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 PDB Ligand
melphalan is an approved drug (FDA (1964), EMA (2020))
Compound class: Synthetic organic
Comment: Marketed formulations may contain melphalan hydrochloride.
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View more information in the IUPHAR Pharmacology Education Project: melphalan

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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Click here for structure editor
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 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

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(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

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
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. Melphalan alkylates DNA at the N7 position of guanine residues to irreversibly interfere with DNA replication, RNA transcription and general disruption of nucleic acid function. This action causes cell death.
External links Click here for help
For extended ADME data see the following:

Electronic Medicines Compendium (eMC)
Drugs.com