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299-75-2,MFCD02258964
Catalog No.:AA00BF29

299-75-2 | Treosulfan

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  • Technical Information
  • Properties
  • Downstream Synthesis Route
  • Literature
  • Request for Quotation
  • Download SDS
  • Technical Information
  • Properties
  • Downstream Synthesis Route
  • Literature
Technical Information
Catalog Number:
AA00BF29
Chemical Name:
Treosulfan
CAS Number:
299-75-2
Molecular Formula:
C6H14O8S2
Molecular Weight:
278.3006
MDL Number:
MFCD02258964
SMILES:
O[C@H]([C@H](COS(=O)(=O)C)O)COS(=O)(=O)C
Properties
Computed Properties
 
Complexity:
345  
Covalently-Bonded Unit Count:
1  
Defined Atom Stereocenter Count:
2  
Heavy Atom Count:
16  
Hydrogen Bond Acceptor Count:
8  
Hydrogen Bond Donor Count:
2  
Rotatable Bond Count:
7  
XLogP3:
-2.2  

Downstream Synthesis Route

[1]Daugey;DeRycke;Brotin;Buffeteau[Chirality,2018,vol.30,#4,p.342-350]

[2]Robbins,MichaelA.;Devine,PaulN.;Oh,Taeboem;Renard,Marc;Ghosez,Léon[OrganicSyntheses,1999,vol.76,p.101-101]

[3]FEIT[Journalofmedicinalchemistry,1964,vol.7,p.14-17]

[4]Devine,PaulN.;Oh,Taeboem[TetrahedronLetters,1991,vol.32,#7,p.883-886]

[5]Park,Soobong;Anderson,Christopher;Loeber,Rachel;Seetharaman,Mahadevan;Jones,Roger;Tretyakova,Natalia[JournaloftheAmericanChemicalSociety,2005,vol.127,#41,p.14355-14365]

[1]Feit,P.W.[TetrahedronLetters,1961,p.716-717]

[1]Feit,P.W.[JournalofMedicinalChemistry,1966,vol.9,p.241-242]

[1]Journalofmedicinalchemistry,1964,vol.7,p.14-17

[2]TetrahedronLetters,1961,p.716-717

[1]Feit,P.W.[JournalofMedicinalChemistry,1966,vol.9,p.241-242]

Literature

Title: Allo-SCT for AML and MDS with treosulfan compared with BU-based regimens: reduced toxicity vs reduced intensity.

Journal: Bone marrow transplantation 20121001

Title: Allogeneic hematopoietic SCT in patients with AML following treosulfan/fludarabine conditioning.

Journal: Bone marrow transplantation 20120901

Title: Phase II prospective study of treosulfan-based reduced-intensity conditioning in allogeneic HSCT for hematological malignancies from 10/10 HLA-identical unrelated donor.

Journal: Annals of hematology 20120801

Title: A prospective multicenter study of treosulfan in elderly patients with recurrent ovarian cancer: results of a planned safety analysis.

Journal: Journal of cancer research and clinical oncology 20120801

Title: Nonmyeloablative conditioning generates autoantigen-encoding bone marrow that prevents and cures an experimental autoimmune disease.

Journal: American journal of transplantation : official journal of the American Society of Transplantation and the American Society of Transplant Surgeons 20120801

Title: Allogeneic hematopoietic stem cell transplantation in thalassemia major: results of a reduced-toxicity conditioning regimen based on the use of treosulfan.

Journal: Blood 20120712

Title: HPLC method for determination of biologically active epoxy-transformers of treosulfan in human plasma: pharmacokinetic application.

Journal: Journal of pharmaceutical and biomedical analysis 20120325

Title: Treosulfan-based conditioning before hematopoietic SCT: more than a BU look-alike.

Journal: Bone marrow transplantation 20120101

Title: Intermediate intensity conditioning regimen containing FLAMSA, treosulfan, cyclophosphamide, and ATG for allogeneic stem cell transplantation in elderly patients with relapsed or high-risk acute myeloid leukemia.

Journal: Annals of hematology 20120101

Title: Low incidence and severity of oral mucositis in allogeneic stem cell transplantation after conditioning with treosulfan and fludarabine.

Journal: European journal of haematology 20120101

Title: Treosulfan-based preparative regimens for allo-HSCT in childhood hematological malignancies: a retrospective study on behalf of the EBMT pediatric diseases working party.

Journal: Bone marrow transplantation 20111201

Title: CD40 ligand deficiency with grade III liver fibrosis, transplanted by a treosulphan-based conditioning regimen.

Journal: Experimental and clinical transplantation : official journal of the Middle East Society for Organ Transplantation 20111001

Title: Reduced-toxicity conditioning with treosulfan and fludarabine in allogeneic hematopoietic stem cell transplantation for myelodysplastic syndromes: final results of an international prospective phase II trial.

Journal: Haematologica 20110901

Title: Treosulfan-based conditioning regimens for hematopoietic stem cell transplantation in children with primary immunodeficiency: United Kingdom experience.

Journal: Blood 20110421

Title: Retrospective analysis of treosulfan-based conditioning in comparison with standard conditioning in patients with myelodysplastic syndrome.

Journal: Bone marrow transplantation 20110401

Title: Conditioning with treosulfan and fludarabine followed by allogeneic hematopoietic cell transplantation for high-risk hematologic malignancies.

Journal: Biology of blood and marrow transplantation : journal of the American Society for Blood and Marrow Transplantation 20110301

Title: Age has no significant impact on overall survival and on treatment tolerability in relapsed stage IV cutaneous malignant melanoma patients receiving Cisplatin, Gemcitabine, and Treosulfan.

Journal: American journal of clinical oncology 20110201

Title: High-dose treosulfan in conditioning prior to hematopoietic stem cell transplantation.

Journal: Expert opinion on investigational drugs 20101001

Title: Molecular basis of chemosensitivity of platinum pre-treated ovarian cancer to chemotherapy.

Journal: British journal of cancer 20100824

Title: The role of reduced intensity preparative regimens in patients with thalassemia given hematopoietic transplantation.

Journal: Annals of the New York Academy of Sciences 20100801

Title: Allogeneic hematopoietic stem-cell transplantation in patients with hematologic malignancies after dose-escalated treosulfan/fludarabine conditioning.

Journal: Journal of clinical oncology : official journal of the American Society of Clinical Oncology 20100710

Title: Treosulfan-based conditioning regimen in a second matched unrelated peripheral blood stem cell transplantation for a pediatric patient with CGD and invasive aspergillosis, who experienced initial graft failure after RIC.

Journal: International journal of hematology 20091201

Title: Chemotherapy: Topotecan or treosulfan--that is the question.

Journal: Nature reviews. Clinical oncology 20091001

Title: Topotecan versus treosulfan, an alkylating agent, in patients with epithelial ovarian cancer and relapse within 12 months following 1st-line platinum/paclitaxel chemotherapy. A prospectively randomized phase III trial by the Arbeitsgemeinschaft Gynaekologische Onkologie Ovarian Cancer Study Group (AGO-OVAR).

Journal: Gynecologic oncology 20090801

Title: Diffusion-weighted imaging as predictor of therapy response in an animal model of Ewing sarcoma.

Journal: Investigative radiology 20090501

Title: Preclinical analysis of treosulfan in combination with total body irradiation as conditioning regimen prior to bone marrow transplantation in rats.

Journal: Immunopharmacology and immunotoxicology 20090101

Title: Treosulphan as an alternative to busulphan for myeloablative conditioning in paediatric allogeneic transplantation.

Journal: British journal of haematology 20081201

Title: Quantitative structure-activity relationship and complex network approach to monoamine oxidase A and B inhibitors.

Journal: Journal of medicinal chemistry 20081113

Title: Treosulfan-based conditioning regimen for allogeneic haematopoietic stem cell transplantation in patients with thalassaemia major.

Journal: British journal of haematology 20081101

Title: Cytotoxic effects of treosulfan and busulfan against leukemic cells of pediatric patients.

Journal: Cancer chemotherapy and pharmacology 20081001

Title: Pharmacokinetics of high-dose i.v. treosulfan in children undergoing treosulfan-based preparative regimen for allogeneic haematopoietic SCT.

Journal: Bone marrow transplantation 20081001

Title: Cisplatin, gemcitabine and treosulfan is effective in chemotherapy-pretreated relapsed stage IV uveal melanoma patients.

Journal: Cancer chemotherapy and pharmacology 20080901

Title: Treosulfan/fludarabine as an allogeneic hematopoietic stem cell transplant conditioning regimen for high-risk patients.

Journal: American journal of hematology 20080901

Title: Preclinical studies of treosulfan demonstrate potent activity in Ewing's sarcoma.

Journal: Cancer chemotherapy and pharmacology 20080601

Title: Treosulfan and fludarabine low-toxicity conditioning for allogeneic haematopoietic stem cell transplantation in chronic myeloid leukaemia.

Journal: British journal of haematology 20080601

Title: Treosulfan-containing regimens achieve high rates of engraftment associated with low transplant morbidity and mortality in children with non-malignant disease and significant co-morbidities.

Journal: British journal of haematology 20080601

Title: Prognostic impact of combined fludarabine, treosulfan and mitoxantrone resistance profile in childhood acute myeloid leukemia.

Journal: Anticancer research 20080101

Title: Lessons of war: progress in transplant conditioning regimens.

Journal: Leukemia & lymphoma 20071201

Title: Fludarabine and treosulfan: a novel modified myeloablative regimen for allogeneic hematopoietic stem-cell transplantation with effective antileukemia activity in patients with acute myeloid leukemia and myelodysplastic syndromes.

Journal: Leukemia & lymphoma 20071201

Title: Cisplatin, gemcitabine, and treosulfan in relapsed stage IV cutaneous malignant melanoma patients.

Journal: British journal of cancer 20071119

Title: Treosulfan impedes the migration of immunocompetent cells.

Journal: Journal of neurology 20071001

Title: Engraftment kinetics and hematopoietic chimerism after reduced-intensity conditioning with fludarabine and treosulfan before allogeneic stem cell transplantation.

Journal: Annals of hematology 20070801

Title: Treatment of active secondary progressive multiple sclerosis with treosulfan.

Journal: Journal of neurology 20070701

Title: Comment on 'determination of treosulfan in plasma and urine by HPLC with refractometric detection; pharmacokinetic studies in children undergoing myeloablative treatment prior to haematopoietic stem cell transplantation' by F.K. Glowka et al. [J. Chromatogr. B 850 (2007) 569-574].

Journal: Journal of chromatography. B, Analytical technologies in the biomedical and life sciences 20070615

Title: Determination of treosulfan in plasma and urine by HPLC with refractometric detection; pharmacokinetic studies in children undergoing myeloablative treatment prior to haematopoietic stem cell transplantation.

Journal: Journal of chromatography. B, Analytical technologies in the biomedical and life sciences 20070501

Title: Reduced-toxicity conditioning with fludarabine and treosulfan prior to allogeneic stem cell transplantation in multiple myeloma.

Journal: Bone marrow transplantation 20070401

Title: Substitution of cyclophosphamide and busulfan by fludarabine, treosulfan and melphalan in a preparative regimen for children and adolescents with Shwachman-Diamond syndrome.

Journal: Bone marrow transplantation 20070201

Title: Fludarabine, treosulfan and etoposide sensitivity and the outcome of hematopoietic stem cell transplantation in childhood acute myeloid leukemia.

Journal: Anticancer research 20070101

Title: Medical treatment of uveal melanoma.

Journal: Tumori 20070101

Title: Cytotoxic effects of treosulfan on prostate cancer cell lines.

Journal: Anticancer research 20070101

Title: A randomized phase II trial of gemcitabine plus treosulfan versus treosulfan alone in patients with metastatic uveal melanoma.

Journal: Annals of oncology : official journal of the European Society for Medical Oncology 20061201

Title: In vitro drug sensitivity predicts response and survival after individualized sensitivity-directed chemotherapy in metastatic melanoma: a multicenter phase II trial of the Dermatologic Cooperative Oncology Group.

Journal: Clinical cancer research : an official journal of the American Association for Cancer Research 20060915

Title: Cytotoxicity of treosulfan and busulfan on pediatric tumor cell lines.

Journal: Anti-cancer drugs 20060701

Title: A prospective single arm phase II study of dacarbazine and treosulfan as first-line therapy in metastatic uveal melanoma.

Journal: Melanoma research 20060601

Title: Reduced-toxicity conditioning with treosulfan, fludarabine and ATG as preparative regimen for allogeneic stem cell transplantation (alloSCT) in elderly patients with secondary acute myeloid leukemia (sAML) or myelodysplastic syndrome (MDS).

Journal: Bone marrow transplantation 20060201

Title: Unrelated donor bone marrow transplantation with treosulfan-based myeloablative conditioning for paroxysmal nocturnal hemoglobinuria--successful treatment despite multiple transplant-related risk factors for hemolysis including major Kidd group incompatibility.

Journal: Bone marrow transplantation 20060101

Title: A randomised comparison of treosulfan and carboplatin in patients with ovarian cancer: a study by the Scottish Gynaecological Cancer Trials Group (SGCTG).

Journal: European journal of cancer (Oxford, England : 1990) 20060101

Title: Myeloablative and immunosuppressive properties of treosulfan in mice.

Journal: Experimental hematology 20060101

Title: Evaluation of chemosensitivity of human bone marrow stromal cells--differences between common chemotherapeutic drugs.

Journal: Anticancer research 20060101

Title: Induction of tolerance across fully mismatched barriers by a nonmyeloablative treatment excluding antibodies or irradiation use.

Journal: Cell transplantation 20060101

Title: Treosulfan, cyclophosphamide and antithymocyte globulin for allogeneic hematopoietic cell transplantation in acquired severe aplastic anemia.

Journal: Annals of transplantation 20060101

Title: The results of treatment of epithelial ovarian cancer after centralisation of primary surgery. Results from North Jutland, Denmark.

Journal: Gynecologic oncology 20051201

Title: A two-cohort phase II clinical trial of gemcitabine plus treosulfan in patients with metastatic uveal melanoma.

Journal: Melanoma research 20051001

Title: [Allogeneic blood stem cell transplantation in high-risk patients after conditioning with treosulfan and fludarabine].

Journal: Deutsche medizinische Wochenschrift (1946) 20050923

Title: Two allogeneic hematopoietic stem cell transplantations without the use of blood-product support.

Journal: Haematologica 20050901

Title: Phase I trial combining gemcitabine and treosulfan in advanced cutaneous and uveal melanoma patients.

Journal: British journal of cancer 20050606

Title: Phase II trial of cisplatin, gemcitabine and treosulfan in patients with metastatic uveal melanoma.

Journal: Melanoma research 20050601

Title: Treosulfan and gemcitabine.

Journal: Journal of cancer research and clinical oncology 20050501

Title: Dose-escalated treosulphan in combination with cyclophosphamide as a new preparative regimen for allogeneic haematopoietic stem cell transplantation in patients with an increased risk for regimen-related complications.

Journal: Bone marrow transplantation 20050201

Title: Myeloablative conditioning in myelofibrosis using i.v. treosulfan and autologous peripheral blood progenitor cell transplantation with high doses of CD34+ cells results in hematologic responses - follow-up of three patients.

Journal: Haematologica 20050201

Title: [Metronomic chemotherapy. Should we change our thinking in the treatment of advanced tumors?].

Journal: Journal der Deutschen Dermatologischen Gesellschaft = Journal of the German Society of Dermatology : JDDG 20050101

Title: Myeloablative conditioning in myelofibrosis using i.v. treosulfan and autologous peripheral blood progenitor cell transplantation with high doses of CD34+ cells results in hematologic responses. A follow-up of three patients.

Journal: Haematologica 20050101

Title: Pharmacokinetics of treosulfan in a myeloablative combination with cyclophosphamide prior to allogeneic hematopoietic stem cell transplantation.

Journal: International journal of clinical pharmacology and therapeutics 20041101

Title: Treosulfan based conditioning for autologous and allogeneic hematopoietic stem cell transplantation.

Journal: International journal of clinical pharmacology and therapeutics 20041101

Title: High-dose treosulfan in patients with relapsed or refractory high-grade lymphoma receiving tandem autologous blood stem cell transplantation.

Journal: Bone marrow transplantation 20040901

Title: A clinical phase I trial of gemcitabine and treosulfan in uveal melanoma and other solid tumours.

Journal: European journal of cancer (Oxford, England : 1990) 20040901

Title: Clinical evaluation of in vitro chemosensitivity testing: the example of uveal melanoma.

Journal: Journal of cancer research and clinical oncology 20040701

Title: Addition of treosulfan to a nonmyeloablative conditioning regimen results in enhanced chimerism and immunologic tolerance in an experimental allogeneic bone marrow transplant model.

Journal: Biology of blood and marrow transplantation : journal of the American Society for Blood and Marrow Transplantation 20040401

Title: Treosulfan and fludarabine: a new toxicity-reduced conditioning regimen for allogeneic hematopoietic stem cell transplantation.

Journal: Blood 20040115

Title: Toward a myeloablative regimen with clinical potential: II. Treosulfan induces specific skin graft tolerance across haploidentical MHC barriers.

Journal: Bone marrow transplantation 20040101

Title: Treosulfan-induced apoptosis in acute myeloid leukemia cells is accompanied by translocation of protein kinase C delta and enhanced by bryostatin-1.

Journal: Experimental hematology 20040101

Title: Treosulfan/fludarabine: a new conditioning regimen in allogeneic transplantation.

Journal: Annals of hematology 20040101

Title: The in vitro effect of gefitinib ('Iressa') alone and in combination with cytotoxic chemotherapy on human solid tumours.

Journal: BMC cancer 20040101

Title: Metronomic oral low-dose treosulfan chemotherapy combined with cyclooxygenase-2 inhibitor in pretreated advanced melanoma: a pilot study.

Journal: Cancer chemotherapy and pharmacology 20031101

Title: Action of treosulfan in myelin-oligodendrocyte-glycoprotein-induced experimental autoimmune encephalomyelitis and human lymphocytes.

Journal: Journal of neuroimmunology 20031101

Title: Treosulfan is an effective inducer of cell death in myeloma cell lines and primary myeloma cells from patients.

Journal: British journal of haematology 20030901

Title: Towards a myeloablative regimen with clinical potential: I. Treosulfan conditioning and bone marrow transplantation allow induction of donor-specific tolerance for skin grafts across full MHC barriers.

Journal: Bone marrow transplantation 20030701

Title: Treosulfan and gemcitabine in metastatic uveal melanoma patients: results of a multicenter feasibility study.

Journal: Anti-cancer drugs 20030601

Title: Antileukaemic activity of treosulfan in xenografted human acute lymphoblastic leukaemias (ALL).

Journal: European journal of cancer (Oxford, England : 1990) 20030401

Title: Femoral head necrosis in three patients with relapsed ovarian cancer receiving high-dose chemotherapy followed by autologous peripheral blood stem cell transplantation.

Journal: Bone marrow transplantation 20030301

Title: Second-line chemotherapy of metastatic malignant melanoma with intravenous treosulfan: a phase II multicentre trial.

Journal: Melanoma research 20030201

Title: Treosulfan in the treatment of metastatic melanoma: from chemosensitivity testing to clinical trials.

Journal: Recent results in cancer research. Fortschritte der Krebsforschung. Progres dans les recherches sur le cancer 20030101

Title: Neoadjuvant gemcitabine/treosulfan chemotherapy for newly diagnosed glioblastoma: a phase II study.

Journal: Journal of neuro-oncology 20020901

Title: CD95/CD95 ligand-independent potentiation of treosulfan cytotoxicity by BSO in malignant glioma cells in vitro and in vivo.

Journal: International journal of oncology 20020701

Title: Use of an ATP-based chemosensitivity assay to design new combinations of high-concentration doxorubicin with other drugs for recurrent ovarian cancer.

Journal: Anti-cancer drugs 20020701

Title: Rationale for combination therapy of chronic myelogenous leukaemia with imatinib and irradiation or alkylating agents: implications for pretransplant conditioning.

Journal: British journal of cancer 20020506

Title: The role of gemcitabine-based doublets in the management of ovarian carcinoma.

Journal: Seminars in oncology 20020201

Title: Chemotherapy versus hormonal treatment in platinum- and paclitaxel-refractory ovarian cancer: a randomised trial of the German Arbeitsgemeinschaft Gynaekologische Onkologie (AGO) Study Group Ovarian Cancer.

Journal: Annals of oncology : official journal of the European Society for Medical Oncology 20020201

Title: Individualized long-term chemotherapy for recurrent ovarian cancer after failing high-dose treatment.

Journal: Anti-cancer drugs 20020201

Title: Treosulfan in the treatment of advanced ovarian cancer: a randomised co-operative multicentre phase III-study.

Journal: Anticancer research 20020101

Title: Progression of Parkinson's disease with impairment of vision under carboplatin/cyclophosphamide therapy for ovarian cancer.

Journal: Cancer chemotherapy and pharmacology 19980101

Title: Nitsch E, et al. Synergistic cytotoxic activity of treosulfan and LY 188011 in pancreatic cancer cell lines. Anticancer Res. 2014 Apr;34(4):1779-84.

Title: Peter T, et al. Programmed erythrocyte death following in vitro Treosulfan treatment. Cell Physiol Biochem. 2015;35(4):1372-80.

Title: Sjöö F, et al. Myeloablative and immunosuppressive properties of treosulfan in mice. Exp Hematol. 2006 Jan;34(1):115-21.

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Tags:299-75-2 Molecular Formula|299-75-2 MDL|299-75-2 SMILES|299-75-2 Treosulfan