General
Preferred name
BUSULFAN
Synonyms
Myleran ()
Busulphan ()
Sulphabutin ()
Busulfex ()
1,4-Dimethylsulfonoxybutane ()
1,4-Butanediol dimethylsulfonate ()
GT 41 ()
X 149 ()
Mablin ()
NSC-750 ()
NSC 750 ()
Busulfan55-98-1 ()
Busulfan (NSC-750) ()
Myelosan ()
Busulfanum ()
Myelosanum ()
Leucosulfan ()
Busilvex ()
NCI-C01592 ()
Busulfan-d8 ()
P&D ID
PD002449
CAS
55-98-1
116653-28-2
Tags
nuisance
natural product
drug
available
Approved by
PMDA
FDA
First approval
1954
Drug Status
investigational
approved
Drug indication
Myeloproliferative syndrome
Max Phase
Phase 4
Probe control
Probe control not defined
Orthogonal probes
0
No orthogonal probes found
Similar probes
0
No structurally similar probes found
Structure
P&D probe-likeness score
Structure formats
[[ format ]]
[[ compound[format === 'MOL' ? 'molblock' : format.toLowerCase()] ]]
Description
(extracted from source data)
MOA
Busulfan is an alkylating agent that contains 2 labile methanesulfonate groups attached to opposite ends of a 4-carbon alkyl chain. Once busulfan is hydrolyzed, the methanesulfonate groups are released and carbonium ions are produced. These carbonium ions alkylate DNA, which results in the interference of DNA replication and RNA transcription, ultimately leading to the disruption of nucleic acid function. Specifically, its mechanism of action through alkylation produces guanine-adenine intrastrand crosslinks. These crosslinks occur through a SN2 reaction guanine N7 nucleophilically 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.
DESCRIPTION
Busulfan is a DNA alkylating agent. It has an immunosuppressive effect on bone marrow, especially inhibiting growth of granulocytes.
(GtoPdb)
[[ p.pathway_name ]]
[[ compound.targets[tid].gene_name ]]
Cell lines
4
Organisms
0
Compound Sets
28
AdooQ Bioactive Compound Library
CeMM library of unique drugs (CLOUD)
ChEMBL Approved Drugs
ChEMBL Drugs
Drug Repurposing Hub
DrugBank
DrugBank Approved Drugs
DrugCentral
DrugCentral Approved Drugs
DrugMAP
DrugMAP Approved Drugs
DrugMatrix
Enamine BioReference Compounds
Guide to Pharmacology
LSP-MoA library (Laboratory of Systems Pharmacology)
MedChem Express Bioactive Compound Library
NCATS Inxight Approved Drugs
NIH Approved Oncology Drugs
NIH Clinical Collections (NCC)
NIH Mechanistic Set
NPC Screening Collection
Nuisance compounds in cellular assays
Prestwick Chemical Library
ReFrame library
Selleckchem Bioactive Compound Library
TargetMol Bioactive Compound Library
The Spectrum Collection
[[ a.name ]]
[[ ligand_id ]]
free of charge
External IDs
45
Molecular Weight
246.02
Hydrogen Bond Acceptors
6
Hydrogen Bond Donors
0
Rotatable Bonds
7
Ring Count
0
Aromatic Ring Count
0
cLogP
-0.28
TPSA
86.74
Fraction CSP3
1.0
Chiral centers
0.0
Largest ring
0.0
QED
0.45
Structural alerts
1
Genotoxic
Nuisance compounds in cellular assays
Related compounds
Custom attributes
(extracted from source data)
MOA
DNA alkylator
DNA inhibitor
Target
DNA
DNA alkylation
DNA alkylator/crosslinker
Apoptosis related,DNA alkylator
Pathway
DNA Damage/DNA Repair
Apoptosis
Cell Cycle/DNA Damage
Indication
chronic myeloid leukemia (CML)
Therapeutic Class
Anticancer Agents
Source data
