Busulfan
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MedKoo CAT#: 100110

CAS#: 55-98-1

Description: Busulfan (Myleran, GlaxoSmithKline, Busulfex IV, Otsuka America Pharmaceutical, Inc.) is a cancer drug, in use since 1959. Busulfan is a cell cycle non-specific alkylating antineoplastic agent, in the class of alkyl sulfonates. Its chemical designation is 1,4-butanediol dimethanesulfonate.


Chemical Structure

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Busulfan
CAS# 55-98-1

Theoretical Analysis

MedKoo Cat#: 100110
Name: Busulfan
CAS#: 55-98-1
Chemical Formula: C6H14O6S2
Exact Mass: 246.02318
Molecular Weight: 246.3
Elemental Analysis: C, 29.26; H, 5.73; O, 38.98; S, 26.04

Size Price Shipping out time Quantity
1g USD 60 Same day
2g USD 80 Same day
5g USD 120 Same day
10g USD 160 Same day
25g USD 250 2 Weeks
50g USD 450 2 Weeks
100g USD 850 2 Weeks
Inquire bulk and customized quantity

Pricing updated 2021-03-03. Prices are subject to change without notice.

Busulfan, purity > 97%, is in stock. The same day shipping out after order is received.

Synonym: BSF; Bussulfam; Busulfanum; busulphan; glyzophrol; methanesulfonic acid tetramethylene ester; Myeleukon; Myeloleukon; Myelosan; Mylecytan; Sulfabutin; tetramethylene bis(methanesulfonate); US brand names: Busulfex; Mitosan; Myleran; Foreign brand names: Mielucin; Misulban; Misulfan; Abbreviations: BU; BUS; Code names: CB2041; GT41; WR19508; Chemical structure names: ; 14bis(methanesulfonoxy)butane; 14bitanediol dimethanesulfonate esters; 14butanediol dimethylsulfonate; 14di(methanesulfonyloxy)butane; 14di(methylsulfonyloxy)butane.

IUPAC/Chemical Name: butane-1,4-diyl dimethanesulfonate

InChi Key: COVZYZSDYWQREU-UHFFFAOYSA-N

InChi Code: InChI=1S/C6H14O6S2/c1-13(7,8)11-5-3-4-6-12-14(2,9)10/h3-6H2,1-2H3

SMILES Code: CS(=O)(OCCCCOS(C)(=O)=O)=O

Appearance:
Solid powder

Purity:
>97% (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 in water

Shelf Life:
>2 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:
2905591000

Certificate of Analysis:

Safety Data Sheet (SDS):

Handling Instructions:

Preparing Stock Solutions

The following data is based on the product molecular weight 246.3 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: McNeill DR, Lam W, DeWeese TL, Cheng YC, Wilson DM 3rd. Impairment of APE1 function enhances cellular sensitivity to clinically relevant alkylators and antimetabolites. Mol Cancer Res. 2009 Jun;7(6):897-906. Epub 2009 May 26. PubMed PMID: 19470598; PubMed Central PMCID: PMC2745049.

2: Gil L, Styczynski J, Dytfeld D, Debski R, Kazmierczak M, Kolodziej B, Rafinska B, Kubicka M, Nowicki A, Komarnicki M, Wysocki M. Activity of bortezomib in adult de novo and relapsed acute myeloid leukemia. Anticancer Res. 2007 Nov-Dec;27(6B):4021-5. PubMed PMID: 18225565.

3: Li J, Tripathi RC, Tripathi BJ. Drug-induced ocular disorders. Drug Saf. 2008;31(2):127-41. Review. PubMed PMID: 18217789.

4: Duraj J, Bodo J, Sulikova M, Rauko P, Sedlak J. Diverse resveratrol sensitization to apoptosis induced by anticancer drugs in sensitive and resistant leukemia cells. Neoplasma. 2006;53(5):384-92. PubMed PMID: 17013532.

5: Stapleton S, Blaney S. New agents for intrathecal administration. Cancer Invest. 2006 Aug-Sep;24(5):528-34. Review. PubMed PMID: 16939963.

6: Lanvers-Kaminsky C, Bremer A, Dirksen U, Jürgens H, Boos J. Cytotoxicity of treosulfan and busulfan on pediatric tumor cell lines. Anticancer Drugs. 2006 Jul;17(6):657-62. PubMed PMID: 16917211.

7: Kopecky M, Semecky V, Nachtigal P. Vimentin expression during altered spermatogenesis in rats. Acta Histochem. 2005;107(4):279-89. Epub 2005 Sep 2. PubMed PMID: 16139876.

8: Witte AB, Anestål K, Jerremalm E, Ehrsson H, Arnér ES. Inhibition of thioredoxin reductase but not of glutathione reductase by the major classes of alkylating and platinum-containing anticancer compounds. Free Radic Biol Med. 2005 Sep 1;39(5):696-703. PubMed PMID: 16085187.

9: Sorg BL, Hull WE, Kliem HC, Mier W, Wiessler M. Synthesis and NMR characterization of hydroxyurea and mesylglycol glycoconjugates as drug candidates for targeted cancer chemotherapy. Carbohydr Res. 2005 Feb 7;340(2):181-9. PubMed PMID: 15639238.

10: Wigington DP, Urben CM, Strugnell SA, Knutson JC. Combination study of 1,24(S)-dihydroxyvitamin D2 and chemotherapeutic agents on human breast and prostate cancer cell lines. Anticancer Res. 2004 Sep-Oct;24(5A):2905-12. PubMed PMID: 15517895.



Additional Information

Busulfan is a synthetic derivative of dimethane-sulfonate with antineoplastic and cytotoxic properties. Although its mechanism of action is not fully understood, busulfan appears to act through the alkylation of DNA. Following systemic absorption of busulfan, carbonium ions are formed, resulting in DNA alkylation and DNA breaks and inhibition of DNA replication and RNA transcription. Check for active clinical trials or closed clinical trials using this agent. (NCI Thesaurus)
 
 
History
Busulfan was the mainstay of the chemotherapeutic treatment of Chronic Myeloid Leukemia (CML) until it was displaced by the new gold standard, Imatinib, though it is still in use to a degree as a result of the drug's relative inexpense. From http://en.wikipedia.org/wiki/Busulfan.
 
DRUG DESCRIPTION
Busulfan is a bifunctional alkylating agent known chemically as 1,4- butanediol, dimethanesulfonate. BUSULFEX® (busulfan) Injection is intended for intravenous administration. It is supplied as a clear, colorless, sterile, solution in 10 mL single use vials. Each vial of BUSULFEX contains 60 mg (6 mg/mL) of busulfan, the active ingredient, a white crystalline powder with a molecular formula of CH3SO2O(CH2)4OSO2CH3 and a molecular weight of 246 g/mole. Busulfan is dissolved in N,N-dimethylacetamide (DMA) 33% vol/vol and Polyethylene Glycol 400, 67% vol/vol. The solubility of busulfan in water is 0.1 g/L and the pH of BUSULFEX diluted to approximately 0.5 mg/mL busulfan in 0.9% Sodium Chloride Injection, USP or 5% Dextrose Injection, USP as recommended for infusion reflects the pH of the diluent used and ranges from 3.4 to 3.9. BUSULFEX is intended for dilution with 0.9% Sodium Chloride Injection, USP or 5% Dextrose Injection, USP prior to intravenous infusion.
 
Mechanism of Action
Busulfan is a bifunctional alkylating agent in which two labile methanesulfonate groups are attached to opposite ends of a four-carbon alkyl chain. In aqueous media, busulfan hydrolyzes to release the methanesulfonate groups. This produces reactive carbonium ions that can alkylate DNA. DNA damage is thought to be responsible for much of the cytotoxicity of busulfan.