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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-06 15:16:49 UTC

Update Date

2022-03-07 02:51:39 UTC

HMDB ID

HMDB0014524

Secondary Accession Numbers

HMDB14524

Metabolite Identification

Common Name

Dexrazoxane

Description

Dexrazoxane, also known as cardioxan or icrf-187, belongs to the class of organic compounds known as alpha amino acids and derivatives. These are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon), or a derivative thereof. Dexrazoxane is a drug which is used for reducing the incidence and severity of cardiomyopathy associated with doxorubicin administration in women with metastatic breast cancer who have received a cumulative doxorubicin hydrochloride dose of 300 mg/m^2 and would benefit from continued doxorubicin therapy. also approved for the treatment of extravasation from intravenous anthracyclines. Dexrazoxane hydrochloride (Zinecard, Cardioxane) is a cardioprotective agent. Extravasation is an adverse event in which chemotherapies containing anthracylines leak out of the blood vessel and necrotize the surrounding tissue. Dexrazoxane is a strong basic compound (based on its pKa). Dexrazoxane is a potentially toxic compound. The exact chelation mechanism is unknown, but it has been postulated that dexrazoxane can be converted into ring-opened form intracellularly and interfere with iron-mediated free radical generation that is in part thought to be responsible for anthryacycline induced cardiomyopathy. It was discovered by Eugene Herman in 1972. Currently, the only FDA and EMA approved cardioprotective treatment for anthracycline cardioprotection is dexrazoxane, which provides effective primary cardioprotection against anthracycline-induced cardiotoxicity without reducing anthracycline activity and without enhancing secondary malignancies. That showed a possibly higher rate of secondary malignancies and acute myelogenous leukemia in pediatric patients treated for different cancers with both dexrazoxane and other chemotherapeutic agents that are associated with secondary malignancies. The IV administration of dexrazoxane is in acidic condition with HCl adjusting the pH.Dexrazoxane has been used to protect the heart against the cardiotoxic side effects of chemotherapeutic drugs such as anthracyclines, such as daunorubicin or doxorubicin or other chemotherapeutic agents. Dexrazoxane was designated by the US FDA as an orphan drug for "prevention of cardiomyopathy for children and adults 0 through 16 years of age treated with anthracyclines".

Structure

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

HMDB0014524
     RDKit          3D
Dexrazoxane
 35 36  0  0  0  0  0  0  0  0999 V2000
    0.6598   -0.9351    1.2952 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3793   -0.4376   -0.1328 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.5904    0.6828   -0.0940 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8317    0.2396    0.4999 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7048    1.3434    0.8039 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6142    1.7061   -0.2865 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7303    2.8640   -0.7465 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3927    0.6048   -0.8094 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8747   -0.7074   -0.5057 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6655   -1.6652   -0.5374 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4576   -0.8543   -0.1785 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6169   -0.0952   -0.8212 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.3173    1.0080   -0.2390 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7518    0.9829   -0.6482 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3331    1.8684   -1.2865 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4644   -0.2031   -0.2305 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.5851   -1.3360   -0.0389 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9040   -2.2159    0.7958 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3701   -1.3319   -0.8741 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5583   -2.0607    1.3483 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6453   -0.6266    1.6443 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0952   -0.5421    2.0093 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0326   -1.2912   -0.6800 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7386    1.1073   -1.1206 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2426    1.5566    0.5070 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0193    2.2088    1.0399 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2322    1.1221    1.7602 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2334    0.7625   -1.3493 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3542   -1.7543    0.4667 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8971   -1.0897   -1.1192 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9155    1.9503   -0.7356 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2850    1.0880    0.8475 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4780   -0.2352   -0.0867 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6803   -1.4919   -1.9349 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7630   -2.2221   -0.5876 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  6  8  1  0
  8  9  1  0
  9 10  2  0
  9 11  1  0
  2 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  2  0
 14 16  1  0
 16 17  1  0
 17 18  2  0
 17 19  1  0
 11  4  1  0
 19 12  1  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
  2 23  1  6
  3 24  1  0
  3 25  1  0
  5 26  1  0
  5 27  1  0
  8 28  1  0
 11 29  1  0
 11 30  1  0
 13 31  1  0
 13 32  1  0
 16 33  1  0
 19 34  1  0
 19 35  1  0
M  END

380
  Mrv0541 02231214382D          

 19 20  0  0  1  0            999 V2000
    5.2224    2.6813    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645    2.6813    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080   -2.6813    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500   -2.6813    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935    1.0313    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791   -1.0313    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935    2.6813    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791   -2.6813    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935    0.2063    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.0791   -0.2063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080    1.4438    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791    1.4438    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
    3.7935   -1.4438    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -1.4438    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080    2.2688    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791    2.2688    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935   -2.2688    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -2.2688    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1 16  2  0  0  0  0
  2 17  2  0  0  0  0
  3 18  2  0  0  0  0
  4 19  2  0  0  0  0
  5  9  1  0  0  0  0
  5 11  1  0  0  0  0
  5 12  1  0  0  0  0
  6 10  1  0  0  0  0
  6 14  1  0  0  0  0
  6 15  1  0  0  0  0
  7 16  1  0  0  0  0
  7 17  1  0  0  0  0
  8 18  1  0  0  0  0
  8 19  1  0  0  0  0
  9 10  1  0  0  0  0
  9 13  1  1  0  0  0
 11 16  1  0  0  0  0
 12 17  1  0  0  0  0
 14 18  1  0  0  0  0
 15 19  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0014524

> <DATABASE_NAME>
hmdb

> <SMILES>
C[C@@H](CN1CC(=O)NC(=O)C1)N1CC(=O)NC(=O)C1

> <INCHI_IDENTIFIER>
InChI=1S/C11H16N4O4/c1-7(15-5-10(18)13-11(19)6-15)2-14-3-8(16)12-9(17)4-14/h7H,2-6H2,1H3,(H,12,16,17)(H,13,18,19)/t7-/m0/s1

> <INCHI_KEY>
BMKDZUISNHGIBY-ZETCQYMHSA-N

> <FORMULA>
C11H16N4O4

> <MOLECULAR_WEIGHT>
268.2691

> <EXACT_MASS>
268.11715502

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_AVERAGE_POLARIZABILITY>
26.12181075550423

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
4-[(2S)-2-(3,5-dioxopiperazin-1-yl)propyl]piperazine-2,6-dione

> <ALOGPS_LOGP>
-1.05

> <JCHEM_LOGP>
-2.6526549413333336

> <ALOGPS_LOGS>
-1.41

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
11.800852844190322

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.198792840713974

> <JCHEM_PKA_STRONGEST_BASIC>
3.595816919458805

> <JCHEM_POLAR_SURFACE_AREA>
98.82

> <JCHEM_REFRACTIVITY>
64.2532

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.04e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
dexrazoxane

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0014524
     RDKit          3D
Dexrazoxane
 35 36  0  0  0  0  0  0  0  0999 V2000
    0.6598   -0.9351    1.2952 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3793   -0.4376   -0.1328 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.5904    0.6828   -0.0940 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8317    0.2396    0.4999 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7048    1.3434    0.8039 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6142    1.7061   -0.2865 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7303    2.8640   -0.7465 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3927    0.6048   -0.8094 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8747   -0.7074   -0.5057 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6655   -1.6652   -0.5374 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4576   -0.8543   -0.1785 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6169   -0.0952   -0.8212 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.3173    1.0080   -0.2390 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7518    0.9829   -0.6482 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3331    1.8684   -1.2865 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4644   -0.2031   -0.2305 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.5851   -1.3360   -0.0389 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9040   -2.2159    0.7958 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3701   -1.3319   -0.8741 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5583   -2.0607    1.3483 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6453   -0.6266    1.6443 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0952   -0.5421    2.0093 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0326   -1.2912   -0.6800 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7386    1.1073   -1.1206 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2426    1.5566    0.5070 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0193    2.2088    1.0399 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2322    1.1221    1.7602 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2334    0.7625   -1.3493 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3542   -1.7543    0.4667 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8971   -1.0897   -1.1192 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9155    1.9503   -0.7356 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2850    1.0880    0.8475 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4780   -0.2352   -0.0867 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6803   -1.4919   -1.9349 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7630   -2.2221   -0.5876 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  6  8  1  0
  8  9  1  0
  9 10  2  0
  9 11  1  0
  2 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  2  0
 14 16  1  0
 16 17  1  0
 17 18  2  0
 17 19  1  0
 11  4  1  0
 19 12  1  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
  2 23  1  6
  3 24  1  0
  3 25  1  0
  5 26  1  0
  5 27  1  0
  8 28  1  0
 11 29  1  0
 11 30  1  0
 13 31  1  0
 13 32  1  0
 16 33  1  0
 19 34  1  0
 19 35  1  0
M  END

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 380                                               
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  O   UNK     0       9.748   5.005   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0       4.414   5.005   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0       8.415  -5.005   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0       3.080  -5.005   0.000  0.00  0.00           O+0
HETATM    5  N   UNK     0       7.081   1.925   0.000  0.00  0.00           N+0
HETATM    6  N   UNK     0       5.748  -1.925   0.000  0.00  0.00           N+0
HETATM    7  N   UNK     0       7.081   5.005   0.000  0.00  0.00           N+0
HETATM    8  N   UNK     0       5.748  -5.005   0.000  0.00  0.00           N+0
HETATM    9  C   UNK     0       7.081   0.385   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.748  -0.385   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       8.415   2.695   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       5.748   2.695   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       8.415  -0.385   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       7.081  -2.695   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.414  -2.695   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       8.415   4.235   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       5.748   4.235   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       7.081  -4.235   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       4.414  -4.235   0.000  0.00  0.00           C+0
CONECT    1   16                                                            
CONECT    2   17                                                            
CONECT    3   18                                                            
CONECT    4   19                                                            
CONECT    5    9   11   12                                                  
CONECT    6   10   14   15                                                  
CONECT    7   16   17                                                       
CONECT    8   18   19                                                       
CONECT    9    5   10   13                                                  
CONECT   10    6    9                                                       
CONECT   11    5   16                                                       
CONECT   12    5   17                                                       
CONECT   13    9                                                            
CONECT   14    6   18                                                       
CONECT   15    6   19                                                       
CONECT   16    1    7   11                                                  
CONECT   17    2    7   12                                                  
CONECT   18    3    8   14                                                  
CONECT   19    4    8   15                                                  
MASTER        0    0    0    0    0    0    0    0   19    0   40    0
END

COMPND    HMDB0014524
HETATM    1  C1  UNL     1       0.660  -0.935   1.295  1.00  0.00           C  
HETATM    2  C2  UNL     1       0.379  -0.438  -0.133  1.00  0.00           C  
HETATM    3  C3  UNL     1      -0.590   0.683  -0.094  1.00  0.00           C  
HETATM    4  N1  UNL     1      -1.832   0.240   0.500  1.00  0.00           N  
HETATM    5  C4  UNL     1      -2.705   1.343   0.804  1.00  0.00           C  
HETATM    6  C5  UNL     1      -3.614   1.706  -0.286  1.00  0.00           C  
HETATM    7  O1  UNL     1      -3.730   2.864  -0.746  1.00  0.00           O  
HETATM    8  N2  UNL     1      -4.393   0.605  -0.809  1.00  0.00           N  
HETATM    9  C6  UNL     1      -3.875  -0.707  -0.506  1.00  0.00           C  
HETATM   10  O2  UNL     1      -4.665  -1.665  -0.537  1.00  0.00           O  
HETATM   11  C7  UNL     1      -2.458  -0.854  -0.179  1.00  0.00           C  
HETATM   12  N3  UNL     1       1.617  -0.095  -0.821  1.00  0.00           N  
HETATM   13  C8  UNL     1       2.317   1.008  -0.239  1.00  0.00           C  
HETATM   14  C9  UNL     1       3.752   0.983  -0.648  1.00  0.00           C  
HETATM   15  O3  UNL     1       4.333   1.868  -1.287  1.00  0.00           O  
HETATM   16  N4  UNL     1       4.464  -0.203  -0.230  1.00  0.00           N  
HETATM   17  C10 UNL     1       3.585  -1.336  -0.039  1.00  0.00           C  
HETATM   18  O4  UNL     1       3.904  -2.216   0.796  1.00  0.00           O  
HETATM   19  C11 UNL     1       2.370  -1.332  -0.874  1.00  0.00           C  
HETATM   20  H1  UNL     1       0.558  -2.061   1.348  1.00  0.00           H  
HETATM   21  H2  UNL     1       1.645  -0.627   1.644  1.00  0.00           H  
HETATM   22  H3  UNL     1      -0.095  -0.542   2.009  1.00  0.00           H  
HETATM   23  H4  UNL     1      -0.033  -1.291  -0.680  1.00  0.00           H  
HETATM   24  H5  UNL     1      -0.739   1.107  -1.121  1.00  0.00           H  
HETATM   25  H6  UNL     1      -0.243   1.557   0.507  1.00  0.00           H  
HETATM   26  H7  UNL     1      -2.019   2.209   1.040  1.00  0.00           H  
HETATM   27  H8  UNL     1      -3.232   1.122   1.760  1.00  0.00           H  
HETATM   28  H9  UNL     1      -5.233   0.762  -1.349  1.00  0.00           H  
HETATM   29  H10 UNL     1      -2.354  -1.754   0.467  1.00  0.00           H  
HETATM   30  H11 UNL     1      -1.897  -1.090  -1.119  1.00  0.00           H  
HETATM   31  H12 UNL     1       1.916   1.950  -0.736  1.00  0.00           H  
HETATM   32  H13 UNL     1       2.285   1.088   0.847  1.00  0.00           H  
HETATM   33  H14 UNL     1       5.478  -0.235  -0.087  1.00  0.00           H  
HETATM   34  H15 UNL     1       2.680  -1.492  -1.935  1.00  0.00           H  
HETATM   35  H16 UNL     1       1.763  -2.222  -0.588  1.00  0.00           H  
CONECT    1    2   20   21   22
CONECT    2    3   12   23
CONECT    3    4   24   25
CONECT    4    5   11
CONECT    5    6   26   27
CONECT    6    7    7    8
CONECT    8    9   28
CONECT    9   10   10   11
CONECT   11   29   30
CONECT   12   13   19
CONECT   13   14   31   32
CONECT   14   15   15   16
CONECT   16   17   33
CONECT   17   18   18   19
CONECT   19   34   35
END

HMDB0014524
     RDKit          3D
Dexrazoxane
 35 36  0  0  0  0  0  0  0  0999 V2000
    0.6598   -0.9351    1.2952 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3793   -0.4376   -0.1328 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.5904    0.6828   -0.0940 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8317    0.2396    0.4999 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7048    1.3434    0.8039 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6142    1.7061   -0.2865 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7303    2.8640   -0.7465 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3927    0.6048   -0.8094 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8747   -0.7074   -0.5057 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6655   -1.6652   -0.5374 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4576   -0.8543   -0.1785 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6169   -0.0952   -0.8212 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.3173    1.0080   -0.2390 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7518    0.9829   -0.6482 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3331    1.8684   -1.2865 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4644   -0.2031   -0.2305 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.5851   -1.3360   -0.0389 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9040   -2.2159    0.7958 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3701   -1.3319   -0.8741 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5583   -2.0607    1.3483 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6453   -0.6266    1.6443 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0952   -0.5421    2.0093 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0326   -1.2912   -0.6800 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7386    1.1073   -1.1206 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2426    1.5566    0.5070 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0193    2.2088    1.0399 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2322    1.1221    1.7602 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2334    0.7625   -1.3493 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3542   -1.7543    0.4667 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8971   -1.0897   -1.1192 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9155    1.9503   -0.7356 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2850    1.0880    0.8475 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4780   -0.2352   -0.0867 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6803   -1.4919   -1.9349 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7630   -2.2221   -0.5876 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  6  8  1  0
  8  9  1  0
  9 10  2  0
  9 11  1  0
  2 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  2  0
 14 16  1  0
 16 17  1  0
 17 18  2  0
 17 19  1  0
 11  4  1  0
 19 12  1  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
  2 23  1  6
  3 24  1  0
  3 25  1  0
  5 26  1  0
  5 27  1  0
  8 28  1  0
 11 29  1  0
 11 30  1  0
 13 31  1  0
 13 32  1  0
 16 33  1  0
 19 34  1  0
 19 35  1  0
M  END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
(+)-(S)-4,4'-Propylenedi-2,6-piperazinedione	ChEBI
(+)-1,2-Bis(3,5-dioxo-1-piperazinyl)propane	ChEBI
Dexrazoxano	ChEBI
Dexrazoxanum	ChEBI
Dextrorazoxane	ChEBI
Desrazoxane	HMDB
Icrf-187	HMDB
ADR 529	HMDB
Cardioxan	HMDB
Cardioxane	HMDB
Dexrazoxane hydrochloride	HMDB
ICRF187	HMDB
Razoxane, (S)-isomer	HMDB
Zinecard	HMDB
ADR-529	HMDB
Razoxane, (S)-isomer, hydrochloride	HMDB
Hydrochloride, dexrazoxane	HMDB
ICRF 187	HMDB
Dexrazoxane	ChEBI

Chemical Formula

C₁₁H₁₆N₄O₄

Average Molecular Weight

268.2691

Monoisotopic Molecular Weight

268.11715502

IUPAC Name

4-[(2S)-2-(3,5-dioxopiperazin-1-yl)propyl]piperazine-2,6-dione

Traditional Name

dexrazoxane

CAS Registry Number

24584-09-6

SMILES

C[C@@H](CN1CC(=O)NC(=O)C1)N1CC(=O)NC(=O)C1

InChI Identifier

InChI=1S/C11H16N4O4/c1-7(15-5-10(18)13-11(19)6-15)2-14-3-8(16)12-9(17)4-14/h7H,2-6H2,1H3,(H,12,16,17)(H,13,18,19)/t7-/m0/s1

InChI Key

BMKDZUISNHGIBY-ZETCQYMHSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as alpha amino acids and derivatives. These are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon), or a derivative thereof.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

Alpha amino acids and derivatives

Alternative Parents

Substituents

Alpha-amino acid or derivatives
Dioxopiperazine
N-alkylpiperazine
1,4-diazinane
Piperazine
Carboxylic acid imide
Dicarboximide
Carboxylic acid imide, n-unsubstituted
Tertiary aliphatic amine
Tertiary amine
Organoheterocyclic compound
Azacycle
Organic nitrogen compound
Organooxygen compound
Organonitrogen compound
Amine
Organic oxygen compound
Hydrocarbon derivative
Organic oxide
Carbonyl group
Organopnictogen compound
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

razoxane (CHEBI:50223 )

Ontology

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	191 - 197 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	10.4 g/L	Not Available
LogP	-2.6	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	10.4 g/L	ALOGPS
logP	-1	ALOGPS
logP	-2.7	ChemAxon
logS	-1.4	ALOGPS
pKa (Strongest Acidic)	11.2	ChemAxon
pKa (Strongest Basic)	3.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	98.82 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	64.25 m³·mol⁻¹	ChemAxon
Polarizability	26.12 Å³	ChemAxon
Number of Rings	2	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]+	162.922	31661259
DarkChem	[M-H]-	159.914	31661259
DeepCCS	[M+H]+	157.892	30932474
DeepCCS	[M-H]-	155.532	30932474
DeepCCS	[M-2H]-	188.824	30932474
DeepCCS	[M+Na]+	164.032	30932474
AllCCS	[M+H]+	159.0	32859911
AllCCS	[M+H-H2O]+	155.5	32859911
AllCCS	[M+NH4]+	162.4	32859911
AllCCS	[M+Na]+	163.3	32859911
AllCCS	[M-H]-	160.9	32859911
AllCCS	[M+Na-2H]-	160.8	32859911
AllCCS	[M+HCOO]-	160.7	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Dexrazoxane	C[C@@H](CN1CC(=O)NC(=O)C1)N1CC(=O)NC(=O)C1	3375.8	Standard polar	33892256
Dexrazoxane	C[C@@H](CN1CC(=O)NC(=O)C1)N1CC(=O)NC(=O)C1	2418.1	Standard non polar	33892256
Dexrazoxane	C[C@@H](CN1CC(=O)NC(=O)C1)N1CC(=O)NC(=O)C1	2552.4	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Dexrazoxane,1TMS,isomer #1	C[C@@H](CN1CC(=O)N([Si](C)(C)C)C(=O)C1)N1CC(=O)NC(=O)C1	2360.4	Semi standard non polar	33892256
Dexrazoxane,1TMS,isomer #1	C[C@@H](CN1CC(=O)N([Si](C)(C)C)C(=O)C1)N1CC(=O)NC(=O)C1	2713.8	Standard non polar	33892256
Dexrazoxane,1TMS,isomer #1	C[C@@H](CN1CC(=O)N([Si](C)(C)C)C(=O)C1)N1CC(=O)NC(=O)C1	4498.1	Standard polar	33892256
Dexrazoxane,1TMS,isomer #2	C[C@@H](CN1CC(=O)NC(=O)C1)N1CC(=O)N([Si](C)(C)C)C(=O)C1	2345.8	Semi standard non polar	33892256
Dexrazoxane,1TMS,isomer #2	C[C@@H](CN1CC(=O)NC(=O)C1)N1CC(=O)N([Si](C)(C)C)C(=O)C1	2706.6	Standard non polar	33892256
Dexrazoxane,1TMS,isomer #2	C[C@@H](CN1CC(=O)NC(=O)C1)N1CC(=O)N([Si](C)(C)C)C(=O)C1	4472.2	Standard polar	33892256
Dexrazoxane,2TMS,isomer #1	C[C@@H](CN1CC(=O)N([Si](C)(C)C)C(=O)C1)N1CC(=O)N([Si](C)(C)C)C(=O)C1	2263.9	Semi standard non polar	33892256
Dexrazoxane,2TMS,isomer #1	C[C@@H](CN1CC(=O)N([Si](C)(C)C)C(=O)C1)N1CC(=O)N([Si](C)(C)C)C(=O)C1	2705.2	Standard non polar	33892256
Dexrazoxane,2TMS,isomer #1	C[C@@H](CN1CC(=O)N([Si](C)(C)C)C(=O)C1)N1CC(=O)N([Si](C)(C)C)C(=O)C1	3720.5	Standard polar	33892256
Dexrazoxane,1TBDMS,isomer #1	C[C@@H](CN1CC(=O)N([Si](C)(C)C(C)(C)C)C(=O)C1)N1CC(=O)NC(=O)C1	2620.1	Semi standard non polar	33892256
Dexrazoxane,1TBDMS,isomer #1	C[C@@H](CN1CC(=O)N([Si](C)(C)C(C)(C)C)C(=O)C1)N1CC(=O)NC(=O)C1	2940.1	Standard non polar	33892256
Dexrazoxane,1TBDMS,isomer #1	C[C@@H](CN1CC(=O)N([Si](C)(C)C(C)(C)C)C(=O)C1)N1CC(=O)NC(=O)C1	4455.0	Standard polar	33892256
Dexrazoxane,1TBDMS,isomer #2	C[C@@H](CN1CC(=O)NC(=O)C1)N1CC(=O)N([Si](C)(C)C(C)(C)C)C(=O)C1	2604.0	Semi standard non polar	33892256
Dexrazoxane,1TBDMS,isomer #2	C[C@@H](CN1CC(=O)NC(=O)C1)N1CC(=O)N([Si](C)(C)C(C)(C)C)C(=O)C1	2937.5	Standard non polar	33892256
Dexrazoxane,1TBDMS,isomer #2	C[C@@H](CN1CC(=O)NC(=O)C1)N1CC(=O)N([Si](C)(C)C(C)(C)C)C(=O)C1	4428.0	Standard polar	33892256
Dexrazoxane,2TBDMS,isomer #1	C[C@@H](CN1CC(=O)N([Si](C)(C)C(C)(C)C)C(=O)C1)N1CC(=O)N([Si](C)(C)C(C)(C)C)C(=O)C1	2743.6	Semi standard non polar	33892256
Dexrazoxane,2TBDMS,isomer #1	C[C@@H](CN1CC(=O)N([Si](C)(C)C(C)(C)C)C(=O)C1)N1CC(=O)N([Si](C)(C)C(C)(C)C)C(=O)C1	3116.5	Standard non polar	33892256
Dexrazoxane,2TBDMS,isomer #1	C[C@@H](CN1CC(=O)N([Si](C)(C)C(C)(C)C)C(=O)C1)N1CC(=O)N([Si](C)(C)C(C)(C)C)C(=O)C1	3610.6	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Dexrazoxane GC-MS (Non-derivatized) - 70eV, Positive	splash10-0m2c-4910000000-46d13032d5f2c6472d9b	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Dexrazoxane GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Dexrazoxane 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
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dexrazoxane 10V, Positive-QTOF	splash10-014i-0490000000-80b0b21a495d2cc911a4	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dexrazoxane 20V, Positive-QTOF	splash10-0a4i-1910000000-5a4bec9ae0f631c4c328	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dexrazoxane 40V, Positive-QTOF	splash10-052b-8900000000-da472776fdfa9ff649dd	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dexrazoxane 10V, Negative-QTOF	splash10-014i-0090000000-3ed9d12564a96e4f79a2	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dexrazoxane 20V, Negative-QTOF	splash10-0006-9010000000-913da0d82e09de14ca70	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dexrazoxane 40V, Negative-QTOF	splash10-0006-9100000000-1b65fef6f408f48c6b59	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dexrazoxane 10V, Positive-QTOF	splash10-0a4i-0910000000-8bbf646c07221a874c7c	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dexrazoxane 20V, Positive-QTOF	splash10-0aor-3790000000-825583366aa2049c6487	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dexrazoxane 40V, Positive-QTOF	splash10-0abc-9610000000-e2da7526d67ac758a836	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dexrazoxane 10V, Negative-QTOF	splash10-014i-0090000000-bd2978e4c0725b5d29bd	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dexrazoxane 20V, Negative-QTOF	splash10-05p6-5890000000-a1cb5b2cd96d828fbdaa	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dexrazoxane 40V, Negative-QTOF	splash10-0006-9400000000-50d8c9f710f08bb20677	2021-09-22	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm

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 DB00380	21059682	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB00380	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

DB00380

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

64479

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Dexrazoxane

METLIN ID

Not Available

PubChem Compound

71384

PDB ID

Not Available

ChEBI ID

50223

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

Hasinoff BB, Herman EH: Dexrazoxane: how it works in cardiac and tumor cells. Is it a prodrug or is it a drug? Cardiovasc Toxicol. 2007;7(2):140-4. [PubMed:17652819 ]
Kik K, Szmigiero L: [Dexrazoxane (ICRF-187)--a cardioprotectant and modulator of action of some anticancer drugs]. Postepy Hig Med Dosw (Online). 2006;60:584-90. [PubMed:17115008 ]
Weiss G, Loyevsky M, Gordeuk VR: Dexrazoxane (ICRF-187). Gen Pharmacol. 1999 Jan;32(1):155-8. [PubMed:9888268 ]
Langer SW: Dexrazoxane for anthracycline extravasation. Expert Rev Anticancer Ther. 2007 Aug;7(8):1081-8. [PubMed:18028016 ]
Hasinoff BB: The use of dexrazoxane for the prevention of anthracycline extravasation injury. Expert Opin Investig Drugs. 2008 Feb;17(2):217-23. doi: 10.1517/13543784.17.2.217. [PubMed:18230055 ]

Enzymes

Enzyme Details

1. DNA topoisomerase 2-beta

General function:: Involved in sequence-specific DNA binding transcription factor activity
Specific function:: Control of topological states of DNA by transient breakage and subsequent rejoining of DNA strands. Topoisomerase II makes double-strand breaks. Indirectly ivolved in vitamin D- coupled transcription regulation via its association with the WINAC complex, a chromatin-remodeling complex recruited by vitamin D receptor (VDR), which is required for the ligand-bound VDR- mediated transrepression of the CYP27B1 gene
Gene Name:: TOP2B
Uniprot ID:: Q02880
Molecular weight:: 183265.8

References

Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284 ]
Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423 ]
Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [PubMed:10592235 ]

Enzyme Details

2. DNA topoisomerase 2-alpha

General function:: Involved in sequence-specific DNA binding transcription factor activity
Specific function:: Control of topological states of DNA by transient breakage and subsequent rejoining of DNA strands. Topoisomerase II makes double-strand breaks
Gene Name:: TOP2A
Uniprot ID:: P11388
Molecular weight:: 174383.9

References

Hasinoff BB, Chee GL, Thampatty P, Allan WP, Yalowich JC: The cardioprotective and DNA topoisomerase II inhibitory agent dexrazoxane (ICRF-187) antagonizes camptothecin-mediated growth inhibition of Chinese hamster ovary cells by inhibition of DNA synthesis. Anticancer Drugs. 1999 Jan;10(1):47-54. [PubMed:10194547 ]
Hasinoff BB, Abram ME, Barnabe N, Khelifa T, Allan WP, Yalowich JC: The catalytic DNA topoisomerase II inhibitor dexrazoxane (ICRF-187) induces differentiation and apoptosis in human leukemia K562 cells. Mol Pharmacol. 2001 Mar;59(3):453-61. [PubMed:11179439 ]
Langer SW, Sehested M, Jensen PB: Dexrazoxane is a potent and specific inhibitor of anthracycline induced subcutaneous lesions in mice. Ann Oncol. 2001 Mar;12(3):405-10. [PubMed:11332155 ]
Hasinoff BB, Takeda K, Ferrans VJ, Yu ZX: The doxorubicin cardioprotective agent dexrazoxane (ICRF-187) induces endopolyploidy in rat neonatal myocytes through inhibition of DNA topoisomerase II. Anticancer Drugs. 2002 Mar;13(3):255-8. [PubMed:11984069 ]
Renodon-Corniere A, Jensen LH, Nitiss JL, Jensen PB, Sehested M: Analysis of bisdioxopiperazine dexrazoxane binding to human DNA topoisomerase II alpha: decreased binding as a mechanism of drug resistance. Biochemistry. 2003 Aug 19;42(32):9749-54. [PubMed:12911317 ]
Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]
Hasinoff BB, Herman EH: Dexrazoxane: how it works in cardiac and tumor cells. Is it a prodrug or is it a drug? Cardiovasc Toxicol. 2007;7(2):140-4. [PubMed:17652819 ]
Kik K, Szmigiero L: [Dexrazoxane (ICRF-187)--a cardioprotectant and modulator of action of some anticancer drugs]. Postepy Hig Med Dosw (Online). 2006;60:584-90. [PubMed:17115008 ]
Hasinoff BB, Abram ME, Chee GL, Huebner E, Byard EH, Barnabe N, Ferrans VJ, Yu ZX, Yalowich JC: The catalytic DNA topoisomerase II inhibitor dexrazoxane (ICRF-187) induces endopolyploidy in Chinese hamster ovary cells. J Pharmacol Exp Ther. 2000 Nov;295(2):474-83. [PubMed:11046078 ]

Showing metabocard for Dexrazoxane (HMDB0014524)

MOL for HMDB0014524 (Dexrazoxane)

3D MOL for HMDB0014524 (Dexrazoxane)

3D SDF for HMDB0014524 (Dexrazoxane)

3D-SDF for HMDB0014524 (Dexrazoxane)

PDB for HMDB0014524 (Dexrazoxane)

3D PDB for HMDB0014524 (Dexrazoxane)

SMILES for HMDB0014524 (Dexrazoxane)

INCHI for HMDB0014524 (Dexrazoxane)

Structure for HMDB0014524 (Dexrazoxane)

3D Structure for HMDB0014524 (Dexrazoxane)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

Enzymes

References

References