Busulfan | CAS# 55-98-1 | anticancer

MedKoo Cat#: 100110 | Name: Busulfan

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Description:

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

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

Busulfan

CAS#55-98-1

Theoretical Analysis

MedKoo Cat#: 100110

Name: Busulfan

CAS#: 55-98-1

Chemical Formula: C6H14O6S2

Exact Mass: 246.0232

Molecular Weight: 246.30

Elemental Analysis: C, 29.26; H, 5.73; O, 38.98; S, 26.04

Price and Availability

Size	Price	Availability
500mg	USD 90.00	Ready to ship
1g	USD 150.00	Ready to ship
2g	USD 250.00	Ready to ship
5g	USD 450.00	Ready to ship

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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

More Info

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. BUSULFEXÂ® (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.

Product Data

Product Data

Certificate of Analysis

View CoA: current batch, Lot#T9C03I04

Safety Data Sheet (SDS)

View Safety Data Sheet (SDS)

Instruction

View handling instruction

Biological target:

Busulfan is a potent alkylator with selective immunosuppressive effect on bone marrow.

In vitro activity:

To further confirm the role of busulfan in platelet apoptosis, antiapoptotic molecule Bcl-2 and proapoptotic molecule Bax, as well as activation of caspase-3, were measured in platelets after busulfan treatment. Consistent with busulfan-induced increased mitochondrial membrane depolarization, significantly reduced expression of Bcl-2, increased expression of Bax, and activation of caspase-3 were observed in platelet treated with busulfan in a dose-dependent manner compared with in vehicle-treated platelets (Figure 3), suggesting busulfan induces platelet apoptosis through regulation of the expression of Bcl-2 and Bax, leading to subsequent increased caspase-3 activation. Reference: Biol Blood Marrow Transplant. 2016 Sep;22(9):1565-1572. https://www.astctjournal.org/article/S1083-8791(16)30137-9/fulltext

In vivo activity:

With busulfan preconditioning, the proportion of human CD45+ leukocytes, various human lymphocytes subsets, DCs and the ratio of CD4+ to CD8+ cells in peripheral blood of NOG mice were significantly higher than those of the untreated group (P < 0.05). Moreover, two subsets of monocytes, classic (CD14+ CD16–) and non-classic (CD14+ CD16+), were also differentiated and showed a significant difference between the two groups (P < 0.05). Reference: Cell Transplant. 2019 Jul; 28(7): 973–979. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6719503/

	Solvent	mg/mL	mM
Solubility
	DMSO	38.6	156.60
	DMSO:PBS (pH 7.2) (1:1)	0.5	2.03
	DMF	16.7	67.80
	Water	1.0	4.06

Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 246.30 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.

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

Formulation protocol:

1. Qiao J, Wu Y, Liu Y, Li X, Wu X, Liu N, Zhu F, Qi K, Cheng H, Li D, Li H, Li Z, Zeng L, Ma P, Xu K. Busulfan Triggers Intrinsic Mitochondrial-Dependent Platelet Apoptosis Independent of Platelet Activation. Biol Blood Marrow Transplant. 2016 Sep;22(9):1565-1572. doi: 10.1016/j.bbmt.2016.06.006. Epub 2016 Jun 9. PMID: 27292166. 2. Mei Q, Li F, Quan H, Liu Y, Xu H. Busulfan inhibits growth of human osteosarcoma through miR-200 family microRNAs in vitro and in vivo. Cancer Sci. 2014 Jul;105(7):755-62. doi: 10.1111/cas.12436. Epub 2014 Jul 3. PMID: 24815002; PMCID: PMC4317920. 3. Leonard A, Yapundich M, Nassehi T, Gamer J, Drysdale CM, Haro-Mora JJ, Demirci S, Hsieh MM, Uchida N, Tisdale JF. Low-Dose Busulfan Reduces Human CD34+ Cell Doses Required for Engraftment in c-kit Mutant Immunodeficient Mice. Mol Ther Methods Clin Dev. 2019 Nov 11;15:430-437. doi: 10.1016/j.omtm.2019.10.017. PMID: 31890735; PMCID: PMC6909187. 4. Guo X, Yin X, Zhu W, Pan Y, Wang H, Liang Y, Zhu X. The Preconditioning of Busulfan Promotes Efficiency of Human CD133+ Cells Engraftment in NOD Shi-SCID IL2Rγcnull (NOG) Mice via Intra-Bone Marrow Injection. Cell Transplant. 2019 Jul;28(7):973-979. doi: 10.1177/0963689719842162. Epub 2019 Apr 15. PMID: 30983406; PMCID: PMC6719503.

In vitro protocol:

In vivo protocol:

1. Leonard A, Yapundich M, Nassehi T, Gamer J, Drysdale CM, Haro-Mora JJ, Demirci S, Hsieh MM, Uchida N, Tisdale JF. Low-Dose Busulfan Reduces Human CD34+ Cell Doses Required for Engraftment in c-kit Mutant Immunodeficient Mice. Mol Ther Methods Clin Dev. 2019 Nov 11;15:430-437. doi: 10.1016/j.omtm.2019.10.017. PMID: 31890735; PMCID: PMC6909187. 2. Guo X, Yin X, Zhu W, Pan Y, Wang H, Liang Y, Zhu X. The Preconditioning of Busulfan Promotes Efficiency of Human CD133+ Cells Engraftment in NOD Shi-SCID IL2Rγcnull (NOG) Mice via Intra-Bone Marrow Injection. Cell Transplant. 2019 Jul;28(7):973-979. doi: 10.1177/0963689719842162. Epub 2019 Apr 15. PMID: 30983406; PMCID: PMC6719503.

1: Buggia I, Locatelli F, Regazzi MB, Zecca M. Busulfan. Ann Pharmacother. 1994 Sep;28(9):1055-62. doi: 10.1177/106002809402800911. PMID: 7803883. 2: O'Marcaigh AS, Betcher DL. Busulfan. J Pediatr Oncol Nurs. 1996 Jul;13(3):150-2. doi: 10.1177/104345429601300308. PMID: 8755444. 3: McCune JS, Holmberg LA. Busulfan in hematopoietic stem cell transplant setting. Expert Opin Drug Metab Toxicol. 2009 Aug;5(8):957-69. doi: 10.1517/17425250903107764. PMID: 19611402. 4: Lawson R, Staatz CE, Fraser CJ, Hennig S. Review of the Pharmacokinetics and Pharmacodynamics of Intravenous Busulfan in Paediatric Patients. Clin Pharmacokinet. 2021 Jan;60(1):17-51. doi: 10.1007/s40262-020-00947-2. Epub 2020 Oct 30. PMID: 33128207. 5: Krivoy N, Hoffer E, Lurie Y, Bentur Y, Rowe JM. Busulfan use in hematopoietic stem cell transplantation: pharmacology, dose adjustment, safety and efficacy in adults and children. Curr Drug Saf. 2008 Jan;3(1):60-6. doi: 10.2174/157488608783333899. PMID: 18690982. 6: ten Brink MH, Zwaveling J, Swen JJ, Bredius RG, Lankester AC, Guchelaar HJ. Personalized busulfan and treosulfan conditioning for pediatric stem cell transplantation: the role of pharmacogenetics and pharmacokinetics. Drug Discov Today. 2014 Oct;19(10):1572-86. doi: 10.1016/j.drudis.2014.04.005. Epub 2014 Apr 16. PMID: 24747172. 7: Das P, Doyle J, Dupuis LL. Appropriate busulfan dosing. Bone Marrow Transplant. 2005 Jan;35(2):199-200. doi: 10.1038/sj.bmt.1704737. PMID: 15516934. 8: Hassan M. The role of busulfan in bone marrow transplantation. Med Oncol. 1999 Sep;16(3):166-76. doi: 10.1007/BF02906128. PMID: 10523796. 9: Vassal G. Pharmacologically-guided dose adjustment of busulfan in high-dose chemotherapy regimens: rationale and pitfalls (review). Anticancer Res. 1994 Nov-Dec;14(6A):2363-70. PMID: 7825973. 10: Hali F, Araqi Houssaini L, Quessar A, Marnissi F, Meftah A, Chiheb S. Une réaction cutanée inhabituelle au busulfan : étude observationnelle de 9 cas [An unusual cutaneous reaction to busulfan: 9 cases]. Therapie. 2022 Sep- Oct;77(5):624-627. French. doi: 10.1016/j.therap.2021.12.019. Epub 2021 Dec 30. PMID: 35034779. 11: Carruthers VA, Lum SH, Flood T, Slatter MA, Gennery AR. Hematopoietic Cell Transplant for CD40 Ligand Deficiency-Comparing Busulfan Versus Treosulfan. J Clin Immunol. 2022 Apr;42(3):703-705. doi: 10.1007/s10875-021-01200-6. Epub 2022 Jan 28. PMID: 35088211. 12: McCune JS, Punt AM, Yeh RF, Dupuis LL, Kweekel DM, Franssen EJF, Ritchie JC, van Maarseveen E, Huitema ADR. Quality Control of Busulfan Plasma Quantitation, Modeling, and Dosing: An Interlaboratory Proficiency Testing Program. Ther Drug Monit. 2021 Oct 1;43(5):657-663. doi: 10.1097/FTD.0000000000000862. PMID: 33675302. 13: Salman B, Al-Khabori M, Al-Huneini M, Al-Rawas A, Dennison D, Al-Za'abi M. Busulfan clearance does not predict the development of hepatic veno-occlusive disease in patients undergoing hematopoietic stem cell transplantation. Int J Hematol. 2020 Aug;112(2):210-216. doi: 10.1007/s12185-020-02891-0. Epub 2020 May 28. PMID: 32468179. 14: Pearl M. Busulfan lung. Am J Dis Child. 1977 Jun;131(6):650-2. PMID: 266839. 15: Grochow LB, Krivit W, Whitley CB, Blazar B. Busulfan disposition in children. Blood. 1990 Apr 15;75(8):1723-7. PMID: 2328321. 16: Morris LE, Guthrie TH Jr. Busulfan-induced hepatitis. Am J Gastroenterol. 1988 Jun;83(6):682-3. PMID: 3376924. 17: Mehta PA, Emoto C, Fukuda T, Seyboth B, Teusink-Cross A, Davies SM, Wilhelm J, Fuller K, Vinks AA, Boulad F. Busulfan Pharmacokinetics and Precision Dosing: Are Patients with Fanconi Anemia Different? Biol Blood Marrow Transplant. 2019 Dec;25(12):2416-2421. doi: 10.1016/j.bbmt.2019.07.014. Epub 2019 Jul 18. PMID: 31326610; PMCID: PMC7219959. 18: Navarro SL, Randolph TW, Shireman LM, Raftery D, McCune JS. Pharmacometabonomic Prediction of Busulfan Clearance in Hematopoetic Cell Transplant Recipients. J Proteome Res. 2016 Aug 5;15(8):2802-11. doi: 10.1021/acs.jproteome.6b00370. Epub 2016 Jul 20. PMID: 27350098; PMCID: PMC5025252. 19: Zao JH, Schechter T, Liu WJ, Gerges S, Gassas A, Egeler RM, Grunebaum E, Dupuis LL. Performance of Busulfan Dosing Guidelines for Pediatric Hematopoietic Stem Cell Transplant Conditioning. Biol Blood Marrow Transplant. 2015 Aug;21(8):1471-8. doi: 10.1016/j.bbmt.2015.05.006. Epub 2015 May 11. PMID: 25977229. 20: Rodríguez Cuartero A, Durán Cara E, Peláez Redondo J. Insuficiencias suprarrenales busulfánicas [Busulfan-induced adrenal insufficiency]. Rev Clin Esp. 1973 Oct 15;131(1):73-8. Spanish. PMID: 4520013.