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.
IUPHAR Pharmacology Education Project (PEP) logo

View more information in the IUPHAR Pharmacology Education Project: mechlorethamine

2D Structure
Click here for help
Click here for structure editor
Physico-chemical Properties
Click here for help
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
Click here for help
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