Details
Stereochemistry | RACEMIC |
Molecular Formula | C9H18Cl3N2O2P |
Molecular Weight | 323.584 |
Optical Activity | ( + / - ) |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
ClCCN(CCCl)P1(=O)OCCCN1CCCl
InChI
InChIKey=UMKFEPPTGMDVMI-UHFFFAOYSA-N
InChI=1S/C9H18Cl3N2O2P/c10-2-6-13-5-1-9-16-17(13,15)14(7-3-11)8-4-12/h1-9H2
Trofosfamide is an orally bioavailable antineoplastic agent. Upon administration, it is predominantly metabolized to the cyclophosphamide analog ifosfamide, which is then metabolized by liver cytochrome P450s to the active isophosphoramide mustard (IPM). IPM alkylates DNA to form DNA-DNA cross-links, which may result in inhibition of DNA, RNA and protein synthesis, and tumor cell apoptosis. Trofosfamide is marketed in Germany by Baxter under tradename Ixoten. It is indicated for the treatment of non-Hodgkin's lymphoma after failure of the standard therapy. The drug was investigated in the clinical trials against soft tissue sarcoma and melanoma.
Approval Year
PubMed
Title | Date | PubMed |
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[Cyclophosphamide and bladder carcinoma (case report) (author's transl)]. | 1978 Jan 6 |
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Studies on the urotoxicity of oxazaphosphorine cytostatics and its prevention--I. Experimental studies on the urotoxicity of alkylating compounds. | 1981 Jun |
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Trofosfamide as salvage therapy for anaplastic large cell lymphoma relapsing after high-dose chemotherapy. | 2002 Dec |
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Relapse after high-dose therapy in relapsed Ewing's tumor patients: effects of maintenance chemotherapy in two selected patients? | 2003 Dec |
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[Hypoglycemia associated with the production of insulin-like growth factor (IGF)-II by a hemangiopericytoma]. | 2003 Feb 7 |
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Phase II trial of trofosfamide in patients with advanced pretreated soft tissue sarcomas. | 2003 Mar-Apr |
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Antiangiogenetic therapy with pioglitazone, rofecoxib, and metronomic trofosfamide in patients with advanced malignant vascular tumors. | 2003 Nov 15 |
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Antiangiogenic therapy with pioglitazone, rofecoxib, and trofosfamide in a patient with endemic kaposi sarcoma. | 2004 Dec |
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Trofosfamide in the palliative treatment of cancer: a review of the literature. | 2004 Dec |
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Dose escalation study for defining the maximum tolerated dose of continuous oral trofosfamide in pretreated patients with metastatic lung cancer. | 2004 Dec |
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Hypersensitivity pneumonitis associated with the use of trofosfamide. | 2004 Jul |
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Investigations on the pharmacokinetics of trofosfamide and its metabolites-first report of 4-hydroxy-trofosfamide kinetics in humans. | 2004 Jun |
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Enzyme-catalyzed activation of anticancer prodrugs. | 2004 Mar |
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Metronomic scheduling of trofosfamide chemotherapy in human NSCLC xenografts highly increases therapeutic efficacy compared to conventional scheduling by inhibition of angiogenesis. | 2004 Nov |
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Surgery and adjuvant dendritic cell-based tumour vaccination for patients with relapsed malignant glioma, a feasibility study. | 2004 Nov 1 |
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Pioglitazone and rofecoxib combined with angiostatically scheduled trofosfamide in the treatment of far-advanced melanoma and soft tissue sarcoma. | 2004 Nov 15 |
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Treatment of primary intraocular lymphoma with oral trofosfamide: report of two cases and review of the literature. | 2004 Sep |
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Recent developments in salvage chemotherapy for patients with metastatic soft tissue sarcoma. | 2005 |
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Primary dissemination of high-grade gliomas in children: experiences from four studies of the Pediatric Oncology and Hematology Society of the German Language Group (GPOH). | 2005 Apr |
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A new therapeutic approach in patients with advanced sarcoma. | 2005 Dec |
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Pharmacokinetics and efficacy of ifosfamide or trofosfamide in patients with intraocular lymphoma. | 2005 Dec |
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[Metronomic chemotherapy. Should we change our thinking in the treatment of advanced tumors?]. | 2005 Jan |
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Anti-inflammatory and angiostatic therapy in chemorefractory multisystem Langerhans' cell histiocytosis of adults. | 2005 Mar |
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Insights into oxazaphosphorine resistance and possible approaches to its circumvention. | 2005 Oct |
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The radiation response of sarcomas by histologic subtypes: a review with special emphasis given to results achieved with razoxane. | 2006 |
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Reversal of resistance to oxazaphosphorines. | 2006 Aug |
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Antiangiogenic therapy in metastatic prostate carcinoma complicated by cutaneous lupus erythematodes. | 2006 Aug |
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Palliative chemotherapy with trofosfamide in advanced prostate cancer. | 2006 Jan-Feb |
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Intraocular lymphoma 2000-2005: results of a retrospective multicentre trial. | 2006 Jun |
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Metronomic trofosfamide inhibits progression of human lung cancer xenografts by exerting anti-angiogenic effects. | 2006 Oct |
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Secondary dissemination in children with high-grade malignant gliomas and diffuse intrinsic pontine gliomas. | 2006 Oct 23 |
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Complete remission of relapsing high-grade angiosarcoma with single-agent metronomic trofosfamide. | 2006 Sep |
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Design of new oxazaphosphorine anticancer drugs. | 2007 |
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Simultaneous determination of gemcitabine, taxol, cyclophosphamide and ifosfamide in wipe samples by high-performance liquid chromatography/tandem mass spectrometry: protocol of validation and uncertainty of measurement. | 2007 |
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Recurrent low- to intermediate-grade chondrosarcoma of the thumb with lung metastases: an objective response to trofosfamide. | 2007 Apr |
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Systemic treatment options for patients with refractory adult-type sarcoma beyond anthracyclines. | 2007 Mar |
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Thyroid function in paediatric and young adult patients after sarcoma therapy: a report from the Late Effects Surveillance System. | 2007 May |
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Diagnosis and management of primary intraocular lymphoma: an update. | 2007 Sep |
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PPARgamma and MEK Interactions in Cancer. | 2008 |
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Potential combination chemotherapy approaches for advanced adult-type soft-tissue sarcoma. | 2008 |
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Peroxisome Proliferator-Activated Receptor-gamma Ligands: Potential Pharmacological Agents for Targeting the Angiogenesis Signaling Cascade in Cancer. | 2008 |
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A pilot study of docetaxel and trofosfamide as second-line 'metronomic' chemotherapy in the treatment of metastatic non-small cell lung cancer (NSCLC). | 2008 Apr |
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Infraorbital cutaneous angiosarcoma: a diagnostic and therapeutic dilemma. | 2008 Aug 11 |
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Low-dose oral metronomic chemotherapy prevents mobilization of endothelial progenitor cells into the blood of cancer patients. | 2008 Nov-Dec |
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Ifosfamide or trofosfamide in patients with intraocular lymphoma. | 2009 Jun |
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Principles of modular tumor therapy. | 2009 Sep |
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Clinical benefit of second-line palliative chemotherapy in advanced soft-tissue sarcoma. | 2010 |
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Metronomic treatment with low-dose trofosfamide leads to a long-term remission in a patient with docetaxel-refractory advanced metastatic prostate cancer. | 2010 |
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Sclerosing epithelioid fibrosarcoma of the bone: a case report of high resistance to chemotherapy and a survey of the literature. | 2010 |
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Oxazaphosphorines: new therapeutic strategies for an old class of drugs. | 2010 Aug |
Patents
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NCI_THESAURUS |
C697
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WHO-VATC |
QL01AA07
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WHO-ATC |
L01AA07
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100000076955
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C1268
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m11217
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DB12902
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65702
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CHEMBL462019
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DTXSID60865031
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244-770-8
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22089-22-1
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2766
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2866
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SUB11331MIG
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109723
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C003726
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38865
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TROFOSFAMIDE
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H64JRU6GJ0
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ACTIVE MOIETY