melphalan flufenamide   Click here for help

GtoPdb Ligand ID: 11605

Synonyms: Melflufen | Pepaxti® | Pepaxto® | Prodrug J 1 | Prodrug J-1
Approved drug
melphalan flufenamide is an approved drug (FDA (2021), EMA (2022))
Compound class: Synthetic organic
Comment: Melphalan flufenamide is a peptide-conjugated prodrug of the cytotoxic DNA alkylating drug melphalan [3]. It is highly lipophilic and is rapidly transported into cells where it is quickly hydrolysed by aminopeptidases that are overexpressed by some cancer cells. Melphalan flufenamide is being evaluated as a treatment for multiple myeloma [2,5-6].
The IUPAC Condensed peptide sequence for melphalan flufenamide is H-Phe(Unk)-Phe(4-F)-OEt.
2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 6
Hydrogen bond donors 2
Rotatable bonds 15
Topological polar surface area 84.66
Molecular weight 497.16
XLogP 4.57
No. Lipinski's rules broken 1
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Canonical SMILES ClCCN(c1ccc(cc1)C[C@@H](C(=O)N[C@H](C(=O)OCC)Cc1ccc(cc1)F)N)CCCl
Isomeric SMILES ClCCN(c1ccc(cc1)C[C@@H](C(=O)N[C@H](C(=O)OCC)Cc1ccc(cc1)F)N)CCCl
InChI InChI=1S/C24H30Cl2FN3O3/c1-2-33-24(32)22(16-18-3-7-19(27)8-4-18)29-23(31)21(28)15-17-5-9-20(10-6-17)30(13-11-25)14-12-26/h3-10,21-22H,2,11-16,28H2,1H3,(H,29,31)/t21-,22-/m0/s1
Classification Click here for help
Compound class Synthetic organic
Approved drug? Yes (FDA (2021), EMA (2022))
Is prodrug? Yes
Active form melphalan
IUPAC Name Click here for help
ethyl (2S)-2-[[(2S)-2-amino-3-[4-[bis(2-chloroethyl)amino]phenyl]propanoyl]amino]-3-(4-fluorophenyl)propanoate
International Nonproprietary Names Click here for help
INN number INN
9493 melphalan flufenamide
Synonyms Click here for help
Melflufen | Pepaxti® | Pepaxto® | Prodrug J 1 | Prodrug J-1
Database Links Click here for help
CAS Registry No. 380449-51-4 (source: WHO INN record)
ChEMBL Ligand CHEMBL4303060
GtoPdb PubChem SID 442878639
PubChem CID 9935639
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UniChem Compound Search for chemical match using the InChIKey YQZNKYXGZSVEHI-VXKWHMMOSA-N
UniChem Connectivity Search for chemical match using the InChIKey YQZNKYXGZSVEHI-VXKWHMMOSA-N