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1,4-Butandiol-dimethylsulfonat
busulphan · 1,4-BUTANEDIOL DIMETHANESULFONATE · myleran · busulfex · Butane-1,4-diyl dimethanesulfonate · gt41 · x149 · mablin
Identifikatoren & physikalische Daten
| CAS No. | 55-98-1 |
|---|---|
| Summenformel | C6H14O6S2 |
| Durchschnittliche Molmasse | 246,3 g/mol |
| Monoisotopische Masse | 246,02318017 g/mol |
| SMILES | CS(=O)(=O)OCCCCOS(C)(=O)=O |
| InChIKey | COVZYZSDYWQREU-UHFFFAOYSA-N |
| PubChem CID | 2478 |
| ChEMBL | CHEMBL820 |
| ChEBI | CHEBI:28901 |
| EC No. | 200-250-2 |
| DTXSID | DTXSID3020910 |
| Lokaler Name | 1,4-Butandiol-dimethylsulfonat |
Chemische & physikalische Eigenschaften
| XLogP | -0,5 |
|---|---|
| Polarare Oberfläche (TPSA) | 104 |
| H-Brücken-Donoren | 0 |
| H-Brücken-Akzeptoren | 6 |
| Frei drehbare Bindungen | 7 |
| Schwere Atome | 14 |
| Formalladung | 0 |
| Komplexität | 293 |
| Arzneimittel | Pharmaceuticals -> Listed in ZINC15 |
| SpringerMaterials Properties | Diamagnetic susceptibility |
| LogP (Verteilungskoeffizient) | log Kow = -0.52-0.3 |
| Color/Form | White needlesCrystals |
| Löslichkeit | Decomposes (NTP, 1992)Solubility in acetone at 25 °C: 2.4 g/100mLin alcohol: 0.1g/100 mL. Practically insoluble in water but will dissolve slowly as hydrolysis takes place.5.16e+00 g/LVery slightly soluble in water, freely soluble in acetone and in acetonitrile, very slightly soluble in ethanol (96 per cent). |
| Human Drugs | Breast FeedingLactationAntineoplastic AgentsAlkylating AgentsFDA approved drugs -> Active ingredientEMA approved medicines: Human medicine |
| Endocrine Disruptors | Potential endocrine disrupting compound |
| Schmelzpunkt | 237 to 244 °F (NTP, 1992)106-107114-118 °C287 °C114-117 °C(lit.) |
| Physical Description | Myleran appears as white crystals or powder. (NTP, 1992)Solid |
| Stability/Shelf Life | ... Solutions of busulfan diluted in 0.9% sodium chloride injection also have been shown to be stable when refrigerated at 2-8 °C for up to 12 hours, during which time the infusion must be completed. |
| Collision Cross Section | 149.55 Ų [M+K]+ [CCS Type: TWMethod: calibrated with polyalanine and drug standards] |
| Siedepunkt | 359.3°C (rough estimate) |
| Dichte | 1.305 (estimate) |
| Brechungsindex | 1.5630 (estimate) |
| Flammpunkt | 9℃ |
| Lagerbedingungen | Inert atmosphere,Room Temperature |
| Aggregatzustand | Crystalline Powder |
| Farbe | Pale Brown |
| Merck | 14,1505 |
| BRN | 1791786 |
| Stabilität | Moisture Sensitive |
| Hauptanwendungen | forensics and toxicologyveterinary |
| 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 |
| SMILES | CS(=O)(=O)OCCCCOS(C)(=O)=O |
| CAS Datenbank | 55-98-1(CAS DataBase Reference) |
| EPA chemische Informationen | Busulfan (55-98-1) |
Sicherheit & Vorschriften
| GHS-Einstufung | DangerH300 (17.6%): Fatal if swallowed [Danger Acute toxicity, oral]P203, P260, P261, P262, P264, P264+P265, P270, P271, P280, P284, P301+P316, P302+P352, P304+P340, P305+P351+P338, P316, P318, P319, P320, P321, P330, P332+P317, P337+P317, P361+P364, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)Aggregated GHS information provided per 51 reports by companies from 10 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.H301: Toxic if swallowed [Danger Acute toxicity, oral] |
|---|---|
| Regulatorische Informationen | Hazard Traits - CarcinogenicityDevelopmental Toxicity |
| Weitere Sicherheitsinformationen | IMAP assessments - 1,4-Butanediol, dimethanesulfonate: Environment tier I assessment |
| DOT-Kennzeichnung | Poison |
| Brandgefahren | Flash point data for this chemical are not available. It is probably combustible. (NTP, 1992) |
| Gesundheitsgefahren | SYMPTOMS: Symptoms of exposure to this compound may include nausea, vomiting, diarrhea, impotence, sterility, amenorrhea, fetal malformation, depression of erythropoiesis leading to aplastic anemia, diffuse pulmonary fibrosis, precipitation of uric acid in kidney tubules and hemorrhages. |
| FDA-Anforderungen | The Approved Drug Products with Therapeutic Equivalence Evaluations List identifies currently marketed prescription drug products, incl busulfan, approved on the basis of safety and effectiveness by FDA under sections 505 of the Federal Food, Drug, and Cosmetic Act. |
| Reaktive Gruppe | Esters, Sulfate Esters, Phosphate Esters, Thiophosphate Esters, and Borate Esters |
| Special Reports | National Toxicology Program. Eleventh Report on Carcinogens (2005). The Report on Carcinogens is an informational scientific and public health document that identifies and discusses substances (including agents, mixtures, or exposure circumstances) that may pose a carcinogenic hazard to human health. 1,4-Butanediol Dimethanesulfonate (Myleran) (55-98-1) is listed as known to be a human carcinogen.[Available from, as of July 31, 2009: http://ntp.niehs.nih.gov/ntp/roc/eleventh/profiles/s026buta.pdf] |
Anwendungen & Verwendung
Beschreibung
Chemically, busulfan is classified as an alkyl sulfonate. One or both of the methylsulfonate ester moieties can be displaced by the nucleophilic N7 of guanine, leading to monoalkylated and cross-linked DNA. The extent of alkyl sulfonate–mediated DNA interstrand cross-linking has been shown to vary with the length of the alkyl chain between sulfonate esters, with the tetramethylene-containing busulfan showing less interstrand cross-linking capability than hexamethylene, methylene, or octamethylene analogues. Intrastrand cross-linking also occurs, preferentially at 5′-GA-3′ but also at 5′-GG-3′ sequences. Alkylation of Cys sulfhydryl groups is yet another mechanism of cytotoxicity.
Verwenden
Busulfan USP (Myleran) is used to treat Chronic granulocytic leukemia; other myeloproliferative disorders.