mechlorethamine   Click here for help

GtoPdb Ligand ID: 7218

Synonyms: Ledaga® | Mustargen® | mustine | nitrogen mustard | nitrogen mustard N-oxide hydrochloride
Approved drug
mechlorethamine is an approved drug (FDA (1949), EMA (2017))
Compound class: Synthetic organic
Comment: Mechlorethamine is a nitrogen mustard and is the prototype alkylating anticancer chemotherapeutic. In addition, mechlorethamine is used in the synthesis of the opioid analgesic pethidine.
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View more information in the IUPHAR Pharmacology Education Project: mechlorethamine

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 1
Hydrogen bond donors 0
Rotatable bonds 4
Topological polar surface area 3.24
Molecular weight 155.03
XLogP 1.59
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 ClCCN(CCCl)C
Isomeric SMILES ClCCN(CCCl)C
InChI InChI=1S/C5H11Cl2N/c1-8(4-2-6)5-3-7/h2-5H2,1H3
InChI Key HAWPXGHAZFHHAD-UHFFFAOYSA-N
No information available.
Summary of Clinical Use Click here for help
Used in the palliative care of patients with various cancers. Ledaga® was EMA approved in 2017 as a treatment for mycosis fungoides-type cutaneous T-cell lymphoma, having been granted EMA orphan designation in 2012 for the treatment of cutaneous T-cell lymphoma.
Mechanism Of Action and Pharmacodynamic Effects Click here for help
Mechlorethamine is a potent DNA alkylating (cross-linking) agent. Treatment with this drug 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:

Drugs.com
European Medicines Agency (EMA)