melphalan   Click here for help

GtoPdb Ligand ID: 7620

Synonyms: Alkeran® | CB-3025 | L-phenylalanine mustard (L-PAM) | L-sarcolysine | melfalan | Phelinun® | Sarcolysin®
Approved drug
melphalan is an approved drug (FDA (1964), EMA (2020))
Compound class: Synthetic organic
Comment: Marketed formulations may contain melphalan hydrochloride.
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 4
Hydrogen bond donors 2
Rotatable bonds 8
Topological polar surface area 66.56
Molecular weight 304.07
XLogP 0.36
No. Lipinski's rules broken 0
SMILES / InChI / InChIKey
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Canonical SMILES ClCCN(c1ccc(cc1)CC(C(=O)O)N)CCCl
Isomeric SMILES ClCCN(c1ccc(cc1)C[C@@H](C(=O)O)N)CCCl
InChI InChI=1S/C13H18Cl2N2O2/c14-5-7-17(8-6-15)11-3-1-10(2-4-11)9-12(16)13(18)19/h1-4,12H,5-9,16H2,(H,18,19)/t12-/m0/s1
InChI Key SGDBTWWWUNNDEQ-LBPRGKRZSA-N
No information available.
Summary of Clinical Use Click here for help
Melphalan is a bifunctional alkylating agent used as a chemotherapy drug. Alkylating agents are active against both resting and rapidly dividing tumour cells. Melphalan is used in the palliative treatment of multiple myeloma and non-resectable ovarian cancer of epithelial origin. Melphalan may also have therapeutic benefit in some patients with advanced breast carcinoma (either alone or in combination with other drugs) or those suffering from polycythaemia vera.
Mechanism Of Action and Pharmacodynamic Effects Click here for help
Alkylating agents inhibit tumour growth by cross-linking guanine bases in DNA double-helix strands. Drug treatment irreversibly interferes with DNA replication, RNA transcription and general disruption of nucleic acid function. This action causes cell death.
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