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| Systematic (IUPAC) name | |
|---|---|
| butane-1,4-diyl dimethanesulfonate | |
| Identifiers | |
| CAS number | 55-98-1 |
| ATC code | L01AB01 |
| PubChem | 2478 |
| DrugBank | APRD00664 |
| ChemSpider | 2384 |
| Chemical data | |
| Formula | C6H14O6S2 |
| Mol. mass | 246.304 g/mol |
| SMILES | eMolecules & PubChem |
| Pharmacokinetic data | |
| Bioavailability | 80% (oral) |
| Protein binding | 32.4% |
| Metabolism | Hepatic |
| Half life | 2.5 hours |
| Excretion | ? |
| Therapeutic considerations | |
| Licence data | |
| Pregnancy cat. | D(US) |
| Legal status | ℞ Prescription only |
| Routes | Oral, parenteral |
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Busulfan is a chemotherapy drug that is a cell cycle non-specific alkylating antineoplastic agent (slows the growth of cancer cells). More specifically it belongs to a subclass of alkylating agents known as alkyl sulfonates. It is marketed in the U.S. by GlaxoSmithKline under the brand name Myleran, and has been in clinical use since 1959. Busulfan is also available in an IV formulation marketed as Busulfex by PDL BioPharma, Inc. Its chemical designation is 1,4-butanediol dimethanesulfonate.
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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.
Currently, its main uses are in bone marrow transplantation, especially in chronic myelogenous leukemia (CML), where it is used as a conditioning drug. Busulfan can control tumor burden but cannot prevent transformation or correct cytogenic abnormalities. Though not as common, it may also be used for Chronic Lymphocytic Leukemia (CLL). The drug was recently used in a study to examine the role of platelet-transported serotonin in liver regeneration.[1]
Myleran is supplied in white film coated tablets with 2mg of Busulfan per tablet. it is also used in the treatment of chronic lymphocytic leukemia
Toxicity may include interstitial pulmonary fibrosis, hyperpigmentation, seizures, hepatic (veno-occlusive disease) and wasting syndrome. Phenytoin may be used concurrently to prevent the seizures.
1,4-Butanediol dimethanesulfonate is listed by the IARC as a Group 1 carcinogen.
Its mechanism of action through alkylation produces Guanine-Adenine intrastrand crosslinks.[2] This occurs through an SN2 reaction in which the relatively nucleophilic guanine N7 attacks the carbon adjacent to the mesylate leaving group. This kind of damage cannot be repaired by cellular machinery and thus the cell undergoes apoptosis.[3] Busulfan also induces thrombocytopenia, a condition of lowered blood platelet count and activity.
The molecular recognition of ureido-cyclodextrin with busulfan was investigated.[4]. The formation of complexes was observed with electrostatic interactions between urea and the sulfonate part of busulfan. A other structure was used for this complextation type, two disaccharidyl units connected by urea linkers to a diazacrown ether organizing platform [5].
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