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MedKoo product information:
Busulfan
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MedKoo Code#: 100110
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Name:
Busulfan
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CAS#: 55-98-1
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: CB-2041; GT-41; WR-19508; Chemical structure names: ;
1,4-bis(methanesulfonoxy)butane; 1,4-bitanediol
dimethanesulfonate esters; 1,4-butanediol dimethylsulfonate;
1,4-di(methanesulfonyloxy)butane; 1,4-di(methylsulfonyloxy)butane.
IUPAC/Chemical name:
butane-1,4-diyl dimethanesulfonate
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Chemical structure:
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Theoretical analysis
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Chemical Formula: C6H14O6S2
Exact Mass: 246.02318
Molecular Weight: 246.30
m/z: 246.02318 (100.0%), 248.01898 (9.0%),
247.02653 (6.5%), 247.02257 (1.6%), 248.02743 (1.2%)
Elemental Analysis: C, 29.26; H, 5.73; O,
38.98; S, 26.04
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Quality control
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Product will be shipped with
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Information about this agent
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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.
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.
11: Mertins SD, Myers TG, Holbeck SL, Medina-Perez W, Wang E, Kohlhagen
G, Pommier Y, Bates SE. In vitro evaluation of dimethane sulfonate
analogues with potential alkylating activity and selective renal cell
carcinoma cytotoxicity. Mol Cancer Ther. 2004 Jul;3(7):849-60. PubMed
PMID: 15252146.
12: Fedier A, Schlamminger M, Schwarz VA, Haller U, Howell SB, Fink D.
Loss of atm sensitises p53-deficient cells to topoisomerase poisons and
antimetabolites. Ann Oncol. 2003 Jun;14(6):938-45. PubMed PMID:
12796033.
13: Fedier A, Steiner RA, Schwarz VA, Lenherr L, Haller U, Fink D. The
effect of loss of Brca1 on the sensitivity to anticancer agents in
p53-deficient cells. Int J Oncol. 2003 May;22(5):1169-73. PubMed PMID:
12684687.
14: Baumhäkel M, Kasel D, Rao-Schymanski RA, Böcker R, Beckurts KT,
Zaigler M, Barthold D, Fuhr U. Screening for inhibitory effects of
antineoplastic agents on CYP3A4 in human liver microsomes. Int J Clin
Pharmacol Ther. 2001 Dec;39(12):517-28. PubMed PMID: 11770832.
15: Nieto Y. Pharmacodynamics of high-dose chemotherapy. Curr Drug Metab.
2001 Mar;2(1):53-66. Review. PubMed PMID: 11465151.
16: van den Bongard HJ, Mathôt RA, Beijnen JH, Schellens JH.
Pharmacokinetically guided administration of chemotherapeutic agents.
Clin Pharmacokinet. 2000 Nov;39(5):345-67. Review. PubMed PMID:
11108434.
17: Sanyal U, Nanda R, Samanta S, Pain A, Dutta S, Verma AS, Rider BJ,
Agrawal KC. Evaluation of dimethylaminosulfonates of alkane diols as a
novel group of anticancer agents. Cancer Lett. 2000 Jul 3;155(1):89-97.
PubMed PMID: 10814884.
18: Reber U, Wüllner U, Trepel M, Baumgart J, Seyfried J, Klockgether T,
Dichgans J, Weller M. Potentiation of treosulfan toxicity by the
glutathione-depleting agent buthionine sulfoximine in human malignant
glioma cells: the role of bcl-2. Biochem Pharmacol. 1998 Feb
1;55(3):349-59. PubMed PMID: 9484802.
19: Navarra P, Preziosi P. Disruptions of the hypothalamo-pituitary-adrenal
axis increase anticancer drug lethality in the rat. Toxicol Lett. 1997
May 16;91(3):219-27. PubMed PMID: 9217242.
20: Pauwels O, Atassi G, Kiss R. Combination of computerized
morphonuclear and multivariate analyses to characterize in vitro the
antineoplastic effect of alkylating agents. J Pharmacol Toxicol Methods.
1995 Feb;33(1):35-45. PubMed PMID: 7727807.
21: Mross K, Bewermeier P, Reifke J, Krüger W, Stockschläder M, Zander
A, Hossfeld DK. Pharmacokinetics of high-dose VP-16: 6-hour infusion
versus 34-hour infusion. Bone Marrow Transplant. 1994 Apr;13(4):423-30.
PubMed PMID: 8019466.
22: Majado MJ, González García C, Marín-Blazquez MD, Morales Lázaro A,
Moreno Moreno M. [Appearance of a chronic myeloid leukemia in
Waldenström's macroglobulinemia]. Sangre (Barc). 1992 Dec;37(6):465-6.
Spanish. PubMed PMID: 1293799.
23: Fujita H. [Clinical pharmacology of anticancer agents. (Part 1)
Introduction, alkylating agents and platinum compounds]. Gan To Kagaku
Ryoho. 1991 Nov;18(14):2481-7. Japanese. PubMed PMID: 1952967.
24: Vassal G, Deroussent A, Hartmann O, Challine D, Benhamou E,
Valteau-Couanet D, Brugières L, Kalifa C, Gouyette A, Lemerle J.
Dose-dependent neurotoxicity of high-dose busulfan in children: a
clinical and pharmacological study. Cancer Res. 1990 Oct
1;50(19):6203-7. PubMed PMID: 2400986.
25: Paolucci G, Rosito P, Di Caro A. [Late data in pediatric oncology].
Pediatr Med Chir. 1990 Jul-Aug;12(4):323-7. Review. Italian. PubMed
PMID: 2075095.
26: Franssen C, Boekema P, De Witte T, Wessels J, Van der Kogel A,
Haanen C. DNA strand breaks in human leukocytes induced by chemotherapy
and total body irradiation. Leuk Res. 1990;14(1):91-7. PubMed PMID:
2406513.
27: Leclerc P, Robillard M. [Respiratory complications of anticancer
chemotherapy]. Rev Pneumol Clin. 1986;42(3):142-9. Review. French.
PubMed PMID: 3534991.
28: Hodel C, Ettlin RA, Zschauer A. Morphological changes produced in
rat testis by anticancer drugs. Arch Toxicol Suppl. 1984;7:147-50.
PubMed PMID: 6595974.
29: Singh B, Gupta RS. Mutagenic responses of thirteen anticancer drugs
on mutation induction at multiple genetic loci and on sister chromatid
exchanges in Chinese hamster ovary cells. Cancer Res. 1983
Feb;43(2):577-84. PubMed PMID: 6848181.
30: Singh B, Gupta RS. Comparison of the mutagenic responses of 12
anticancer drugs at the hypoxanthine-guanine phosphoribosyl transferase
and adenosine kinase loci in Chinese hamster ovary cells. Environ
Mutagen. 1983;5(6):871-80. PubMed PMID: 6317371.
31: Gola A, Orzechowska-Juzwenko K. Toxicity interactions and ways of
reducing side effects of anticancer drugs. Folia Haematol Int Mag Klin
Morphol Blutforsch. 1982;109(4):521-32. PubMed PMID: 6184274.
32: Kawazoe Y, Tamura N. Synthesis and antitumor effect of new
biological alkylating agents, isethionic acid esters. Gann. 1981
Dec;72(6):862-7. PubMed PMID: 6281116.
33: Chiuten DF, Rozencweig M, Von Hoff DD, Muggia FM. Clinical trials
with the hexitol derivatives in the U.S. Cancer. 1981 Feb
1;47(3):442-51. Review. PubMed PMID: 6784907.
34: Mizushima Y. [Enhancement of the antitumor transplantation
resistance in rats by the antileukemia drug busulfan (author's transl)].
Hokkaido Igaku Zasshi. 1980 Nov;55(6):537-42. Japanese. PubMed PMID:
7274985.
35: Pak K, Iwasaki T, Miyakawa M, Yoshida O. The mutagenic activity of
anti-cancer drugs and the urine of rats given these drugs. Urol Res.
1979 Jun 22;7(2):119-24. PubMed PMID: 382571.
36: Soots A, Häyry P. Prolongation of rat cardiac allograft survival by
donor pretreatment. Screening of antineoplastic drugs. Transplantation.
1978 May;25(5):259-64. PubMed PMID: 349802.
37: Flubacher P, Meier V, Obrecht JP, Hartmann D. [Cytostatic
pneumopathy following chemotherapy for metastasizing breast neoplasm].
Schweiz Med Wochenschr. 1977 Oct 8;107(40):1412-7. German. PubMed PMID:
918593.
38: Stutzman L, Sokal JE. Use of anticancer drugs during pregnancy. Clin
Obstet Gynecol. 1968 Jun;11(2):416-27. Review. PubMed PMID: 4879373.
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