Record Information |
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Version | 5.0 |
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Status | Expected but not Quantified |
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Creation Date | 2012-09-06 15:16:49 UTC |
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Update Date | 2022-03-07 02:51:39 UTC |
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HMDB ID | HMDB0014524 |
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Secondary Accession Numbers | |
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Metabolite Identification |
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Common Name | Dexrazoxane |
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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". | Read more...
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Structure | C[C@@H](CN1CC(=O)NC(=O)C1)N1CC(=O)NC(=O)C1 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 |
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Synonyms | Value | Source |
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(+)-(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 |
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Chemical Formula | C11H16N4O4 |
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Average Molecular Weight | 268.2691 |
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Monoisotopic Molecular Weight | 268.11715502 |
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IUPAC Name | 4-[(2S)-2-(3,5-dioxopiperazin-1-yl)propyl]piperazine-2,6-dione |
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Traditional Name | dexrazoxane |
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CAS Registry Number | 24584-09-6 |
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SMILES | C[C@@H](CN1CC(=O)NC(=O)C1)N1CC(=O)NC(=O)C1 |
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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 |
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InChI Key | BMKDZUISNHGIBY-ZETCQYMHSA-N |
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Chemical Taxonomy |
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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. |
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Kingdom | Organic compounds |
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Super Class | Organic acids and derivatives |
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Class | Carboxylic acids and derivatives |
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Sub Class | Amino acids, peptides, and analogues |
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Direct Parent | Alpha amino acids and derivatives |
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Alternative Parents | |
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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
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Molecular Framework | Aliphatic heteromonocyclic compounds |
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External Descriptors | |
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Ontology |
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Physiological effect | Not Available |
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Disposition | |
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Process | Not Available |
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Role | |
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Physical Properties |
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State | Solid |
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Experimental Molecular Properties | Property | Value | Reference |
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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 |
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Experimental Chromatographic Properties | Not Available |
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Predicted Molecular Properties | | Show more...
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Predicted Chromatographic Properties | Predicted Collision Cross SectionsPredicted Kovats Retention IndicesUnderivatizedDerivatizedDerivative Name / Structure | SMILES | Kovats RI Value | Column Type | Reference |
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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 |
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Spectra |
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| GC-MS SpectraSpectrum Type | Description | Splash Key | Deposition Date | Source | View |
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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 SpectraSpectrum Type | Description | Splash Key | Deposition Date | Source | View |
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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 SpectraSpectrum Type | Description | Deposition Date | Source | View |
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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 |
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Biological Properties |
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Cellular Locations | |
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Biospecimen Locations | |
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Tissue Locations | Not Available |
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Pathways | |
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Normal Concentrations |
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Blood | Expected but not Quantified | Not Quantified | Not Available | Not Available | Taking drug identified by DrugBank entry DB00380 | | details | Urine | Expected but not Quantified | Not Quantified | Not Available | Not Available | Taking drug identified by DrugBank entry DB00380 | | details |
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Abnormal Concentrations |
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| Not Available |
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Predicted Concentrations |
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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 |
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Associated Disorders and Diseases |
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Disease References | None |
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Associated OMIM IDs | None |
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External Links |
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DrugBank ID | DB00380 |
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Phenol Explorer Compound ID | Not Available |
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FooDB ID | Not Available |
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KNApSAcK ID | Not Available |
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Chemspider ID | 64479 |
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KEGG Compound ID | Not Available |
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BioCyc ID | Not Available |
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BiGG ID | Not Available |
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Wikipedia Link | Dexrazoxane |
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METLIN ID | Not Available |
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PubChem Compound | 71384 |
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PDB ID | Not Available |
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ChEBI ID | 50223 |
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Food Biomarker Ontology | Not Available |
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VMH ID | Not Available |
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MarkerDB ID | Not Available |
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Good Scents ID | Not Available |
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References |
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Synthesis Reference | Not Available |
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Material Safety Data Sheet (MSDS) | Not Available |
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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 ]
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