busulfan   Click here for help

GtoPdb Ligand ID: 7136

Synonyms: Busulfex IV® | Myleran®
Approved drug
busulfan is an approved drug (FDA (1954), EMA (2003))
Compound class: Synthetic organic
Comment: Busulfan is a DNA alkylating agent. It has an immunosuppressive effect on bone marrow, especially inhibiting growth of granulocytes.
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Ligand Activity Visualisation Charts

These are box plot that provide a unique visualisation, summarising all the activity data for a ligand taken from ChEMBL and GtoPdb across multiple targets and species. Click on a plot to see the median, interquartile range, low and high data points. A value of zero indicates that no data are available. A separate chart is created for each target, and where possible the algorithm tries to merge ChEMBL and GtoPdb targets by matching them on name and UniProt accession, for each available species. However, please note that inconsistency in naming of targets may lead to data for the same target being reported across multiple charts.

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View interactive charts of activity data across species

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View more information in the IUPHAR Pharmacology Education Project: busulfan

2D Structure
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2D Structure

An image of the ligand's 2D structure. For small molecules with SMILES these are drawn using the NCI/CADD Chemical Identifier Resolver. Click on the image to access the chemical structure search tool with the ligand pre-loaded in the structure editor. For other types of ligands, e.g. longer nucleotides and peptides, a manually drawn representation of the molecule may be provided.

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Physico-chemical Properties
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Physico-chemical Properties

Calculated molecular properties are available for small molecules and natural products (not peptides). Properties were generated using the CDK toolkit. All properties were selected to enable the prediction of the Lipinski Rule-of-Five profile or ‘druglikeness’ for each ligand. For more info on each category see the help pages.

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Hydrogen bond acceptors 6
Hydrogen bond donors 0
Rotatable bonds 7
Topological polar surface area 103.5
Molecular weight 246.02
XLogP -1.23
No. Lipinski's rules broken 0
SMILES / InChI / InChIKey
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SMILES / InChI / InChIKey

SMILES (Simplified Molecular Input Line Entry Specification) A specification for unambiguously describing the structure of chemical molecules using short ASCII strings. Canonical SMILES specify a unique representation of the 2D structure without chiral or isotopic specifications. Isomeric SMILES include chiral specification and isotopes.

Standard InChI (IUPAC International Chemical Identifier) and InChIKey InChI is a non-proprietary, standard, textual identifier for chemical substances designed to facilitate linking of information and database searching. An InChIKey is a simplified version of a full InChI, designed for easier web searching.

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Canonical SMILES CS(=O)(=O)OCCCCOS(=O)(=O)C
Isomeric 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
InChI Key COVZYZSDYWQREU-UHFFFAOYSA-N
No information available.
Summary of Clinical Use Click here for help
Busulfan is used as palliative care in patients with chronic myeloid leukemia (CML). It is also used to pre-condition (ie immunosuppress) patients prior to undergoing bone marrow transplant (autologous or allogenic hematopoietic stem cell transplantation) as treatment for leukemias.
Mechanism Of Action and Pharmacodynamic Effects Click here for help
As a DNA alkylating (cross-linking) agent, busulfan treatment irreversibly interferes with DNA replication, RNA transcription and general disruption of nucleic acid function. This action causes cell death. Due to the complex and varied nature of nucleic acids we do not include DNA or RNA as targets on this database.
External links Click here for help
For extended ADME data see the following:

Electronic Medicines Compendium (eMC)
Drugs.com
European Medicines Agency (EMA)