TROFOSFAMIDE

Possibly Marketed Outside US

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

Structure Search

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

HIDE SMILES / InChI

Molecular Formula	C9H18Cl3N2O2P
Molecular Weight	323.584
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Description
Sources: https://www.cancer.gov/publications/dictionaries/cancer-drug/def/trofosfamide | https://www.baxter.de/sites/g/files/ebysai1301/files/2019-01/ixoten_fs.pdf | https://www.ncbi.nlm.nih.gov/pubmed/15591719

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
Oxazaphosphorines: new therapeutic strategies for an old class of drugs.	2010-08	20446865
SRD5A2 V89L polymorphism and prostate cancer risk: a meta-analysis.	2010-02-01	19760631
Circulating tumor cells: a window into cancer biology and metastasis.	2010-02	20071161
Clinical benefit of second-line palliative chemotherapy in advanced soft-tissue sarcoma.	2010	20508840
Metronomic treatment with low-dose trofosfamide leads to a long-term remission in a patient with docetaxel-refractory advanced metastatic prostate cancer.	2010	20396674
Sclerosing epithelioid fibrosarcoma of the bone: a case report of high resistance to chemotherapy and a survey of the literature.	2010	20396630
Establishment of canine hemangiosarcoma xenograft models expressing endothelial growth factors, their receptors, and angiogenesis-associated homeobox genes.	2009-10-14	19825192
Bleomycin, vinorelbine and trofosfamide in relapsed stage IV cutaneous malignant melanoma patients.	2009-10	19229537
Principles of modular tumor therapy.	2009-09	19593676
Ifosfamide or trofosfamide in patients with intraocular lymphoma.	2009-06	19099202
Low-dose oral metronomic chemotherapy prevents mobilization of endothelial progenitor cells into the blood of cancer patients.	2009-02-03	19181016
Cyclooxygenase 2 (COX2) and Peroxisome Proliferator-Activated Receptor Gamma (PPARG) Are Stage-Dependent Prognostic Markers of Malignant Melanoma.	2009	19639032
Systems biology: a therapeutic target for tumor therapy.	2008-12	19308694
Infraorbital cutaneous angiosarcoma: a diagnostic and therapeutic dilemma.	2008-08-11	18694495
A pharmacokinetic and pharmacodynamic study on metronomic irinotecan in metastatic colorectal cancer patients.	2008-04-22	18362940
A pilot study of docetaxel and trofosfamide as second-line 'metronomic' chemotherapy in the treatment of metastatic non-small cell lung cancer (NSCLC).	2008-04	18418020
Treatment of children with metastatic soft tissue sarcoma with oral maintenance compared to high dose chemotherapy: report of the HD CWS-96 trial.	2008-04	18286501
PPARs Mediate Lipid Signaling in Inflammation and Cancer.	2008	19125181
Clinical Use of PPARgamma Ligands in Cancer.	2008	19125177
The Role of PPARs in the Endothelium: Implications for Cancer Therapy.	2008	19043612
PPARgamma and MEK Interactions in Cancer.	2008	18596912
Potential combination chemotherapy approaches for advanced adult-type soft-tissue sarcoma.	2008	18572972
Peroxisome Proliferator-Activated Receptor-gamma Ligands: Potential Pharmacological Agents for Targeting the Angiogenesis Signaling Cascade in Cancer.	2008	18464916
Targeted combined anti-inflammatory and angiostatic therapy in advanced melanoma: a randomized phase II trial.	2007-12	17992118
Diagnosis and management of primary intraocular lymphoma: an update.	2007-09	19668478
Thyroid function in paediatric and young adult patients after sarcoma therapy: a report from the Late Effects Surveillance System.	2007-05	17381483
Recurrent low- to intermediate-grade chondrosarcoma of the thumb with lung metastases: an objective response to trofosfamide.	2007-04	17396043
Systemic treatment options for patients with refractory adult-type sarcoma beyond anthracyclines.	2007-03	17264755
C-reactive Protein in Patients with Metastatic Clear Cell Renal Carcinoma: An Important Biomarker for Tumor-associated Inflammation.	2007-02-07	19690640
Design of new oxazaphosphorine anticancer drugs.	2007	17430192
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	17340557
Secondary dissemination in children with high-grade malignant gliomas and diffuse intrinsic pontine gliomas.	2006-10-23	17047647
Metronomic trofosfamide inhibits progression of human lung cancer xenografts by exerting anti-angiogenic effects.	2006-10	16761121
Complete remission of relapsing high-grade angiosarcoma with single-agent metronomic trofosfamide.	2006-09	16940811
Reversal of resistance to oxazaphosphorines.	2006-08	16918308
Antiangiogenic therapy in metastatic prostate carcinoma complicated by cutaneous lupus erythematodes.	2006-08	16887488
Palliative chemotherapy with trofosfamide in advanced prostate cancer.	2006-06-03	16739316
Intraocular lymphoma 2000-2005: results of a retrospective multicentre trial.	2006-06	16228920
The radiation response of sarcomas by histologic subtypes: a review with special emphasis given to results achieved with razoxane.	2006	17040092
A new therapeutic approach in patients with advanced sarcoma.	2005-12	16369750
Pharmacokinetics and efficacy of ifosfamide or trofosfamide in patients with intraocular lymphoma.	2005-12	16219622
Insights into oxazaphosphorine resistance and possible approaches to its circumvention.	2005-10	16154799
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).	2005-04	15925999
Anti-inflammatory and angiostatic therapy in chemorefractory multisystem Langerhans' cell histiocytosis of adults.	2005-03	15725096
[Metronomic chemotherapy. Should we change our thinking in the treatment of advanced tumors?].	2005-01	16353744
Recent developments in salvage chemotherapy for patients with metastatic soft tissue sarcoma.	2005	15631540
Antiangiogenic therapy with pioglitazone, rofecoxib, and trofosfamide in a patient with endemic kaposi sarcoma.	2004-12	15611430
Metronomic scheduling of trofosfamide chemotherapy in human NSCLC xenografts highly increases therapeutic efficacy compared to conventional scheduling by inhibition of angiogenesis.	2004-11	15598036
Studies on the urotoxicity of oxazaphosphorine cytostatics and its prevention--I. Experimental studies on the urotoxicity of alkylating compounds.	1981-06	7308258
[Cyclophosphamide and bladder carcinoma (case report) (author's transl)].	1978-01-06	620650

Patents

Substance Class	Chemical Created by `admin` on `Mon Mar 31 19:15:31 GMT 2025` Edited by `admin` on `Mon Mar 31 19:15:31 GMT 2025`
Record UNII	H64JRU6GJ0
Record Status	`Validated (UNII)`
Record Version

Download

Name

Type

Language

A-4828

Preferred Name

English

TROFOSFAMIDE

Official Name

English

NSC-109723

Code

English

Trofosfamide [WHO-DD]

Common Name

English

TROFOSFAMIDE [MI]

Common Name

English

TROFOSFAMIDE [MART.]

Common Name

English

trofosfamide [INN]

Common Name

English

3-(2-CHLOROETHYL)-2-(BIS(2-CHLOROETHYL)AMINO)TETRAHYDRO-2H-1,3,2-OXAZAPHOSPHORIN 2-OXIDE

Systematic Name

English

Z-4828

Code

English

Classification Tree Code System Code

NCI_THESAURUS

C697