dechloroethylifosfamide)

  Mrv0541 06191310212D          

 11 11  0  0  0  0            999 V2000
    8.7176   -6.0763    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    8.7176   -3.2185    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
    9.4319   -2.8060    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.1301   -3.9331    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.0031   -2.8060    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.3051   -3.9331    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.0031   -1.9812    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7176   -1.5687    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4319   -1.9812    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7176   -4.6475    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3051   -5.3620    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1 11  1  0  0  0  0
  2  3  1  0  0  0  0
  2  4  2  0  0  0  0
  2  5  1  0  0  0  0
  2  6  1  0  0  0  0
  3  9  1  0  0  0  0
  5  7  1  0  0  0  0
  6 10  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
 10 11  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0013858

> <DATABASE_NAME>
hmdb

> <SMILES>
ClCCNP1(=O)NCCCO1

> <INCHI_IDENTIFIER>
InChI=1S/C5H12ClN2O2P/c6-2-4-8-11(9)7-3-1-5-10-11/h1-5H2,(H2,7,8,9)

> <INCHI_KEY>
DZKGMGPLDJOVCX-UHFFFAOYSA-N

> <FORMULA>
C5H12ClN2O2P

> <MOLECULAR_WEIGHT>
198.588

> <EXACT_MASS>
198.032491857

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
17.70515295622222

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-[(2-chloroethyl)amino]-1,3,2λ⁵-oxazaphosphinan-2-one

> <ALOGPS_LOGP>
-0.54

> <JCHEM_LOGP>
-0.7916182229999997

> <ALOGPS_LOGS>
-0.99

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.733572788306645

> <JCHEM_PKA_STRONGEST_BASIC>
-2.1069199326491885

> <JCHEM_POLAR_SURFACE_AREA>
50.36

> <JCHEM_REFRACTIVITY>
44.23810000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.03e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3-dechloroethylifosfamide

> <JCHEM_VEBER_RULE>
0

$$$$
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3D-SDF for HMDB0013858 (3-Dechloroethylifosfamide)

HMDB0060881
     RDKit          3D
Dechloroethyl cyclophosphamide
 23 23  0  0  0  0  0  0  0  0999 V2000
   -0.1042    0.2002    1.4966 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0248    0.5586    0.0191 P   0  0  0  0  0  5  0  0  0  0  0  0
    1.5554    1.0866   -0.4263 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.5572    0.8541    0.5914 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4182   -0.3474    0.2707 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0671   -1.0173    1.7949 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -0.5880   -0.7830   -0.9162 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9764   -1.0437   -0.8401 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8901    0.0368   -0.4296 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3431    1.1692    0.3538 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2085    1.7625   -0.2090 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8118    0.6640   -1.3417 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1311    0.7407    1.6058 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2400    1.7386    0.6270 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7865   -1.1227   -0.1891 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2996   -0.0699   -0.3388 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0066   -1.6034   -0.6799 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1145   -1.9747   -0.2313 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2959   -1.3622   -1.8683 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6874   -0.4261    0.2094 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4554    0.4730   -1.2931 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1145    1.9607    0.3999 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0708    0.8816    1.3950 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  2  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11  2  1  0
  3 12  1  0
  4 13  1  0
  4 14  1  0
  5 15  1  0
  5 16  1  0
  7 17  1  0
  8 18  1  0
  8 19  1  0
  9 20  1  0
  9 21  1  0
 10 22  1  0
 10 23  1  0
M  END
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PDB for HMDB0013858 (3-Dechloroethylifosfamide)

HEADER    PROTEIN                                 19-JUN-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   19-JUN-13         0                                  
HETATM    1 Cl   UNK     0      16.273 -11.342   0.000  0.00  0.00          Cl+0
HETATM    2  P   UNK     0      16.273  -6.008   0.000  0.00  0.00           P+0
HETATM    3  O   UNK     0      17.606  -5.238   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0      17.043  -7.342   0.000  0.00  0.00           O+0
HETATM    5  N   UNK     0      14.939  -5.238   0.000  0.00  0.00           N+0
HETATM    6  N   UNK     0      15.503  -7.342   0.000  0.00  0.00           N+0
HETATM    7  C   UNK     0      14.939  -3.698   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      16.273  -2.928   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      17.606  -3.698   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      16.273  -8.675   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      15.503 -10.009   0.000  0.00  0.00           C+0
CONECT    1   11                                                            
CONECT    2    3    4    5    6                                             
CONECT    3    2    9                                                       
CONECT    4    2                                                            
CONECT    5    2    7                                                       
CONECT    6    2   10                                                       
CONECT    7    5    8                                                       
CONECT    8    7    9                                                       
CONECT    9    3    8                                                       
CONECT   10    6   11                                                       
CONECT   11    1   10                                                       
MASTER        0    0    0    0    0    0    0    0   11    0   22    0
END
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3D PDB for HMDB0013858 (3-Dechloroethylifosfamide)

COMPND    HMDB0060881
HETATM    1  O1  UNL     1      -0.104   0.200   1.497  1.00  0.00           O  
HETATM    2  P1  UNL     1      -0.025   0.559   0.019  1.00  0.00           P  
HETATM    3  N1  UNL     1       1.555   1.087  -0.426  1.00  0.00           N  
HETATM    4  C1  UNL     1       2.557   0.854   0.591  1.00  0.00           C  
HETATM    5  C2  UNL     1       3.418  -0.347   0.271  1.00  0.00           C  
HETATM    6 CL1  UNL     1       4.067  -1.017   1.795  1.00  0.00          CL  
HETATM    7  N2  UNL     1      -0.588  -0.783  -0.916  1.00  0.00           N  
HETATM    8  C3  UNL     1      -1.976  -1.044  -0.840  1.00  0.00           C  
HETATM    9  C4  UNL     1      -2.890   0.037  -0.430  1.00  0.00           C  
HETATM   10  C5  UNL     1      -2.343   1.169   0.354  1.00  0.00           C  
HETATM   11  O2  UNL     1      -1.209   1.762  -0.209  1.00  0.00           O  
HETATM   12  H1  UNL     1       1.812   0.664  -1.342  1.00  0.00           H  
HETATM   13  H2  UNL     1       2.131   0.741   1.606  1.00  0.00           H  
HETATM   14  H3  UNL     1       3.240   1.739   0.627  1.00  0.00           H  
HETATM   15  H4  UNL     1       2.786  -1.123  -0.189  1.00  0.00           H  
HETATM   16  H5  UNL     1       4.300  -0.070  -0.339  1.00  0.00           H  
HETATM   17  H6  UNL     1       0.007  -1.603  -0.680  1.00  0.00           H  
HETATM   18  H7  UNL     1      -2.115  -1.975  -0.231  1.00  0.00           H  
HETATM   19  H8  UNL     1      -2.296  -1.362  -1.868  1.00  0.00           H  
HETATM   20  H9  UNL     1      -3.687  -0.426   0.209  1.00  0.00           H  
HETATM   21  H10 UNL     1      -3.455   0.473  -1.293  1.00  0.00           H  
HETATM   22  H11 UNL     1      -3.114   1.961   0.400  1.00  0.00           H  
HETATM   23  H12 UNL     1      -2.071   0.882   1.395  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3    7   11
CONECT    3    4   12
CONECT    4    5   13   14
CONECT    5    6   15   16
CONECT    7    8   17
CONECT    8    9   18   19
CONECT    9   10   20   21
CONECT   10   11   22   23
END
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SMILES for HMDB0013858 (3-Dechloroethylifosfamide)

ClCCNP1(=O)NCCCO1
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INCHI for HMDB0013858 (3-Dechloroethylifosfamide)

InChI=1S/C5H12ClN2O2P/c6-2-4-8-11(9)7-3-1-5-10-11/h1-5H2,(H2,7,8,9)
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View in JSmolView NMR AssignmentsView Stereo Labels
Synonyms
ValueSource
DechloroethylcyclophosphamideHMDB
N-(2-Chloroethyl)-1,3,2-oxazaphosphinan-2-amine 2-oxideHMDB
N-(2-Chloroethyl)-2-oxo-1,3,2$l^{5}-oxazaphosphinan-2-amineHMDB
(+-)-Isomer OF dechloroethylcyclophosphamideHMDB
(R)-Isomer OF dechloroethylcyclophosphamideHMDB
N-Dechloroethyl-cpaHMDB
(S)-Isomer OF dechloroethylcyclophosphamideHMDB
3-DCE-iffHMDB
3-DClIFHMDB
Chemical FormulaC5H12ClN2O2P
Average Molecular Weight198.588
Monoisotopic Molecular Weight198.032491857
IUPAC Name2-[(2-chloroethyl)amino]-1,3,2λ⁵-oxazaphosphinan-2-one
Traditional Name3-dechloroethylifosfamide
CAS Registry Number36761-83-8
SMILES
ClCCNP1(=O)NCCCO1
InChI Identifier
InChI=1S/C5H12ClN2O2P/c6-2-4-8-11(9)7-3-1-5-10-11/h1-5H2,(H2,7,8,9)
InChI KeyDZKGMGPLDJOVCX-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as phosphoric monoester diamides. These are organophosphorus compounds containing a monoamide derivative of a phosphoric acid diester functional group. They have the general structure R1OP(=O)(N(R2)R3)N(R4)R5, where R1 = organyl group and R2-R5 = H or organyl.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassOrganic phosphoric acids and derivatives
Sub ClassOrganic phosphoramides
Direct ParentPhosphoric monoester diamides
Alternative Parents
Substituents
  • Phosphoric monoester diamide
  • Oxazaphosphinane
  • Organoheterocyclic compound
  • Azacycle
  • Oxacycle
  • Alkyl chloride
  • Hydrocarbon derivative
  • Organic oxide
  • Organopnictogen compound
  • Organic oxygen compound
  • Organic nitrogen compound
  • Organooxygen compound
  • Organonitrogen compound
  • Organochloride
  • Organohalogen compound
  • Alkyl halide
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
Disposition
Biological locationSource
Process
Naturally occurring process
RoleNot Available
Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
Predicted Chromatographic Properties
Spectra
Biological Properties
Cellular Locations
  • Extracellular
Biospecimen Locations
  • Blood
  • Urine
Tissue Locations
  • Kidney
  • Liver
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID102819
KEGG Compound IDC16550
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound114861
PDB IDNot Available
ChEBI ID238115
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. Kurowski V, Wagner T: Urinary excretion of ifosfamide, 4-hydroxyifosfamide, 3- and 2-dechloroethylifosfamide, mesna, and dimesna in patients on fractionated intravenous ifosfamide and concomitant mesna therapy. Cancer Chemother Pharmacol. 1997;39(5):431-9. doi: 10.1007/s002800050594. [PubMed:9054957 ]
  2. Aleksa K, Matsell D, Krausz K, Gelboin H, Ito S, Koren G: Cytochrome P450 3A and 2B6 in the developing kidney: implications for ifosfamide nephrotoxicity. Pediatr Nephrol. 2005 Jul;20(7):872-85. doi: 10.1007/s00467-004-1807-3. Epub 2005 May 4. [PubMed:15875221 ]
  3. Kerbusch T, Mathot RA, Keizer HJ, Kaijser GP, Schellens JH, Beijnen JH: Influence of dose and infusion duration on pharmacokinetics of ifosfamide and metabolites. Drug Metab Dispos. 2001 Jul;29(7):967-75. [PubMed:11408362 ]

Enzymes

Enzyme Details
1. Prostaglandin G/H synthase 1
General function:
Involved in peroxidase activity
Specific function:
May play an important role in regulating or promoting cell proliferation in some normal and neoplastically transformed cells.
Gene Name:
PTGS1
Uniprot ID:
P23219
Molecular weight:
68685.82
References
  1. Zhou SF, Zhou ZW, Yang LP, Cai JP: Substrates, inducers, inhibitors and structure-activity relationships of human Cytochrome P450 2C9 and implications in drug development. Curr Med Chem. 2009;16(27):3480-675. Epub 2009 Sep 1. [PubMed:19515014 ]
Enzyme Details
2. 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. Lokiec F: Ifosfamide: pharmacokinetic properties for central nervous system metastasis prevention. Ann Oncol. 2006 May;17 Suppl 4:iv33-6. [PubMed:16702183 ]
  2. Chen CS, Jounaidi Y, Waxman DJ: Enantioselective metabolism and cytotoxicity of R-ifosfamide and S-ifosfamide by tumor cell-expressed cytochromes P450. Drug Metab Dispos. 2005 Sep;33(9):1261-7. Epub 2005 May 26. [PubMed:15919850 ]
  3. Zhou SF, Zhou ZW, Yang LP, Cai JP: Substrates, inducers, inhibitors and structure-activity relationships of human Cytochrome P450 2C9 and implications in drug development. Curr Med Chem. 2009;16(27):3480-675. Epub 2009 Sep 1. [PubMed:19515014 ]
  4. Roy P, Yu LJ, Crespi CL, Waxman DJ: Development of a substrate-activity based approach to identify the major human liver P-450 catalysts of cyclophosphamide and ifosfamide activation based on cDNA-expressed activities and liver microsomal P-450 profiles. Drug Metab Dispos. 1999 Jun;27(6):655-66. [PubMed:10348794 ]
  5. Preiss R, Schmidt R, Baumann F, Hanschmann H, Hauss J, Geissler F, Pahlig H, Ratzewiss B: Measurement of 4-hydroxylation of ifosfamide in human liver microsomes using the estimation of free and protein-bound acrolein and codetermination of keto- and carboxyifosfamide. J Cancer Res Clin Oncol. 2002 Jul;128(7):385-92. Epub 2002 Jun 11. [PubMed:12136253 ]
  6. 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 ]
Enzyme Details
3. Cytochrome P450 2C9
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 oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. This enzyme contributes to the wide pharmacokinetics variability of the metabolism of drugs such as S-warfarin, diclofenac, phenytoin, tolbutamide and losartan.
Gene Name:
CYP2C9
Uniprot ID:
P11712
Molecular weight:
55627.365
References
  1. Lokiec F: Ifosfamide: pharmacokinetic properties for central nervous system metastasis prevention. Ann Oncol. 2006 May;17 Suppl 4:iv33-6. [PubMed:16702183 ]
  2. Zhou SF, Zhou ZW, Yang LP, Cai JP: Substrates, inducers, inhibitors and structure-activity relationships of human Cytochrome P450 2C9 and implications in drug development. Curr Med Chem. 2009;16(27):3480-675. Epub 2009 Sep 1. [PubMed:19515014 ]
  3. 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 ]
Enzyme Details
4. Cytochrome P450 2C19
General function:
Involved in monooxygenase activity
Specific function:
Responsible for the metabolism of a number of therapeutic agents such as the anticonvulsant drug S-mephenytoin, omeprazole, proguanil, certain barbiturates, diazepam, propranolol, citalopram and imipramine.
Gene Name:
CYP2C19
Uniprot ID:
P33261
Molecular weight:
55944.565
References
  1. Roy P, Yu LJ, Crespi CL, Waxman DJ: Development of a substrate-activity based approach to identify the major human liver P-450 catalysts of cyclophosphamide and ifosfamide activation based on cDNA-expressed activities and liver microsomal P-450 profiles. Drug Metab Dispos. 1999 Jun;27(6):655-66. [PubMed:10348794 ]
  2. 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 ]
Enzyme Details
5. Cytochrome P450 2C18
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 oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics.
Gene Name:
CYP2C18
Uniprot ID:
P33260
Molecular weight:
55710.075
References
  1. Roy P, Yu LJ, Crespi CL, Waxman DJ: Development of a substrate-activity based approach to identify the major human liver P-450 catalysts of cyclophosphamide and ifosfamide activation based on cDNA-expressed activities and liver microsomal P-450 profiles. Drug Metab Dispos. 1999 Jun;27(6):655-66. [PubMed:10348794 ]
  2. 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 ]
Enzyme Details
6. Cytochrome P450 2B6
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 oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Acts as a 1,4-cineole 2-exo-monooxygenase.
Gene Name:
CYP2B6
Uniprot ID:
P20813
Molecular weight:
56277.81
References
  1. Lokiec F: Ifosfamide: pharmacokinetic properties for central nervous system metastasis prevention. Ann Oncol. 2006 May;17 Suppl 4:iv33-6. [PubMed:16702183 ]
  2. Chen CS, Jounaidi Y, Waxman DJ: Enantioselective metabolism and cytotoxicity of R-ifosfamide and S-ifosfamide by tumor cell-expressed cytochromes P450. Drug Metab Dispos. 2005 Sep;33(9):1261-7. Epub 2005 May 26. [PubMed:15919850 ]
  3. Zhou SF, Zhou ZW, Yang LP, Cai JP: Substrates, inducers, inhibitors and structure-activity relationships of human Cytochrome P450 2C9 and implications in drug development. Curr Med Chem. 2009;16(27):3480-675. Epub 2009 Sep 1. [PubMed:19515014 ]
  4. Roy P, Yu LJ, Crespi CL, Waxman DJ: Development of a substrate-activity based approach to identify the major human liver P-450 catalysts of cyclophosphamide and ifosfamide activation based on cDNA-expressed activities and liver microsomal P-450 profiles. Drug Metab Dispos. 1999 Jun;27(6):655-66. [PubMed:10348794 ]
Enzyme Details
7. Cytochrome P450 3A5
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 oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics.
Gene Name:
CYP3A5
Uniprot ID:
P20815
Molecular weight:
57108.065
References
  1. Lokiec F: Ifosfamide: pharmacokinetic properties for central nervous system metastasis prevention. Ann Oncol. 2006 May;17 Suppl 4:iv33-6. [PubMed:16702183 ]
  2. Zhou SF, Zhou ZW, Yang LP, Cai JP: Substrates, inducers, inhibitors and structure-activity relationships of human Cytochrome P450 2C9 and implications in drug development. Curr Med Chem. 2009;16(27):3480-675. Epub 2009 Sep 1. [PubMed:19515014 ]
  3. Roy P, Yu LJ, Crespi CL, Waxman DJ: Development of a substrate-activity based approach to identify the major human liver P-450 catalysts of cyclophosphamide and ifosfamide activation based on cDNA-expressed activities and liver microsomal P-450 profiles. Drug Metab Dispos. 1999 Jun;27(6):655-66. [PubMed:10348794 ]
Enzyme Details
8. Cytochrome P450 3A7
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 oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics.
Gene Name:
CYP3A7
Uniprot ID:
P24462
Molecular weight:
57525.03
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 ]
Enzyme Details
9. Cytochrome P450 2C8
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 oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. In the epoxidation of arachidonic acid it generates only 14,15- and 11,12-cis-epoxyeicosatrienoic acids. It is the principal enzyme responsible for the metabolism the anti-cancer drug paclitaxel (taxol).
Gene Name:
CYP2C8
Uniprot ID:
P10632
Molecular weight:
55824.275
References
  1. Lokiec F: Ifosfamide: pharmacokinetic properties for central nervous system metastasis prevention. Ann Oncol. 2006 May;17 Suppl 4:iv33-6. [PubMed:16702183 ]
  2. 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 ]
Enzyme Details
10. Cytochrome P450 2A6
General function:
Involved in monooxygenase activity
Specific function:
Exhibits a high coumarin 7-hydroxylase activity. Can act in the hydroxylation of the anti-cancer drugs cyclophosphamide and ifosphamide. Competent in the metabolic activation of aflatoxin B1. Constitutes the major nicotine C-oxidase. Acts as a 1,4-cineole 2-exo-monooxygenase. Possesses low phenacetin O-deethylation activity.
Gene Name:
CYP2A6
Uniprot ID:
P11509
Molecular weight:
56517.005
References
  1. Lokiec F: Ifosfamide: pharmacokinetic properties for central nervous system metastasis prevention. Ann Oncol. 2006 May;17 Suppl 4:iv33-6. [PubMed:16702183 ]
  2. Roy P, Yu LJ, Crespi CL, Waxman DJ: Development of a substrate-activity based approach to identify the major human liver P-450 catalysts of cyclophosphamide and ifosfamide activation based on cDNA-expressed activities and liver microsomal P-450 profiles. Drug Metab Dispos. 1999 Jun;27(6):655-66. [PubMed:10348794 ]
  3. 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 ]