Treosulfan

    WARNING: This product is for research use only, not for human or veterinary use.

MedKoo CAT#: 205652

CAS#: 299-75-2

Description: Treosulfan is the product of a bifunctional sulfonate alkylating agent with myeloablative, immunosuppresive, and antineoplastic activities. Under physiological conditions, treosulfan converts nonenzymatically to L-diepoxybutane via a monoepoxide intermediate. The monoepoxide intermediate and L-diepoxybutane alkylate DNA at guanine residues and produce DNA interstrand crosslinks, resulting in DNA fragmentation and apoptosis. In escalated doses, this agent also exhbits myeloablative and immunosuppressive activities.


Chemical Structure

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Treosulfan
CAS# 299-75-2

Theoretical Analysis

MedKoo Cat#: 205652
Name: Treosulfan
CAS#: 299-75-2
Chemical Formula: C6H14O8S2
Exact Mass: 278.01301
Molecular Weight: 278.3
Elemental Analysis: C, 25.89; H, 5.07; O, 45.99; S, 23.04

Size Price Shipping out time Quantity
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Pricing updated 2021-03-02. Prices are subject to change without notice.

Treosulfan is not in stock, may be available through custom synthesis. For cost-effective reason, minimum 1 gram order is requested. The product will be characterized by NMR, HPLC and MS analysis. Purity (HPLC) is usually >98%. CoA, QC data, MSDS will be provided when product is successfully made. The estimated lead time is 2-3 months. Please send email to sales@medkoo.com to inquire quote.

Synonym: NSC 39069; NSC39069; NSC-39069; Treosulfan; (2S,3S)-2,3-Dihydroxybutane-1,4diyl dimethanesulfonate.

IUPAC/Chemical Name: (2S,3S)-2,3-dihydroxybutane-1,4-diyl dimethanesulfonate

InChi Key: YCPOZVAOBBQLRI-WDSKDSINSA-N

InChi Code: InChI=1S/C6H14O8S2/c1-15(9,10)13-3-5(7)6(8)4-14-16(2,11)12/h5-8H,3-4H2,1-2H3/t5-,6-/m0/s1

SMILES Code: O[C@@H](COS(C)(=O)=O)[C@@H](O)COS(C)(=O)=O

Appearance:
Solid powder

Purity:
>98% (or refer to the Certificate of Analysis)

Shipping Condition:
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition:
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility:
soluble in DMSO, not soluble in water.

Shelf Life:
>5 years if stored properly

Drug Formulation:
This drug may be formulated in DMSO

Stock Solution Storage:
0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code:
2934.99.9001

Handling Instructions:

Preparing Stock Solutions

The following data is based on the product molecular weight 278.3 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Select a batch to recalculate based on the batch molecular weight:
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL

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1: Choudhary D, Sharma SK, Gupta N, Kharya G, Pavecha P, Handoo A, Setia R, Katewa S. Treosulfan-Thiotepa-Fludarabine-Based Conditioning Regimen for Allogeneic Transplantation in Patients with Thalassemia Major: A Single-Center Experience from North India. Biol Blood Marrow Transplant. 2012 Nov 15. doi:pii: S1083-8791(12)00480-6. 10.1016/j.bbmt.2012.11.007. [Epub ahead of print] PubMed PMID: 23160007.

2: Galaup A, Paci A. Pharmacology of dimethanesulfonate alkylating agents: busulfan and treosulfan. Expert Opin Drug Metab Toxicol. 2012 Nov 16. [Epub ahead of print] PubMed PMID: 23157726.

3: GłÃ³wka FK, Romański M, Teżyk A, Żaba C. Direct high-performance liquid chromatography method with refractometric detection designed for stability studies of treosulfan and its biologically active epoxy-transformers. J Pharm Biomed Anal. 2013 Jan;72:145-9. doi: 10.1016/j.jpba.2012.10.005. Epub 2012 Oct 16. PubMed PMID: 23146239.

4: Ghosh S, Schuster FR, Fuchs I, Laws HJ, Borkhardt A, Meisel R. Treosulfan-based conditioning in DOCK8 deficiency: complete lympho-hematopoietic reconstitution with minimal toxicity. Clin Immunol. 2012 Dec;145(3):259-61. doi: 10.1016/j.clim.2012.10.003. Epub 2012 Oct 14. Review. PubMed PMID: 23128504.

5: Beier R, Schulz A, Hönig M, Eyrich M, Schlegel PG, Holter W, Stachel KD, Ehlert K, Greil J, Nürnberger W, Wößmann W, Bader P, Urban C, Müller I, Suttorp M, Sauer M, Gruhn B, Meisel R, Zimmermann M, Sykora KW. Long-term follow-up of children conditioned with Treosulfan: German and Austrian experience. Bone Marrow Transplant. 2012 Oct 22. doi: 10.1038/bmt.2012.188. [Epub ahead of print] PubMed PMID: 23085832.

6: Bernardo ME, Piras E, Vacca A, Giorgiani G, Zecca M, Bertaina A, Pagliara D, Contoli B, Pinto RM, Caocci G, Mastronuzzi A, La Nasa G, Locatelli F. Allogeneic hematopoietic stem cell transplantation in thalassemia major: results of a reduced-toxicity conditioning regimen based on the use of treosulfan. Blood. 2012 Jul 12;120(2):473-6. doi: 10.1182/blood-2012-04-423822. Epub 2012 May 29. PubMed PMID: 22645178.

7: Mahner S, Oskay-Özcelik G, Heidrich-Lorsbach E, Fuxius S, Sommer H, Klare P, Belau A, Ruhmland B, Heuser T, Kölbl H, Markmann S, Sehouli J. A prospective multicenter study of treosulfan in elderly patients with recurrent ovarian cancer: results of a planned safety analysis. J Cancer Res Clin Oncol. 2012 Aug;138(8):1413-9. doi: 10.1007/s00432-012-1221-3. Epub 2012 Apr 15. PubMed PMID: 22526159; PubMed Central PMCID: PMC3397225.

8: Michallet M, Sobh M, Milpied N, Bay JO, Fürst S, Harousseau JL, Mohty M, Nicolini FE, Labussière H, Tedone N, Morisset S, Vigouroux S, Baumgart J, Tabrizi R, Blaise D. Phase II prospective study of treosulfan-based reduced-intensity conditioning in allogeneic HSCT for hematological malignancies from 10/10 HLA-identical unrelated donor. Ann Hematol. 2012 Aug;91(8):1289-97. doi: 10.1007/s00277-012-1429-y. Epub 2012 Feb 25. PubMed PMID: 22362122.

9: Shimoni A, Shem-Tov N, Volchek Y, Danylesko I, Yerushalmi R, Nagler A. Allo-SCT for AML and MDS with treosulfan compared with BU-based regimens: reduced toxicity vs reduced intensity. Bone Marrow Transplant. 2012 Oct;47(10):1274-82. doi: 10.1038/bmt.2012.4. Epub 2012 Feb 13. PubMed PMID: 22327135.

10: GłÃ³wka FK, Romański M, Teżyk A, Zaba C, Wróbel T. HPLC method for determination of biologically active epoxy-transformers of treosulfan in human plasma: pharmacokinetic application. J Pharm Biomed Anal. 2012 Mar 25;62:105-13. doi: 10.1016/j.jpba.2011.12.021. Epub 2011 Dec 24. PubMed PMID: 22260969.

11: Casper J, Holowiecki J, Trenschel R, Wandt H, Schaefer-Eckart K, Ruutu T, Volin L, Einsele H, Stuhler G, Uharek L, Blau I, Bornhaeuser M, Zander AR, Larsson K, Markiewicz M, Giebel S, Kruzel T, Mylius HA, Baumgart J, Pichlmeier U, Freund M, Beelen DW. Allogeneic hematopoietic SCT in patients with AML following treosulfan/fludarabine conditioning. Bone Marrow Transplant. 2012 Sep;47(9):1171-7. doi: 10.1038/bmt.2011.242. Epub 2011 Dec 12. PubMed PMID: 22158386.

12: Heli U, Eeva J, Anne N, Tapani R, Liisa V. Low incidence and severity of oral mucositis in allogeneic stem cell transplantation after conditioning with treosulfan and fludarabine. Eur J Haematol. 2012 Jan;88(1):87-8. doi: 10.1111/j.1600-0609.2011.01732.x. Epub 2011 Nov 22. PubMed PMID: 22103782.

13: Ruutu T, Volin L, Beelen DW, Trenschel R, Finke J, Schnitzler M, Holowiecki J, Giebel S, Markiewicz M, Uharek L, Blau IW, Kienast J, Stelljes M, Larsson K, Zander AR, Gramatzki M, Repp R, Einsele H, Stuhler G, Baumgart J, Mylius HA, Pichlmeier U, Freund M, Casper J. 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. Haematologica. 2011 Sep;96(9):1344-50. doi: 10.3324/haematol.2011.043810. Epub 2011 Jun 9. PubMed PMID: 21659356; PubMed Central PMCID: PMC3166105.

14: Chemnitz JM, von Lilienfeld-Toal M, Holtick U, Theurich S, Shimabukuro-Vornhagen A, Krause A, Brossart P, Hallek M, Scheid C. 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. Ann Hematol. 2012 Jan;91(1):47-55. doi: 10.1007/s00277-011-1253-9. Epub 2011 May 17. PubMed PMID: 21584670.

15: Danylesko I, Shimoni A, Nagler A. Treosulfan-based conditioning before hematopoietic SCT: more than a BU look-alike. Bone Marrow Transplant. 2012 Jan;47(1):5-14. doi: 10.1038/bmt.2011.88. Epub 2011 Apr 11. Review. PubMed PMID: 21478921.

16: Slatter MA, Rao K, Amrolia P, Flood T, Abinun M, Hambleton S, Nademi Z, Goulden N, Davies G, Qasim W, Gaspar HB, Cant A, Gennery AR, Veys P. Treosulfan-based conditioning regimens for hematopoietic stem cell transplantation in children with primary immunodeficiency: United Kingdom experience. Blood. 2011 Apr 21;117(16):4367-75. doi: 10.1182/blood-2010-10-312082. Epub 2011 Feb 16. PubMed PMID: 21325599.

17: Wachowiak J, Sykora KW, Cornish J, Chybicka A, Kowalczyk JR, Gorczyńska E, Choma M, Grund G, Peters C; EBMT Pediatric Diseases Working Party. Treosulfan-based preparative regimens for allo-HSCT in childhood hematological malignancies: a retrospective study on behalf of the EBMT pediatric diseases working party. Bone Marrow Transplant. 2011 Dec;46(12):1510-8. doi: 10.1038/bmt.2010.343. Epub 2011 Feb 7. PubMed PMID: 21297673.

18: GłÃ³wka FK, Romański M, Wachowiak J. High-dose treosulfan in conditioning prior to hematopoietic stem cell transplantation. Expert Opin Investig Drugs. 2010 Oct;19(10):1275-95. doi: 10.1517/13543784.2010.517744. Review. PubMed PMID: 20836619.

19: Nemecek ER, Guthrie KA, Sorror ML, Wood BL, Doney KC, Hilger RA, Scott BL, Kovacsovics TJ, Maziarz RT, Woolfrey AE, Bedalov A, Sanders JE, Pagel JM, Sickle EJ, Witherspoon R, Flowers ME, Appelbaum FR, Deeg HJ. Conditioning with treosulfan and fludarabine followed by allogeneic hematopoietic cell transplantation for high-risk hematologic malignancies. Biol Blood Marrow Transplant. 2011 Mar;17(3):341-50. doi: 10.1016/j.bbmt.2010.05.007. Epub 2010 May 26. PubMed PMID: 20685259; PubMed Central PMCID: PMC2974965.

20: Hilgendorf I, Wolff D, Gromke T, Trenschel R, Elmaagacli AH, Pichlmeier U, Junghanss C, Freund M, Beelen DW, Casper J. Retrospective analysis of treosulfan-based conditioning in comparison with standard conditioning in patients with myelodysplastic syndrome. Bone Marrow Transplant. 2011 Apr;46(4):502-9. doi: 10.1038/bmt.2010.153. Epub 2010 Jun 28. PubMed PMID: 20581886.



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