Busulfan

An alkylating antineoplastic agent used primarily in myeloablative conditioning regimens before hematopoietic stem cell transplantation and historically in the treatment of chronic myeloid leukemia. Busulfan forms covalent DNA adducts and interstrand cross-links, disrupting DNA replication and inducing cell death, particularly in rapidly proliferating hematopoietic cells. It produces profound bone marrow suppression and is administered orally or intravenously. Major toxicities include myelosuppression, hepatic sinusoidal obstruction syndrome, pulmonary toxicity, and seizures; therapeutic drug monitoring is often used to optimize exposure during transplantation conditioning

CAS Number: 55-98-1

Molecular Mass: 246.3 g/mol

Formula: C₆H₁₄O₆S₂

Smiles: CS(=O)(=O)OCCCCOS(C)(=O)=O

Synonymes:

Busulfan, busulfan, 55-98-1, Myleran, Busulphan, Sulphabutin, Leucosulfan, Busulfex, Myelosan, Myeloleukon, Sulfabutin, Mablin, Mielucin, Misulban, Mitostan, Mylecytan, Mielevcin, Mielosan, Milecitan, Mileran, Myeleukon, 1,4-BUTANEDIOL DIMETHANESULFONATE, 1,4-Dimesyloxybutane, 1,4-Butanediol, dimethanesulfonate, Busulfano, Busulfanum, Myelosanum, 1,4-Dimethanesulfonoxybutane, Tetramethylene dimethane sulfonate, Busilvex, Mitosan, 1,4-Dimethylsulfonyloxybutane, NCI-C01592, 1,4-Bis(methanesulfonoxy)butane, 1,4-Butanediol dimethylsulfonate, NSC-750, 1,4-Bis(methanesulfonyloxy)butane, GT 41, Tetramethylene bis(methanesulfonate), 1,4-Butanediol dimethanesulphonate, CB 2041, Methanesulfonic acid, tetramethylene ester, NSC 750, Tetramethylenester kyseliny methansulfonove, C.B. 2041, Bisulfex, NSC750, DTXSID3020910, 4-(methanesulfonyloxy)butyl methanesulfonate, Tetramethylene bis[methanesulfonate], G1LN9045DK, 1,4-Bis[methanesulfonoxy]butane, CHEBI:28901, DTXCID10910, BUSULFAN FRESENIUS KABI, 4-04-00-00019 (Beilstein Handbook Reference), CB-2041, Bussulfam, Joacamine, Misulfan, 1,4-di(methanesulfonyloxy)butane, GT-41, RefChem:5626, Tetramethylenedimethanesulfonate, 1,4-di(methylsulfonyloxy)butane, L01AB01, 1, 4-Bis(methanesulfonoxy)butane, methanesulfonic acid tetramethylene ester, 1,4-Bitanediol Dimethanesulfonate Esters, WR-19508, 200-250-2, Glyzophrol, Wellcome, Busulfan, Citosulfan, Buzulfan, butane-1,4-diyl dimethanesulfonate, Busulphane, 1,4-Dimethanesulfonyloxybutane, 4-methylsulfonyloxybutyl methanesulfonate, 1,4-Dimethylsulfonoxybutane, AN 33501, 1,4-Dimethanesulphonyloxybutane, X 149, GT 2041, 1,4-Butanediol, dimethanesulphonate, MFCD00007562, 2041 C. B., G.T. 41, s1692, NCGC00090905-06, Busulfanum [INN-Latin], Busulfano [INN-Spanish], Methanesulfonic, CAS-55-98-1, CCRIS 418, Busulfan, Butane-1,4-diyl di(methanesulfonate), SR-01000765405, EINECS 200-250-2, BRN 1791786, UNII-G1LN9045DK, AI3-25012, Busulfan/Myleran, Busulfex IV, Busulfan [USP:INN:BAN:JAN], Busulfan CRS, HSDB 7605, Tetramethylenester kyseliny methansulfonove [Czech], Prestwick_989, Tetramethylene {bis[methanesulfonate]}, 1,4-Butanediol-dimethanesulfonate Esters, Spectrum_000092, BUSULFAN [HSDB], BUSULFAN [IARC], BUSULFAN [INN], BUSULFAN [JAN], 2041 C.B., BUSULFAN [MI], BUSULFAN [VANDF], Spectrum2_000067, Spectrum3_000320, Spectrum4_000259, Spectrum5_000928, BUSULFAN [MART.], BUSULFAN [WHO-DD], BUSULFAN [WHO-IP], CHEMBL820, NCIMech_000192, SCHEMBL4373, BUSULFAN [EMA EPAR], MYELOSANUM [WHO-IP], WLN: WS1&O4OSW1, BSPBio_001920, KBioGR_000698, KBioSS_000512, MLS001076666, Busulfan (Myleran, Busulfex), DivK1c_000847, SPECTRUM1500152, Busulfan (JP18/USP/INN), SPBio_000253, BUSULFAN [EP IMPURITY], BUSULFAN [ORANGE BOOK], GTPL7136, orb1310165, orb3141182, BUSULFAN [EP MONOGRAPH], BUSULFAN [USP MONOGRAPH], COVZYZSDYWQREU-UHFFFAOYSA-, HMS502K09, KBio1_000847, KBio2_000512, KBio2_003080, KBio2_005648, KBio3_001420, butane-1,4-diyldimethanesulfonate, BUSULFANUM [WHO-IP LATIN], NINDS_000847, GLXC-07732, HMS1920I07, HMS2091O09, HMS2233H04, HMS3259G15, HMS3370E11, HMS3655A21, HMS3712A20, HMS5079P12, Pharmakon1600-01500152, HY-B0245, MSK10327, Tox21_111038, Tox21_201848, Tox21_300318, 1, {4-Bis[methanesulfonoxy]butane}, 2041CB, AC-198, BDBM50237623, CCG-35458, EBC-03587, NSC755916, AKOS003614975, Tox21_111038_1, DB01008, FB19365, KS-5212, NC00498, NSC-755916, IDI1_000847, NCGC00090905-01, NCGC00090905-02, NCGC00090905-03, NCGC00090905-04, NCGC00090905-05, NCGC00090905-07, NCGC00090905-08, NCGC00090905-09, NCGC00090905-10, NCGC00090905-11, NCGC00090905-12, NCGC00254038-01, NCGC00259397-01, 4-(methylsulfonyloxy)butyl methylsulfonate, NCI60_041640, SMR000058613, SY029743, TETRAMETHYLENE DI(METHANESULFONATE), SBI-0051300.P003, B1022, NS00010142, ST45022142, SW198555-3, C06862, D00248, D88731, EN300-118686, 4-[(Methylsulfonyl)oxy]butyl methanesulfonate #, AB00051929-10, AB00051929-11, AB00051929_12, AB00051929_14, Busulfan, analytical standard, for drug analysis, F001734, Q348922, SR-01000765405-2, SR-01000765405-3, SR-01000765405-7, BRD-K23204545-001-15-6, BRD-K23204545-001-16-4, BRD-K23204545-001-18-0, Busulfan Working Standard (Secondary Reference Standard), Busulfan, European Pharmacopoeia (EP) Reference Standard, Z276508890, InChI=1/C6H14O6S2/c1-13(7,8)11-5-3-4-6-12-14(2,9)10/h3-6H2,1-2H3

Bioactivity: Bifunctional DNA-alkylating agent; alkylsulfonate antineoplastic drug; myeloablative agent

Solubility in Different Solvents

Solvent	Temperature [K]	Crystal form	Solubility [mg/mL]	Reference
1-Butanol	278.15	-	0.0186	[132]
1-Butanol	283.15	-	0.0296	[132]
1-Butanol	288.15	-	0.04649	[132]
1-Butanol	293.15	-	0.07156	[132]
1-Butanol	298.15	-	0.113	[132]
1-Butanol	303.15	-	0.1692	[132]
1-Butanol	308.15	-	0.2454	[132]
1-Butanol	313.15	-	0.3553	[132]
1-Butanol	318.15	-	0.5029	[132]
1-Butanol	323.15	-	0.721	[132]
1-Propanol	278.15	-	0.015	[132]
1-Propanol	283.15	-	0.027	[132]
1-Propanol	288.15	-	0.04733	[132]
1-Propanol	293.15	-	0.079	[132]
1-Propanol	298.15	-	0.1327	[132]
1-Propanol	303.15	-	0.2178	[132]
1-Propanol	308.15	-	0.3471	[132]
1-Propanol	313.15	-	0.5584	[132]
1-Propanol	318.15	-	0.8885	[132]
1-Propanol	323.15	-	1.419	[132]
2-Butoxyethanol	278.15	-	0.3067	[132]
2-Butoxyethanol	283.15	-	0.3943	[132]
2-Butoxyethanol	288.15	-	0.4929	[132]
2-Butoxyethanol	293.15	-	0.6227	[132]
2-Butoxyethanol	298.15	-	0.7793	[132]
2-Butoxyethanol	303.15	-	0.9709	[132]
2-Butoxyethanol	308.15	-	1.222	[132]
2-Butoxyethanol	313.15	-	1.494	[132]
2-Butoxyethanol	318.15	-	1.871	[132]
2-Butoxyethanol	323.15	-	2.266	[132]
2-Methoxyethanol	278.15	-	1.413	[132]
2-Methoxyethanol	283.15	-	2.131	[132]
2-Methoxyethanol	288.15	-	3.268	[132]
2-Methoxyethanol	293.15	-	4.66	[132]
2-Methoxyethanol	298.15	-	6.85	[132]
2-Methoxyethanol	303.15	-	9.634	[132]
2-Methoxyethanol	308.15	-	13.56	[132]
2-Methoxyethanol	313.15	-	18.75	[132]
2-Methoxyethanol	318.15	-	26.18	[132]
2-Methoxyethanol	323.15	-	36.09	[132]
Butyl acetate	278.15	-	0.3966	[132]
Butyl acetate	283.15	-	0.5455	[132]
Butyl acetate	288.15	-	0.7548	[132]
Butyl acetate	293.15	-	1.026	[132]
Butyl acetate	298.15	-	1.459	[132]
Butyl acetate	303.15	-	1.778	[132]
Butyl acetate	308.15	-	2.241	[132]
Butyl acetate	313.15	-	3.2	[132]
Butyl acetate	318.15	-	3.968	[132]
Butyl acetate	323.15	-	5.082	[132]
Dimethyl sulfoxide	298.15	-	131.7	[132]
Dimethyl sulfoxide	303.15	-	165.4	[132]
Dimethyl sulfoxide	308.15	-	205.8	[132]
Dimethyl sulfoxide	313.15	-	254.5	[132]
Dimethyl sulfoxide	318.15	-	315.4	[132]
Dimethyl sulfoxide	323.15	-	389.6	[132]
Dimethylformamide	278.15	-	38.13	[132]
Dimethylformamide	283.15	-	49.45	[132]
Dimethylformamide	288.15	-	63.74	[132]
Dimethylformamide	293.15	-	81.27	[132]
Dimethylformamide	298.15	-	104.3	[132]
Dimethylformamide	303.15	-	130.7	[132]
Dimethylformamide	308.15	-	164.0	[132]
Dimethylformamide	313.15	-	203.9	[132]
Dimethylformamide	318.15	-	256.4	[132]
Dimethylformamide	323.15	-	317.6	[132]
Ethanol	278.15	-	0.06651	[132]
Ethanol	283.15	-	0.1062	[132]
Ethanol	288.15	-	0.1675	[132]
Ethanol	293.15	-	0.2567	[132]
Ethanol	298.15	-	0.3922	[132]
Ethanol	303.15	-	0.5942	[132]
Ethanol	308.15	-	0.876	[132]
Ethanol	313.15	-	1.301	[132]
Ethanol	318.15	-	1.89	[132]
Ethanol	323.15	-	2.673	[132]
Ethyl acetate	278.15	-	0.9889	[132]
Ethyl acetate	283.15	-	1.468	[132]
Ethyl acetate	288.15	-	2.05	[132]
Ethyl acetate	293.15	-	2.817	[132]
Ethyl acetate	298.15	-	4.017	[132]
Ethyl acetate	303.15	-	5.201	[132]
Ethyl acetate	308.15	-	7.108	[132]
Ethyl acetate	313.15	-	9.347	[132]
Ethyl acetate	318.15	-	12.83	[132]
Ethyl acetate	323.15	-	17.13	[132]
Glycol monoethyl ether	278.15	-	0.4296	[132]
Glycol monoethyl ether	283.15	-	0.6562	[132]
Glycol monoethyl ether	288.15	-	0.9952	[132]
Glycol monoethyl ether	293.15	-	1.493	[132]
Glycol monoethyl ether	298.15	-	2.169	[132]
Glycol monoethyl ether	303.15	-	3.226	[132]
Glycol monoethyl ether	308.15	-	4.499	[132]
Glycol monoethyl ether	313.15	-	6.471	[132]
Glycol monoethyl ether	318.15	-	9.122	[132]
Glycol monoethyl ether	323.15	-	12.67	[132]
Glycol monopropyl ether	278.15	-	0.3677	[132]
Glycol monopropyl ether	283.15	-	0.4818	[132]
Glycol monopropyl ether	288.15	-	0.6713	[132]
Glycol monopropyl ether	293.15	-	0.8588	[132]
Glycol monopropyl ether	298.15	-	1.14	[132]
Glycol monopropyl ether	303.15	-	1.481	[132]
Glycol monopropyl ether	308.15	-	1.925	[132]
Glycol monopropyl ether	313.15	-	2.489	[132]
Glycol monopropyl ether	318.15	-	3.265	[132]
Glycol monopropyl ether	323.15	-	4.11	[132]
Methanol	278.15	-	0.2674	[132]
Methanol	283.15	-	0.4288	[132]
Methanol	288.15	-	0.6539	[132]
Methanol	293.15	-	1.012	[132]
Methanol	298.15	-	1.518	[132]
Methanol	303.15	-	2.276	[132]
Methanol	308.15	-	3.316	[132]
Methanol	313.15	-	4.828	[132]
Methanol	318.15	-	7.004	[132]
Methanol	323.15	-	9.905	[132]
Methyl acetate	278.15	-	2.829	[132]
Methyl acetate	283.15	-	3.435	[132]
Methyl acetate	288.15	-	5.605	[132]
Methyl acetate	293.15	-	7.707	[132]
Methyl acetate	298.15	-	9.983	[132]
Methyl acetate	303.15	-	13.85	[132]
Methyl acetate	308.15	-	18.09	[132]
Methyl acetate	313.15	-	24.0	[132]
Methyl acetate	318.15	-	32.46	[132]
Methyl acetate	323.15	-	43.82	[132]
N-Methyl-2-pyrrolidone	278.15	-	45.58	[132]
N-Methyl-2-pyrrolidone	283.15	-	56.82	[132]
N-Methyl-2-pyrrolidone	288.15	-	70.41	[132]
N-Methyl-2-pyrrolidone	293.15	-	86.96	[132]
N-Methyl-2-pyrrolidone	298.15	-	106.8	[132]
N-Methyl-2-pyrrolidone	303.15	-	130.3	[132]
N-Methyl-2-pyrrolidone	308.15	-	158.7	[132]
N-Methyl-2-pyrrolidone	313.15	-	193.7	[132]
N-Methyl-2-pyrrolidone	318.15	-	234.3	[132]
N-Methyl-2-pyrrolidone	323.15	-	284.4	[132]
Propyl acetate	278.15	-	0.349	[132]
Propyl acetate	283.15	-	0.6467	[132]
Propyl acetate	288.15	-	1.009	[132]
Propyl acetate	293.15	-	1.391	[132]
Propyl acetate	298.15	-	2.148	[132]
Propyl acetate	303.15	-	2.895	[132]
Propyl acetate	308.15	-	4.113	[132]
Propyl acetate	313.15	-	5.7	[132]
Propyl acetate	318.15	-	8.034	[132]
Propyl acetate	323.15	-	11.01	[132]

Molecule 3D descriptors

Descriptor	Value
PMI1	479.0250
PMI2	2407.3294
PMI3	2618.4845
NPR1	0.1829
NPR2	0.9194
RadiusOfGyration	3.3429
InertialShapeFactor	0.0019
Eccentricity	0.9831
Asphericity	0.5505
SpherocityIndex	0.2257
PBF	0.7900