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uramustine   Click here for help

GtoPdb Ligand ID: 7621

Synonyms: U-8344 | Uracil Mustard®
Approved drug
uramustine is an approved drug
Compound class: Synthetic organic
Comment: Chemically uramustine is a derivative of nitrogen mustard and uracil. It is used clinically as a DNA alkylating anti-cancer chemotherapeutic.
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 Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/). 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 3
Hydrogen bond donors 2
Rotatable bonds 5
Topological polar surface area 68.96
Molecular weight 251.02
XLogP 1.56
No. Lipinski's rules broken 0

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
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.

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)

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Canonical SMILES ClCCN(c1c[nH]c(=O)[nH]c1=O)CCCl
Isomeric SMILES ClCCN(c1c[nH]c(=O)[nH]c1=O)CCCl
InChI InChI=1S/C8H11Cl2N3O2/c9-1-3-13(4-2-10)6-5-11-8(15)12-7(6)14/h5H,1-4H2,(H2,11,12,14,15)
InChI Key IDPUKCWIGUEADI-UHFFFAOYSA-N

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
No information available.
Summary of Clinical Use Click here for help
Antineoplastic action is used to treat lymphatic malignancies eg non-Hodgkin's lymphoma. However, there is no information regarding approval of this drug on either the US FDA or EMA websites. Individual national approval agencies may have granted marketing authorisation for this drug.
Mechanism Of Action and Pharmacodynamic Effects Click here for help
Uramustine binds preferentially to the guanine and cytosine nucleotides in DNA, leading to DNA cross-linking, and subsequently inhibits DNA synthesis and function. This results in cell death. At high doses RNA and protein synthesis are also inhibited.