4-(methanesulfonyloxy)butyl methanesulfonate

• ChemBase ID: 881
• Molecular Formular: C6H14O6S2
• Molecular Mass: 246.30176
• Monoisotopic Mass: 246.02318017
• SMILES: S(=O)(=O)(OCCCCOS(=O)(=O)C)C
• Canonical SMILES: CS(=O)(=O)OCCCCOS(=O)(=O)C
• InChI: InChI=1S/C6H14O6S2/c1-13(7,8)11-5-3-4-6-12-14(2,9)10/h3-6H2,1-2H3
• InChIKey: COVZYZSDYWQREU-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 4-(methanesulfonyloxy)butyl methanesulfonate
• IUPAC Traditional name: busulfan
• Brand Name: Busulfex; Citosulfan; Leucosulfan; Mablin; Mielevcin; Mielosan; Mielucin; Milecitan; Mileran; Misulban; Mitosan; Mitostan; Myeleukon; Myeloleukon; Myelosan; Mylecytan; Myleran; Myleran Tablets
• Synonyms: 1,4-Butanediol-dimethanesulfonate Esters; CB-2041; GT-41; Misulban; Busulfan; 4-(methanesulfonyloxy)butyl methanesulfonate; 1,4-Butanediol dimethanesulfonate; 1,4-Butanediol dimethanesulfonate; Butanedioldimethanesulfonate; Busulphan; Busulphane; Buzulfan; Sulfabutin; Sulphabutin; Tetramethylene Dimethane Sulfonate; Tetramethylenester Kyseliny Methansulfonove; busulfan; Busulfan; Myleran; Busulfex; 1,4-丁二醇二甲烷磺酸盐; 白消安; 白消安; 1,4-双(甲基磺酰氧)丁烷

Database IDs

• CAS Number: 55-98-1
• EC Number: 200-250-2
• MDL Number: MFCD00007562
• Beilstein Number: 1791786
• PubChem SID: 160964344; 46506234; 24891664
• PubChem CID: 2478

CALCULATED PROPERTIES

JChem

• H Acceptors: 4
• H Donor: 0
• LogD (pH = 5.5): -0.7590282
• LogD (pH = 7.4): -0.7590282
• Log P: -0.7590282
• Molar Refractivity: 49.5686 cm^3
• Polarizability: 21.777626 Å^3
• Polar Surface Area: 86.74 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: -0.9
• LOG S: -1.68
• Solubility (Water): 5.16e+00 g/l

PROPERTIES

Physical Property

• Solubility: 6.9E+004 mg/L; Acetonitrile; DMSO; Methanol
• Apperance: White Solid
• Melting Point: 114 - 117°C; 114-116°C; 114-117 °C(lit.); 114-118; 115-117 °C
• Hydrophobicity(logP): -0.3; -0.592

Safety Information

• Storage Condition: -20°C; Hygroscopic, Refrigerator, Under Inert Atmosphere; Room Temperature (15-30°C)
• RTECS: EK1750000
• European Hazard Symbols: Toxic (T); Highly toxic (T+)
• UN Number: 2811
• German water hazard class: 3
• Hazard Class: 6.1
• Packing Group: 3; III
• Australian Hazchem: 2X
• Risk Statements: 45-26/27/28; R:45
• Safety Statements: 53-36/37/39-45; S:28-36/37/39-45-53
• EU Classification: T2
• EU Hazard Identification Number: 6.1B
• Emergency Response Guidebook(ERG) Number: 154
• GHS Pictograms: GHS06; GHS08
• GHS Signal Word: Danger
• GHS Hazard statements: H301-H310-H330-H350
• GHS Precautionary statements: P201-P260-P280-P284-P301 + P310-P302 + P350
• Personal Protective Equipment: Eyeshields, Faceshields, full-face particle respirator type N100 (US), Gloves, respirator cartridge type N100 (US), type P1 (EN143) respirator filter, type P3 (EN 143) respirator cartridges
• RID/ADR: UN 2811 6.1/PG 3

Pharmacology Properties

• Gene Information: human ... CYP1A2(1544)

Product Information

• Purity: ≥99.0% (CH); 95%
• Grade: analytical standard, for drug analysis; purum
• Salt Data: Free Base
• Linear Formula: CH3SO2O(CH2)4OSO2CH3

DETAILS

MP Biomedicals - 02154906

(1,4-Butanediol dimethanesulfonate)

DrugBank - DB01008

• Drug Groups: approved; investigational
• Description: An alkylating agent having a selective immunosuppressive effect on bone marrow. It has been used in the palliative treatment of chronic myeloid leukemia (myeloid leukemia, chronic), but although symptomatic relief is provided, no permanent remission is brought about. According to the Fourth Annual Report on Carcinogens (NTP 85-002, 1985), busulfan is listed as a known carcinogen. [PubChem]
• Indication: For use in combination with cyclophosphamide as a conditioning regimen prior to allogeneic hematopoietic progenitor cell transplantation for chronic myelogenous leukemia (FDA has designated busulfan as an orphan drug for this use). Also used as a component of pretransplant conditioning regimens in patients undergoing bone marrow transplantation for acute myeloid leukemia and nonmalignant diseases.
• Pharmacology: Busulfan is an antineoplastic in the class of alkylating agents and is used to treat various forms of cancer. Alkylating agents are so named because of their ability to add alkyl groups to many electronegative groups under conditions present in cells. They stop tumor growth by cross-linking guanine bases in DNA double-helix strands - directly attacking DNA. This makes the strands unable to uncoil and separate. As this is necessary in DNA replication, the cells can no longer divide. In addition, these drugs add methyl or other alkyl groups onto molecules where they do not belong which in turn leads to a miscoding of DNA. Alkylating agents are cell cycle-nonspecific and work by three different mechanisms, all of which achieve the same end result - disruption of DNA function and cell death.
• Toxicity: Signs of overdose include allergic reaction, unusual bleeding or bruising, sudden weakness or unusual fatigue, persistent cough, congestion, or shortness of breath; flank, stomach or joint pain; pronounced nausea, vomiting, diarrhea, dizziness, confusion, or darkening of the skin, chills, fever, collapse, and loss of consciousness.
• Affected Organisms: Humans and other mammals
• Biotransformation: Mainly Hepatic. Busulfan is predominantly metabolized by conjugation with glutathione, both spontaneously and by glutathione S-transferase (GST) catalysis.
• Absorption: Completely absorbed from the gastrointestinal tract.
• Half Life: 2.5 hours
• Protein Binding: 32.4%
• Elimination: Following administration of 14C- labeled busulfan to humans, approximately 30% of the radioactivity was excreted into the urine over 48 hours; negligible amounts were recovered in feces.
• Clearance: * 2.52 ml/min/kg [Following an infusion of dose of 0.8 mg/kg every six hours, for a total of 16 doses over four days]
• References: Lesurtel M, Graf R, Aleil B, Walther DJ, Tian Y, Jochum W, Gachet C, Bader M, Clavien PA: Platelet-derived serotonin mediates liver regeneration. Science. 2006 Apr 7;312(5770):104-7. [Pubmed] ; Valdez BC, Andersson BS: Interstrand crosslink inducing agents in pretransplant conditioning therapy for hematologic malignancies. Environ Mol Mutagen. 2010 Jul;51(6):659-68. [Pubmed] ; Hall AG, Tilby MJ: Mechanisms of action of, and modes of resistance to, alkylating agents used in the treatment of haematological malignancies. Blood Rev. 1992 Sep;6(3):163-73. [Pubmed] ; Ciurea SO, Andersson BS: Busulfan in hematopoietic stem cell transplantation. Biol Blood Marrow Transplant. 2009 May;15(5):523-36. Epub 2009 Feb 12. [Pubmed] ; McCune JS, Holmberg LA: Busulfan in hematopoietic stem cell transplant setting. Expert Opin Drug Metab Toxicol. 2009 Aug;5(8):957-69. [Pubmed] ; 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. [Pubmed] ; Nath CE, Shaw PJ: Busulphan in blood and marrow transplantation: dose, route, frequency and role of therapeutic drug monitoring. Curr Clin Pharmacol. 2007 Jan;2(1):75-91. [Pubmed]
• External Links: Wikipedia; RxList; Drugs.com

Selleck Chemicals - S1692

Research Area: Cardiovascular Disease
Biological Activity:
Busulfan(Myleran, Busulfex) is a cell cycle non-specific alkylating antineoplastic agent, in the class of alkyl sulfonates. Its chemical designation is 1,4-butanediol dimethanesulfonate. 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). [1]

Sigma Aldrich - B2635

包装
10, 25 g in poly bottle

Toronto Research Chemicals - B689900

Alkylating agent with antileukemic activity. Antineoplastic.

REFERENCES

• Lesurtel M, Graf R, Aleil B, Walther DJ, Tian Y, Jochum W, Gachet C, Bader M, Clavien PA: Platelet-derived serotonin mediates liver regeneration. Science. 2006 Apr 7;312(5770):104-7. Pubmed
• Valdez BC, Andersson BS: Interstrand crosslink inducing agents in pretransplant conditioning therapy for hematologic malignancies. Environ Mol Mutagen. 2010 Jul;51(6):659-68. Pubmed
• Hall AG, Tilby MJ: Mechanisms of action of, and modes of resistance to, alkylating agents used in the treatment of haematological malignancies. Blood Rev. 1992 Sep;6(3):163-73. Pubmed
• Ciurea SO, Andersson BS: Busulfan in hematopoietic stem cell transplantation. Biol Blood Marrow Transplant. 2009 May;15(5):523-36. Epub 2009 Feb 12. Pubmed
• McCune JS, Holmberg LA: Busulfan in hematopoietic stem cell transplant setting. Expert Opin Drug Metab Toxicol. 2009 Aug;5(8):957-69. Pubmed
• 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. Pubmed
• Nath CE, Shaw PJ: Busulphan in blood and marrow transplantation: dose, route, frequency and role of therapeutic drug monitoring. Curr Clin Pharmacol. 2007 Jan;2(1):75-91. Pubmed
• http://en.wikipedia.org/wiki/Busulfan
• Ehrsson, H., et al.: Clin. Pharmacol. Ther., 34, 86 (1983)
• Bishop, J.B., et al.: Mutat. Res., 168,15 (1983)
• Tariq, M., et al.: Anal. Profiles Drug Subs., 16, 53 (1983)