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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:49 UTC
Update Date2022-03-07 02:51:39 UTC
HMDB IDHMDB0014524
Secondary Accession Numbers
  • HMDB14524
Metabolite Identification
Common NameDexrazoxane
DescriptionDexrazoxane, 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
Data?1582753189
Synonyms
ValueSource
(+)-(S)-4,4'-Propylenedi-2,6-piperazinedioneChEBI
(+)-1,2-Bis(3,5-dioxo-1-piperazinyl)propaneChEBI
DexrazoxanoChEBI
DexrazoxanumChEBI
DextrorazoxaneChEBI
DesrazoxaneHMDB
Icrf-187HMDB
ADR 529HMDB
CardioxanHMDB
CardioxaneHMDB
Dexrazoxane hydrochlorideHMDB
ICRF187HMDB
Razoxane, (S)-isomerHMDB
ZinecardHMDB
ADR-529HMDB
Razoxane, (S)-isomer, hydrochlorideHMDB
Hydrochloride, dexrazoxaneHMDB
ICRF 187HMDB
DexrazoxaneChEBI
Chemical FormulaC11H16N4O4
Average Molecular Weight268.2691
Monoisotopic Molecular Weight268.11715502
IUPAC Name4-[(2S)-2-(3,5-dioxopiperazin-1-yl)propyl]piperazine-2,6-dione
Traditional Namedexrazoxane
CAS Registry Number24584-09-6
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 KeyBMKDZUISNHGIBY-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.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentAlpha 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 FrameworkAliphatic heteromonocyclic compounds
External Descriptors
Ontology
Not AvailableNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point191 - 197 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility10.4 g/LNot Available
LogP-2.6Not Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility10.4 g/LALOGPS
logP-1ALOGPS
logP-2.7ChemAxon
logS-1.4ALOGPS
pKa (Strongest Acidic)11.2ChemAxon
pKa (Strongest Basic)3.6ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area98.82 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity64.25 m³·mol⁻¹ChemAxon
Polarizability26.12 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+162.92231661259
DarkChem[M-H]-159.91431661259
DeepCCS[M+H]+157.89230932474
DeepCCS[M-H]-155.53230932474
DeepCCS[M-2H]-188.82430932474
DeepCCS[M+Na]+164.03230932474
AllCCS[M+H]+159.032859911
AllCCS[M+H-H2O]+155.532859911
AllCCS[M+NH4]+162.432859911
AllCCS[M+Na]+163.332859911
AllCCS[M-H]-160.932859911
AllCCS[M+Na-2H]-160.832859911
AllCCS[M+HCOO]-160.732859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
DexrazoxaneC[C@@H](CN1CC(=O)NC(=O)C1)N1CC(=O)NC(=O)C13375.8Standard polar33892256
DexrazoxaneC[C@@H](CN1CC(=O)NC(=O)C1)N1CC(=O)NC(=O)C12418.1Standard non polar33892256
DexrazoxaneC[C@@H](CN1CC(=O)NC(=O)C1)N1CC(=O)NC(=O)C12552.4Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Dexrazoxane,1TMS,isomer #1C[C@@H](CN1CC(=O)N([Si](C)(C)C)C(=O)C1)N1CC(=O)NC(=O)C12360.4Semi standard non polar33892256
Dexrazoxane,1TMS,isomer #1C[C@@H](CN1CC(=O)N([Si](C)(C)C)C(=O)C1)N1CC(=O)NC(=O)C12713.8Standard non polar33892256
Dexrazoxane,1TMS,isomer #1C[C@@H](CN1CC(=O)N([Si](C)(C)C)C(=O)C1)N1CC(=O)NC(=O)C14498.1Standard polar33892256
Dexrazoxane,1TMS,isomer #2C[C@@H](CN1CC(=O)NC(=O)C1)N1CC(=O)N([Si](C)(C)C)C(=O)C12345.8Semi standard non polar33892256
Dexrazoxane,1TMS,isomer #2C[C@@H](CN1CC(=O)NC(=O)C1)N1CC(=O)N([Si](C)(C)C)C(=O)C12706.6Standard non polar33892256
Dexrazoxane,1TMS,isomer #2C[C@@H](CN1CC(=O)NC(=O)C1)N1CC(=O)N([Si](C)(C)C)C(=O)C14472.2Standard polar33892256
Dexrazoxane,2TMS,isomer #1C[C@@H](CN1CC(=O)N([Si](C)(C)C)C(=O)C1)N1CC(=O)N([Si](C)(C)C)C(=O)C12263.9Semi standard non polar33892256
Dexrazoxane,2TMS,isomer #1C[C@@H](CN1CC(=O)N([Si](C)(C)C)C(=O)C1)N1CC(=O)N([Si](C)(C)C)C(=O)C12705.2Standard non polar33892256
Dexrazoxane,2TMS,isomer #1C[C@@H](CN1CC(=O)N([Si](C)(C)C)C(=O)C1)N1CC(=O)N([Si](C)(C)C)C(=O)C13720.5Standard polar33892256
Dexrazoxane,1TBDMS,isomer #1C[C@@H](CN1CC(=O)N([Si](C)(C)C(C)(C)C)C(=O)C1)N1CC(=O)NC(=O)C12620.1Semi standard non polar33892256
Dexrazoxane,1TBDMS,isomer #1C[C@@H](CN1CC(=O)N([Si](C)(C)C(C)(C)C)C(=O)C1)N1CC(=O)NC(=O)C12940.1Standard non polar33892256
Dexrazoxane,1TBDMS,isomer #1C[C@@H](CN1CC(=O)N([Si](C)(C)C(C)(C)C)C(=O)C1)N1CC(=O)NC(=O)C14455.0Standard polar33892256
Dexrazoxane,1TBDMS,isomer #2C[C@@H](CN1CC(=O)NC(=O)C1)N1CC(=O)N([Si](C)(C)C(C)(C)C)C(=O)C12604.0Semi standard non polar33892256
Dexrazoxane,1TBDMS,isomer #2C[C@@H](CN1CC(=O)NC(=O)C1)N1CC(=O)N([Si](C)(C)C(C)(C)C)C(=O)C12937.5Standard non polar33892256
Dexrazoxane,1TBDMS,isomer #2C[C@@H](CN1CC(=O)NC(=O)C1)N1CC(=O)N([Si](C)(C)C(C)(C)C)C(=O)C14428.0Standard polar33892256
Dexrazoxane,2TBDMS,isomer #1C[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)C12743.6Semi standard non polar33892256
Dexrazoxane,2TBDMS,isomer #1C[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)C13116.5Standard non polar33892256
Dexrazoxane,2TBDMS,isomer #1C[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)C13610.6Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Dexrazoxane GC-MS (Non-derivatized) - 70eV, Positivesplash10-0m2c-4910000000-46d13032d5f2c6472d9b2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Dexrazoxane GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Dexrazoxane GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dexrazoxane 10V, Positive-QTOFsplash10-014i-0490000000-80b0b21a495d2cc911a42016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dexrazoxane 20V, Positive-QTOFsplash10-0a4i-1910000000-5a4bec9ae0f631c4c3282016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dexrazoxane 40V, Positive-QTOFsplash10-052b-8900000000-da472776fdfa9ff649dd2016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dexrazoxane 10V, Negative-QTOFsplash10-014i-0090000000-3ed9d12564a96e4f79a22016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dexrazoxane 20V, Negative-QTOFsplash10-0006-9010000000-913da0d82e09de14ca702016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dexrazoxane 40V, Negative-QTOFsplash10-0006-9100000000-1b65fef6f408f48c6b592016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dexrazoxane 10V, Positive-QTOFsplash10-0a4i-0910000000-8bbf646c07221a874c7c2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dexrazoxane 20V, Positive-QTOFsplash10-0aor-3790000000-825583366aa2049c64872021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dexrazoxane 40V, Positive-QTOFsplash10-0abc-9610000000-e2da7526d67ac758a8362021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dexrazoxane 10V, Negative-QTOFsplash10-014i-0090000000-bd2978e4c0725b5d29bd2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dexrazoxane 20V, Negative-QTOFsplash10-05p6-5890000000-a1cb5b2cd96d828fbdaa2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dexrazoxane 40V, Negative-QTOFsplash10-0006-9400000000-50d8c9f710f08bb206772021-09-22Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00380 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00380 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 IDDB00380
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID64479
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkDexrazoxane
METLIN IDNot Available
PubChem Compound71384
PDB IDNot Available
ChEBI ID50223
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. 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 ]
  2. 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 ]
  3. Weiss G, Loyevsky M, Gordeuk VR: Dexrazoxane (ICRF-187). Gen Pharmacol. 1999 Jan;32(1):155-8. [PubMed:9888268 ]
  4. Langer SW: Dexrazoxane for anthracycline extravasation. Expert Rev Anticancer Ther. 2007 Aug;7(8):1081-8. [PubMed:18028016 ]
  5. 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

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
  1. 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 ]
  2. 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 ]
  3. 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 ]
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
  1. 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 ]
  2. 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 ]
  3. 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 ]
  4. 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 ]
  5. 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 ]
  6. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]
  7. 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 ]
  8. 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 ]
  9. 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 ]